Matt Mullenweg, cofounder of WordPress and CEO of Automattic, embarks on a journey to understand the future of work. Having built his own company with no offices and more than 1,300 employees in 76 countries, speaking 95 different languages, Mullenweg examines the benefits and challenges of distributed work and recruiting talented people around the globe.
On this episode of Distributed, we dig into the good, the bad, and the karaoke-filled history of Automattic meetups. Before the COVID-19 pandemic, our annual Grand Meetup brought the entire company together for a week. The time spent together — along with team-specific meetups scattered throughout the year — helped us strengthen relationships with our colleagues located around the world. Now, as companies and workers grapple with returning to the office, it’s a perfect chance to consider in-person time as an important complement to the autonomy and flexibility of distributed work.
We spoke with Automatticians about how to stay connected in a distributed work culture. You’ll hear from Toni Schneider, Automattic’s first CEO, Josepha Haden Chomphosy, Executive Director of the WordPress Project, and Nick Gernert, CEO of WordPress VIP, along with a wide range of Automatticians.
The full episode transcript is below and has been lightly edited for clarity.
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MATT MULLENWEG: Howdy howdy. This is Matt Mullenweg, the co-founder of WordPress and the CEO of Automattic, and you are listening to the Distributed podcast, which is back after a – I’m embarrassed to say – 500 day hiatus, roughly. I wasn’t as drawn to do more Distributed episodes last year. One because I got super busy and, you know, 2022 I started running Tumblr directly and WordPress.com.
So, things at work got pretty busy, but also just felt like everyone was doing it. Everyone had kind of figured out the remote and distributed thing. And it was going fine. So like, the reason I started the podcast was done so the purpose, the goal I set out to accomplish was completed.
However, recently there’s been a lot of news about companies who are rolling back their employee flexibility and forcing people back into the office 2, 3, 4, 5 days a week. Sometimes, they might be doing this as a way to lay people off. It’s hard to tell the motivations of some of these executives.
But some, I think, in good faith are saying that they were missing something when people weren’t getting together and that employees that joined during the pandemic maybe weren’t as productive as employees who joined prior. It got me thinking and I started to wonder if what they were missing was meetups.
So there is something magic, some frisson that happens in person, that’s impossible to recreate. At Automattic, we just don’t think that needs to be 52 weeks a year. Just like a little salt makes the dish, getting together in person a few times a year is a key ingredient of Automattic’s culture. So I wanted to share with the world and podcast listeners who are now seeing this pop up after 500 days.
How we do meetups at Automattic and why it’s so key. So, I tapped my colleague Chenda Ngak to gather some stories and best practices from Automatticians of how we do meetups. We’ll also put together some guides on the distributed.blog website, after this episode is up. But please get together. Seeing people is important.
And without further ado, I’ll pass you over to the Chenda.
CHENDA NGAK: Grand meetups at Automatic are the stuff of legends. We paused them because of the pandemic and have slowly restarted smaller meetups over the last year. Meetups have been an important tradition ever since the first meetup in 2006. Now, I’d never been to a grand meetup, so I wanted to hear what it was like from Automatticians who have attended.
I started with Lori McLeese. She leads our global people team from Asheville, North Carolina. I couldn’t think of a better person to give me a crash course in meetups. She’s been at Automattic for a decade, and her team is connected to every Automattician around the world.
LORI MCLEESE: So, the different types of meetups that Automattic are our Grand Meetup, which is when the whole company comes together. Unfortunately, we have not had an all company meetup since the end of 2019 because of the pandemic. However, when we were having them before that, it usually lasted about seven to eight days and we usually held them in September or October, and it was a week when the whole company could get together.
We could learn from each other. We could do projects. We could hear amazing speakers, you know, spend time together, both as teams and with people that maybe you don’t work with on a normal basis and just have fun and build relationships. So, that’s one type of meetup.
A second type of meet up is team meetups, which is very similar to the Grand Meetup, but on a much, much, much smaller scale. So, team meetups are usually anywhere from four to 10 people. The team actually decides where to go, what to do, what type of social activities they want to be involved in.
And as a company, we give them a budget and then the teams make all that decision. And we ask people after their meetups to actually write a summary on our internal, we call it Meetomattic and it’s a P2 or a website where all the teams record experiences of their meetup and actually rate the location about whether it would be good for other teams to go.
CHENDA NGAK: So, for those who don’t know, Lori is talking about an internal network of blogs called P2. The recaps on P2 are like a mini city guide with best restaurants, activities, the team’s itinerary for the week, and the average cost of throwing a meetup in cities around the world.
LORI MCLEESE: And then a third type of meetup is a division meetup, and that’s when several teams within the division get together. And I would say that those depending on the division run from like 75 to maybe 200 people. So, it’s a little bit of a mash up between team and Grand Meetup.
CHENDA NGAK: Why do you think that meetups are so important for our culture?
LORI MCLEESE: While it’s great to work from home, work distributedly, work from anywhere, there is something missing when all you ever have is either text communication or perhaps even video communication and I think one of the best things about meetups is that that’s where spontaneity can occur.
CHENDA NGAK: I wanna expand on that and see if we can talk a bit about what meetups mean for team morale and inclusion.
LORI MCLEESE: For team morale, there is an excitement not only of being at the meetup, but also planning the meetup and talking about what do we want to do together? Whether that’s the work activities or the social activities, and learning about people’s preferences for inclusion. It’s also really important because we have a pre-meetup survey that we ask each attendee to complete as the team members are planning the meetup.
And you know, it’s not just dietary needs, which are important, but it’s things like how far are you comfortable walking? Are you comfortable speaking up in public or would you rather have the questions beforehand? And so it gives you an understanding of people’s work styles, which are very different and helps the organizers to really plan a much more inclusive event.
And those learnings then carry over after you get back from the meetup when you’re working online so that you can remember like, oh, this person doesn’t like to be called out on the spot. They like to have questions in advance so that they can think about it before presenting an answer.
CHENDA NGAK: Now that Lori has explained the different types of meetups, I thought it would be interesting to get background on why we started doing them. So, I caught up with Toni Schneider who joined Automattic in 2006 as its first CEO, just six months after the company was founded.
TONI SCHNEIDER: I think the reason we started having meetups right away and they worked right away is because there was a meeting of the existing team that was already distributed and working together via open source and really liked meeting in person every once in a while.
So, that was already a pattern that was established and in my background, coming from other startups and spending a little bit of time at Yahoo, at a bigger company, kinda seeing if we fast forward this, if WordPress gets huge and we have a huge team, how can we make this work at scale? That’s gonna be different than those big companies.
And the big companies I saw were, when they were doing meetups, it was really offsites and they were awkward, in my opinion, because people were already spending all day together at work. And they’re like, “How do we have to now go somewhere else and spend even more time?” And they’d be very scripted and all about the product roadmap and all these things. And I knew we didn’t want that at all.
We flipped it upside down and said, what if we had a meetup and did essentially no work, nothing extra, nothing scripted, purely focus it on social time, purely focus it on bonding because that’s what we need more of.
And then we saw things that came out of the meetups that I don’t think would’ve arisen otherwise. And I think that’s why we kept doing them too. Things like P2 came out of the meetup and that became hugely important for the company.
We had town halls and we had flash talks, things like that. I think, are examples of things that just happen when you get together in person and just kinda see what arises for people. WordCamps were another example. You know, the first WordCamp was essentially a brainstorm in one of our meetups and said, “Let’s try it.”
CHENDA NGAK: Do you have any practical advice for startups that wanna throw a meet up today?
TONI SCHNEIDER: Yeah, I think it’s important to set the expectations. And we have to be pretty explicit and say, “No, this is part of the job. This is part of your expectation. You can’t skip these.” And it’s really important to say that up front to people and say, “Look, there’s 52 weeks in a year. You know, you’re gonna maybe work, I don’t know, 40-some of those. And most of that’s gonna be at home and you’re totally in control, but you know, probably two or three weeks a year, you’re gonna participate in these types of activities.”
CHENDA NGAK: Another thing that I was curious about is if you’ve noticed meetups come up in other conversations with any startups that you’ve been working with, or in the tech industry in general.
TONI SCHNEIDER: Oh, absolutely. I mean, I am now with True Ventures. We have ours, a little shorter, usually three days every quarter, four times a year. Most of the startups I work with – we have over 200 in our portfolio. At True, everybody is at least partially remote or fully remote, and everybody’s trying to figure out how to spend time together.
So, it’s on everybody’s mind. I think a lot of people are adopting these kinds of, you know, best practices that fully distributed companies have come up with. I think it’s working. I feel like there’s a whole set of tools in the industry growing up around it. Right? There’s a lot of people going, “OK, we can host some of these meetups and retreats and be a great place for people to get together. We can be a platform where people can organize their meetups.”
And I think one of the companies we invested in called Happy does that. And there’s a huge demand for it, especially from big companies who are saying, “OK, all of our teams want to meet in person and we’re not set up for it, help us figure out how to do these things.” And I think we’ll just see more and more of it.
I have friends who are essentially building retreat centers around this notion and saying, we don’t need more hotels. We need more places where these teams can gather and spend several days and be creative together. It’s really nice to be in a place where you feel like, “Oh, it’s just us. We get to do our thing.”
I think all of our initial meetups were like, there was like a ranch in Arizona where it was just us and there was like a bed and breakfast in Mexico where it was just us. And we could bring our Wii and play Wii tennis and be goofy and stay up till two in the morning and nobody cared. And I think that’s important too, to pick venues that allow for that to happen versus again, the more scripted, “Here’s, you know, a place with good wifi and good presentation system.” And let’s all sit in a conference room. We’ve always avoided that.
I see a lot of teams gravitating towards the more retreat type setting. And I think hopefully there’ll be a lot more of it. I think there’s still, there’s a huge untapped market for it because it’s still hard to find something that’s like a retreat, but also has really good internet and you actually can be connected. We would find these places like, “Oh my God, this looks amazing.” “Oh no, we don’t have internet people come here to disconnect.” “Oh no, that’s not us.” We’re gonna be the opposite. We’re gonna get there and you know, 20 or 30 laptops are gonna open and your internet’s gonna come to a halt.
CHENDA NGAK: What do you think our legacy has been for remote companies today?
TONI SCHNEIDER: Yeah, it’s hard to tell, but I always assumed that it’s amazing as WordPress is. I think our long term impact might be just as much that we showed that a remote model can work. I definitely remember the early days and it was very, very different when we tell people that we were distributed. A lot of people didn’t like the idea.
They wanted to argue why it was a bad idea or they just didn’t think it was ever gonna scale. There was a lot of like, “Oh, that’s great, but you’re just 20 people just wait till you’re 50 people just wait till you’re a hundred people. It’s definitely gonna break at 200 people.” So there was just a lot of disbelief that this actually works. I think we kind of chipped away and it’s not like we started the company to prove that distributed can work. It just worked for us and we thought, well, let’s keep going and let’s make it work even better. And let’s really lean into it.
And just leading by example, I guess, other companies now look and go, “Oh yeah, that’s an option. It’s not the only option. There’s lots of ways to build an organization, but this is a real option. This can work.” We’re 2,000 people now and it’s working and it’s a great organization. So, I really think it has helped tremendously to just make it available to other entrepreneurs and, and be able to say, “Oh look, they did it, WordPress did it.”
It’s funny to think back, but there was a lot of skepticism. We even had employees who would say, “Can you send a message to my parents and tell them that this is real, this isn’t like some weird scam?” Even the employees were like, “I love it, but like my friends and family think I’m crazy.” So, we’ve come a long way. I’m proud that we’ve been able to help this model gain more mainstream acceptance. And obviously with COVID, it kind of kicked into hyper drive and 10 years of adoption happened in like 10 days.
I think all that work of slowly perfecting the model and showing that it works, sort of, at the right time was all available for people to go, “Oh OK, let’s try that.” And then I think the other thing that happened is we had less to do with all the tools that started to become available.
In the beginning we built all our tools ourselves, and then we realized, “Oh, now we can use Slack; now we can use Zoom.”
I think a lot of companies when COVID hit realized that they were already using all the tools. So, I would give a lot of credit to those companies, as well, for popularizing tools that companies didn’t even totally realize you already have all the infrastructure in place. And I know a lot of companies I worked with were shocked how easy it was to just work from home. They’re like, “Oh wait, we don’t even have to change anything. We just already have it all in place.”
And I think that was huge. So, that lined up really well as well.
CHENDA NGAK: I wanted to hear more about the vibe and social aspects of meetups. So I rounded up a few members of our house band, the Automusicians. There are hundreds of musicians in this group. They discuss songs and set lists on our internal blog system, P2, and then they sign up to perform at the Grand Meetup. I could only get time with Matt, Leif, and Paul who are based in South Africa, Germany and Austria, respectively. Paul works with me on WordPress.com while Leif and Matt work on WooCommerce.
How does the band prepare for a show when all of the members are distributed?
LEIF SINGER: For me, there’s two things to it, right? The practice week together, where you get to know everyone, you make music together which is just fun and makes people bond. Right. But you’re working towards this goal, which is the last evening, and that is an evening where you get to be a rockstar for one day a year.
PAUL BONAHORA: I guess everybody managed it differently, in their own way, but I recall there was like a spreadsheet where we would put in who would want to practice. Because we had a couple of practice rooms. There were two or three, at least at the one meetup that I’ve been to two of them.
And there was a spreadsheet where everybody would book their slot. So, we had these practice slots where the band would show up for their practice slot and we would get to get the instruments and just practice the songs, which would be a really cool way to bond.
CHENDA NGAK: I would love to hear more about the vibe of a Grand Meetup.
MATT COHEN: Yeah, there’s, there’s definitely an energy to it. Compared to a smaller team gathering of five to 10 people. That’s one thing. Coordination is really straightforward there. You’re all kind of in the same room or nearby to each other. At a big event, like a Grand Meetup, there’s several hundred people. Maybe even a thousand people or more.
It’s electric, you’re not always seeing people that you work with day to day. I think most times you’ll actually see a lot more people that you don’t often see, which is somewhat intentional in some contexts like around meal time and things like that.
But it’s nice to embrace every aspect of the meetup as an opportunity for that kind of connection. So, standing in a buffet line at a meal, for example, and you look across the table and you see someone you haven’t seen in three years, who’s now moved to a different division in the company and you say, “Oh wow. So nice to see you. How are you? How’s your kids? How’s, you know, how’s life on your end of the world?” You know, being that we’re in 90 plus countries as well. It’s powerful.
LEIF SINGER: The magic starts even at the airport, like, especially coming from Europe, for example. There’s usually one or two hubs that basically everyone goes through.
So, as I have headphones on at the airport, I listen to music and I walk to the gate from my previous flight and I sit down. And then suddenly I realize I sit among a dozen other colleagues whom I can identify through their backpacks with WordPress logos and stuff. Right?
And, they’re like, “Oh, you probably belong to us. We have never met before, but ‘howdy.’”
That’s where it starts, right? And then you start to see other people trickle in that, maybe you’ve worked with before that you’ve met. And then you have these, “Oh, we haven’t met in two years. How you been, good to see you again.” Then after the full day of travel again, coming from Europe, when it’s usually in the U.S., there’s like 10 hour travel and quite some time zone difference, right?
So, when we arrive there at, say 8:00 pm, we’re super tired, but there are so many people from the events team, welcoming everyone. It’s such a buzz in the air. Like you feel instantly welcome and among friends. That’s super touching.
PAUL BONAHORA: Yeah, I can totally relate to that feeling of getting excited there. And then after being on the plane, you know, for 10 hours that kind of simmering down, but then going back up when, when, once you get to the venue and you start meeting more and more folks, so it’s very energizing.
CHENDA NGAK: What are some of your favorite social moments from previous meetups?
MATT COHEN: It’s tough to pick just one. The two that jumped to mind and I’ll go through them individually. But the first one was those ad hoc moments where you’re all just sitting around and having a discussion about something, but it’s a very deep discussion. And then also at the recent GM, the activities around mindfulness and breath work and, and meditation, and things that are less tech, but still extremely important. Right? Those two really stood out to me.
The sitting around at a table, there’s so many spaces in a, in a hotel or a resort for those impromptu connections. And I think we’ve done that really well at GM’s overall, is creating those spaces. Whether it doesn’t have to be around a bar or a restaurant, it can be just couches in the hotel and just finding those nooks and saying, well, let’s have a deep discussion about the one that comes to mind is the history of Scotland, for example and common law in Scotland. And that is a completely random subject that would’ve never come up if it weren’t for the people at that nook, at that time.
And that really stands out and you, you know, you carry that through. In building the connection with that other person. It’s not about the topic necessarily, but it’s a way of creating that bond, right. That, that really stands out to me. It’s purely social.
LEIF SINGER: My immediate thoughts go to big events, like for example, the closing party or the silent disco was always really, really great. I usually don’t dance, but that is a really, really safe space and I loved it. As Matty says, the small moments are where the real, like there’s a sparkle to it.
For example, Seth, I knew him from a previous meetup where we bonded a bit, because we were the first to arrive, but at the Grand Meetup, then we were all super busy meeting, new people, talking to everyone. And on day two, I hadn’t met Seth yet, but we were walking down the hallway – each of us deep in a conversation with someone else – but we saw each other, we had a quick hug, smiled at each other and went our ways. There’s no function to that really but it’s great for the heart, for the soul.
CHENDA NGAK: If you didn’t know, we have a huge team of Automattic called Happiness. They are a direct connection to our customers and have a real pulse on how we’re doing. This team works 24 hours a day. So, they’re spread all around the world. I caught up with Nagesh Pai who is based in India.
Nagesh is actually on rotation with another team right now, but that’s another story for another day. Nagesh, what’s it like to be at a Grand Meetup?
NAGESH PAI: In a single word, surreal you’re surrounded by some of the most talented people, I would say, I’ve ever seen. People whom I’ve always looked up to as a small person within the WordPress ecosystem. Maybe I began as a hobby blogger, and then as a freelancer, but always I’ve been wondering who are these wonderful people and great minds that contribute to it.
CHENDA NGAK: I was thinking about the Happiness team and how it’s so big and spread out globally. I would love it if you could talk about how important it is for you all to meet up.
NAGESH PAI: It’s very imperative to have very good connections amongst ourselves within the team so that we are following the same path we are following the same great vision of what we aspire to do as a company, to our users.
And at a personal level, it’s also important to develop best practices and learn the best things from each other. So while there is a standard set of things that we do as a routine on a day to day basis, we are scheduled to work six hours a day. It’s equally important to take a step back and see what are the individual flavors that we can add to these standard things that we do.
And that’s something which is very important to pick from our colleagues who are in our close circle. And that’s precisely where sort of a time out for those seven days, which we enjoy as a team meetup. It certainly helps a lot.
CHENDA NGAK: We mentioned that you’re on rotation now on a different team. That is something that is really unique to Automattic. I think it’s a really cool thing that we do. People can go on rotation to a different team for six months and just fully work there. Do you feel like, because you had been at a bunch of meetups before, it helped you transition to your rotation a lot easier?
NAGESH PAI: Certainly, I would like to add here that Automattic has a wonderful opportunity for each of its employees to try out different skills. And some of us have come with different backgrounds in the past, I’ve worked in marketing and corporate as well.
I also have a background as an engineer, not in computer science, but I like fixing things. During these meetups, I had an opportunity to chat with colleagues who are full-time into those roles and ask myself what next for me within this company to grow individually and also wherein I can contribute in a better way to the company.
And it’s not just about rotating to the coding role or the developer role that I’m trying right now. In the past, I had the opportunity of being a lead for my team for some time. I also did a rotation within Happiness to the WooCommerce division.
So for all of this, I had to ask opinions from people who already done this.
All the answers to these questions I could get firsthand from people who’ve already done that. So this is precisely what I got from some of these meetups, across a dinner table or a nice pleasant drink.
CHENDA NGAK: I had already started interviewing Automatticians for this episode when I was tagged in a P2 post that felt almost serendipitous. Steve Blythe works on our Trust and Safety team on legal processes. He wrote a blog post talking about the importance of meetups at Automattic. It was exactly what I was building this episode around. Can you summarize what your post was about? And give me a little bit of insight into your inspiration on why you wrote it.
STEVE BLYTHE: I’ve been at Automattic almost nine years. I’ve been to a lot of meetups, a lot of different kinds of meetups over the years. Team meetups, Grand Meetups, you know, the Grand Meetup when it was 200 people versus 2,000 odd or whatever we’re at now. I think that especially over the pandemic because we haven’t been able to meet the kind of the dynamics in terms of our relationship with meetups has changed.
I wanted to share that internally because the company has grown so much over the past few years, even like throughout the pandemic. And there’s lots of people who’ve never been at a meetup, lots of people who’ve never met any other Automattician in person.
The summary of the post was to advocate for the importance of meetups, because there’s the danger, I guess, that, you know, having not had meetups for a long time, either people won’t want to go to them, won’t understand why they’re important, and will prefer to stay at home without really understanding what they’re all about. Or maybe I’ve just got used to not being around people. And It was to try and kind of, yeah, give that perspective I think.
CHENDA NGAK: You know, I was thinking about how people collaborate with each other in social settings at meetups. How do you think that translates to how we work together?
STEVE BLYTHE: Ooh, that’s a good question. I’d never actually made that connection before, or maybe not recently, but I think that, I think it’s the other way around, maybe like in the sense of we have these people that have got amazing strengths or particular skills and are often used to working very independently, cause they’re online might not be obtain their time zone or whatever it is.
And at Automattic we’ve always been kind of early spins started. We were always encouraged. Well, not just encouraged, I don’t wanna say forced, but we were pushed to discover things for ourselves and seek out answers rather than asking other people. So the autonomy part of working Automattic translates well into those situations where people can each bring something? I think that we want to make sure meetups have the opportunity for that, as opposed to just presentational style things, because in those cases, you’re given people that are used to working very independently and expecting them to sit there and listen, which, you know, you, you need to have a balance of that.
CHENDA NGAK: After talking to Steve, I wanted to hear from one of our leaders about why meetups are so important for the business. Nick Gernert is the head of WordPress VIP. They’re the enterprise team that powers huge websites like CNN and Salesforce. Do you have any favorite moments for meetups that you’ve attended over the years?
NICK GERNERT: I started on a Monday, I think it was September 23rd and September 27th was the start of Automattic’s 2013 Grand Meetup. I think there were almost 200 people at Automattic at that time. So it was, it was a great way to just jump right in and get to meet a lot of folks. I feel very fortunate that I got to do that and come into the company in that way. A lot of my fondest memories and like my formative memories around my time at Automattic have come, through meetups.
So, we have our Grand Meetup, which is like everyone at Automattic gets together in the same place. And then depending on what part of the business we’re in, we also get together within our teams. And so the team I was joining at that time was less than 15 people. And so we were having our team meetup.
This was my first team meetup and as part of the meetup we launched the homepage of Time.com. So it’s like, we’re all getting together for this first time. And you get to take this storied media property hundred plus years of just amazing journalism and being there through so many incredible historic moments. And here we are a team of 10 people or so sitting around the table and we’re launching the homepage of Time.com.
CHENDA NGAK: I wanted to get your perspective on meetups from a business standpoint. Why do you think they’re so important for companies like ours that are distributed?
NICK GERNERT: So inherently, you know, we’ve bought into this idea that like, we’re going to work from wherever we’re most comfortable for the majority of our time. And so there’s great flexibility with that. There’s great power that comes with being able to source talent and work from anywhere and things like this.
But then there’s always this fundamental belief that we, as human beings, are also social beings. The most high fidelity form of communication comes from being in the same physical space you could pick up on social cues. You can pick up on body language and just lots of things in the environment that influence that.
And so there’s this case for like, we still need to come together as human beings on a cadence and, and occupy this physical space and this high bandwidth sort of collaboration and communication. And I will admit, Chenda, it’s a bit anecdotal and I want to do more digging into this with like our data on our side, around just retention.
But as a bonding and just really getting folks, you know, brought together as a common and retention and retaining of these teams. A lot of our team has really bonded and it’s formed through these moments where we come together. Which may make you think like, well, yeah, if you were just together all the time, then you would also get that same benefit.
But there’s something really magical about this fact that you have this balance of flexibility and working and residing where you’re most effective. And then when you come together with the teams, it’s like this high energy focused, like you wanna maximize every moment of it cause you know, it’s a finite period of time.
And so you come together and it’s highly effective. So we also tend to think about meetups as what do we wanna accomplish through coming together? Which may just be like, look, our team’s very new and we need to just like help it help us form as an organization. So when you think about formations of teams and things like that, super important in doing things like that.
The other thought from the business perspective, as I thought about this, Chenda, is it just evolves over time. So when I think about, you know, the group that I’m part of was like, you know, less than 15 people, when I joined Automattic and a meetup meant like we could get all 15 of us around the table. Very easily. Like, this business is now 300 plus people in it. And so our concept of how do we leverage meetups evolves over time because the scale of the business matters and that context matters.
CHENDA NGAK: I was wondering if you had any tips for balancing your time at meetups, because it can be so overwhelming.
NICK GERNERT: One of the primary objectives in just coming together as a team in that space is really just bonding as a team. It’s great to have a shared sense of an outcome or an objective, but don’t overly index on those things. Like, don’t come into one of these settings and then put a very ambitious target on it, which then takes all of the focus away from coming together in a way that it’s, you don’t typically get to collaborate.
So, I think not over programming is a big thing. And then what’s been interesting as meetups have evolved, especially when we bring big groups together, like in the Grand Meetup is creating spaces both physically. And then just in the timelines that just allows folks to disconnect from the meetup for a little bit.
And then one thing that also just comes to mind for me, as I think about like how to learnings and programming is just really the importance of bringing folks together that may not collaborate day-to-day and building empathy for how we really are all contributing to common objectives, even though it may not always be obvious how, you know a sales team is working with product or customer support is working with sales or product or any of these other things.
And so how can we bring folks together and build empathy across the business.
CHENDA NGAK: I love that you brought up empathy because it reminds me of the importance of creating psychological safety. And I feel like these meetups really provide that. So, I was wondering if you could touch on that a little bit.
NICK GERNERT: Yeah. It’s so interesting. The concept of psychological safety is, like, once we’ve met each other in person, how it totally changes our perception of day to day interactions. Because when you think about a distributed work style and especially where we commit deeply to the idea of asynchronous collaboration. I may send you something, Chenda, and may have a question for you, but I don’t expect that you’re gonna respond in 60 seconds. You may respond to me the next day or later that day or whatever it is, but it’s not immediate.
So, there’s a lot of text based communication and you lose a lot of signals that, you know, when you and I are just conversing. And so once you’ve been able to really meet someone in person and you understand how they communicate. Once you’ve put a face to the name and met in person done all this, you just have a totally different interpretation once you leave. You really do remind yourself. It’s like, hey, we’re all just people. We are all really trying to just do our best work for common goals. And I feel a lot safer now in the collaboration around that.
CHENDA NGAK: What sort of impact did you see when meetups paused during the pandemic? And what observations did you make?
NICK GERNERT: I think we lived both sides of this as an organization because up and through 2019, we just took for granted that we had this cadence of meetups that, you know, it was recommended once a year. We’re gonna get the whole business together. Once every nine to 12 months, you’re gonna get your particular team together.
You’ll probably attend another cross-functional, cross-divisional, gathering and you had these moments to check in and reset and it really did help prevent things like burnout because it can be very isolating when you’re working in your particular space for extended periods of time.
And you can’t just easily reset humanity behind everything that we’re doing day to day. And even for us as a distributed company, as we went into 2020, meetups were essentially frozen no more, if we’re not gonna be meeting up. And we don’t know when we’re gonna meet up again.
So it created disparity around that and you could start to see how that was like weighing over the extended period of time. And at a certain point after a year goes by and no one’s meeting up. You can see this impact of like, gosh, if we could all get together and just bond again as individuals, and you could just see a collective exhale, because we’re all feeling the tension of just kind of like being in our respective space day after day after day and not having that moment to come together as people again. So, it really crystallized the importance of just, we need that time where we can come together as individuals and bond and share.
CHENDA NGAK: Ama Osei-Oppong is one of our HR Wangers based in Scotland. She connects with people every day for work. So she has great insights on the importance of strong connections. Ama can you tell me why it’s so important to feel that sense of belonging at a meetup?
AMA OSEI-OPPONG: I mean, I would say that the sense of belonging, and this is for me personally, other people may have their own views, but I just feel like you’re seeing and being around people that absolutely get the mission. They absolutely get what we’re trying to do at Automattic and, you know, it’s just that understanding and that collaboration, like for me, it’s a collaboration that I love the most. And sometimes, you know, it can be challenging. Not being all together to do that.
So it just allows you that additional option of getting together, working through, you know, projects or initiatives and actually just spending time with each other, getting to know each other as people, because sometimes you can come in and work and you maybe don’t always have that.
And there is something to be said, you know, when you’re working with people and you know more about them and they know more about you, it helps build that trust. And also helps you, you know, it helps you be comfortable and it helps you be creative as well.
CHENDA NGAK: We spoke about why meetups are great. Are there any downsides or challenges of meetups?
AMA OSEI-OPPONG: Downsides or challenges of meetups – I think one of the challenges are to actually keep focused. I think there’s the excitement of seeing your colleagues and seeing people, especially after COVID that you’ve maybe never met. And I think sometimes, you know, if there’s a session where there’s a business objective, sometimes it can kind of feel like it’s getting lost because there’s excitement of meeting everyone.
And I think the way to overcome that is when you’re really looking at the setup of your meetup and almost looking at the agenda, having adequate time for that social time – that getting to know each other and balance that off with your working sessions. So, that you’ve got that kind of delineation.
I’d also say possibly one of the downsides, and this is possibly an after effect of the meetup is that sometimes you all get together and there’s some conversations where like, you know what face to face conversation is probably better for that particular scenario. And sometimes it’s like, you have the energy of the meetup. You know, when everyone gets home, the day to day of the job kind of comes in and sometimes those ideas can get lost.
And actually it’s almost that way of really – there needs to be a commitment that whatever is agreed and discussed at the meetup there’ll be like an absolute commitment to see those along when everyone gets back home.
CHENDA NGAK: Meetups have been part of Automatic’s culture since the start. Donncha O Caoimh has been at the company for 17 years. He’s experienced the good and bad parts of meetups.
DONNCHA Ó CAOIMH: I think practically the only time we get to talk about personal issues and just talk about life is at the meetups and at our team meetups.So that really does help to help us bond. And even besides that, it helps, helps us brainstorm issues.
It’s a great way of just getting to know my colleagues, because we can walk along the streets to a cafe or a restaurant where we’re going for dinner and we’ll talk about personal things that you’re not gonna talk about during a work Zoom call because a Zoom call is just an hour where you have to concentrate on what you’re doing, and you should talk about business issues or you’re talking about programming problems.
Whereas when you’re in ordinary life, you’re walking along with another person and you get to talk about ordinary things. It helps to build that relationship with the people I go with.
CHENDA NGAK: But there are challenges for folks who are more introverted as the company has grown. The dynamic of meetups has changed. Trying to connect with a hundred people is different than meeting 2,000.
DONNCHA Ó CAOIMH: It can be stressful because you’re you go from sitting at a desk for, 48, 50 weeks of the year, maybe communicating with a single group of people that you know, pretty well and suddenly you’re thrust into this confusion of faces that can be tough.
CHENDA NGAK: The next person I spoke to makes tough decisions on a daily basis.
David Watkis is Automattic’s Director of Trust and Safety. His team oversees policy and content moderation for WordPress.com and Tumblr. He spends a lot of brain power thinking about complex situations. If anyone could talk about building trust and how meetups help with that surely it has to be him.
DAVID WATKIS: Meetups tend to be unique depending on what the primary goal is of that meetup, depending on who’s attending, and even just where in the world we’re located. I think there are some through lines, however. Some similarities that I would say are our takeaways from every meetup. For me, the biggest thing is just the ability to make leaps forward in the work, whether that’s discussions that we’re having, particular projects we’re working on and deep trust and safety policy decisions that need to be wrapped up. These things can happen online and certainly they do.
But when you have sort of six months of like asynchronous work, it can become a little more difficult to land the plane. When you have everybody in the same room, it’s really nice to sort of tie up those loose ends and. Move to the next milestone or indeed move to completion. They’re also really grounding experiences.
It’s easy to lose the thread a little bit when you’re working strictly remotely, or certainly primarily in text. So, when you’re on the ground and in the same place as somebody, it’s just a good reminder of how great your colleagues are, why we’re all at Automattic and, and now we’re all on the same team and sort of pulling in the same direction.
CHENDA NGAK: So when I was thinking about trust and safety, I thought this is a role that requires clear thinking, a calm mind and trust within your own team. I would love it if you could talk to me about the importance of connecting to build that trust within your team.
DAVID WATKIS: Yeah. So building trust within teams, whether that’s trust and safety, whether that’s any team in Automattic is so important. And meetups, in my mind anyway, are one of the primary ways in which we can do that. We’re certainly making those connections online in trust and safety, certainly.
We assume positive intent with one another. When we’re discussing policies, when we’re making decisions, we have frameworks for giving one another, the confidence checks we need when we are not feeling so confident or so sure about a decision about a course of action, but all of those things are, you know, one step above one step further when we’re together at a meetup.
It’s just different when you’re breathing the same air as somebody and sitting down in the same room with them. We can hear the intonation in each other’s voices. We can see the mannerisms, the other cues as we’re, as we’re talking and, and listening. There’s also typically a social component at these meetups, whether that’s just hanging out after dinner to talk shop to get to know one another or even something more structured, like going on a food tour or attending an art class together, you know, what, whatever it might be.
It really creates these team bonding moments that just aren’t possible when we’re remote or working strictly online. I would say it’s also a bit easier to be vulnerable and to be ourselves when we’re all together in the same room. So, if there’s somebody, a colleague, a teammate who’s perhaps suffering from imposter syndrome or who’s been struggling to complete a task, it’s a lot easier to raise your hand and ask for that support when you’re with your colleagues in the same room.
CHENDA NGAK: Do you find that there are unrelated skills that you pick up while you’re there meeting with other Automatticians?
DAVID WATKIS: You know, my line of work is such that the applicable skills tend to be quite specific. Having said that, a conversation that stays with me probably daily, is advice that I receive from another Automattician and another area of the company at a Grand Meetup, which was, “Never waste a crisis.”
Which took me some time to digest and understand exactly what that means or how to apply it. But I would argue true regardless of field, but certainly in trust and safety, when things go sideways and they inevitably do go sideways, it’s a great opportunity to pause, to reflect, and course correct in a way that hopefully allows you to sidestep a similar crisis or that same crisis, in the future.
In the trust and safety field, we tend to be problem solvers when the issue presents itself. It’s, “How do we get to the solution as soon as possible?” But acknowledging that crisis, not wasting that opportunity to have a teaching moment, have a learning experience. So that we’re not rushing into the same issue, the same pitfalls in the future is incredibly valuable.
And that is a piece of advice that I got at a meetup, in a random conversation with someone outside of the trust and safety field. And so a great example of how those minor connections and those minor sparks can blossom into things that indeed become guiding lights as you navigate this career and, and these different areas of focus that we all have.
CHENDA NGAK: One of the absolute unsung heroes of a grand meetup are the folks that orchestrate the whole thing. Megan Marcel has been with Automattic for six years, leading internal events. If you need tips on how to throw a week-long gathering for a thousand people, hit her up. Okay. So tell me, what does it take to pull off an event of that size?
MEGAN MARCEL: Yeah, so I think one of the first key things that we try to do is get together the key stakeholders and really outline, “What are the objectives and goals for the meetup?” What do they wanna get out of it? We also, a lot of times, will survey folks at Automattic to hear.
In addition to what leadership is hoping to get out of this, what do the employees wanna get out of this? And I think really helping to meld that all together is super important. So, after getting that kind of buy-in from key stakeholders, what I will usually do is prepare a bit of a draft like block agenda, if you will.
I think that social is just as important as the business, while we’re on site, just because of why we’re meeting and being remote. So making sure that there’s a really good balance between the two. Also people are used to working from home every day, as I mentioned. And so it can be tiring. So, making sure to put in a good balance of breaks, just so this way, when people are showing up, they are really present.
So once we kind of go through that and have a general agenda in place, we’ll start locking in speakers, workshops, breakouts.Some of those being led internally, some of them maybe will bring in external speakers and then finding little elements that we can add in throughout to just bring the culture of Automattic.
CHENDA NGAK: How do you go about finding a venue for our meetups?
MEGAN MARCEL: We definitely wanna be mindful that we don’t have the bulk of people traveling 16 plus hours and some traveling only one hour. It’s not always possible that everyone has a short journey, but we do try our best to look at a central spot. Given the budget, we also will just try to keep in mind, staying away from any high season.
Being flexible on location. We have really strong relationships with some hotels where we’ll use our global salesperson to help us, you know, really just hone in, on places that feel Automattic. And what I mean by that is just really the whole vibe of the space.
Say it’s a meetup for 250 people. We don’t want to be in a hotel that’s for 3,000 people. We really want to feel like it’s our home base for the week and not get lost in it. We try to keep that in mind. We also try to look at locations where it may be a bit easier for people with visa requirements.
Being a global company, we do have people from all around the world attending. And so we try to get ahead of that when we can, we try to help build travel history through other events and meetups during the year. And that’s one of the things that we look at. So, while it might not be a perfect science, we try to look at all of these different things.
And then, you know, how much space do we need? We are a big team. We have breakouts. And so having a meeting space, that’s a big enough size. I would say we always get creative there. Sometimes we might use a suite in the hotel if there’s not enough meeting rooms or maybe there’s a restaurant that we can grab a private room in and have that for during the week, if we don’t have enough meeting rooms necessarily.
So, just trying to get creative where we can keep in mind costs, also you know, when we look at the dates. Availability becomes a big thing, especially a group our size, but we also wanna make sure that we avoid any holidays, times where it would be really hard for people to be away from home. And so incorporating that into our search.
CHENDA NGAK: I believe we have more than 2000 Automatticians in almost a hundred countries. Now, how do you approach logistics with everyone being so spread out?
MEGAN MARCEL: We have channels set up where people can ask questions on different routes that they might be considering taking. And so just a lot of support on that, wherever we can help provide it. I think it does a lot for people to feel comfortable attending.
Also just taking into account cultural norms where people might be and can we incorporate any of that into the meetup? Is that through food? Is it having a prayer room set up? Like what can we do in those instances so that when people are away from home for such an extended amount of time, they feel comfortable, they have what they’re used to. Maybe not in everything, but we definitely try to take it into consideration.
CHENDA NGAK: Now that I’ve heard all the great stories from past meetups and why they’re so important, I thought it would be great to hear about how to optimize our time at meetups. So I spoke to someone that has so much wisdom to share.
JOSEPHA HADEN CHOMPHOSY: My name is Josepha Haden Chomphosy. I am in Southern California. And what I do here at Automattic is I run our division that focuses on the open source practice, specifically for WordPress.
CHENDA NGAK: What’s it like for you to attend a meetup as a team lead?
JOSEPHA HADEN CHOMPHOSY: For team leads, if you’re leading a group of people, when you go to a meetup, it’s really important that you kind of realize that your event starts the moment that your team knows about it.
It’s not always the case that the team lead is the organizer. Sometimes the team kind of organizes your event together. I think also as attendees, there’s a lot that you have to do ahead of time to make sure that you are using your time, the best and you’re looking after your own energy. Like in order to make events really functional as a way to move through problems that you find when you’re working in a distributed way, it just, you have to bring a lot of intention to it.
CHENDA NGAK: Can you share any tips on how to make the most of our time together?
JOSEPHA HADEN CHOMPHOSY: One of the things about in person events, in a distributed sort of ecosystem in a distributed organization, is that you really have to put a lot of effort into making sure that it is the most effective, the most efficient that it can be. Cause it happens so rarely. I like to remind any of my leaders and certainly anyone on my teams, that 90% of your work, if you are doing any of the leading, needs to happen before anyone actually gets there.
Then, also, if you are going to an event as an attendee, you really do have a bit of research you have to do ahead of time, just to make sure that like, everything that could be done ahead of time is already done so that you don’t necessarily have to figure that out once you get there. And so some of the things that anyone can do to make sure that their event is the most effective, the most efficient use of their time and their team member’s time is one, always keep in mind the level of ask that you’re bringing to that event. You have so much you have to do ahead of time.
And so if you are a team lead, if you’re a leader, one of the things you have to know for sure is the reason behind why you’re gathering. You have to know why you believe it is that you are better together. So, if you’re bringing folks, in order to learn or to plan something or, or simply just to get connected, It’s good to know what that is. And then you have to ask yourself some important secondary questions, where are my weakest relationships, or where have I seen the weakest relationships within my teams?
What questions do we not ask ourselves often enough? Or how can we get to a shared vision and make sure that what we are working on is what everyone should be working on? So, those are the sorts of questions you have to ask yourself.
CHENDA NGAK: Do you have any personal life hacks, any routines that you do before you attend a meetup?
JOSEPHA HADEN CHOMPHOSY: Yes. So, any time that you’re attending a meetup, but certainly right now, one of the most important things that you will not believe before you get there is that it is exhausting. Like you’re working in a different way. Physically, you’re working in a different way. Mentally, you’re working in a different way. Emotionally, your brain is working in a different way.
Like everything about working with people, especially over the course of a week or two or three days is so different from working with people when it’s just text based. One of the things that you have to remember as you’re headed into these events is that you’re going to need to pace yourself. You need to think about how you need to be able to show up over the course of the event. And so you have to look and make sure that you are accounting for consistency of showing up over time, as opposed to the average of showing up over time.
And so the thing that I do before every event is sit down and look at who is going to be there and who I would like to make sure I connect with for whatever reason and then message them ahead of time.
CHENDA NGAK: We really consider meetups to be our secret sauce at Automattic. Why do you think that is?
JOSEPHA HADEN CHOMPHOSY: I think it’s generally true that one Automattic believes that many eyes makes all bugs shallow. Right? We believe that we can go further together because we believe we are better together.
But also, I believe that Automatticians, like, people who work at Automattic are inherently kind of social animals. And we really commit to the idea that all of our combined experience is better than any individual person’s experience. I think that’s true for folks who work at Automattic, we tend to attract that sort of attitude.
MATT MULLENWEG: Hey everybody, Matt Mullenweg here again. It was great to hear my colleagues share their stories and speak from the heart. As you heard from Megan Marcel, it takes a lot of work to organize a company-wide meetup. People fly in from all over the world, spend a week away from their families.
So, I appreciate why they’re meaningful from diverse perspectives across Automattic.
Like many companies across the world, Automattic is very closely watching its budgets right now and how much we’re spending and trying to reign things in a macroeconomic instability. However, especially post pandemic, we decided to invest in meetups and getting colleagues to see each other in person.
It’s kind of funny that after, you know, 17 years of telling everyone to be distributed and remote, that now I’m beating the drum of people getting together in person. And of course, we all want to be connected to our colleagues, to our work, to our communities, to the fruits of our labor. And meetups are our fantastic way to do that.
Thanks to everyone who took the time to share their stories and the Chenda for going on this journey of discovery. Hope this episode inspires other leaders to invest in bringing people together. Thank you so much for listening. See you next time.
Episode 29: Dylan Field, Figma Co-founder, Talks Design, Digital Economy, and Remote Culture with Host Connie Yang
Nov 19, 2021
Nearly ten years ago, Dylan Field and Evan Wallace turned a Thiel Fellowship into a solution to the ‘single source of truth’ problem for design systems.
Their interest in design collaboration and WebGL laid the foundation for the origin story of Figma, today’s ubiquitous browser-based design tool — and rapidly-growing company.
“The more (we) pulled this thread, the more we learned there’s so much to do in terms of making design better, and in making it so more people can access design within the organization,” says Dylan of their early pursuis. (Spoiler: drone technology was a runner up in their technology explorations).
The latest episode of the Distributed podcast pairs Dylan, Figma’s CEO and Co-founder, and guest host Connie Yang, Head of Payments Design at Stripe, with past design leadership posts at Coinbase and Facebook.
Connie’s passion — uncovering the bits of magic surrounding us in everyday life — guides their friendly dialogue from design to remote culture and much more. Early in the show, Dylan shares what he’s learned about instilling culture in a rapidly-growing company, especially amid the changes brought on by the pandemic. “The main thing that changes once you go from in-person to remote is you can no longer rely on physical context to instill culture,” says Dylan. “It matters even more to elevate the role of design, and elevate anything you think is really important in that digital context.”
Dylan also builds on a recurring Distributed podcast theme over the past year, adding “It’s really important to be intentional about creating serendipitous moments.” Figma’s playful approach to collaboration influenced its recently-launched FigJam, a digital whiteboard that can help fill the need for serendipity.
Dylan speaks with the unique authority of a tech leader who has not only prioritized design but, with his team and products, greatly influenced it in a way that seems to have happened just in time for distributed collaboration.
“We’ve gone from a physical economy to a digital economy. I don’t think these are new trends or new things that happen but now, all of a sudden it happened all at once, and accelerated massively,” he says, echoing Matt’s May 2020 post Gradually, Then Suddenly.
“I think that we’re seeing every part of the economy shape around design,” says Dylan, noting how Figma has even observed collaboration in the product, beyond design, on days when other workplace chat tools were down.
Why does it matter? Because now, Dylan says, “Design leads to winning.”
Thank you to both of our guests for this latest episode of Distributed. We hope you enjoy it.
The full episode transcript is below.
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CONNIE YANG: Hey everyone, welcome to the Distributed Podcast. I’m your host for today, Connie Yang. I am the Head of Payments Design at Stripe and I want to give a huge thanks to Matt Mullenweg for allowing me the opportunity to host this podcast.
I am super excited to have an opportunity to talk to one of the leaders in advancing design technology and changing how we all in the industry work together. Dylan Field is not only co-founder and CEO of Figma, a collaborative design tool used by some of the biggest design teams in the space, he is also a leading advocate for bringing more designers into companies and the importance of the role of design in building successful products. He is also a huge proponent of community and an open source approach to design.
Dylan, thank you so much for joining us today.
DYLAN FIELD: Thanks, Connie. It’s really good to see you.
CONNIE: Good to see you too. Dylan, before we even get into Figma and all the momentum you’ve built let’s start by talking about design itself.
DYLAN: Okay.
CONNIE: It seems like you had some amazing insight nearly ten years ago now on the importance of designers on teams, the way we work with one another and how we work with even non-designers. What did you discover about design in those early days that motivated you to dive into this world of design and creativity?
DYLAN: Yeah so I’ve always been interested in design and excited about design product. But I think I started getting really excited about and interested in how do we make design tools better when I started working full-time as a design intern at Flipboard. And at the time I was kind of watching how the tools worked, we were in Fireworks pretty much every single day and collaborating through a Dropbox folder.
We kind of had attempts to do a blog where we could post work in progress but honestly all the collaboration was kind of a mess and that was with a very design-forward team. Flipboard was very excited about let’s go make.. Flipboard was really into let’s go make design a really core part of the product experience and how we build product.
And leaving Flipboard I was thinking a lot about creative tools with my co-founder Evan and should we go and build a company around this. And on the list was always design. We thought this would be a great area to go into is interface design but we weren’t sure the market was big enough. But honestly it was. Once we figured out that the market was there, the problems were very clear.
It was.. the experience of designing product was not synchronous at all. It was you had all these different sources of truth, there was no one source of truth you could rely on. I remember the version problem where you have final underscore, final underscore two, you never know which one is the latest version.
And then I started interviewing people at larger organizations and would hear stories about how a file would go halfway across the org at a super large enterprise and suddenly you’ve got some random product manager somewhere who’s mad at some other product manager because they think they’re doing something that they’re not even doing anymore because that was like two months ago. And the single source of truth problem was really huge.
I think as we started to think about okay, what does it take to scale design teams up, design systems are incredibly important in that role and without a design system, it was really hard to keep things consistent or scalable. The more we pulled this thread, the more we learned in terms of there is so much to do in terms of making design better. And also so much to do in terms of making it so that more people can access design within the organization.
And I think we started to have this thesis about it’s just really important to get more people to do more design and for companies to invest more in design and that’s how companies will win or lose in the future. And I think that has played out and is playing out now, which is really exciting to see.
CONNIE: Yeah, I mean now has been a really interesting time.
DYLAN: Yes.
CONNIE: Especially for Figma, right? So we’re almost two years into the pandemic, lots of change, what are some of the top trends that you’ve seen change with designing remotely and the way that we work?
DYLAN: I think there’s a lot of changes generally in the way that work happens right now, especially for teams that were not distributed before. The teams that have been distributed this entire time, I don’t know how much change they’ve seen during the pandemic in terms of the way that they work.
But I think that the main thing that changes once you go from in-person to remote is you can no longer rely on physical context to instill culture and it matters even more to elevate the role of design and elevate anything you think is really important in that digital context. And digital contexts have no walls, they are flat, but they are not.. they still have these systems in place were, for example, if I (imagine a digital?) context, if I don’t intentionally make time to talk with somebody, that conversation will not happen. Whereas in an office, we might run into each other on the way to the bathroom or something or waiting for a drink in the kitchen.
I think it’s really important to be intentional about creating serendipitous moments. And also I think to elevate the things that you hold dear as a company.
I think that the other thing that’s happened as we’ve all gone remote and during the pandemic is that we’ve gone from a physical economy to a digital economy. And we’ve gone from physical spaces to digital spaces in terms of where we congregate. And I don’t think these are new trends or a new thing that has happened. I think that actually has been happening for decades. But now we’re at a place where all the sudden it happened all at once and it accelerated massively.
So as you go from a physical economy to a digital economy, it is really important to create a great digital product experience, otherwise you’re not gonna win. And it turns out that everyone, every company needs to do this to survive right now, whether you’re at Stripe and you’re creating a payments API, it actually does matter how good your design is. Whereas maybe 10-20 years ago people would assume actually it doesn’t matter at all.
If you’ve a bank, if you want to survive against a challenger bank, you better have a great design. If you are a company that’s doing logistics or industrial, you need to actually have really well designed processes inside the company and good internal tools. And if you don’t design those well you might lose that to Amazon. So I think that we are seeing every part of the economy shape around design and realize that design is a core part of how they win or lose.
CONNIE: Yeah and I love hearing all these specific examples that you’re bringing up of how these different companies should be thinking about building products. This is kind of a funny question. How do you think companies are.. Do you think they’re getting better at designing remotely whether they use Figma or not? Is it even possible to design remotely without Figma now?
DYLAN: Well we definitely saw a lot of people that, as they went into a remote design scenario, they really wanted Figma.
CONNIE: Yeah.
DYLAN: So I’m not an expert on the work flows outside of Figma as much but I think it is less painful to design in Figma than not in Figma in general. And that’s definitely true for remote teams. But what do you think? Because you’re in Figma a lot.
CONNIE: We are. We are definitely a Figma oriented team. I was trying to imagine what was that world like? You know, we had the issues with updated files and (getting things across?), and all this stuff that you brought up earlier. So I sort of can’t imagine with the speed that we have to work now and the amount of distributed teams that we have, I can’t imagine designing without Figma. That’s pretty rough for me. But hey, props.
DYLAN: Okay, thank you. I’ll take that.
CONNIE: I definitely appreciate the tool. So Dylan, you and I have actually met a number of times before.
DYLAN: Yup.
CONNIE: Including co-judging a really big hackathon for crypto projects a few years ago. But big events like this are still not happening live and some will probably be forever remote from now on. So it’s a changing landscape. How can we still support events like this? Is Figma doing anything?
DYLAN: Well, I think that again it’s about going from physical space to digital spaces. And if you look at how people are interacting online right now, there is so much happening, whether it’s just on Twitter but also in virtual spaces, whether that’s VR or Gather.Town or people are finding stuff like Clubhouse or Twitter spaces. We’ve even seen it in Figma. People have started to hang out in Figma and that inspired FigJam, which is our digital white boarding tool.
And we started watching how people were interacting in Figma, which is basically this abstracted canvas, how they were greeting each other, how they were talking to each other, they were typing text. And we saw Slack went down one day and people started to really interact with each other over Figma instead. I’m not saying that we’re competing with Slack, we’re not, [laughs] no interest in that. But I think as we have seen more people go in these spaces they just want a place to play and they want a place to have these experiences and to be with people and to be collaborative.
And I think that design is a really interesting place and role and activity to do where you’re visually creating with each other. And the more that you’re visually creating, the less you’re coming from a place of fear during a pandemic, the less that you have ego involved. You’re just able to get in the sandbox and play. I’ve been really excited to see people do that in Figma, in FigJam.
I think in terms of the literal interpretation of your question around getting people together in person or together in event space, I think there’s just so much around that. We have thrown a few conferences during the pandemic. We threw one recently around design systems called Schema through a Config, every year.
And just find ways to have people gather around an event, around a.. maybe it’s a product announcement or maybe it’s a topic that everyone cares about. But both finding ways to bring people together but also not have the wideness of the internet be a distraction. There’s so many ways that people that are trolls can come in or noise can get high, and so you have to be very intentional about that too, while also making it so people are able to have that access.
Because that’s the beautiful thing, I think, about digital events is that they are not exclusive anymore. Right? You don’t have to find your way to San Francisco to come to Config and it’s hard to imagine going back from that. Even though there’s real benefits to having a physical event, it’s just really lovely to have that access for everyone in our community.
CONNIE: Yeah, it’s like opening a gate, why would you close that again?
DYLAN: Yeah.
CONNIE: I really liked how you referenced so much of the word ‘play’ when describing Figma. And one side bar I want to dig into a little bit, when you say you watch designers or you see people using it in the space, what is that kind of user research like for you? Are you literally watching designers?
DYLAN: Well, we do a combination of things. I mean, we talk to people, we watch people user research sessions use Figma, we talk about their lived experience and ask them questions about how they use it, what artifacts people create. We look at the way we use it ourselves, too. That’s a huge way we learn.
And then I think also just.. for example for FigJam, one of the things I heard most about was how people were excited to do these playful things. And we watched ourselves use it and that’s what inspired the name FigJam. It’s a playful name. We’re using it and we’re trying different things and seeing what resonated with our own team. And the playfulness part was definitely the thing we came away with, like wow, there’s so many directions it can go but play and fun and getting too to flow with your team, that is such a big part of FigJam which [00:11:02.26] to ideate and brain stormings are there.
And from there it was like, okay, how do we double down on this. And so we did a design sprint for a day and we came up with maybe 60 ideas and three of them we’ve implemented, around three. We did stuff like curser chat, emoji reactions, (stamps?), audio chat, and plus widgets were starting to be born there, which is a way to basically embed a widget onto the FigJam canvas, you can use it on your whiteboard, and many more things that we haven’t shipped yet.
But it was like one day with one clear intention and it was amazing what came out of it. And that’s when I think we knew, we were like, okay, we’re onto something here.
CONNIE: Wow, that’s awesome. I’d love to dig into that story a little bit more later. But for now, another question about design overall. What are some of the hardest problems about remote design that you haven’t been able to solve yet?
DYLAN: I think it goes back to serendipity, what we were talking about earlier. I think that tools are doing a better job of this more and more but still there is so much to do to try to figure out how do you create serendipity in digital environments and across the suite of teams.
One thing we have tried, which is.. Actually it’s interesting we’re talking this week because it’s a (maker?) week right now for us –
CONNIE: Oh wow.
DYLAN: – and we always try to have different little attempts to figure what we can do here during (maker) weeks. And so one thing we’re doing right now is we have these little crews.. We have a space theme and it’s called Figmaverse this week. Every (maker) week has a different theme and last year in the winter it was Figmaland. And this time they were like, we’ve gotta think bigger, Figmaverse.
CONNIE: Awesome.
DYLAN: Not my idea but someone on our team, Anthony, came up with it. And it’s cool because they have these little.. they call them “squads” or crews, I think. With your crew you can all come together, you’ve got like six to eight people, you can bounce ideas off each other, share what you’re up to but also play this meta game on top of maker week. And it’s a random assortment of people you might not meet otherwise in the company but just trying to create those connections that otherwise you might not have. And I think the more you can do that across the company, the more you can create these experiences people can bond over.
Another thing I’ve done are new hire breakfasts, just trying to get people that have joined the company that are new.. six to eight at a time, we have breakfast together and just talk about whatever people want to talk about. And it’s totally casual, usually not super related to Figma, though if people want to talk about that we can. And it’s just a way for people to get to know each other across the company and start to connect those notes.
CONNIE: Yeah. I loved hearing about ways you’re intentionally trying to bring more serendipity into the space. And it’s not always about work. It can be about anything.
DYLAN: Yeah. I think that can be done not just on the company wide context but also in a team context. And so while [00:13:38.20] that’s not about design, it’s about.. just broadly about companies I think that it’s true for designers as well. And it’s so important for designers to be invigorated and challenged and inspired by people that are coming from lots of different backgrounds and from lots of different areas of the company. Otherwise they’re not going to do their best work. They won’t think of the challenge cases in their head, they won’t think of the random idea that might solve the problem. It’s important to get input from everywhere.
CONNIE: Yeah, absolutely. So you’ve become a really well respected thought leader about the role of design and how we work. What is something really important that you’ve learned about designers that influences your vision for Figma and your leadership of the company?
DYLAN: One thing I’ve learned about design and designers, I feel like it’s similar to many of my other answers, but I think it’s really important, is just how inclusive the best designers are and how much they bring other people into the fold. I’ve seen this with the best designers I’ve worked with and I suspect you’ve seen the same.
But there’s just a stereotype among designers, or at least there was, of the designer that goes off into the ivory tower or the corner and they put their headphones and they just type on their Mac for a while or use the pen to [00:14:49.03] –
CONNIE: Yes, heard of those.
DYLAN: – tablet and they are just.. they’re solitary, they’re a genius, they come up with the idea, they come to crit, they present it, everyone’s jaw drops on the floor and that’s it and you ship it. And like, that’s just not how it works. [laughs]
And so that was our hypothesis going to Figma but I think just to see it play out and to see how much is the truth and how much designers as well appreciate that myth breaking down and appreciate the collaborative process that can come along with design and breaking down those barriers and bringing more people in and how it results in just better work.
Like, I think a myth that exists is that collaboration, more voices at the table, can sometimes lead to worst results. And I think we see this implicitly all the time. I’ve even caught myself implicitly doing it and accidentally started this myth when I have said things like, oh, I just want to have a small meeting here or whatever because I want to get this done. And I think it’s a balance, you don’t want to have thousands of people in a meeting, that’s not going to be productive either. But if there’s ways you can bring more people into the process, I do think that you get to better results usually, and often times simpler results, which is also interesting.
Like, we’ve seen for example, one of the case studies that we found during the pandemic was Kimberly-Clark. Do you remember the toilet paper shortage?
CONNIE: Oh yeah, yeah who could forget?
DYLAN: Yeah so they were trying to solve that. And they were trying to come up with an order form that was going from 14 fields or something crazy to much less. And so they all got on Figma and started to figure out how to reduce the number of forms on their order form. And despite a lot of people collaborating on that together they were able to come up with a much simpler experience for the user placing the orders than they had before.
And you hear stories like this and you go wow, bringing more people into the process can actually help. It’s not just always distract.
CONNIE: Yeah the ivory tower idea is an interesting one. I mean the reason it became an idea is that it works for some designers, a very, very small amount. And there are some companies that have been known and are quite successful for operating that way. Have you seen that change?
DYLAN: I guess I would challenge it a little bit. A lot of times that people act in that way, I think that they are not propagating the right knowledge amongst their teammates. A lot of times you end up with a bus factor problem, a lot of times you end up with one person who is kind of like seen as an individual leader on the team but no one else can critique their work properly because of social norms that start to take place.
So I do wonder if it’s actually a constructive pattern for organizations. And I think that just because it’s a working style that has existed doesn’t mean it’s the most productive one. And I also wouldn’t say that they’re working alone. A lot of times they’re building on the knowledge of others, they are building on patterns that have existed for a long time and they are definitely bringing on the people to complete the project and those people usually..
I usually find that designers and engineers working together, once they’ve had like [00:17:59.26] and help from product, in that implementation phase even, there’s so much that gets defined and figured out when you’re implementing something. So if nothing else, I would claim that a designer that’s working with an engineer, even looking at that atomic unit of collaboration, that is a time where you’re getting a lot of different back and forth that’s happening. And the engineer is pushing back and saying well what about this edge case, what about this edge case? And unless you’re (inputting yourself?) you’re just not going to think of those things.
CONNIE: Yeah, absolutely.
DYLAN: But what about you? What’s your presumption and what you’ve seen there?
CONNIE: I also think we’re stronger in numbers. One of my personal design principles is that we should make complex things as simple and as accessible to people. And you have to keep your audience in mind for that. And so the more audience or individuals that you talk to and the more variety that you understand, that’s when you really start to get what’s the common baseline for users, that’s how you have a broader audience, that’s how you grow, that’s how you make things as simple as possible.
So I am a huge believer in that kind of inclusivity. But sometimes it’s.. different people have different processes. That’s the way I think about it but there’s lots of different ways out there.
DYLAN: Totally.
CONNIE: So let’s back up a little bit. We’re going to start talking about Figma as a company. You’ve had a lot of big moments this year. You launched FigJam, you’ve had significant fundraising, how do you describe Figma as a product today if you were to pitch it to someone?
DYLAN: Yeah. Well, I think of it as kind of like we’re trying to serve the entire project design lifecycle. So we’re going all the way from ideation with FigJam and white boarding and brainstorming to the design phase with Figma where you’re really fleshing out mockups and you’re trying to work with other stakeholders all the way to prototyping and buy in from other people and eventually production where you’re trying to turn your work into code. And we are trying to serve that entire lifecycle.
CONNIE: Gotcha. And if you could take us back to the beginning, if we could get into a little bit of an origin story, you started Figma in 2012 as a Thiel fellow and you were exploring other ideas at the time.
DYLAN: Yes.
CONNIE: How did you choose this particular problem to solve and how did you get started?
DYLAN: Yeah so my cofounder and I knew that we wanted to do creative tools and we even wanted to work with WebGL. And I think that sometimes as you are figuring out a new business, one thing that happens is people really focus on like problem, solution, what is the total market that’s addressable and how much are you going to charge people and [00:20:14.26]. And these are all really good questions to ask but for us instead we really focused on what’s the technology that we’re going to use. And for us, that was WebGL. The backup was going to be drones but my cofounder Evan was not into that.
CONNIE: Drones?
DYLAN: Yeah, I thought drones were really exciting and I still do. We also saw that there’s a lot of regulation there, a lot of just privacy concerns and so that’s why we didn’t go into that area.
CONNIE: Harder to design with a drone too.
DYLAN: I don’t know if [00:20:40.02] yeah. But hey, it’s cool toys. But no, I think my cofounder had actually built drones in college and did a lot of programming with drones and he was like, no, the hardware run to bug loop, it sucks, I don’t want to do that. So we kind of focused more on WebGL and creative tools.
And the from there it was like, okay, WebGL is the why now here. It’s the reason why this [00:21:02.28] exists that hasn’t existed before. And then the question is like what is it we’re going to make and what takes advantage of WebGL more than anything else? And we explored photo editing, (combinational?) photography and even a more Photoshop like approach where you blend a lot of things together before we realized that interface designer was (beginning of market?) and that was always on the list, always something I wanted to do, and then we (went to that?).
CONNIE: Yeah. And for people who may not know the intricacies of WebGL, what would you say was so unique about that that made you want to use that for sure?
DYLAN: Yeah so WebGL is the way to use the GPU in your computer in the browser. And by doing that, you are able to take apps that traditionally would’ve been desktop apps siloed offline and move them to the cloud. And so I think that basically any creative tool but also any game, honestly, could be made with WebGL (as well as?) just a browser. And that way if I sent you a link to a Figma file, you can learn it right away as long as you have a browser.
And that means it’s platform agnostic. It doesn’t matter if you’re on a Chromebook, a [00:22:00.04] machine, Mac, you can use Figma. And that became really important I think because as we saw Figma spread, there’s sort of this heterogeneous mix of competing environments people are coming with in different organizations and also entire areas and countries that had never switched to things like Sketch because they didn’t have Macs.
And it turns out Macs are like.. If you think about the designer stereotype you might have in your head, kind of going back to they’re on their Mac, they’re in a cafe, they have the headphones on, they probably have a really nice Moleskine, whatever that is in your head, it’s still not the reality for most of the world. I think a lot of our users are on PC or on Linux or more low end hardware. And not everyone is on a Mac. So it’s really important.
CONNIE: Yeah, again, thinking about people beyond what is immediately around us. It comes back again.
DYLAN: Yes.
CONNIE: So how long did it take between when you started trying to build Figma and then when you actually first launched to any group of people?
DYLAN: It was a long time. So we started talking about the company December 2011, started.. I got the Thiel Fellowship April or May of 2012. I was still an intern at Flipboard at the time. I told them six months, I finished that six months. So we were talking a bit more at that point. And then August 2012, we started full time. It probably wasn’t until June 2013 that we really were like okay, let’s go build what became Figma today and focus on interface design. And even then, we thought of it as interface design plus other things. And it wasn’t clear what those other things were.
And there was a point where we had to really define that and say we’re going to focus on interface design and really had a nice (white board?) session with the team where we just crossed all these t things off. It’s like, what do we all think we’re doing? Okay, let’s cross them off one by one until we get to what we’re actually doing. And we used a cool framework, omit, raise, (use?), create.. from this book Blue Ocean Strategy to figure out okay, what are we doing that’s different than the competition, what are we not doing that the condition is doing? What are we doing worse and where are we going to make this brand new?
Yeah, from there we didn’t launch our closed beta until December of 2015. And our [00:24:05.17] release was not until October 2016 and didn’t start charging until summer of 2017. So it was a very, very long road and it took a long time to get to the point where we actually had Figma.
CONNIE: Wow. And it’s funny as me as working in the industry, I remember those milestones.
DYLAN: You were there.
CONNIE: Yeah, yeah absolutely.
DYLAN: Yeah I remember Coinbase was a really early user and y’all took a bet and I really appreciate it.
CONNIE: Yeah we had some big fans.
DYLAN: Cool. It was mutual.
CONNIE: So when my team at Coinbase first got started on Figma, we weren’t even remote, we just kind of thought oh it’s a great tool, it seems collaborative, it seems easy, the file systems, all that seemed so much better. Do you see it now as a product for distributed creative process or would you say it’s still not specifically designed for remote teams?
DYLAN: I think we are trying to get better about.. I think every team now is a distributed remote team basically even if you’re not all remote, literally, you’re all distributed. And as is increasingly the truth, you want to make sure that you’re especially good for that environment. That’s where I think the play, the focus on digital space comes in. And how do you make it really great for that environment.
But yeah, I would say that we should also work really well if you’re all in an office together. And hopefully in things like FigJam, the experience you have in FigJam white boarding is even better than the physical equivalent. So I think a real metric of success could be okay, we are all in a room with a white board, what makes it so that we want to use FigJam instead of the white board that’s on the wall?
CONNIE: Hmm, yeah, that’s a great mission, a north star, to be aiming for. You mentioned that there is a difference between a remote team and a distributed team. What is that difference for you?
DYLAN: A remote team is when no one is in the office, a distributed team is where you maybe have multiple people that are congregating in physical spaces together. That’s my view. What do you think? We’re on the Distributed Podcast, so you’re probably an expert. [laughter]
CONNIE: It sounds good to me. And I think one of the things that we all realize is that even though we’ve all been adapting to this world, it is still really different from team-to-team, company-to-company. Everybody has different definitions and different ideas of what they think works best and how they build products best.
DYLAN: Totally.
CONNIE: What are some of the key moments in growth at Figma where you could see that you were really on track for the bigger vision, for where you ultimately wanted Figma to go?
DYLAN: I think the first time that someone told me please charge for Figma was the big moment for me.
CONNIE: Hmm..
DYLAN: Because we were free for a long time. And I always thought of it as like okay, we just gotta get to product market fit, we’re not there yet, it’s going to take a long time. And at some point this morass of just grinding, someone was like, hey, we really want to spread Figma at the big company I work at, like major enterprise, Fortune 100 company, and I can’t do it right now because y’all don’t charge and everyone thinks you’re going to go out of business.
CONNIE: That’s funny.
DYLAN: And it was this double reaction of oh my god, we’ve made it and oh gosh, how have we not charged yet? I thought that being free would help growth, not block it. [laughs] So it was like, oh shoot.
CONNIE: The things we get surprised by.
DYLAN: Yeah, exactly.
CONNIE: That’s awesome. That’s a fun milestone to really remember.
DYLAN: Their big one was just seeing people that are non-designers start to get into Figma without formal design training. So I’ve had like now a ton of founders come up to me and tell me how they’ve designed the first version of their product with Figma and really dived into design. I think that’s so important as you’re building a business to just be design driven and to have somebody that has a design point of view and propagating that from the top.
And so if we can help inspire the next generation of companies to be more design driven, to hire more designers, to put more people in design roles, I think that’s really, really important.
CONNIE: Absolutely. One of the points actually that I recalled as you were explaining that was that when we were again, getting on board Figma at Coinbase and we had to convince not just designers to use it, we had to convince PMs, engineers, everybody else to use it, and an aha moment that we had was when a PM realized oh, he could edit text directly in Figma –
DYLAN: Yup.
CONNIE: – and then just be done with it. That was a major aha moment. I could see the light in his eyes. I was like, oh, that’s why I switch. That’s pretty incredible. I don’t know if I’ve ever told you that.
DYLAN: That’s awesome. Yeah, the copy editing on the canvas is big but also just like I think being able to leave comments and conversation around the asset itself and have that be collocated is another one that’s really big. And then just getting to the point where you can use the design system and a product manager can start doing some of their own (blocks?) rather than just like oh yes, I need a designer to help me draw things. It’s like, no product manager, you can do that on your own, really, I promise you. [laughs]
CONNIE: Yeah, makes it as easy as possible.
DYLAN: It makes it so the designer can focus on harder tasks.
CONNIE: Absolutely. Do you have any dream companies or teams that you wish would start using Figma, like where you really think it could make a huge difference?
DYLAN: I would love government to start using it more.
CONNIE: That’s what I was thinking too. [laughter] Do you think they use it at all?
DYLAN: Uhh.. I don’t know if I can comment on that. [laughter]
CONNIE: Noted. So we started talking a little bit about the non-designers, PMs, engineers, writers, researchers, so many people who all have to come together to make products look really good. What impact do you really think Figma has had for those people that’s really important for you?
DYLAN: I think again the more you can get people in the design process, the better designed products can be. I think also just the roles around what design mean and who does design are blurring so much. So I think that a [00:29:47.14] engineer versus a designer, that is converging more than I think a lot of people realize and both could be really additive to the other’s process.
We could debate the next hour or two the difference between product and design or even research and what that trifecta looks like in that Venn Diagram but I think that all of them have to talk to customers, all of them need to think about strategy, all of them need to think about the future of what the product could be and paint an inspiring vision. And because all of them have use cases for Figma that are important, even if they have different orientations in a day to day job.
What I have also been inspired to see is the amount the executives and people that are stakeholders outside of product engineer design are starting to use Figma to visually communicate, or ideate in the case of FigJam, but also just to really be on the ground and thinking about what it will take to win for the company through design. I think it’s interesting too because designers as an archetype are kind of more in touch with emotions, they are more in touch with the soft side of the business. But at the end of the day, design leads to winning. [laughs] And I think that people don’t realize that enough.
CONNIE: Did you say design needs to..?
DYLAN: No, design leads to winning.
CONNIE: Oh design leads to winning.
DYLAN: Exactly.
CONNIE: Great phrase, yeah, I love that.
DYLAN: In my opinion. I mean.. Somebody out there might challenge that but I really think it’s the case.
CONNIE: Speaking of winning, and you had touched briefly earlier about competition and how Figma starting from a small place, what is your competition like now? What do you think about, what do you worry about?
DYLAN: We have obviously a major competitor in this in Adobe. And I think it’s really important to just have a super healthy respect for your competition. Adobe in our case is like they’re the daddy of the creative tools industry, you know, they literally back in the late 1980s made Illustrator and in the 1990s acquired Photoshop. This is all before I was born, basically. [laughs]
CONNIE: Oh, right.
DYLAN: Obviously some of these products have bloat, some of them have long histories, but they also exist after decades and decades and decades. And I think just the work Adobe has done has been really inspirational for a lot of people, including myself.
So I think you can learn from these companies that have been around for a long time, you can learn about how to create good software, you can learn about the traps of trying to build something for a long time, you can learn about the traps of trying to put too many things into one place. And I think it’s good for us to have strong, challenging competitors. That’s the way that we’ll become a better business in the long term.
CONNIE: Yeah, it is a good way to look at that. I remember also that’s how I got started learning about design.
DYLAN: Totally.
CONNIE: It’s using those tools.
DYLAN: Yup.
CONNIE: That was kind of the originator. Do you think they learn from you and your team as well on how to make it more collaborative?
DYLAN: Judging by the recent releases, yes. But I think it’s hard. The fact is that we’re able to take assumptions about being cloud first that they can’t really take. And so having to accommodate a lot of off-line workflows.. it really constrains what you can do and it makes a lot harder to create great product experience people.
CONNIE: Yeah that makes sense.
DYLAN: So we’re lucky in that sense.
CONNIE: All right, we’re going to go back to FigJam for a minute, which I love.
DYLAN: Sure!
CONNIE: You’ve made Figma somehow even easier for new people to use and there are so many creative ways that people have been playing around in FigJam. Like, within our team, we use it to play games in team building events. We even have a Figma height chart. [laughter] Since you don’t know anyone’s heights while you’re remote, we made a chart of where everybody is so it can be a little more connected.
DYLAN: In case you’re wondering, I’m on the bottom. [laughter]
CONNIE: So it has been super fun. And you touched a little bit on what it took to create that but it felt like you seized the moment. Like, somehow you knew this is THE tool to make during this remote time and you spun it up really quickly. What actually happened there? Can you tell us a little more about that?
DYLAN: Sure. So we had long intended to go into white board diagraming space, that was something that we had seen people use (before?) along with lots of other use cases for a long time. And obviously it’s not ideal for Figma proper to do that because, as you try to expand it to more people and bring more people in, there’s all this stuff that we’ve done for design that gets in the way. So it’s like, okay, how do you create a tool around white boarding, diagraming and ideations use case that is just really excellent for anyone to bring in from the product team?
And then the pandemic hit. And we already had this in our minds and right away we realized that people were doing way more of this activity in Figma than they were before and they were having challenges doing it. And we realized, okay, we just have to move as fast as we can, get this to market, because the pandemic is not going anywhere, it’s going to be a long road ahead.
And so we spun up a team and this is a few months of research first, we make sure we really understood the problem. And then it was probably fall of 2020 we spun up the team and it was maybe six, seven months before we launched, which I’m really proud of.
CONNIE: Wow.
DYLAN: And I think a big part of that was just the team knowing that this was such an important use case for our community and that we really needed to get this out there for our user base. And that the pandemic was.. it was just important for people to have a digital white board during the pandemic, which is now endemic. It’s not ending. And so as we go into that world, it’s like, it’s 2021, everyone needs a digital white board, how can we help serve our customers there?
And the other thing we did was we weren’t sure what the prices were at first and so we did a higher price and then as we watched people use it, we realized that entire teams were using it and not only entire teams, entire companies. And as it expanded out more, we thought to ourselves, okay, the range that we’re seeing in terms of who will use FigJam justifies it actually going to a more competitive price point. And so we have.. actually now its three dollars if you’re on Pro, five dollars if you’re an org for FigJam and it’s free if you just wanted to start off on your own. And again, we’re trying to really go for access with those price points.
CONNIE: Yeah, that makes sense. You mentioned it was about six or seven months before it came out, which is really short for that kind of product development.
DYLAN: Yes.
CONNIE: Can you tell us a bit about the team that you put together? How did they get this done?
DYLAN: Yeah, it’s an amazing team. I think all Figma is an amazing team. But I think with every release you kind of have quality, deadline, feature set in this triangle. And I definitely was like, okay, features and deadline, that’s what we’re optimizing for. And of course the Figma team is very quality oriented so they also care about that too.
But it was I think a deliberate move to say this is different than going and iterating on an existing product. We’re building this new thing from scratch, there’s real time pressure, we have to get this out, what can we do to move fast here? And having that entire team have this mindset around shipping quickly made a huge impact. But also they’re just incredible people.
CONNIE: Yeah, awesome.
DYLAN: So, I feel very lucky to work with all my Figmates.
CONNIE: And I love that description, I love that word Figmates, it’s so cute.
DYLAN: They’re amazing.
CONNIE: What was the actual make-up of the team? Was it one designer, was it multiple..? How did that get set up?
DYLAN: Yeah, I mean, it was one designer, one product manager, a few engineers (spanning to?) multiple designers over time and more engineers over time. And then because the engine behind Figma and FigJam is the same, we’re able to pull in additional people as needed from other teams. So it’s kind of like, the teams became a somewhat permeable membrane that people could flow back and forth between.
It also was a good forcing function to do things that we long wanted to do in Figma. So, for example, bullet points is something that we’ve wanted to do forever in Figma and it just never rose to the top of the priority list. And then for FigJam it was a key thing that if you don’t have bullet points, what are you doing? So that became something that we prioritized on the Figma side that also works for FigJam.
And what we’ve seen too is that some of the experiments we can do around digital space and bringing people together and having fun in FigJam people like them so much they flow right back to Figma as well. And it’s just nice to have this sandbox that we can play in, try things out, and then you can improve the core Figma experience after that as well.
CONNIE: Yeah. And I love hearing about how it started with one designer and then there became more. I’d love to dive in for a quick second on how –
DYLAN: And research too. I should not forget research.
CONNIE: Yeah, absolutely.
DYLAN: Research have played a heavy role in FigJam and continues to, to this day. We are lucky to have a great research team.
CONNIE: Yeah. I would love to hear a bit more about how.. If it’s a designer and a researcher, they get started, how do they collaborate with everybody else? Like, I feel like your team must be the best at using Figma. That’s my guess, so how do you do it? [laughter]
DYLAN: You know, I’m not always sure because there’s a lot of teams that have like.. I think the amazing thing about creating a tool, and I’m sure you’ve seen this in Stripe, is just the amount of ways that people take these legal pieces and put them together. And this is true for Crypto too. People, once they have generic tools or generic things that they can use, the ways that people stream them together and compose, is just infinite and perplexing and awe inspiring.
So yeah, I don’t have any like.. here’s the one thing that we did in the collaboration side. I think most of them would ring relatively true for a lot of companies. But yeah, it’s been exciting to see just the way that people collaborate across Figma and what that means.
CONNIE: Yeah, that’s awesome to hear about. And talking a little bit more about your culture. It looks like you’ve reopened your San Francisco a few months ago.
DYLAN: We did.
CONNIE: Yeah, congrats on that. Gotta ask a tough question here that I’m pretty curious about. So, Figma is a tool that seems right now like so focused on remote design and distributed design and you’re not a fully remote team. Why not? What’s your thinking here?
DYLAN: Yeah, I did a survey back in May or June of 2020 and just basically asked a lot of questions of our entire employee base at the time. And I expected some teams, like Engineering, to be more remote heavy in terms of preferences for the future, some teams like Sales to be more in-person heavy. And the reality was that everyone was a mix. The only pattern was there was no pattern. And some teams had more distribution than others. Like, Engineering surprisingly wanted to be more in the office, although still a lot of people in Engineering wanted to be remote too and Sales want to be more remote but still have people who want to be in the office and every permutation you can imagine for every other team as well.
And it was.. We kind of reflected on it and we thought, okay, I did all the game theory and thought through what will happen during this pandemic, where are all these companies gonna end up at? And where we landed was let’s have hubs. Anyone can come into those hubs if they chose to. If you do come into a hub and you decided to affiliate with a hub, you have to come in two days a week at minimum and those two days are gonna be set and we’ll have it be the same two days for everyone because otherwise communities don’t form, you have this weird affect where people don’t come in and when they don’t come in it feels like it’s kind of an empty, dead space. And you want the space to feel alive and you want things to be happy in there. You want these communities to form in this space, especially for people that are right out of college, new grads, it’s really important for them to have this physical community.
And then if you don’t want to come into a hub, that’s also totally fine because we’re in a pandemic so a lot of people are not going to want to do that, especially if you’re care taking or you’ve got kids at home that don’t have the vaccine yet. So if you’re in that situation, fine, don’t come in. You have the option but you don’t get to arbitrarily choose, okay, well this day I’m going to come in the office, this day I’m not going to. You kind of have to make a choice and then (your pay is localized?) depending on what city you’re in.
We tried to be very clear about that at the start, relatively at the start of the pandemic. I think we announced it internally around June or July. I announced it to the world in August 2020 and from there we’ve just been very clear with everybody about where we’re at. In the future, I mean, I think it’s (not at the table?) we one day go remote. I don’t think that’ll be any time soon, we just made this major investment in our office and we’re scouting offices in different hub locations. And I do think there is value to physical community too.
But I also think that it’s important, just for the empathy of our customer base, of like understanding hybrid as well as remote. And I think we have a pretty good understanding of remote after being all at home for a while with the pandemic. So I think hybrid is a really important one to get a handle on as well.
CONNIE: Do you think more teams will end up being hybrid rather than fully remote given another few years?
DYLAN: Oh, good question. What kind of teams? Software teams..?
CONNIE: Yeah, let’s say software or whatever you might count as your main audience.
DYLAN: In what time frame?
CONNIE: Two to five years.
DYLAN: Oh, I think the one to two years’ time frame I think we’ll see more teams be hybrid than fully remote. And I think beyond two years it’s hard to say but I would guess that we see divergence from hybrid into either full remote or full in-person for a lot of things because I think hybrid is hard. And I wouldn’t be surprised if a lot of people go back to in-person if they are given the option to.
But I think we’ll probably see more remote teams than hybrid teams in [00:42:38.16], I could be off though. I just think for software in particular there’s such an amazing community out there globally that can do this core work. And if you’re limiting yourselves to cities like San Francisco as your talent base it’s just really hard to hire, at least right now in boom times. Maybe in a year from now, if we’re not in the current bubbly world that we’re in right now in the Bay Area, perhaps that changes. But right now I think that’s the case.
CONNIE: Yeah. And I love how that leads into community, which is something that I can tell is relay important to you and to Figma. It literally has a really prominent position inside of the Figma product itself, right?
DYLAN: Yup.
CONNIE: You can access community from the top left pull down menu. Why that intentional emphasis on community? What is that for you?
DYLAN: It’s actually funny because at the start of Figma, we thought we’d be a community first and a SAS tool second. And so the first version of the Figma product is (when we had editor?) but the main file browser experience was just a feed. On the right hand.. at the center was the feed and the right hadn’t side were your drafts. And you could remix anything. I put that in air quotes. No one else can see the air quotes I realize because we’re on a podcast but you could “remix” anything that was in the feed and you could open up the file in your editor and that became a draft on your right handsome and if you wanted, you could repost your remix to the feed later.
And so we had this ambition to do this right away. And as we observed people in that early alpha period using Figma, we realized that just so many people are spending most of their creative energy at their work day-to-day and for a small base of users, it didn’t make sense to try to, like, do the community-first approach. But we always had that ambition.
So we just kind of pivoted our approach to be more a SAS tool first and we thought, okay, community will be a fast follow. That fast follow ended up being four or five years before we got to that. Fast follow is not always as fast as you want them to be, but to me it’s just so important to have this open source mentality about design.
And if you think about the way that engineers have been open source for a long time now, there’s this amazing job of just not recreating the wheel over and over and over again. And yet, how many times as designers have we recreated the most basic elements we use every day? And are we actually open to the inspiration that we can get from others? I just think there’s so much we can learn from the open source because it’s done in engineering when it comes to more creative work. And that is a big part of why we are leaning into community there.
But also I hope that over time the Figma community is a place where not only are you sharing resources but you’re also congregating as designers. So if you’re trying to learn about design, if you’re trying to teach design, if you’re trying to just hang out and get to know other designers, where do you go? You could go to Twitter and read some snarky tweets on design Twitter, nothing against that but maybe there’s a more constructive place that we can create for people too. And if we can create that third place for design, I’d be really excited about that. That’s where I want to hang out.
CONNIE: Yeah. And I love that you’re really bringing so much about the ethos of open source into design. And that’s part of why you have.. so much of the Figma files, they’re under a creative commons license, right?
DYLAN: In the community, yes.
CONNIE: In the community, which is really interesting. Do you ever feel like you get caught into.. some people can’t share because of copyright..? How do you think about that trade off?
DYLAN: Yeah, there are some people that have definitely raised that to us but actually I’ve been really surprised by how few people have that reaction. And also, people from fields that are [00:46:02.02] interface design that are really eager for their work to be shared and used because that actually adds value to your work paradoxically.
I think that one thing I have thought about and ruminated a lot recently on is the idea that basically for a meme, and that meme can be visual, that meme can be more of a thought, whatever it is, for it to gain value, the more that people [00:46:27.21] the more people add onto it the more valuable it is. And I think it’s definitely true of work that people create as well.
So I think the scarcity mindset around this is designers have had their work stolen for a long time, everyone has had this experience with a client who doesn’t pay or somebody that rips off work on the internet. And these are really negative experiences and so I understand how people are coming from that mindset. The abundance mindset is one where if you actually do share your work, get it out there, and people re-use it, repackage it and its attributable to you and people know that it’s yours, that actually can do a major.. have major effects in terms of creating your stature in the ecosystem and giving you social status.
And if we can help enforce that and to propagate those norms in Figma, with I’m not saying we’re doing a perfect job of today, I think we can do much better, but if we can boost people that are coming into design even more with our platform, then I think it could be a really constructive thing for the ecosystem overall.
CONNIE: Yeah, absolutely. At the end of 2020, you wrote a blog post called Meet Us in the Browser where you talked about Figma’s vision of making design accessible to everybody and that Figma itself is – and I love this quote – is more than a digital extension of our physical self, it’s an invitation to leave ego at the door and create shared consciousness with others. It seems like openness, transparency and access has always been a theme for your work with Figma and that refocusing on the community is the next extension of that. Is that the case or is that something that you’ve realized along the way?
DYLAN: Yeah, definitely. I think implicit in what you’re saying though is also velocity and I think that’s one area that we have to improve still is like how do you actually make it so that it’s not just I create something, it exists for a while and then it just gets remixed? How do you make it so that you’re able to move really fast and have high velocity across these shared experiences and collaborations? And that’s something that I am thinking a lot about right now in terms of how do we enable that.
CONNIE: Interesting. Do you mean velocity in the design process or merely how people learn about or see new designs?
DYLAN: Well so again, going back to that term shared consciousness, right? If we’re having a conversation, even if it’s a visual conversation in the case of design, then if I send you a letter and then a month later you send me a letter back, that’s a very different shared consciousness than if were having a conversation on a podcast. And so what does that mean for Figma? What does it mean for visual communication?
CONNIE: That’s a nice analogy. Have you sent a letter recently?
DYLAN: I haven’t, I should send letters.
CONNIE: Yeah, sending letters, sending cards, it’s great, it’s a great thing to do.
DYLAN: Well, I’ll get your address after this and we can be pen pals.
CONNIE: Oh let’s do it, that would be so much fun.
DYLAN: I’m down.
CONNIE: And since it is the Distributed Podcast, we like to hear a little bit about how you work and have your own office set up. So can you tell us a bit about what your home office is like and what are some of the most important two or three things that you can’t work without?
DYLAN: You know, I have a very minimalist answer partially because I just moved and I haven’t.. It’s really interesting because I used to have this really epic bookshelf behind me that my wife made and it’s like.. It’s funny because the colors are based off of a painting my friend Hannah made and it was sitting on top of the bookshelf. And at some point I was like, wait, these are very similar to Figma colors.
CONNIE: Amazing.
DYLAN: It was this great bookshelf with all these great design books on it and other books I loved. And then I moved to this new place and now I’ve got a filing cabinet behind me. I have the same desk, I have the same laptop. The only thing that’s missing is the notebook because I haven’t found my notebook yet in the move. And I’ll find it, I think I know where it is.
But I think it’s the only thing that’s like atypical I would point out here, which is I find that if I’m writing things down or in a conversation I just recall them so much better later. And it’s like, I don’t even have to look at it later, although it’s nice to sometimes. Just the mere act of writing things down really, really helps me. Other than that, I don’t have the one tip or trick. I’m pretty minimalist in my set up.
CONNIE: And is that the same for your actual office/office set up?
DYLAN: The office/office set up, we actually have a.. people are going between desks, it’s more like a (hotelier?) model. And so we don’t have physical here’s your spot and you get to claim it forever yet. Maybe we’ll [00:50:38.16] in the future but for now you actually rotate in. People have a monitor, a keyboard, a mouse if they want it, and they can plug in, it’s really simple.
CONNIE: I really like that you referenced the word serendipity so much because that’s actually a distinct theme of the distributed podcast for this year. What else are you doing now that you’re back in the office part time, we’re all adapting to our normal at-home lives, what else are you doing to add some more serendipity to your life?
DYLAN: Well to my life versus to the Figma life?
CONNIE: Both.
DYLAN: Okay. I think Figma, just the more you can empower people that are wanting to start organizations inside of Figma or groups, the more that you can get people to create culture events on their own, it’s always winning over, you know, top down, here’s what we’re going to do, I think it’s much better to have it bottoms up. And that creates serendipity whether it’s in the office or its remote.
In my own life, literally just walking around the city or going to new places, travel to places that are in driving distance, even, finding a cheap Air B&B. Now I’m lucky that’s affordable for me, not everyone is the case, but I think even just a bus ride or a drive to a new place that you haven’t been, can add a lot of serendipity and creativity and inspiration to your life.
And yeah, I find that when I get outside, which it’s so easy to go a full day and just be working and there’s always more to do. But just getting outside, listening to music, reading, learning, these are things that add a lot of serendipity in my life as well as conversations with loved ones and friends, like, it’s not.. it’s nothing that people are not used to but it’s just amazing, like, making the time for that, how much it matters. Getting exciting. Like, if you don’t get excited, like, what are you doing?
CONNIE: I love excitement.
DYLAN: Yes.
CONNIE: Can I ask, what else are you doing to generally maintain your mental fitness especially as this, as you pointed out, this pandemic is just going to keep going. What else do you do to keep yourself fit, happy, healthy?
DYLAN: Sleep, spending time with my wife Helena. She’s due right now so we’re excited. She’s due in December.
CONNIE: Wow, congratulations.
DYLAN: Thank you, yeah.
CONNIE: That’s amazing.
DYLAN: So I think just having the humility of oh my gosh she is literally growing a human, what am I doing today? [laughs]
CONNIE: Perspective, it’s great. [laughter]
DYLAN: Perspective, yeah, that’s another word for it. But yeah, just having the perspective I think is really a great way to have that mental fitness, as (you put it?). Because a lot of the things that are like these are the little challenges we run into every day, they kind of all fade away in that grand horizon.
CONNIE: Yeah. Do you have any daily rituals like meditation or anything else that lends itself to that?
DYLAN: I should definitely meditate more. I think it always makes me happy. But I wouldn’t say it’s a daily ritual yet, although that would be great if it was. I am not a very good ritual person. I think so many people are great at this and I have never found my groove of a ritual for some amount of time. But I think the only ritual I would say that.. it’s not necessarily the same time of day but if I don’t learn something during the day that’s usually not my top day. So I’m always trying to figure out something that I can learn from people.
CONNIE: That’s a great philosophy to have. I’d like to move to a special section at the end that I like to call the lightning round of questions.
DYLAN: Oh, oh boy. [laughter]
CONNIE: It doesn’t have to be that fast but they’re meant to be quick little top of mind responses. Starting with an easy one, so, since you talked about being really excited about things and how that is awesome for you, what is something that you’re really excited about right now that’s totally outside what we have been discussing?
DYLAN: Yeah, well, we were talking about crypto earlier because you were formerly at Coinbase and I think that one thing that I’m really excited about right now is just DAOs.
CONNIE: Awesome, thank you. All right, next question. What job would you be absolutely terrible at?
DYLAN: If I was in a very heavy operational role I don’t think you’d want me in that role. And that goes for running a very operational business as well. Like, something like DoorDash I think I would not excel at.
CONNIE: Noted. What is a nice compliment that you’ve received recently?
DYLAN: You said a lot of nice things today. Thank you, Connie.
CONNIE: Oh, you’re welcome. What’s something that you wish more people did?
DYLAN: Think from first principles. I think it’s so easy, especially in today’s day and age, to take whatever you read online, whatever you’ve seen in media, and just repeat it without thinking about it first. And I think that the world would be a much better place if we all did our research and thought deeply about the things that we were taking on as opinions and didn’t just give everyone right access to our brain.
CONNIE: You mentioned that you really, really like learning and that in fact if you didn’t learn something it’s probably not your top day. What’s some thought nugget you learned recently that you really like?
DYLAN: It’s not really a thing I learned but one thing I’ve been reflecting on is how fear blocks compassion.
CONNIE: How fear blocks compassion? Hmm.
DYLAN: Yeah. I think that for me at least, maybe it’s different for the people, but a lot of times when I find myself lacking compassion I can trace it back to I’m being fearful of something. And if I can figure out why I’m being fearful that I can unblock that compassion. So yeah, it’s been applicable for a lot of different parts of my life recently.
CONNIE: It’s such a great philosophy. It’s very closely linked with meditation, which is interesting that you have that view.
DYLAN: What is the meditation viewpoint there?
CONNIE: Just very similar to that, that there’s a lot about compassion about.. Buddhist meditation, the default is the world is suffering and it’s compassion and understanding that gets people through that and helps you live and be empathetic to all of the fellow people that inhabit this world with you. What do you think enabled you to get to that kind of realization?
DYLAN: Just a lot of thought about the pandemic and the things that I was not being compassionate about and the people that I was not being compassionate towards and I asked myself why.
CONNIE: Really nice reflection. All right, this is a question I’ve been really enjoying asking people recently and it’s kind of a fun one I was first asked by my 19-year-old cousin, which is what are some of your hot takes?
DYLAN: Hot takes. Well, give me a subject or a point of view and I’ll try to give you a hot take on it.
CONNIE: Absolutely. A hot take on food.
DYLAN: Oh, well, I have really bad acid reflux so I try not to drink caffeine and I also try to stay away from night shades and tomato. But the biggest hot take I have on food is that I hate chocolate.
CONNIE: Oh wow.
DYLAN: Yeah. I just have always hated chocolate. It’s almost like this thing where I feel like I’m in The Truman Show and everyone else is gonna at some point be like ha ha, I got you and I took a bite of chocolate and pretend it’s good because I’ve just been pushed this way my entire life but really it’s not good, it sucks, I don’t know what y’all are thinking.
CONNIE: That’s amazing. What about chocolate with nuts?
DYLAN: It’s gross.
CONNIE: Still gross. Kit-Kats?
DYLAN: Everything chocolate is gross. It’s disgusting.
CONNIE: Wow, that’s a great hot take. I’ll confess one. I don’t like pizza. That freaks people out.
DYLAN: That’s fair. Yeah, I mean, it’s bread and cheese, it’s not exactly the most healthy food.
CONNIE: It’s kind of goopy, it’s a little hard to deal with. I want to get a couple more hot takes, I think this is a fun question.
DYLAN: Okay, okay.
CONNIE: What is a hot take on San Francisco?
DYLAN: I’ll give three. One is its beautiful and it’s a majestic place that has endured as a creative hub for many decades and that’s not going anywhere. The second is that it is no longer, along with the Bay Area, going to be the top hub in tech.
And the third is, as a resident of San Francisco, is that I will put a political opinion out there, which is that I really believe that we have to actually care about crime and if we see stores shutting down because they’re getting so many people shoplifting, at least we should have a conversation about it. I’m seeing some people saying that’s just not happening and denying it’s happening and that really frustrates me.
CONNIE: Understood. Hot take on space travel?
DYLAN: Love it, go to the stars. I think there’s some perspective from people that says we have so many problems on earth, why are we going and exploring new frontiers? Why not go and solve those problems on earth? For example, a lot of people criticized Jeff Bezos for his work on Blue Origin. That was also after he donated or committed a ton of money to climate change. So I think it’s not an ‘or’ it’s an ‘and.’
And I have nothing but respect for people that are pushing the frontiers of technology, science and trying to figure out ways to make sure that in a worst case scenario, if we blow ourselves up, that some part of our human consciousness remains.
Also, if there were aliens, I think that we’d all be very focused on the state of space travel. I’m not saying there are, I’m saying that the government has been very quiet about the subject. And they have been willing to admit that there’s a lot of UFOs out there and we have no idea what they are. So either that means that we are behind on their mission in terms of military or that there’s phenomenon we can’t explain. In either case, I think you want to invest a lot in space travel and aeronautics right now.
CONNIE: I’m into that, I’m a huge, huge fan of space. It seems really cool. All right, well thanks for diving into the hot takes segment.
DYLAN: Sure. That was fun.
CONNIE: Yeah, learned a lot. What is keeping you up at night?
DYLAN: I mean, for Figma we’re growing so fast and so it’s just like how to maintain culture when we’re distributed, when we’re growing really quickly, that’s super important. So trying to make sure that we do a good job of that.
CONNIE: Absolutely. What is one piece of advice that you have for companies who want to be excellent at design?
DYLAN: Oh, I think it comes from the top. So if your leadership doesn’t care about design, make a case for that. Make sure that they start caring. And if you are leadership at a company, start caring about design, start talking to your designers more, start talking to your product people more, anyone who is working on the digital project experience. That, I suspect, will be the reason you win or lose the business.
CONNIE: Hmm, I would love for you to expand on that. Like, if you pretend you’re talking to maybe some skeptical leader out there, what is your pitch right now for why they should care about design?
DYLAN: Well the entire world is going from physical to digital, like we talked about. And if you ignore that transition and you say that the ways of the past are going to serve you and you don’t have to continue to innovate and to keep pushing on the design of your experience, I just think that some competitor is going to come find you and they’re going to beat you.
And so if you want to maintain your market position, even as an incumbent or a laggard and certainly if you want to gain market position against others, design can be a differentiator. And you either have to be leaning into that to go on the offensive or leaning into that in order to be on the defensive. But either way, it is an arms race and if you don’t participate in it, you’re just going to lose.
CONNIE: All right, Dylan, I’ve got one more hot take for you.
DYLAN: All right, let’s do it.
CONNIE: What’s your hot take on becoming a dad?
DYLAN: I’m so excited. [laughs] It’s gonna be awesome. I can’t wait to meet this kid.
CONNIE: That’s so great. Dylan, thank you so much. This is such an exciting time for you between the growth and momentum of Figma and the opportunities that you and your team have created for all of us designers in the tech community, it has been real swell to talk to you about all of that today.
DYLAN: Thank you. Thank you for supporting us and for having me today.
CONNIE: Absolutely. Thank you for sharing your thoughts. And here’s to more success for you and a great year ahead for Figma and for everyone listening out there as well. Stay healthy a stay positive. Thanks, all.
DYLAN: Thank you.
End.
Episode 28: Erica Pandey of Axios on Returning to Work
Jul 22, 2021
We admire journalists today more than ever. Whether getting their start as a solo blogger on their own beat, or growing up in a thriving newsroom, journalists must forge their own unique work life as they write the first draft of history.
So it’s no surprise that this episode of the Distributed podcast with Matt Mullenweg and special guest Erica Pandey, business journalist and writer of the What’s Next newsletter at Axios, moves fast and covers a lot of ground, from Erica’s career, to how she works with her Axios colleagues in different cities and bureaus, to what she is seeing as she covers the intersection of technology, business and people.
Erica has recently written about how workers are discovering their own ‘Third Workplace,” and shared insight on how HR departments can improve childcare benefits for working parents. “Childcare has always been a problem. The pandemic just spotlighted it, and hopefully now something will be done about it,” says Pandey.
She balances Axios’ Smart Brevity style with authoritative reporting on complex topics, seeking multiples perspectives, from data to experts to people on the ground. Says Erica, “One of my greatest joys is being able to talk to people.”
The lively conversation centers on how we’re all returning to work after so much change and adaptation, including the rise of hybrid workplaces.
“The best possible form of hybrid – and this is not just me, this is what HR experts are trying to game out here – is everybody meeting, and (then) everybody at home, at the same time,” says Pandey. “The benefits of being in person, which are social interaction, which may be rubbing shoulders with leadership, which may be the innovation that happens on the spot when you are talking with someone at the coffee maker, happen when everyone is there. And then when everyone’s home, they can work on solo projects or get longer term projects done.”
“When you make it so that there is no penalty for not being in the office,” Matt later agrees, “you’re not missing opportunities, you’re not missing socialization, you’re not missing anything. That is to me the superpower (of distributed work).”
The duo see that this moment may represent – as Erica names it – a ‘code switch’ from prioritizing a job near your family and social life, to adjusting your work to where you live. But it’s an adjustment for everyone, she adds, including journalists:
“Journalism is also so much about the energy of the newsroom. There’s the camaraderie of it too. When you’re always distributed…and you don’t get to come back to your desk with all of your colleagues typing away furiously, you do lose a sense of the team sport of it.”
And that may be what we can all learn from journalists: at home, out for an interview, writing from a Third Workplace or with the team in the newsroom, figuring out how and where we work our best, deadlines and all.
“We’re not work from home evangelists. We’re kind of like ‘Work from wherever you’re going to be most effective’ evangelists,” says Matt. “I can’t wait for people to experience a good version of work from anywhere – not where you’re isolated, and fearing for your life or your family, but where you can actually really get out and enjoy your community.”
Thanks to Erica for joining and sharing her insight. And thanks for listening.
The full episode transcript is below
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MATT MULLENWEG: All right, howdy everybody and welcome to the Distributed podcast. I’m your host, Matt Mullenweg. Today’s guest is a hard-working reporter covering the intersection of business, technology and people.
Erica Pandy is a business writer for Axios and author of the What’s Next newsletter. The last few months of her coverage has included biometric tracking, pandemic-driven migration patterns and a subject near and dear to my heart, which is the fried chicken shortage. We follow her most closely for her extensive coverage of the changing workplace, including diversity hiring, gender inequalities and other trends surrounding the return-to-work discussion.
Erica has been writing a lot about hybrid office culture, hybrid schools and even hybrid concerts and weddings. So you can imagine we’re going to be talking about one of our favorite topics – distributed work. Axios is an exciting publisher as well and Erica is right in the middle of some of the most relevant trends in reporting. So I’m excited to learn from someone whose work is all about learning from others in business, tech and beyond.
So, Erica, thank you so much for joining today.
ERICA PANDY: Thanks, Matt. It is awesome to be here.
MATT: So, where are you joining us from today just out of curiosity?
ERICA: So I actually am living out the trends that I’m writing. I lived in Brooklyn, New York, I was a classic millennial living in Brooklyn having that perfect hipster lifestyle. And after the pandemic hit, I have since moved to Hoboken, New Jersey. So, New Jersey has been one of the biggest beneficiaries of the pandemic era exodus from New York and I am definitely part of that. I never saw myself as a New Jersey person but there’s more space and if I’m not going to be having to go to the office every single day I don’t mind being in a different state.
MATT: How did you choose Hoboken?
ERICA: A couple reasons. It’s just cheaper, first of all, than Brooklyn and I wanted to.. Also I’m one of those people who decided to buy during the pandemic. I had rented before this and for the price of something in Hoboken, I’d be living in a studio in Brooklyn. And there’s a little bit more space, there’s a little bit.. it’s a little quieter, a better place to raise a puppy. I also got a pandemic puppy. I’m really hitting all the stereotypes here. So, yeah, a plethora of reasons but yeah, not.. New York kind of shutting down for a year made me realize that I didn’t need to be in the thick of it all the time.
MATT: How is it feeling over there? I’ve heard New York is feeling a lot of energy and almost back to normal.
ERICA: Yeah, it really is. I mean, everything from the restaurant scene to the entertainment scene is back. And some of the things that the city is holding onto I think are great too. You know, all of those outdoor dining set ups that people really grew to love are staying up through the summer. And I think there is a real desire for that space that restaurants and people took over from cars in cities. So I’m hoping that the New York of the future will be a little bit more community driven and a little bit less just cars and parking.
MATT: It also feels like restaurants that happen to have street front have disproportionately benefited from that from like a restaurant in a basement or a second floor.
ERICA: Absolutely. It’s nice to see those kind of speakeasy type spots coming back too now that people aren’t really afraid to be in a cellar somewhere, in close quarters with others. Because that’s also quintessentially part of the New York experience. But that outdoor dining set up is basically like free advertising. You walk by, you see a well decorated outdoor dining set up, it’s covered, you go right ahead.
And one interesting thing that I’ve seen in New York, I don’t know if it’s happening as much in other cities, is restaurants, which as you and I know have been battered by the pandemic, are using this new world to make money in new ways. Like, there’s some cafes here in New York that opened for dinner at five or six but during the day they rent out their table space to remote workers so you can work from a place that’s not the home or the office.
MATT: Wow, and have you tried this yet?
ERICA: Yes. I tried it at a cafe in the East Village called Kindred. They’re like Eastern European food at night and a classic dinner spot but during the day, for $25 you get a table for eight hours, you get to have free Wi-Fi access, you have outlets right there and free coffee all day. And they’ve built in the outlets into the outdoor dining set up so you can sit outside but in a sort of closed, less-chaotic space.
It’s this rise of the third workplace. I like the flexibility of working in isolation on my own times sometimes, but you get sick of being in your house, especially if you’re a New Yorker and being in your house means being with three roommates.
MATT: Are there any studies or surveys you’ve come across that say how many people want to do this or how often it’s happening?
ERICA: Well, there aren’t really studies on this call it the third workplace yet because it’s so new. But the overwhelming majority of people, like around 60 or 70 percent, across different studies, want to do hybrid work. And what we’re learning is that hybrid work doesn’t really mean just home or the office, it means all sorts of things.
So, maybe you want to go to L.A. for a couple of days and visit friends but you only want to take one of the days off and you work there. Maybe you want to rent some space in a WeWork that’s closer to where you live rather than commute 40 minutes to the office. So, hybrid just encompasses all of these things where you’re just taking your laptop and sitting down and work happens where you are.
And then there’s only about 10 or 15 percent of people who want in-person all the time or at-home all the time. So it’s very much those are the two extremes and everybody else kind of wants to be a floater.
MATT: What feels tricky about the term ‘hybrid’ is you can kind of bring to it almost anything. Like, arguably, Automattic, which has been distributed for 15 years, was hybrid because we would do meet-ups. So we would try to see colleagues sometimes, it was just once year for the whole company and then a few weeks a year for each team. So I guess that is a form of hybrid. But I’m curious, if you were to describe the best possible form of hybrid and the worst possible form of hybrid, which would each archetype be?
ERICA: So, the best possible form of hybrid, and this is not just me, this is what some HR experts are trying to game out here, is every.. like you’re saying with Automattic, everybody meeting and everybody at home at the same time. So, if you’ve really going to do a hybrid work week what that would look like is everybody comes to the office on Mondays or Wednesdays, for example, and everybody is home on the other three days. The worst possible form of hybrid is when people just come and go as they please, which is unfortunately what a lot of companies are leaning towards.
And I will explain why each of those is. The best works the best because then the benefits of being in-person, which is that social interaction, which may be rubbing shoulders with leadership, which may be the innovation that happens on the spot when you are talking to someone at the coffee maker, happens when everyone is there. And then, when everyone is home, they can work on solo projects or get longer term projects done. If people are just coming and going as they please you might come to an empty office or you might stay home on the day where everyone else is there. So it doesn’t really work for anybody.
If you’re trying to make it a little bit more structured then you please your employees who want the social interaction but you also make your employees happy who want to be home more. If you just let people do whatever, you end up in a situation where maybe someone really wants to come to the office and then they arrive and they realize I’m coming in on days when no one else is here, I don’t like this energy, I’m leaving and going to a different company. But obviously it’s not as simple as that.
MATT: Can you just ask your colleagues, like, hey are you going to be there on Wednesday?
ERICA: I’ve kind of been doing that with Axios, trying to set up days where everyone comes in. But again, it’s not that simple because there’s some folks who want to work from home all the time and hybrid policies do let them do that. So I have honestly no idea what the future is going to look like.
I do sympathize with my colleagues who have kids or who have moved deeper into Brooklyn or further away and they don’t want to commute to an office in Chelsea every day, or ever. So we’ll see what it looks like. But I do think there’s going to be some redistributing of people towards companies that have work philosophies that align more with what they want.
MATT: That’s funny because what you said is the best, that few days a week in, a few days out, I would actually say is the worst of all worlds. [laughter]
ERICA: Yeah. You have a point too because if you have a days in, a few days out, then if I’m someone who really wants to move far away, I have to kind of have one foot in the door all the time. So that doesn’t have its (perks either?).
What you’re saying is great too. I mean, if you want to be an all-remote company but then do very intentional, big budget retreats where you bring everyone together in a way that’s fun and cool, that also works. So yeah, we’ll have to see where different companies land. Yeah, I don’t think anyone really knows. That is such a good example of how convoluted it all is that we have opposite ideas of what’s good, what’s bad.
MATT: [laughs] Yeah, for me so much of the power of working from anywhere is that ability to, like you said, travel for a week or two or even for a few days, or just leave that kind of commuting, what’s it called, like the commuting geographic boundary of where that office happens to be. Because then you unlock access to all the talent that either never lived there in the first place or all the talent that is thinking about something different, something further afield in Hoboken for optimizing their life and integrating their life with their work and their family as best as they could.
ERICA: Mhm.
MATT: So, when you make it so there’s no penalty for not being in the office – you’re not missing opportunities, you’re not missing socialization, you’re not missing anything, that is to me the superpower of it and something companies have to do anyway, by the way, as soon as they get big enough where they’re going to have multiple offices or even multiple floors in the same office. Like, how much of that benefit of in-person work if your team is spread across three different floors and only sees each other every now and then are you really getting?
I’m curious, like, the really objective challenge of the sort of hand wave-y benefits of in-person work, especially after we had a year, a year and a half, of companies doing some of the best ever, certainly by stock market performance, at a time when we literally couldn’t see each other.
ERICA: Yeah. I think also going a little bit back on what works.. I think my perspective is a little bit warped just by my age too. I’m in that kind of mid to late twenties contingent and I really like the office. I mean, 25 percent of people are still meeting their spouses at the office. And I think there’s a lot of.. I talked to a lot of recently minted college grads who are finally ready to venture out into the world and have that daily commute in L.A. or New York and suddenly it’s like, oh, people don’t really come in anymore, you can if you want to but no one is really here.
So, I think you’ll see a little bit of tension there too between people who have families, who have established networks, who are very much happy to work from anywhere, stay home, or do their own thing, and then people who really are relying on coming into the office, finding a mentor, building a network because they just don’t have that yet.
MATT: Hmm. What does that say about the paucity of our social life as well, the whole idea of bowling alone, that the third place also has to be work related? Maybe it would be a good measure. Certainly as a manager, I’d prefer if less people met each other at work and had romantic entanglements. So maybe if that 25 percent went down, it doesn’t necessarily need to be a bad thing. It could also mean that we’re connecting more with community organizations, churches, volunteer organizations, sports, music, fun stuff that could be more interest or passion based than necessarily happening to work for the same company.
ERICA: I mean, that’s such a good point. So many of our other relationships, like our friendships and our family relationships, we conduct remotely just so we can have our work relationships in person. So, maybe it’s a code switch that we as a society, as a country, have to go through where work becomes a remote thing and family and friends and hobbies and interests become the in-person thing.
MATT: That is a really interesting way to put it. I wouldn’t have used those terms but I like it a lot.
ERICA: Mhm.
MATT: I feel like journalists and reporters have always been a little more adapted to distributed work because often your beats or your reporting is going to take you away from the office. So how did you see that with your work and your colleagues?
ERICA: Absolutely true. I mean we’ve always had to have different bureaus and the tech reporters are out in San Francisco, some of the businesspeople are up in New York and then you’ve got politics in D.C. So we’re definitely used to that. And also, reporting involves work trips.
But journalism I think also is so much about the energy of the newsroom. A lot of people grow up watching those movies and TV shows about all the journalists on deadline, at computers. So there is a camaraderie of that too. So I think when you’re always distributed and you don’t have.. maybe you do the work trip and you don’t get to come back to your desk with all your colleagues typing away furiously, you do lose a sense of the team sport aspect of it.
And journalists have been through a lot. I mean, covering crisis after crisis, whether its political crises or public health crises with the coronavirus, has been really, really taxing on journalists’ mental health. And I think the sense of community being lost was not great. But we have Zoom, we have all of these technologies that let us connect again. And I’m sure newsrooms will be among the first to kind of have retreats and bring everyone together as soon as it’s safe to do so. And some are already doing so.
MATT: I can’t wait for people to experience a good version of work from anywhere. Not where you’re isolated and fearing for your life with your loved ones but where you can actually get out and really enjoy your community because that is a, at least I would say a qualitatively, like, order of magnitude different than certainly what I and many of my colleagues experienced in the past year.
ERICA: That is so true. I hear this when I talk to people who have been doing remote work and remote teams before the pandemic and I hear them but I can’t really relate because I haven’t been there yet. But yet people have said it’s very simple – working from home doesn’t always mean working from home during a public health crisis. It’s not always like this.
So I think once people start to loosen that negative association they have it could be really great. And realizing that you can do retreats and meet up whenever you need to.. For example, we have this great thing happening at Axios right now where our editorial leadership, our editor-in-chief and other top editors are doing a tour to our different bureaus and coming to the reporters instead of all the reporters having to fly out to headquarters. And that has been great for them to have an ear to the ground and it has been great for people to have the editor-in-chief come to their city.
I mean, Axios has expanded into local coverage. So we’ve got a bureau in northwest Arkansas now, we’ve got one in Des Moines. So, having the leadership come there is great.
MATT: As a leader I also found it also just.. you get a sense of the place so much more from being around the people in their home territory than you would if they were visiting a headquarters or making a pilgrimage. So I’m excited to hear that.
I actually, I guess it was last month now in New York, I was on a visit for a separate reason and I realized that so many of the folks I worked most closely with in the company were in the New York area or within an hour flight. So, I was actually able to have like ten one-on-one lunches and dinners and things with some of these colleagues who I’m very, very fond of and we work very closely. But it was almost.. We probably talked about work less as a percentage than we normally do in meetings just because it was so nice to connect again as humans and I really appreciated that.
ERICA: Yeah, that is such a big part of it too. When those interactions with leadership happen in your hometown, when you’re showing them the local spot to eat rather than everyone at HQ and at a company retreat it is a lot more generative and a lot more.. Like you said, it’s a lot more fulfilling than just all right, the CEO is at the headquarters, everybody report there and sit for meetings or seminars.
MATT: You had mentioned the verve of a newsroom and it sounds like you might be based with.. Axios has an office in New York?
ERICA: Yes, we do have an office in New York, right in the Chelsea, right by Penn Station area. And one of my fears in the middle of the pandemic was that we were going to shut that down because our headquarters is D.C., New York was always a side office. But I respect that our founders seem to have a great desire to have a presence in New York and even if most people want to work from home or they just..
Because the New York office here at Axios tends to be more design and tech and engineering folks, so not necessarily people who are craving the energy of a newsroom. But we’re going to keep it open and I think we’re going to keep expanding the team up here. So that’s great for me.
MATT: Yeah. I think especially New York is one of those cities where a lot of people are working from home or their workplace options are not the best.
ERICA: Yes, exactly. And you’re seeing new things. Like, WeWork has tried to become the Uber for the office market, which I think is interesting. You can book WeWork space by the hour now instead of getting a long-term lease for lots and lots of money for your company, you can just go in as a single person and say I’m going to have a desk there for four hours today. And then this restaurant model that I’m telling you about.
So I do think there are some opportunities for businesses to get creative here, to accommodate the rise of the third workplace. You might see it improve. But for now, trying to set up shop in a coffee shop in New York where you’re probably not going to have an outlet, you might get glares from people saying why did you buy one croissant and now you’ve been here for three and a half hours.. [laughter] So, as of now it’s not great but I am hopeful for the future.
MATT: I also think about the privacy of conversations. Like, what if you’re having a sensitive conversation with a source or something like that? Do you want to do that in a coffee shop where there’s ten people listening to you?
ERICA: Absolutely not. And even if you know that no one can listen or no one can hear you, just having the source hear the hullabaloo in the background and realizing you’re in public is just not a great look.
MATT: I have always been such a fan of journalism and journalists and you mentioned watching movies or the idolization that might have caused people to get into it. I’m curious what was your moment where you decided this might be something you’d want to pursue as your career and as your passion?
ERICA: It’s really interesting because it wasn’t really a movie that got me excited. Most of the movies that I watched the journalists were the annoying guys or the bad guys, I’m thinking about The West Wing, which I loved and the journalists were always the ones that came and spoiled all the fun by telling everyone the secret thing that was happening at the White House. [laughter]
But for me, I just kind of.. I never really latched onto one subject at school, I kind of liked a little of everything. And that made me confused, you know, what am I going to go into? And then I realized that journalism is the kind of profession where you can become an expert in a different thing every week and then just completely move onto something else and revisit it when you want to. And that idea of just floating around and diving into these micro passions I think really landed well with me.
Like you were saying, I mean, I wrote about weddings a couple of weeks ago, I’ve written about surveillance, I’ve written about China, I have written about stuff that I personally find interesting. My family is from Nepal, I wrote a story for Axios about Nepal’s geopolitical role in Asia as between these stalwarts, India and China. And then I moved onto a business beat and was able to cover remote work and all kinds of stuff. So, fun stuff, serious stuff, and just the range of things you can do rather than just doing the same thing every day I think was what really appealed to me.
MATT: As a funny aside and a correlation I have realized.. We’ve hired thousands of people over the years and we definitely have hired some who thought why would enjoy distributed work and ended up really wanting to be in a company with an office, which I think that is a completely fair reason and a good reason to leave Automattic. But I noticed that a really high percentage of the folks who wanted that office experience were obsessed with the show West Wing. Like could quote the episodes.
ERICA: Really?
MATT: I love the show as well but there is something about that energy of that fictional West Wing, which was definitely infectious. Like, who wouldn’t want to live in a place where.. or work in and spend all your hours in a place like that environment?
ERICA: We were just talking about work being life. And that show was about work being life and they made it look pretty cool.
MATT: And there was such fun.. I did notice on those folks as well, they would just make everything a little more exciting on the good end and a little more dramatic on the bad end, kind of like the show does. You know? Like normal stuff would happen and it would be clever and funny. It wasn’t running into a tree; it was a sudden arboreal stop. And you’re like, oh that’s so good.
ERICA: Right, exactly, exactly. You become kind of entranced by office politics with that show and there’s a few others like it but it’s just so.. yeah. And journalists are like that too. When you are a reporter and your whole job is about seeking out information and learning things, you realize that you want to do that about your own colleagues and your own company. So I think the office politics and office gossip in newsrooms is a cut above everywhere else.
MATT: And how the media covers media I’ve noticed as well is I think with added vim and vigor than almost any other topic.
ERICA: Absolutely. Some of the most voraciously consumed content by journalists is media journalism because what is more interesting than your own life? All of my colleagues have become obsessed with the show Succession for the same reason. It’s about media, it’s about the business of media, which is just so interesting.
MATT: Is that the one loosely inspired by the Murdoch family?
ERICA: Yes, yes that’s the one.
MATT: You mentioned moving between these topics, which is very different than many, many roles because you are writing authoritatively as part of the first draft of history on.. it could be a different thing every week. So how do you approach boot strapping your knowledge in the (fundamentalism area?) to write about it in that authoritative way?
ERICA: So, I think it’s just about talking to the right people and you have to go from the top down. So, say you’re writing about the effects of virtual learning on students with learning disabilities, which is something I’ve done, and you have two weeks to pull together a story on it. Obviously, my beat is not education primarily so it’s not something I’m too well versed in so I’d start by talking to education professors who are really looking at this from the big picture view.
Then you go a level below that and you talk to teachers and non-profits, people who run non-profits on this issue. And then you go right to the source and you talk to families or students who are dealing with this on a day-to-day basis. And I think getting those three perspectives from the 30,000-foot view to a level down to right on the ground really helps you form a picture in a way that you can write authoritatively on any topic.
That method has worked for me well and I also love talking to people. And I have friends who say I could not cold call all day or I could not spend my day talking to strangers but it’s I think one of my greatest joys is being able to talk to different people, especially the families, who are dealing with this. Or, you know, for my story on the future of weddings, I spoke to an actual couple who had a hybrid wedding. And people just sharing their stories is the most interesting part of it. And so many reporters now just talk to the experts and ignore the people so I think doing both is the perfect balance.
MATT: What do you do when the experts and what you’re hearing on the ground isn’t congruent?
ERICA: That’s why you keep the numbers and you go back to them. I’ve had experts tell me remote work works for everybody, it’s great. And you take that, this person has been studying remote work, they’ve been studying remote teams, they probably know what’s what. Then you talk to someone saying remote work is driving me crazy, I’m sitting and my two roommates are taking meetings, the wi-fi never works, I feel like I’ve lost my sense of self.
You go back to the experts and say but some people are saying this, what do you say? The experts can usually riff right there on the spot and say well, it might not work for everybody, here’s some examples that I found that I didn’t share with you on that first call. So, just taking your sources back to each other so they are almost having conversations through you also I think makes any story better.
MATT: The role of studies and surveys, it seems like when an article comes out, it gets covered very extensively in journalism and that becomes common knowledge. But also studies are constantly being reversed, like social science findings that maybe they don’t replicate or that changes and often that doesn’t get picked up as much. Or surveys might have flaws in their methodology. So, how do you balance that? Do you have to be an amateur statistician as well?
ERICA: I think with the rise of Twitter we’ve just become such headline-oriented news consumers. So you see so many people just taking a stat from a study, pasting it at the top and publishing that. And that has its place but I always think studies should be reported with a lot more context. I don’t think they should ever be.. in the first sentence of the story, you shouldn’t.. if you have that study you should add in a few more, unless it’s something like a big paper that came out in a scientific journal.
But there are so many studies that are done, for example, saying how many people want to do remote work versus hybrid work and there’s different stats on each one, including a few.. I like to wait until there’s a few that have the same headline and then you can write about it in a more qualitative way. And most newsrooms now have dedicated people on staff who are on there to gut check and make sure that what we are reporting is.. the methodology stands and is reportable and has integrity.
And newsrooms are also doing their own surveys. So I feel like surveys should be taken with a grain of salt but once you start seeing four or five surveys that are saying the same sort of thing then maybe it’s okay to lean into it a little bit.
MATT: Yeah and also as a journalist you know the incredible power of a question. And I’ve seen it while running surveys. Phrasing a question even a word or two differently can drastically change the outcome and how people respond to it.
ERICA: Absolutely, yeah. So, sometimes you ask people do you like hybrid work, for example, and they will say no but you forget to ask them, like you say, would you like hybrid work if you weren’t stuck at home because of the pandemic and then it completely changes.
MATT: Yeah. I wonder that about the 15 percent that say they want to be remote all the time. Does that truly mean never, ever seeing your colleagues, ever?
ERICA: Yeah.
MATT: [00:28:40.22] (Attributing?) that to 15 percent of us seems high there. Like, who would..? You want to see them at least maybe once a year or once a decade, something.
ERICA: Yeah, well I mean you’re so right. Do those people think that this is a world without any retreats or do they think this is a world where the holiday party still happens, I just don’t have to go into the office? And you don’t know that until you conduct the survey yourself. So I think you’ll see more and more newsrooms do that, too.
But my feeling is that the people who say they want all remote are people who say I don’t want to even live within commuting distance of my workplace. I want to be able to be anywhere, whether that’s move across the country or move to a different country and still be a part of this. But I’m sure, like you said, those people do want that occasional meet-up even if it’s once a year or once every six months.
MATT: We have experimented so much with this over the decades really and ended up in a place where we said hey, work from anywhere, like literally we could care less and we want you to be able to be productive but expect three to four weeks of travel per year. And it was really important to communicate that up front because people might need childcare or pet sitting or someone to water the plants – they might need a plan for being away from home for three or four weeks.
And I also want them.. we don’t have any special subsidies around that so I want them to take that into account with their compensation, like at this salary, knowing that you’ll need to be away from home for three or four weeks per year, is that something you want to accept? Because we’re not going to, say, pay for pet sitting or any of those other things that.. costs you might incur from being away from home.
ERICA: And speaking of subsidies like you’re saying, we also have to figure out the new model for how we pay for the actual office. Because a lot of people have dealt with the cost of their office being offset onto them, whether that’s through wi-fi or electricity or having to buy a desk or a set up or whatever it is. And lots of companies have given stipends for this kind of thing. But if this is going to be, if remote work is going to be a big part of the working moving forward, companies are going to have to figure out what helping people set up their offices and keep their offices running looks like when they’re not in the central office building.
MATT: Yes. We’ve actually for many years had remote ergonomics consultants as well, so people who you can go on Zoom and walk them through your home set up – the monitor, the chair, everything like that. And it can make a huge difference. You get that stuff for free in an office, sort of, but the downside is you also get lowest common denominator of the desk, the chair, etcetera.
So we just say a budget, I forget exactly what it was, maybe it’s a $1000 or $1500 or something to set up your home office, and you can get whatever chair you want, whatever desk you want, etcetera. So there is a lot more variety and personalization in how people can configure it, given that they have the space and the timing to do so, which if you have to commute into a certain location, you might be making tradeoffs to be within a reasonable commute time.
I don’t have the survey here but almost no one is like wow, I love my two hour a day commute. [laughter] It does feel like one of those under.. or overrated things about any sort of office work is that commute time.
ERICA: Yeah, that’s kind of become the truth of the times is that people might like the office but they definitely hate the commute. And so I think that’s going to influence decisions going forward too.
I’m curious though, from what you’re saying, have you thought about the third workplace before the pandemic? I’m sure it’s come up. Because I’m thinking about employees of yours that may be sharing apartments with people or not able to set up the ideal home office. I wonder what strategies they have.
MATT: Yeah it’s worth saying because we do very few paid stipends or benefits at Automattic partly because it’s difficult to administer across 80 countries but we just also want to give people a choice. We don’t want to be too paternalistic so we want to pay people fantastic salaries and then they can direct that as they choose.
But two exceptions are obviously the retreats or meet-ups, which we have a $250 per person, per day budget for lodging and everything while you’re there. And the $250 also shows up one other place, which is we have a co-working stipend. So, up to $250 per person, per month you can put towards a WeWork equivalent. Or we have had a lot of people do exactly what you described in the past – find a bar or a restaurant that’s closed during the day and just get access. Or we allow you to put that $250 towards if you need to buy that croissant to not get kicked out of the coffee shop, that’s kind of all included.
Remarkably, it’s not used as much as you would think. But we’re not work from home evangelists, we’re kind of like work wherever you’re going to be most effective evangelists and giving people the choice and autonomy there. So if that is a WeWork for you, awesome. And I actually love that there can be creative juxtapositions of folks working on not just different teams but different companies but interacting, grabbing lunch together and what those creative collisions can inspire.
ERICA: Absolutely. I think that the other hard part for a lot of people during the pandemic experimenting with remote work has been every day is something new. You wake up, your dog might be feeling particularly loud today and that throws a wrench in your plans, your kid might be having a particularly tough day at school, you might try to go to a coffee shop and find there’s no seats. So I think the more people are a little bit more intentional about this and figure out what they like and figure out a routine for them, the better it works.
My parents recently moved to Manhattan during the pandemic, they were the rare move in. And I have been picking a day a week to go and work from their apartment and be with them and just knowing on Sunday that I’m going to do that on a Tuesday makes me feel better than waking up and just seeing where the day takes me.
MATT: That must be really beautiful for them as well. So that’s cool you’re able to do that.
ERICA: Yeah, that’s another trend I’ve been following is the evolving of family relationships during all this. It was kind of a renaissance for families at the beginning of the pandemic with.. you had multi-generational households for the first time in a long time, at least in the U.S., and people were loving it. Grandparents were loving spending time with grandchildren even if it was just because parents didn’t want to deal with childcare during remote school.
And you had a lot of young kids obviously, recent graduates having to move back in with mom and dad rather than to start life. And some families hated it but others loved it. So there were definitely some perks there. So I think it has been a good time for families.
And I think you’ll see a lot of those boomerang folks, those people who moved away before the pandemic but then maybe moved back home to a smaller town so they could be close to their parents for childcare, you’ll see a lot of them stick around because childcare is expensive and hard. And if your mom and dad are close by and you trust them and they’re good with your kids and both parties are happy, then why move back, why not just keep working remotely from your hometown?
MATT: Yeah. One thing you’ve written about that I actually found very alarming was the difference in experience between genders, men and women, on experiencing the pandemic, wanting to return to work, remote work, etcetera. So, what’s the latest there? What have you found and what do you think that bodes for this return to normalcy that hopefully we have over the coming year or two?
ERICA: The big trend right now that people are talking about is this idea of the great resignation, upwards of 40 percent of people might leave their jobs or are considering leaving their jobs and that has been painted as such a positive story, it is an era of worker power, there’s open jobs, you can decide to go to a different job if you like a working style better or if you want to switch careers.
But the dark side of that is, like you said, a lot of women have really suffered. About a million mothers have left the workforce due to the pandemic and due to child-care burdens and it is unclear if many of them go back. There’s a remote school that’s continuing that’s keeping people at home. And a lot of times, specifically for women, I mean, we’ve seen this with maternity leave, it can be hard to reenter at the same salary or at the same level if you leave and try to go to a different job. It’s maybe hard to get back into the swing of things if you have a kid now and you can’t go to that after work drinks or those happy hours where a lot of networking and rubbing shoulders happens.
So the pandemic has made that worse. And I think if you’ll see a future in which families have realized that staying home is better for childcare and they decide only one parent is going to go back to the office and the other parent is going to pursue remote work, it’s typically going to be, in heterosexual couples, the husband going back to work and the wife staying home with the kids. And I worry about an out of sight, out of mind culture in these hybrid workplaces where typically women are staying home and they’re losing out on raises or promotions or worse.
MATT: Well that would be terrible. Definitely we don’t want a regression in that, we’ve had a lot of progress in the past century there.
ERICA: Mhm. And one more thing on this, that’s why I think one of the biggest challenges HR departments are going to have to tackle, and one of the best ways to recruit and retain is going to be beefing up your childcare benefits in the workplace, giving parents actual money to put towards childcare or giving them flexible schedules and making sure that having a kid isn’t something that you just don’t talk about anymore, it’s more front and center.
But that’s been one of the sad things about covering specifically childcare during the pandemic is I don’t have a kid but I have talked to so many colleagues and sources and they’ve said, yeah, this is just how it is, finally people are paying attention now because the numbers are so stark and people are on Zoom calls and they’re seeing what my kids are like in the background. But childcare has always been a problem, the pandemic just spotlighted it and hopefully something now will be done about it.
MATT: I think there’s also an opportunity there for companies that can be truly distributed where you don’t need to be at the after-work drinks to get ahead. And we have seen the flexibility being the key thing there.
Even a hybrid, you know, one version of hybrid is you don’t have to be in an office at all but you have to work the same hours, kind of like nine to five, standard hours in a given time zone. And I think that also loses a lot of the benefits of that true flexibility. So if you are able to design.. accomplish the same in a given week as someone who works at the office nine to five but slice and dice it however best fits your schedule, maybe that means off a bit in the morning, off a bit in the afternoon to take your kids, pick your kids up, those types of things.
But we’ve found people do that very naturally. I think this is something parents have always done, which is figure out how to make things work. But it’s.. in an office environment, I think just culturally, the social mores of leaving the office in the middle of the day, even if the company was supportive of it, would feel weird to do because people equate being in the chair or being in meetings with working.
ERICA: Right and that was such a given up until the pandemic. I really do think that a lot of these norms are breaking down. Who knows if they’ll stay that way. But it’s a good thing to see not just are we rethinking where we work from, we are also rethinking the hours we work.
One great point I saw made in The Economist by Adam Grant, who is a work psychologist at Wharton was why is it that the workday ends at five and the school day ends at three? That makes no sense. We have had this forever where parents have these two hours, three to five, where they are constantly worried – where do I put my kid, do I pay for after school? Why don’t we just have the workday end at three and start earlier if it needs to or just have a shorter workday? I think just rethinking just everything from the place to the times to the structure of teams that the pandemic has allowed us to really do is a great thing.
MATT: Yeah, it’s not often where you get the opportunity to make these experiments, go through it all at the same time. Right? Usually it’s like – I’ve heard this so many times – like, ohh that stuff works for Automattic but it would never work for my company or something like that.
But I was amazed actually at how quickly so many companies that had probably never thought they could operate without people going into the office were able to adapt in this emergency situation. And I think it’s actually something I’m just really proud of the world on is that, given a crisis, so many people really made it work.
ERICA: Yeah. We think about it in the news, like, the New York Times still came out every day. They never missed a beat and no one was in the office. So it really can be done under pressure.
MATT: What do you see around the corner? You cover so many things, you probably get hints of what’s in the future more than most. So what do you think listeners should keep in mind for what’s coming up?
ERICA: There are so many little things but the big thing is just we are just going go lead much more tech-infused lives than we did before. And we have done it in the pandemic a lot but it is because the pandemic has accelerated it. When you think about things that you didn’t think of having a tech component in the past, they will in the future.
One of my most favorite stories I’ve written most recently is the one about weddings, like I told you. So many people want to have a small, intimate wedding and they can’t because their parents or their relatives want all these people to be invited and they feel all this pressure to have the wedding that everybody else wants them to have rather than the one that they want. So now you have that intimate wedding and then everybody else gets to be a part of it for free, via Zoom. You don’t have to pay that per-plate cost.
Concerts is a huge one. Dua Lipa had five million viewers at her concert. She is the next big thing in pop. Five million viewers at her virtual concert. And not only was that a great success and it had a huge budget but just that online concert raised tickets sales for her in-person concert by 75 percent. So, not only was it a way to get her music out there but it was a way to market her in-person show, which is how artists make money, through tours and shows.
So you’ll see a lot more virtual events for people to raise the hype and get the word out there and get more people to be a part of their music without putting all of that effort into a stage and close quarters and a limited amount of tickets.
And the other side of this is think of all the charity galas where they spend almost as much money as they raised because it’s all fancy and you’ve got a big venue booked. There were a lot of charity galas during the pandemic that raised the same amount of money just over Zoom. So you’ll see a lot more of that too, you know, more of the money going towards the cause rather than towards the fancy dinner.
So, I feel like tech is going to be a part of everything we do more and more. Another big area I cover is the future of payments in stores and contactless payment was this niche thing and you saw more and more people downloading Apple Pay or getting touch-less cards because they didn’t want to.. they wanted to minimize their touch points at a store for safety. That’ll keep going. More of that Just Walk Out, Amazon Go technology. Really, the pandemic has been an accelerant for tech everywhere.
MATT: Yeah, I started to see the Just Walk Out in I think it was JFK or Newark, I forget which one. But they had it at one of those airport convenience stores. I was like, wow, I expected this from a tech company, I didn’t expect this from Hudson or whatever it is that always has those little stores.
ERICA: Right.
MATT: I guess the concert thing is also really counterintuitive to me because, as a musician and also a lover of music, there’s always been that energy of being in the room.
But now when you started saying that I also started to think about movies. I used to love going to movie theaters. I guess I still do a little bit. But that at-home experience, if you invest a little bit more in a TV and sound and then you could have your friends, your own drinks, your own food, your own comfort, you can pause it, all that sort of stuff is actually much, much nicer. And I’ve become so attached to that, I don’t feel like I’m missing that much from the slightly bigger screen or better sound.
ERICA: Right. It almost becomes two different experiences. Obviously going to the concert is a big night, it’s fun in and of itself. But Brandi Carlisle did this Christmas show where she was in her living room in the Christmas sweater and everything and live streaming into other people’s living rooms. So that’s a whole other type of experience where it’s way more intimate. The artist isn’t in this crazy cool costume on a stage, they are right there with you, it feels a lot more like I’m just in your house with you. So, fans of hers can enjoy her in that way and also go to a show and enjoy the big production of it.
MATT: I also hope that makes, you know, as a lover of people learning to make music and being participatory in music, I hope that also makes it a little more accessible, right? You see a Beyonce show and it just seems so unattainable. But you see a few folks sitting on a couch in the living room and it feels like something you and your friends can do too, which I think would maybe be a good outcome as well.
ERICA: Right, it really lowers that barrier to entry.
MATT: It makes it more accessible. Well I appreciate it that we were able to end on that note of some exciting things coming around the corner. And Erica, thank you so much. Already your coverage has been influential and I really appreciate following your work. Thank you so much for coming on the Distributed podcast.
ERICA: Thanks. Thanks so much, Matt. This was a lot of fun.
MATT: All right, have a good one. Take care. And all the listeners, we’ll see you see you next time.
End.
Distributed by Default: Matt Mullenweg on The Knowledge Project
Jun 10, 2021
“Aren’t people lonely because they don’t have their friendships at work?”
On a recent appearance of The Knowledge Project with Shane Parrish of Farnam Street, Matt Mullenweg revealed that he hears this question often, and that the answer is one of many benefits of a company built to be distributed from the start.
“If your only social network is at work, you might be lonely if you weren’t working with people physcally,” answered Matt. “But then what does that open up? It opens up the opportunity for you to choose people around you geographically to spend time with.”
The conversation evolved to the Five Levels of Autonomy (spoiler: many companies made it to Level Two during the pandemic) and how it allows teams to focus on the work. “Part of our model of distributed work also provides a fair amount of autonomy in how people get their work done,” Matt said. “I like that it creates a lot more objectivity and focus around what the actual work is.”
The episode was first published in January, but it is a great listen today as many companies that became distributed by necessity in 2020 make decisions about returning to work places.
Shane and Matt also talk about blending the cultures of different business units within a company like Automattic, the future of proprietary software, and how Open Source is like kids banding together on a playground, for the greater good of the open web.
This was the 100th episode of The Knowledge Project, whose recent guests have also included Angela Duckworth, Jim Collins and Josh Kaufman.
You can listen to the full episode on your favorite podcast platform, watch it on YouTube, and read Shane’s highlights from the conversation over at The Knowledge Project.
Episode 27: Leading with Values: Sid Sijbrandij joins Matt Mullenweg to talk about GitLab, Transparency and Growing a Distributed Company
May 21, 2021
“Every company has a poster on the wall,” says Matt Mullenweg in the latest episode of The Distributed Podcast. Matt welcomes Sid Sijbrandij, Co-founder and CEO of GitLab, another pioneering company with Open Source origins and a long-running commitment to a completely distributed workforce. Sid and Matt settle into a conversation about GitLab’s six values – which have been cut down from the original 13, and which are always visible in Sid’s video background – are reinforced in 20 ways at the fully-distributed company. GitLab, now with more than 1,300 employees, updated its values over 300 times in the last calendar year.
“They have to be reinforced,” says Sid, “and be alive in that way.”
And as for sharing just about everything publicly? “Transparency is sunlight.”
The values are part of the publicly-viewable GitLab Handbook that, with over 10,000 pages, details data both interesting and “mundane,” from compensation to how employees should interact with Hacker News. An example: “I think what’s really interesting is our engineering metrics. We pay very close to what we call the MR rate: how many merge requests did an engineer make over a month; how many did a team make over a month?” Sid shares. “If you push on that, people start making the changes that they make smaller to kind of increase that rate. The whole process becomes more efficient.”
Sid and Matt – an observer on GitLab’s board – get into the details: taking time off, leadership development programs, scheduling coffee chats that actually work, and much more. And they revisit predictions Sid made on Twitter in May, 2020, about the post-Pandemic future of distributed work. Check out the full episode above, or on your favorite podcasting platform.
The full episode transcript is below.
***
MATT MULLENWEG: Howdy everybody and welcome to the Distributed Podcast. I am your host, Matt Mullenweg. Today’s guest is a like-minded leader of a software company that is driven by its values, supports open source and happens to be distributed too. Sid Sijbrandij is the Co-Founder and CEO of GitLab, a fast-growing company and a single application for the entire DevOps (life?) cycle.
GitLab has been distributed basically from the beginning. But last May, two months into the pandemic, Sid made some predictions that we will talk about today. Even more so, Sid very often talks about the values that drive GitLab and how they experience each day as a growing company, a really rapidly growing company, actually.
So it’s rare to get to talk to someone who has been such an advocate for distributed teams as long. And also as full disclosure, I am a board observer of GitLab, so I have had an inside view to some of what y’all have been building and it has been amazing to have a seat at that table. So Sid, thank you so much for joining.
SID SIJBRANDIJ: Yeah, you’re welcome. And thanks for being at that table at GitLab.
MATT: Yeah. Talk to me. Let’s start off with just a little bit of the values that you hold as a company because I think every company has a poster on the wall – and you have one on your distributed wall – but how does it actually come into play for y’all?
SID: Yeah, I think you can tell how serious a company is about its values in two ways – how often they update the values, our values got updated over 300 times last calendar year.
MATT: Wow.
SID: So it is a living document. And then the other thing is how do they reinforce the values. We have now 20 ways to reinforce our values. So it’s not that that document doesn’t matter, it is are they really lived. And for them to be lived, they have to be alive themselves and they have to frequently be reinforced and be alive in that way.
MATT: I saw you could reinforce the values by complimenting people but you could also put a virtual background with one of the values on it as one of the 20 things?
SID: Yes. If you see my Zoom, I will always have six logos above me. And those represent our six values. And yeah, I like the complimenting as well. We have a thanks channel and in that thanks channel people thank each other and then people can comment and they frequently do that with emojis that represent our values and then we keep count of who was particularly good in expressing certain values throughout the year.
MATT: Do you tie them into performance reviews? Like, do people talk about the values as part of performance reviews?
SID: With those emojis, that is linked to our annual event and we select the people who best represent a certain value and those emojis are used to create a short list and a group of people decides who best represented it. So it’s input. It’s not ideal but it gives a good way to make a short list.
And then, yes, performance reviews, the values tie into that but also into hiring decisions. And for example, I think the most important thing is promotion documents. Every promotion document at GitLab is shared with everyone in the company and its primary structure is the values.
MATT: To put you on the spot, can you name the six values?
SID: Yes. We had 13 values before and even I couldn’t name them so that was a good reminder to rationalize. So our values spell the word credit. It’s the credit we give each other by assuming good intent. The first C stands for collaboration, the R stands for results, the E for efficiency, D for diversity, inclusion and belonging, the I stands for iteration and the T for transparency.
MATT: I guess with D you kind of expanded it. It stands for multiple words, but that works.
SID: Yeah, first it was D&I and now that we added belonging it.. I am open to changing the whole thing but I think having one letter per value is defensible.
MATT: Since you have a backronym or an acronym that spells things out does that make it harder to add values of certain letters or make it more incentivized, like certain letters to be added, like maybe it would be easy to add a value with an S but it would be hard to add a value that started with X.
SID: Yeah, Credits. Yeah. I guess there’s a certain amount of sunk cost there or inertia to overcome to change it. I think there hasn’t been a big push to add a value. We have had diversity changed to diversity and inclusion and now diversity, inclusion and belonging, that has been the major thing. Other than that, people talk about how do the values relate to each other and we have a lot of sub values.
So for example, today I am having a call with Dara and Dara said, look, some of our sub values are more important than others. So the six values I mentioned are core values but then we have sub values that are kind of.. that relate to certain examples and that make it more concrete because otherwise it’s just words and they are very open to interpretation. The sub values makes them actionable. And Dara, her very good point was some of our sub values are more important and more actionable than others so maybe we should cull some of them or maybe we should elevate some of them.
MATT: What were some of the values you got rid of or renamed? What were some of the seven that got cut out?
SID: Yeah, I forgot about them so that’s good. But I think we found some overlap. The exercise we did is we wrote down all the values we had, we wrote down some that we thought we should have and started grouping them and we came to this. And actually it wasn’t a big exercise, it was me and my CEO coach who did that one afternoon in a couple of hours. And then I proposed it and it was clearly better and that’s how that happened.
MATT: This is probably a good time to introduce the GitLab handbook. So all of these values and the 20 ways you can put them into effect and everything like that is all public on your website.
SID: Yes. I think our handbook is now over 10,000 pages and it has all of our process and procedures, like how you work. And now just the boring ISO stuff but really what you would need to know if you join our company.
MATT: What does ISO stand for?
SID: Sorry, I’m from Europe and a lot of companies follow the ISO standards for documenting process. And that left a big impression on me because those ISO handbooks were not what really happened in those companies. There was the written ISO process which you could update once a year and the other was what people really did.
So there was the paper handbook they haven’t touched in two months and there were the sticky notes on the computer how to really do things. And I was like, look, if you’re going to have something, it should be easy to change because how you work changes every day so it should be a living thing that people use every day and it gets updated every day.
MATT: So let’s say I’m an employee at GitLab and I would like to update one of the values. Could I submit.. the entire handbook is in GitLab, I could submit a merge request?
SID: For sure.
MATT: And what would happen?
SID: You don’t have to be an employee. You don’t even have to be a board observer. You can just.. anyone in the world can make a suggestion to improve them. And then if you think I should have a look at it, I suggest you at mention me on Twitter or send me a DM. But most of the time also people kind of check it out and escalate it within the company. We have a values Slack channel that will probably pay some attention to it.
MATT: To give people a sense of the scale, its 10,000 pages but these are very, very distinct. So it has onboarding. Do you still have the org chart and everything on there?
SID: Yeah for sure.
MATT: Salary. And occasionally you will run into something that links to an internal google doc that you only have access to as a GitLab employee. But there is, yeah, what I can only describe as a radical transparency that the organization practices, that’s different than I have seen really anywhere else, even other companies that really practice a ton of open source thinking.
SID: Yes. And I think what has been cool, I gave a talk at YCombinator recently and there was a bit of what would GitLab do. So if you have a question (started?) the first thing is like try to see.. Google the question with GitLab and see if it is already in our handbook. And that is probably a decent starting point. And that is just because we kind of document a lot of mundane stuff. Like, I don’t know, I’m not sure we documented trademark registrations but it would totally be something we document. So because we document so many mundane sales, marketing, engineering for processes, it’s a good starting off point if you have to make something yourself.
MATT: You know, there’s often CEO backchannels where you’ll ping another CEO and be like, so how does this work at your company or what do you do for this? And I would say that you are the one I ping. And 99.9 percent of the time it’s a link to your public handbook. I mean you don’t say Matt, let me Google that for you but [laughs] I’ve started just.. I’m probably pinging you a little less because just everything is on the website. I’m like, oh, how does GitLab do sales on boarding? I know you brought your time to productivity down quite a bit and your time to hire, some things you’ve been improving. So that’s all there, including what you’re trying to improve.
SID: Yes. And Matt, rest assured that every time I send the link I’m just very, very proud that we have written it down. It’s not dinging anybody for not looking it up. It is very counterintuitive that that is out there and that it’s big. So it’s not.. Google really helps but it’s not always easy to find something.
MATT: What is something that listeners might find surprising that you have public on the handbook?
SID: I think our compensation ranges. Its maybe not as surprising anymore but it is always something people care a lot about. I think all the mundane stuff, like how we interact with hacker news, like people in the team should probably not post GitLab articles to that, we don’t want to be perceived as astroturfing, disclose who you are. I think there’s just a whole lot of mundane things.
I think what is really interesting is our engineering metrics. So in engineering we pay very close attention to what we call the MR rate, how many merge requests did an engineer make over a month or did the team make over a month correlated to the team’s size. We found if you push on that people start making the changes that they make smaller to increase that rate, which is great because then it becomes easier to write, easier to test, easier to review and the whole process becomes more efficient.
MATT: That is interesting because developer productivity is notoriously hard to track and measure. What is the rate that you aim, an engineer at GitLab might aim for?
SID: Yes, so we are around 8.8 right now.
MATT: Merge requests per month?
SID: Yes.
MATT: Oh, so that’s.. I had expected the number.. is that where you want to be or is that where you’re at?
SID: We always want to be a little bit higher. So, like nine, ten-ish would be great but we are also in the middle of a global pandemic so we have not pushed very hard on it recently. So yeah it also differs a bit between teams and what they are assigned to. But I think it’s a great rate. And I think the awesome thing is it only counts if you actually got it all the way to the end user, people started using your code. And I think that helps to keep things small and to reinforce one of our top three values – iteration.
MATT: How fast does GitLab iterate?
SID: So I think it is very important to quickly get things out to users but I think in the end it is like how productive is an individual. So I think that 8.8 captures our productivity.
MATT: 8.8?
SID: 8.8. Sorry. 8.8 merge requests per month.
MATT: Oh, yeah, yeah. But to that question, you ship major new releases is it once a month and have for like a bajillion months?
SID: Yes. We now.. I think we get code into production after it’s merged within 12 hours, so released on GigLab.com and it’s a continuous process. We just bundle it up per month because we have a lot of self-managed users, they kind of need a version number to make it digestible and a blog post to make it digestible but it’s really a continuous release. And every month we have over 50 substantial things that we ship, at least substantial enough to mention in the release post. So I think we are extremely productive considering the whole company is about 1200 people and engineering on features is about 500 people.
MATT: You mentioned maybe working with ISO in the past. Was there anything earlier in your experience or life, personal or work, that drove you to create a company which was so ruthlessly documented and relentlessly documented and process driven but in a really, really positive and enabling way?
SID: Yes. I think a lot of GitLab values can be explained by my scar tissue. And I did a lot of things. I built recreational submarines, I was a part-time civil servant, I worked at Proctor & Gamble and IBM. I thought it was so inefficient.
If you have to ask somebody else, like, how is this done.. It’s not just inefficient for the people on-boarding but I think it is most inefficient when you have to change something. If you want to change something what you had to do is you had to build up all that context for this is what I’m talking about and then say okay, and this part we are going to change and then present that to the whole company. And then a person onboarding a month later would now have that presentation.
So, like, how does that work? It kind of works but it’s really silly. And I think one of the biggest benefits of having a handbook is that you can change something and it’s.. You don’t have to build up all the context because the context exists in all the links from the documents so everyone understands what you are talking about. And it is relatively easy to change, it’s easy to make the suggestion, anybody can do it, it is easy to discuss that suggestion. And then when that is merged, when that is pulled in, it’s clear to everyone from then on that that is effective.
MATT: By the way, this has been very influential on me as well in that I have been asking a lot, actually for a few years now, like, why can’t we make more of our stuff public? And the answer is generally just that it takes time. There’s not a real reason that anything in our internal field guide needs to be private, most of it. And so that makes me think that if you do this from the beginning it is just so much easier. So I would encourage anyone listening that is curious about this, just start publishing things as soon as possible.
What would you say to people who think it’s scary or we have things that are proprietary to our company or if our competitors know what we’re going to do they’re going to be able to out-maneuver us?
SID: I think there is a page at the bottom of our strategy page from Peter Drucker, strategy is a commodity, execution is an art. I think the really great companies, they have a super obvious strategy, they just do it better than anybody else. I think if you depend on your strategy being a secret it’s first of all very hard. Some of your people are going to quit and then talk to the competition, so it is very hard to keep it secret.
I think it is actually very hard for everyone in your organization to know your strategy. Most companies I have been with, like, people didn’t even understand the strategy, the people who worked there. So I think in general optimize for more people knowing your strategy, not fewer people knowing it. And we have found that having our roadmaps public and things like that has been a bit benefit. It has been such a big benefit that we might have inspired our competitors who are also now publishing their roadmaps.
MATT: And you are in a highly, highly competitive space.
SID: Yes. And I think a lot of the things you do are not differentiated. No one is going to buy from GitLab because our accounts reconciliation process. Like, people don’t care. But it should be efficient and the best we can do but it’s not like we lose our ability to compete if our competitor implements the same process. In general, people have a super hard time embracing even just best practices, let alone their competitors’ practices.
And I think you lose a lot and you win a lot, I think. Transparency (and sunlight?) makes you do better work. You get a bigger.. an easier ability to change. And yeah, there is a bit of hesitation that is from being afraid. I think that doesn’t make sense. I think what does make sense is that it is more work. When you want to make a change, changing it in the right context takes more work than firing off an email.
So I think while the change is more work, it is more durable. So over time you can start reaping the benefits but it’s a.. Short term it is more work and then it pays off over the long term.
MATT: And that is because, and this is my understanding, that the change isn’t actually.. it isn’t real until it’s in the handbook, right?
SID: Yes.
MATT: So we can’t say we’re going to do this for a month and then we will put it in the handbook later?
SID: Oh no. That doesn’t work. So we are very adamant about handbook first. The only way you can communicate a change is when it’s done in the handbook. And then commonly you just refer to the (dif?), like this is what changed, you link directly to it. What we cannot have is someone emailing, presenting, talking about a change that is not in the handbook.
Because if you instill in the company oh you can document it later, it’s not going to happen. Like, people have jobs to do, they will move on. So it has been one of the hardest things to enforce in the company, to work handbook first, but it prevents what happens at 99 percent of the companies where the knowledge base is very big but most of it, a lot of it, is out of date.
MATT: What is maybe underappreciated about this approach as well is that due to the fact that everything is in version control you have essentially an organizational block chain of every way the company has run and every change and who made that change and when it happened going back to when the handbook started, which.. was it at the very beginning of GitLab or a little later in its life?
SID: Yeah, no from 2015, so from when we were ten people. So I think someday hopefully if we continue growing, some organizational research is going to have a field day. Because I think we are the best documented instance of a really steep growth trajectory for a startup and how your processes changed and what’s important. And it’s all kind of.. it’s to the letter dated and everything else. You could see all the comments. I think that’s gonna be an amazing research if you’re into organizational research.
MATT: It is the code that runs the organization, which I think, like you said, super fascinating, I hope it gets studied. Is –
SID: Yes, we both have a software engineering background and I think we just moved onto a higher level language, namely English.
MATT: [laughs] It’s less deterministic for sure, I don’t know.
SID: Yes and it’s hard to trouble shoot and there’s no tests for it and there’s no indentations.. Well, the indentation standards are pretty okay but it’s much harder but it’s much more powerful.
MATT: To give a sense for the listeners who might not be familiar with GitLab, you mentioned ten people in 2015. What are some of the growth milestones since then, in terms of people? And I think some valuation has even been public in the press.
SID: Yes. So I think our craziest year was 2019 where we tripled from 800 to 1000, or something. We are now 1300 people. And the last public metric we share was a valuation of $6 billion.
MATT: That is pretty incredible because I think that.. You know, one of the criticisms, I don’t know if you heard this much in the early days of GitLab, but that distributed or remote companies or open source companies can be nice lifestyle businesses or some of these approaches work if you’re like base camp and only 50 or 60 people but it doesn’t turn into hyper scale or blitz scaling, as Reid Hoffman might say. But you did that. You went from 300 to 900 or 1000 in a 12-month-ish period. What broke that year?
SID: Actually not a lot. It was kind of hard to do recruiting at such a scale. I think we relied a lot on in-bound. So we got 15,000 applications every month and I think now that we grow a bit less fast we are better able to reach out to people who will add diversity to the company. And any time you grow faster, that’s tougher.
I think I have to thank you because WordPress was the number one example to convince investors that we’d be able to scale fast a distributed company, an all-remote company. So thank you for giving that example. I don’t think we could have convinced them otherwise.
MATT: I appreciate it.
SID: And now looking back on it I’m like how can you scale when you don’t’ have a handbook, when you have not documented things? Like, that is ridiculous. If two-thirds of the people at the end of the year are new, how do you do that? So I think having all these practices has enabled us to scale. And I think in general, all remote, you don’t have to do special things for it, you just have to do things that would be good for any company and you are forced to do them sooner.
MATT: There are stories I hear from friends that have hyper scaled around like they can’t find enough desks in the office and so they’re squeezing people into the same desk and things, which is such a quaint concept if everyone has their own office because they work wherever they’re coming from. So I wonder what might be a..
I have heard kids now don’t know what the disk icon, it represents a floppy disk so when they see a floppy disk they’re like oh, cool, you 3D printed a save icon. It’s totally lost the original metaphor. So I wonder if there’s other metaphors around work that have completely changed maybe permanently even now with the pandemic.
SID: Yes, it seems that most companies are going back to the office but I think.. I don’t know, I look back on cubicles as super outdated and I think one day we’ll look back on the open plan offices as something super outdated. Like, how could you be productive there?
MATT: How does your values impact your meetings?
SID: Transparency impacted that most meetings.. Like, my calendar.. Most meetings are shared with the rest of the company. In advance you, because of efficiency, you link a Google doc with the agenda and then the notes are taken in line and most documents are open to the entire company. [crosstalk] [00:26:33.16]
MATT: So while we’re meeting someone will be taking notes on the shared Google doc so people will have both up on the screen?
SID: Yes, multiple people will be taking notes. And if you ask questions you also commonly put them in written before and then you get to verbalize them.
MATT: Are there any external meetings? Like, let’s say the board that you also run in a similar manner?
SID: Yes. We are blessed with board members who have an open mind and I’m learning a lot about how to run better board meetings with their feedback. What they have embraced is running it from a document and that’s been super successful. They actually start putting in questions like days before and we already start answering them. So when the board meeting actually comes around a lot of things are like well that’s already answers, we can skip that. And like any board meeting, we can fill the time but it’s just they have much more opportunity to get their questions answered.
MATT: It also requires a lot of pre-work. Do you want to talk about what you expect people to do before a meeting and for board meetings and I imagine internal meetings as well?
SID: Yes. Board meetings are quite special. They require more work than any other meeting. Of course you can Google GitLab board meetings but I’ll do some of the highlights. I think one thing that we do throughout all meetings is no presentations in the meeting. It has been one of the toughest things to enforce. People really like a captive audience.
So before the board meeting I will send out a video with my overview, our go to market leaders from Sales and Marketing will send out a video where they review that. My notes kind of sound like an earnings call because we kind of.. we aspire one day to be a public company. So those videos are sent up front plus a deck plus a doc for them to ask their questions.
MATT: Do you have a sense for the scale for like how many slides, how long the documents, etcetera?
SID: I think our worst has been 140 slides, which is not good, so I think now we’re back to like 60 slides or something like that. And I think what is essential is like how do you allocate the time in the meeting. So we have three key questions or key discussion points that we state up front, this is what we like to talk about as a company.
So as a company we are going, we are thinking about this new product offering, give us feedback about the pricing, about the implementation, about the roll out, what do you foresee. As a company we are struggling with X, Y, Z, do you know people who might be able to help, what do you think about our current approach. I think board members should want to help, they give you advice, if you don’t indicate what you need help on, they will start helping you on stuff you don’t need help with, which can be a big distraction so channel all that energy into something that they can help with because they will do a great job.
And we spend most of the time on that. And then there is Q&A, in which they can ask about anything. But that has been a really big improvement. And I think that should be true for every meeting in general. In our internal meetings my policy is I want to discuss a proposal, I do not want to do brainstorming or something like that. Have a proposal and we can review it, that is a much more better spend of all of our time.
MATT: So if everyone asks the questions before and reads everything and watching everything before and you answer them before, you don’t run out of stuff to do in the meeting?
SID: No, you don’t because people build on each other. And even if you might’ve like tried to answer the question many times you still verbalize the question. So I mentioned an example of something that.. where people would say oh its already answered, we can skip it. That tends to be about trivial stuff. It’s important that we don’t skip, like, hey you asked this question and even though it’s already answered –
MATT: So they present the question?
SID: Yes, they present the question. And frequently you learn more. They will say it in a certain way, they will have more intonation, they will have enthusiasm or worry or be pensive or other things and they’ll tend to say more, like it’s easier speaking than writing so they tend to elaborate it a bit more. And then we call it reenactment. We reenact the question and answer so that the answer.. they answer people too, they reenact their answer. And then hearing all of that in the rest of the room, now suddenly, now that they have heard that, they have something to add as well. So no, we don’t run out of stuff.
MATT: It makes sense for why the sort of reenactment of the question and answer might give additional information that is not on the page. But couldn’t you make that same argument for the entire presentation?
SID: Yes. And so I think it is really good to, if you want to present, to do that. Just record it and send it to everyone upfront asynchronous and don’t want for the super expensive, synchronous time to do it.
MATT: So it’s maybe about the amount of time?
SID: I think meetings are for back and forth.
MATT: Because interrupting a presentation could be good, right? Like we are having a real time conversation so we can jump in, like I just did?
SID: Yes. I think that’s the benefit of this, right? We can go back and forth. I think interruptions are great because if I say too much or too little it’s easy to give me feedback in the moment. I think most presentations, especially remote, there’s not enough interruptions, interruptions are awkward. We just (did delay?) because it’s kind of hard to hear someone breathing in to ask a question. Maybe you can look at who is un-muting their mic but it’s much harder. So we find that in general there’s not a lot of interruptions so you might as well just do your presentation and then have people ask questions during the meeting.
MATT: A hybrid meeting makes that especially hard. I remember when I first joined I was.. I thought everyone was going to be remote. Everyone else was in the room. I think I was the only one remote and it was very, very difficult to both hear and jump in.
SID: Yes, hybrid is horrible and I’m very glad that our board meetings are now all remote.
MATT: I remember we also talked about sending people some microphones and some other things because there was some varying audio quality.
SID: Yes, we did that. Thanks for the suggestion. A lot of board members received that Sennheiser microphone you suggested.
MATT: It’s like the cheapest way to make a meeting better, if you’re going to have a couple hours together. The collective value at that time is huge, particularly because you have so much of the team there, like, might as well spend a couple hundred bucks to make it sound better.
SID: Yeah it’s a $100,000 meeting, you better make the most of it. I send a lot of people I meet with, I send them cameras and microphones kind of as a thank you for meeting or just to help them out.
MATT: To go back to transparency as a value, like, you have started broadcasting many meetings, not the board meeting but lots of others?
SID: Yes. So by default we put our meetings on GitLab unfiltered on YouTube. So most meetings can probably be public and we just live stream them from Zoom to YouTube.
MATT: The only other organization (that has a way of?) doing this is probably Mathematica, the Wolfram [00:34:40.16] stuff, (Steven?) Wolfram. But what is that like? I have watched some of these or I have tuned in to some that are happening live because YouTube will ping me.
SID: Well you have trouble sleeping because most of these meetings are very boring so I assume you watched them because you had trouble falling asleep.
MATT: Yeah ya know, I find it kind of fascinating because I’m an organizational voyeur. I am very fascinated on how different companies work and how they solve problems. And also I feel like as a duty, as someone trying to contribute to GitLab, to get to know the organization as well as possible. But also, YouTube pings me about it because you’re one of the only channels I follow that does live broadcasts basically all the time. Who watches these besides GitLab employees and has anything interesting ever come out of that?
SID: I think it has been great in finding and convincing potential team members. So I think like what you always want to know is like what is that company like on the inside. You go talk to people, you go have lunch with someone who works there and they say stuff but there is nothing like being in the meeting, that boring meeting that no one cares about on Thursday at 3PM about some boring subject where everyone is kind of bored.
Like, that’s what a company is really like. So I think it’s amazing for potential team members. People watch that and like, okay, this is a boring meeting but it’s a better boring meeting than at my old company because like they’re efficient about stuff, they are transparent with each other, they are really goal oriented. They try to make.. try to come to actions and to agreements, it’s well documented, people screen share, people try to contribute, people are positive, people assume good intent.. this is better boring than the company I’m at now. And then they apply for a job.
MATT: So all of your culture around meetings doesn’t make them more exciting?
SID: No. No. I don’t think they get more exciting, I think they get more effective.
MATT: This approach to meeting culture sounds very efficient. But how do people get to know each other better?
SID: Yes, you have to organize that too. So I think one of our biggest lessons is to be intentional around informal communication. There’s a web page we have with 20 ways to kind of stimulate informal communication. And most of it is like have a meeting but have it explicitly not be about work. And that is tough and the concept doesn’t always translate well.
I just had a meeting with a country manager of ours, an international country manager, and like we tried to signal to him hey, this is going to be a coffee chat, it’s going to be a social call, this is.. here’s how coffee chats work. And still like, I can’t imagine out of the blue you’re going to talk with the CEO, you have some backup slides about the business. And he did that, he had the slides ready but he was like, oh, this is a different meeting than I expected.
It’s a coffee chat, so it’s informal and can be a bit about work or a bit about our private life. I wanted to kind of set the tone, this was just getting to know each other better and get a feel for how he was experiencing his work and our support for what he was doing. And that’s one example, we’ve got a ton.
But I think what is most important is that you make it okay to do that because it feels really weird, it feels like somehow when you’re on Zoom it feels like you should be working and then people are not always working but they’re always not working when they are not on Zoom. And you have to make it okay, like, hey, two of us are in a call and we are not working and that is okay and we can just hang out together.
So that water cooler chat, organizing that, that has been hard. I think we’re the most effective at it, that doesn’t mean it’s perfect and we do try to augment it with in-person meetings where that’s a lot easier to do.
MATT: Yes. So if I were to try to be more social in a more goal driven meeting would that get shut down or do you have some space for people to goof off a little?
SID: Yes, I think it’s appreciated when the meeting hasn’t started yet. So people at GitLab tend to come early to meetings. So in the first few minutes you joke around a bit. I had an interaction like that today in a meeting where I joined a few minutes early and we had some banter but then we tend to start on the dot, so on the top or the bottom of the hour.
MATT: Literally on the dot almost to the second, correct?
SID: Yes.
MATT: Tell me about your personal thoughts on timeliness. Does this translate into your personal life as well as professional and how have you gotten the whole culture – because you have people from dozens of countries – to make this important?
SID: Yes, I think we set the standard, like, hey you start on time, you don’t wait for people to arrive. So if you say in a meeting we have quorum or everyone is here and so we start, I will remind you, no, we’re starting because it’s time. And everyone is here because we start on time and we don’t wait for them. And then also very important, you end on time.
And we do speeding meetings at GitLab, which is a settings in Google Calendar that means 25 or 50 minutes, not 30 or 60. So you have some time in between the meetings to do whatever you want to do.
MATT: And for you, how important are meetings to how you do work? Like, how much of your week is meetings?
SID: Most of my week is meetings. I think if you radiate a lot of information it’s a very efficient way to work. For me also, it’s.. because its interactive, it’s easy to ask for a little more or a little less information and to speed things up. So I think there’s a bit of a burden on the other side but I’m.. because I tend to be on the busy side I optimize for my own time. And I think also as the company progressed, I get more and more interrupt driven where I just have to respond to things so I set up the mechanisms that force me to.. that send out pings where I just have to respond to it.
MATT: In terms of other unusual things, that probably hits transparency as well. You have a shadow program. Could you talk a little bit about that? And is it just for you or is it also other roles in the company?
SID: Yes, it’s called a CEO Shadow Program and it’s two people who go to most of my meetings. And the idea is we are a functional organization, as a CEO I’m the level at which all those parts come together. So it is an opportunity for them to look across, see more than just their own function and see all those other functions.
So its two weeks, it’s an opportunity to learn and get a broad perspective. They also have to work. They take a lot of notes during meetings and they sometimes get assigned small changes to the handbook that come up during the meeting. I think it’s a great opportunity. Look at the bottom of the CEO Shadow page, you’ll find videos from alumni and how they experienced the program. And hopefully it is a way to create that next level of leadership at GitLab.
MATT: How has it evolved over time? It used to be one person, now it’s two?
SID: It used to be three weeks. So I was inspired.. First of all, it was trigged by when I was recruiting for a chief of staff and they said well it’s great because for the chief of staff you have one person a year that kind of.. you graduate one person a year that knows the entire organization. And I was like, wow, that’s not fast enough. [laughter]
So I’m like how about three weeks? See one, do one, teach one, which is kind of a medical thing. And then they were, well, the see one made a ton of sense, to learn from the old person, the teach one makes a ton of sense but to do one is kid of.. well, when you see one, you can do one. So we cut out the middle week also to make it more approachable for people who couldn’t be away from their family when it was still in person.
Now luckily [00:43:44.13] like I have a lot of external meetings and those used to be in-person but I think that even after the pandemic a lot of those can keep happening online so we might keep the program remote to keep it more accessible from other places.
MATT: Yes, I recall when I was a board member you even were like hey can this shadow join this meeting. And for some of them it made sense and for some I think we were going to discuss something private and so I was like well maybe not this one.
SID: Yes, so they attend board meetings and things like that.
MATT: How do people respond to it?
SID: Well people never tell you the negative stuff so maybe some people are weirded out. But in general it gets a really positive reception and I think it drives home that we are a really transparent company. You have to be pretty transparent and have a high bar for sharing.. or not a high bar but be comfortable with sharing things to even have such a program. So I think in the meeting with external parties they exemplify our values.
MATT: I think a common question people would have – oh well we could do that but what if something private comes up? So what do you do both for the shadows if something private comes up, or sensitive, and for these broadcast things?
SID: You say bye shadows. And I say it a lot. I think I said it three times yesterday. But we tend to.. It happens mostly during one-on-ones where we have to discuss performance of one of the reports of the.. my reports.
MATT: So your one-on-ones are really three-on-ones.
SID: Yeah, they’re one-on-ones but with two shadows in the room. But what we tend to do is we put it on the agenda, so there’s confidential subject, and then at the end we, depending on how many there are, we take five or ten minutes without the shadows.
MATT: How about for any of these live broadcast meetings? Does ever anything come up that you need to take down later or you turn off the broadcast, maybe dealing with a specific customer issue or things you want to keep confidential?
SID: Yes, that happens as well. So we just had our product key meeting, live streamed publicly to YouTube and there was a question about CI abuse and we don’t want to have the.. the people who abuse our CI, I mean it’s.. to have them be aware of how we are trying to counteract that. It’s kind of a cat and mouse game. So there was one question about that that gets placed at the bottom in between the.. I’ll take it offline now. So we say oh, there’s now.. There were I think eight public questions and now we took it off air and we have one private question.
MATT: You’ve been remote distributed almost since you started, right?
SID: Yes.
MATT: How has the pandemic changed.. how are these ways of people connecting, how is it working? Would you say it’s 50 percent as good as when you used to do meetups or 80 percent? And how did you think about.. let’s say pretend the world is fully healed and vaccinated and safe, what do you want to get back to in terms of in-person?
SID: I think meeting with external organizations has gotten so much better, just that everyone can get on Zoom and like audio and video quality and internet quality is so much better. And we really are looking forward to the world opening up again, obviously these people are vaccinated and safe and we won’t be suffering from this pandemic and people don’t have to fear for their loved ones and kids can go to school as they should be.
But as a company we are looking forward to doing local meetups. We used to have, or we still have but it’s in active, a travel stipend where you can visit other team members. But most of all we have a yearly get-together and this year we are hoping to have that in the September time frame and I think we’ll be able to make it with more than half of the team. So super looking forward to that.
MATT: Applause for that. We actually decided to not do the grand meetup this year, our equivalent of this annual get-together just because it’s still unrolling so differently across 80 countries that we are in. And you’re probably in a similar.. Actually how many countries are you in, do you know?
SID: 67
MATT: 67, yeah.
SID: So it has been a topic of conversation. It is clear right now that not everyone will be able to make it, not everywhere there will be vaccines. The majority of our team members are in America and Europe. America is looking like a lot of people will be vaccinated and Europe is also looking like September will be.. there will be a lot of vaccinations. But it’s a daily topic of conversation and it’s not a clear-cut decision at all.
We do think it’s super important for us to have the event. Past events have been really a boost in moral. So we’re going to keep monitoring it but for now it’s on.
MATT: It’s kind of the beautiful paradox of distributed organizations is that being distributed most of the time is fantastic but then that makes getting in person that much more fun and that much more exciting.
SID: Yes, it makes it more exciting and also I think it allows you to do something extra special. Like we do a week. We commonly go to a destination that’s interesting. So I think you are able make a little bit more of it.
MATT: How do you try to incorporate customers into these?
SID: Yeah, we did that. What tended to happen is that if they are at the actual event they are the.. team members are no longer there for themselves but for the customers, which makes sense, right? Customers are super important to us. But it didn’t really work. I think what might work is have the team event and then tag on a few days where there’s customers but don’t make that part of your team event.
I think it was different for contributors, for contributors to GitLab, having them as part of the main event. That felt much more natural and that’s what we keep doing – the core team members commonly are invited.
MATT: So at your company meetups you’ll have people attending who aren’t part of the company?
SID: Yes. We also once had a journalist attending. I think that was tricker.
MATT: Hmm. Yes, the one I remember going to, I think it was in New Orleans and it was interesting. There were customers there, there was all sorts of different folks. A lot of companies say customers first. And I believe you explicitly don’t so what is first at GitLab?
SID: I think results first. So, whatever gets you to the results.
MATT: I think I read friends and family.
SID: Oh yes, friends and family first, yes, thank you. That was a lay-up and I totally missed it.
MATT: No it’s no worries. I was just reading the handbook.
SID: And that’s not.. Look, I don’t think that there is an easy.. is it your contributors, is it your suppliers, is it your team members or is it your customers. I think picking between that is like who is your favorite child. It depends. I don’t think there is a clear-cut answer.
MATT: It depends on the day who your favorite child is.
SID: No you’re not going to pick a favorite. And it depends on the question of what you’re going to do and it shouldn’t be based on favoritism. I think it’s not about customers versus team members, it’s about work versus your life outside of work and family and friends is a way to represent that. And there we have a clear opinion – family and friends come first and work comes second.
And I think if you ask anybody in your friend group, like, what’s more important to you, work or family and friends? Everyone’s like, well, family and friends, obviously. And there’s a lot of companies which kind of pretend that work is the most important thing in your life and I never quite got that, that doesn’t make sense to me, I think it’s disingenuous and it forces everyone to pretend something.
And I think by saying that explicitly it opens up the possibility for people to say hey when something important is happening with my family or my friends, I’m going to take time off work to pay attention to that or I’m going to move.. I’m not going to be in this meeting because.. And I think that flexibility is a great benefit to people.
It doesn’t mean that at GitLab we don’t work hard or we don’t care about the result. I think on average we are very ambitious and put work.. work is really important to most people at GitLab. But yeah, we can just be.. We don’t have to pretend to like it more than our family and friends.
MATT: And have you been doing family and friend day, like days off for the whole company, essentially? And how did that start and how is it going?
SID: Yes. During the pandemic we saw productivity inch up. We saw the (MI?) rate inch up, especially in the beginning. We’re like, what’s happening? It didn’t make sense. People had kids at school, were distracted.. But people were super bored so they just started filling that time with work. We were like, hey, this is probably not a sustainable thing and we want to prevent burnout and we want to.. We don’t think this is the right thing.
And to set as a company a direction, kind of indicate what we thought about it, we said hey, we’re going to take some Fridays and we’re going to treat them as holidays. So treat them as a holiday, everyone is off. You can tell people to take time off but if you are the only one taking time off then your inbox fills up with stuff that you have to take care of. It’s harder to do unless it’s.. it’s easier to do when it’s coordinated.
MATT: One of my favorite things about the GitLab handbook is that there’s also the FAQs. So often you will hear about a policy, like Google’s 20 percent time or something like that, and you’re like, okay, how does that work? And for you, you can actually look at the day for Family and Friends Day and it has the questions, like, well what if I need to work because I’m on call or something like that? And it’s like, well it’s very common sense. It’s like, talk to your manager, take the next business day if you can, all these sorts of things.
SID: Yes.
MATT: I’m glad that’s been going well. Do you do anything else on Fridays that’s different from other companies?
SID: Oh yeah, no meeting Fridays. So we have now made that permanent. They were a big success. They were called Focus Fridays and we try to not schedule Zoom meetings. I think for a lot of people it’s nice to have uninterrupted time where you can work on something without having a meeting in between and Focus Fridays helps us to organize that.
MATT: I know other people do this on Wednesday’s and things because they worry if they do it on Fridays everyone just, I don’t know, takes the day off or.. How did you end up with Friday?
SID: Yeah, I think it enables people to take the day off if they think that’s better.
MATT: Cool. I know there’s some people who research organizational design and things like that. I really hope that more people study GitLab, one because you are open to it, literally they wouldn’t even need your permission, so much is open. But two, I think one of the challenges in even talking to relatively new GitLab-ers is that they internalize your culture so quickly that it becomes almost like water to a fish. They don’t realize it’s there. There’s really quite a bit that’s like very unique and unusual and arguably controversial at other companies in the way that you do things.
SID: Yeah, thanks for that. And we’re seeing that with the people who come back. So often people who leave GitLab they leave because there’s a lot more options now, right? The only way to work for an up and coming start up when they joined was – in their area – was GitLab. And now there’s like a thousand options because everyone is hiring remote.
So they make a move and then they are like wow, this company, they do work remote but they do it so much worse. And some of them bring the GitLab practices to their new companies, so that is very cool, and some of them return to GitLab. I think, yes, especially for people for whom GitLab was their first remote job they assume that remote means the GitLab practices but it can be very different.
MATT: Our name for that internally is boomerang.
SID: Yes.
MATT: People will go.. And actually I really appreciate it. It’s never great to lose a colleague you enjoy working with but many of folks who’ve returned have brought in some perspective and there is nothing that recreates actually working someplace else. They’ll say like okay this worked, this doesn’t, this is what I know about Automattic now that I’ve been outside of it for a few years and been successful someplace else. And so I really find that a valuable, valuable input.
SID: Yeah, me too. And I think.. we say you’re the CEO of your own career, so it makes total sense to interview externally even if you’re not looking. And a lot of GitLab people get approached by companies because those companies know that GitLab team members have a lot of great remote work practices. So great if they end up advancing their careers because they spent time at GitLab.
MATT: We have started seeing the same thing, especially in 2021, where a bunch of companies are like, oh no, how do we do this distributed thing better? We’ve been doing it for a while and we want to get good at it.
You know, I’m curious, you mentioned in-person being warmer, building trust.. And I see how this kind of more scheduled, social or non-work time can work internally because you can kind of force people to do it and it feels weird but then once they do it I imagine it feels better, right?
SID: Yes, exactly.
MATT: It’s [00:58:23.20]. But for customers, I feel like there’s almost a prisoner’s dilemma where no one is meeting with the client in person now but in let’s say a few months some sales person, and you’re a very sales driven organization, is going to get on a plane from a competitor and if you lose a deal because of that then it’s going to start almost like the dominos falling of everyone feeling like they need to do that for the client to take it seriously or to build a deeper relationship. It’s not just signaling, it can be actually true deepness of understanding the customer problem.
SID: Yes, I totally agree. Those organized, informal communication is.. it has to be kind of sponsored by the company, like the company has to tell you about it, give the name, make it okay, help with scheduling and it is hard to do that with external parties. And so we still have an exception process now where sales people have to request meeting customers because of Covid but it’s certainly ramping up and I think that’s.. the in-person for external especially customer meetings is going to come back.
MATT: What have you seen be effective for deepening relationships? Because you’ve grown a lot in the past year when you haven’t been meeting people. For deepening relationships and building that kind of sales-driven trust and understanding when you can’t get together in person.
SID: Yes. I think that there has been a big shift in that customers are now much more okay with taking Zoom meetings. I think I have not seen kind of informal communication during the meeting. There’s no banter or stuff like that in the meeting. It’s interesting, yeah. I think we have not been able to do that. I think I have personally done a lot more gift-sending, which is like you figure out during a call something that might be relevant to the person and you send it because that’s a thing we can still do with Covid. Other than that I don’t have any great suggestions.
MATT: Well good to keep in mind. I know you’ll share it when you do figure it out.
SID: For sure, yeah. That’s a great question.
MATT: Explicitly remote is not a value even though you’re one of the most famous remote or distributed companies. Why not?
SID: I think remote is a work practice that we have. I don’t think it should be a value. Making it a value feels like a cart before the horse. Values are deeper principles and I think it makes total sense if you are transparent and you want to be effective and you want to have a diverse organization to be remote, like it’s an outcome of that. I think making it a value feels strange.
MATT: So it is derived from these deeper values. You’re like, well if you want to do this you can end up with distributed. But if there were a scenario where an office made sense for being more inclusive, more transparent, etcetera, you’d do that?
SID: Yeah. I don’t know, one time I argued hey, should we have an office at a beach in Mexico for people to just hang out, like you can work but you can still hang out in a nice atmosphere. And then people pushed me on oh what’s the first iteration? Well, I have a house in Netherlands that I hardly use so people can just go there and see whether people like that.
And then we did that and what didn’t end up happening was like I said hey, this week it’s co-working week at my place without me there, do people want to join? And people were like, well I’m not gonna go with other people. And I said okay well it’s no longer co-working week but you can just go to my place. And then that was amazingly popular. So to this day we have the CEO house where you can just.. as long as it’s available you can stay in my house for free.
So that works but all getting together didn’t quite work. Maybe we should buy a small village of houses but that’s expensive.
MATT: Are you still looking at that? Is there going to be a GitLab village somewhere?
SID: No. I have given up on that. Given up.. it’s not a priority. Maybe some of our team members hear this and are like a village of houses in Mexico? It sounds interesting. So we’ll see.
MATT: I have also fantasized about something like that because it would be really fun to see colleagues more in a fun setting. And I know some companies have tried it. It just gets a little tricky.
One thing that I would say that distributed companies don’t develop a strong muscle for is facilities management and managing a physical space, especially a high volume one or especially one that people actually live in maybe with family and kids, etcetera, is a lot of overhead and you start to get into something more like running a hotel than changing dev ops works in the world or democratizing publishing. And so like it goes outside some core competencies. And at that point there’s lots of places you can pay to do that.
SID: Yeah. I think if you go hey, you’re basically running a hotel, I totally agree, and that come with a lot of things, like you are responsible for making sure it’s a great environment and there’s not any HR violations and that there’s security people and things like that. So if you do a hotel you might as well bring the whole company together on the same week because it’s kind of nice to have a bigger group there. So you have a yearly event like we are having now instead of a much smaller group somewhere for a year.
MATT: What I tried to do a few years ago was take the grand meetup, which was the whole company, and split it up. Because I enjoyed the smaller ones when we were hundreds of people as opposed to more over 1,000. And Automattic is organized as almost essentially separate companies internally so I thought it would make sense to split it up. But people pushed back so much that I kind of surrendered to that idea. I even announced on stage this is our last grand meetup. And we just kept doing it. Obviously it stopped last year, but..
It is amazing how much people enjoy getting together and how much value that week comes. It is also stressful as well. You’re not around people for a while, I imagine this will be especially acute on the first one. So it can be tiring to be surrounded by people constantly.
But you can iterate your way into better versions of that too. Like, we often do kind of a quiet zone. So it’ll be a little area that’s marked off where you can go in here to just have no one talk to you. [laughs] So that’s kind of a I just want to reset and recharge zone. And hotels are actually really nice because then people each have their own room and they can go back and recharge and have their own private space, which gets tricker in shared houses or Air B&Bs or things that aren’t hotels essentially.
SID: I totally agree. It can get very overwhelming. We make a ton of things optional and we are super lenient if people want to leave early or things like that. It can be overwhelming and it’s not for everyone. I do think that there’s something to like having most of the company in one location. And yeah, maybe someday that is – I don’t know – a stadium or something like that. And yeah it will be very different. Yeah, you don’t get to talk to everyone and it’s a different vibe but it’s.. it’s different but not necessarily worse.
MATT: People still go to conferences that are thousands or tens of thousands of people and they get value out of it.
SID: Yes.
MATT: It’s just different from meeting every single other person. Internally it comes up where people say I feel like part of the reason this team is having friction is because we haven’t had a meetup in a while. And I try to push back on that because there’s lots of reasons why someone couldn’t make a meetup and we want to make sure we develop the ability to have a team be super cohesive and aligned and everything regardless of whether they’re getting together in person or not.
But I do personally miss it and I think there is a real desire to return to seeing people in person, which brings us a little bit to your Twitter thread. You wrote this last May. Do you want to recap or could you recap a little bit of these predictions you made in May of 2020, so about two months into the pandemic?
SID: Oh wow. Is this the one that’s pinned on my Twitter profile?
MATT: It is pinned, yes.
SID: And it starts with [01:07:22.09].
MATT: It’s still pinned a year later so I thought it would be interesting to return to it.
SID: A year later, well it’s the only successful thing I have ever done on Twitter with 1,000 retweets. So let’s see. I haven’t looked at it for a while. Yeah, no, I’ll.. the first point is remote work will be allowed at Twitter, Square, Facebook and Shopify. Great. And that’s.. many of them are going to continue.
Many companies are learning that their workers are just as or even more productive working from home. And I think that is true as far as I’ve heard of other people but my sources might be a bit biased. But a lot of companies actually got more effective, like more work got done, it’s just that people said they were unhappy and I attribute that to not having enough informal communication.
And I kind of acknowledge here that I thought it took all these practices to do remote work right and it turns out without [01:08:20.03] practices you could still do remote work and it still was better than in-office work. So co-located work was even less useful than I thought.
I think this is important. Somehow the lesson that companies deduced from this isn’t that they should go all remote – but this works really well – but that they should go hybrid, combining remote and collocated work. I think that hybrid is much harder and less likely to be successful and I am still of that opinion. So that’s going to play out over the next couple of years.
Also these companies are going hybrid for the wrong reasons. Social bond building, culture, creativity, white boarding and brainstorming needs to happen at the office. I totally disagree. You can do those things but you have to organize it just like you have to do facilities management. Like it doesn’t happen automatically. Put some effort into it. I have a list of 17 reasons why Google Docs is better than white boarding. With the social bond building you gotta organize informal communication.
MATT: It sounds like you agree with a lot of this still.
SID: Yes. Where do you think it went sideways?
MATT: Well there’s a few things there. Is some ways, we are hybrid organizations in that we, in non-pandemic times, tell people we’re going to get together for a few weeks out of the year, which technically is a hybrid. Right? It’s not fully you’re never going to see your employees.
SID: I think the hybrid I’m rallying against is not that sometimes you bring everyone together or you have local meet ups. The hybrid I’m rallying against is that some people are never remote and some people are never at the office. And I think that is going to create A teams and B teams where the people have an information and a visibility advantage.
MATT: Especially if things aren’t documented or transparent. Kind of like we described meetings earlier, a meeting where some people are in person and some people aren’t is kind of the worst type of meeting, no matter how good the conference room system is.
SID: Exactly.
MATT: I think what people over weight is they look back at the office.. Well, one, they really want to see people again, just in general. They look at rose colored glasses of the best things that could possibly happen in an office versus what actually happens in an office 99 percent to the time. and I think they over weight office and underweight commute.
And if you look at something that actually the meet-up version of hybrid does is we kind of amortize a really big commute, probably flying across the world a couple times of year and then you stay there at that place, versus the everyday driving 15 to 60 minutes each way to get to an office, or commuting, I think can be.. is actually the hardest thing on people. It’s more about the commute than actually the office environment.
SID: Yes, I totally agree. I bet that most people commute longer than that they have super valuable informal communication at the office. Like how much water cooler talk are you going to do? For most people it’s less than an hour and their commute both ways is probably more than an hour. And it doesn’t mean like don’t do water cooler talk anymore and don’t do the commute, like, skip the commute and just organize that water cooler talk.
MATT: And like you said, it can feel awkward at first but then gets better. Y’all use the donut. I think Automattic uses this too, a donut pairing bot, right?
SID: Yes, ‘do not be strangers,’ a great plugin for Slack that for people who want to kind of introduces them to one new team member every week at random and you set up a call together. I think it’s a bit weird but you just send a calendar invite to someone for a coffee chat. And I think it really helps if the company names the concept – this is a coffee chat, informal, you don’t have to prep anything – and then also introduces new team members to it. If you join GitLab you have to do 12 coffee chats.
MATT: Wow. There is also something to the.. like you do these as well. You lead by example in all this.
SID: Yes. I had a coffee chat yesterday. And I encourage people to schedule them. I think it’s really important to lead by example. Another big thing has been taking time off. I like my time off. I have an argument to do even more of it because I have to be a leader and then I try to be really visible and talk about it a lot. Vacation and time off is not something that you have to be ashamed of (or hide?), it should be a point of pride that you’re taking care of yourself.
MATT: That’s something I need to get better at. I think pre-pandemic I was better at taking time off and talking about it and then post-pandemic I’ve been a lot worse.
SID: Two weeks ago I took half the week off. I just took on from noon and went biking for a week.
MATT: Oh cool. In some ways I love thinking about how the distributed intentional version of this can be even better than in-person. I have definitely seen and experienced where in-person social pairings can kind of by default fall into cliques and not even maliciously but folks who you maybe know better and are more comfortable with. But when you are randomly paired by a bot it breaks up all the cliques because everyone is being randomly paired with everyone else.
SID: Yes. And I think for example if you’re remote it’s easy to do a quiz about like guess whose team member does this or that. It’s kind of interesting. It gives you something to talk about. It’s like there’s a reason there’s pop quizzes. I think they are pretty easy to organize when you are remote and it’s easy to screen share and everyone is online anyway.
It’s also super fun to hang out in person. It’s not a.. we are not trying to find a substitute for that. We are trying to find a substitute for some of the informal communication.
MATT: People underweight screen sharing too. I find myself often screen sharing some Google photos or something like that, like you might take out your phone and show someone something. It’s a nice way to jump in and out of things.
SID: I think if you look at like per-hour how many times is this screen share button pressed, I bet that is a great indicator of how remote proficient an organization is.
MATT: Wow. That is probably a good place to end. Sid, where can people check out more about you and GitLab?
SID: Yeah, if you type ‘GitLab about’ you’ll find a good starting point, or GitLab handbook if you want to dive into those 10,000 pages immediately.
MATT: What is your handle on Twitter?
SID: @sytses
MATT: And more than most interviews I would encourage listeners to really dive into these (resources?). It’s almost like a Wikipedia of GitLab, which also happens to be a Wikipedia for some of the best practices in the world for how to run a distributed organization, I truly believe that. And I find myself referring to it often. And thank you for doing that.
It didn’t start as the easy path. Maybe it’s easy now to keep doing it but when you started it was probably not easy to convince the world, the investors, everyone else that you should publish every single thing about the internals of your company.
SID: It was funny in the beginning. I tweeted out our OKRs and one of our investors said I almost had a heart attack, suddenly seeing oh my goodness you publish your OKRs, you shouldn’t do that. No, like, we’ve been doing that for years, it’s fine. But it’s certainly gotten easier and I am really grateful for you clearing that path and I think there’s now a whole bunch of companies following in WordPress, in their footsteps.
MATT: The lane is getting wider. I think GitLab opened it quite a bit and now both distributed and open source and open core I think is getting more and more common.
As an exercise for the reader, I would encourage folks to check out.. there’s a lot of published read-mes about .gitlab, which are basically like developer documentation but for people and including a CEO one that talks about Sid’s… Well, describe it really quickly.
SID: Yeah, if you Google GitLab CEO you’ll probably end up on my handbook page and I just try to define my interface, how do you interact, how do you get a meeting…but also like what are my flaws, what are things that I frequently do wrong and how to be aware of that, how to… if you wonder how to tell me, how to point me at those things to correct them. It used to have my favorite restaurants. It makes.. the whole goal is to make someone more approachable.
I think with remote you have sometimes less of an opportunity to be an observer. So we do a lot of practices to make that easier – CEO Shadows, the live streaming of videos are examples but we also try to give a read-me, like this is how I tend to work, this is what I care about, this is how I am best.. here’s how to enable me in processing information quickly.
MATT: I think one of the best compliments I could give GitLab is it’s a very self-aware organization. Thank you for leading by example and thank you for joining.
You have been listening to the Distributed Podcast with Sid Sijbrandij of GitLab and Matt Mullenweg. Have a great day. See you next time.
End.
Hiring For Distributed Companies & Angel Investing: This Week in Startups with Jason Calacanis
May 11, 2021
The angel investing-themed episode opens with both investors sharing their approaches to early-stage companies, supporting entrepreneurs, and making an ecosystem-building impact, on top of return-on-investment.
The conversation soon shifts toward the outlook for distributed work. “What do you think the world’s going to look like in six months when everybody’s got their shots and is back to work, in at least the United States and Europe?” Jason asks. Matt shares a hiring insight for distributed, global companies, from the changing perspective of a talented individual who can now work from many more places: “You can really build a robust social network with folks you choose to connect with…(anything) that gives you that sense of community, not just where you happen to work.”
Matt’s latest appearance on the show – he first appeared on Episode 26 in 2010, according to Jason, and again in 2013 – touches on Automattic’s business structure, using collaboration tools like P2 to onboard new employees, cryptocurrency, and the value of editors. “I haven’t met a single writer – or any of my own writing – that hasn’t been vastly improved by really great editing,” says Matt. “Engaging your ideas with another human just improves them every single time.”
500-page bound merger agreements, office printers, and libraries lined with law books. Legal work looks a lot different now that most in-house counsel (and law firms for that matter) have adopted some form of distributed work.
But that doesn’t mean the work itself has changed. Contracts still need to be written and signed, litigation still needs to happen, and employment law might be more important than ever. What’s become clear over a year into a global pandemic is that legal work can be even more effective without the office. To make it happen, however, lawyers need to adapt their communication mediums and technology in a way that fits company culture and mission.
Automattic’s General Counsel, Paul Sieminski, recently joined the Technically Legal podcast to talk about how legal work can thrive in a fully distributed company. “It’s aimed at a legal audience, and I love to remind my fellow layers how much value we can add to a distributed organization,” said Paul of his appearance on the podcast. “We are trained to communicate clearly, and especially to write cogently and persuasively. These are invaluable skills in any environment, but especially in an environment where writing is paramount…like a distributed company.” Paul has written on the topic in other places, such as Modern Counsel. He talks about communication starting just after the 23:00 mark with host Chad Main. For that discussion, and legal topics spanning the advantages of creating a searchable document database, to what tools and protocols we use to communicate transparently while protecting confidentiality, you can learn more about legal work in the distributed model by listening to the full episode here.
Growing as a Leader: Matt Mullenweg on the Starting Greatness Podcast with Mike Maples Jr.
Apr 20, 2021
“Was there a palpable time when you felt like…you had to have a new kind of thought as you got bigger?” asks Mike Maples Jr., host of the Starting Greatness podcast in an April conversation with Automattic founder and CEO Matt Mullenweg.
Matt shares several such pivotal moments in an episode full of stories and insight from the growth of Automattic, and of his own journey and leadership evolution.
“For better or worse, you become close personal friends with everyone because you’re kind of in the trenches,” Matt said, sharing a story about when the company almost accepted an acquisition offer at a time of friction among the small, but growing, Automattic team. “So when you fight, it kind of feels like you’re fighting with your partner, your significant other.”
Matt reflects on a journey from his Palm Pilot user group to first meeting Jeffrey Zeldman of A List Apart (and now a Principal Designer at Automattic), and later his first visit to San Francisco, all before committing full-time to WordPress and Automattic. Mike and Matt also touch on the difference between a learn-it-all and a know-it-all, and even some books that have been influential along the way.
Maples, partner in venture capital firm Floodgate, has also hosted Annie Duke, Mark Cuban, Tim Ferriss and David Sacks in the second season of Starting Greatness, a podcast dedicated to startup founders who want to go from “nothing to awesome, super fast.” You can listen to the full Starting Greatness episode, and all others, right here.
Episode 26: Jack Dorsey and Matt Mullenweg on Remote Collaboration, Finding Serendipity, and the Art of Deliberate Work
Dec 16, 2020
Join us for the latest episode of Distributed, as Matt Mullenweg interviews Jack Dorsey, co-founder and CEO of Twitter and Square. They discuss how both companies have embraced remote collaboration, the underrated value of deliberate work, and how questioning preconceived models from the get-go can change everything.
This spring, Jack Dorsey told Twitter and Square employees they could work from home forever if they choose. But a year earlier –– before the global pandemic happened –– he had already started working from home two days a week. There wasn’t the noise or the distraction. It was a place and a time where he felt more freedom and creativity.
Now, he reflects on how his way of working has evolved alongside Twitter and Square over the past year. From leading thousands of employees as a self-described introvert, to why he planned (and still does) to work from Africa for an extended period (spoiler: largely, to support entrepreneurs on the continent), Matt and Jack share ideas for combining the deliberate, thoughtful pace of asynchronous work with the serendipity that occurs in the office.
“If we can run the company without missing a beat,” says Dorsey of planning to work in Africa, “it really opens the door for a lot, especially our ability to hire anywhere as well.”
Tune in to learn how meetings work at fully distributed Twitter and Square, what open source and the punk scene have in common, why bringing thoughtfulness into collaboration is more important than ever, and if Jack Dorsey ever wants to go back to the old board meetings. Plus a whole lot more.
The full episode transcript is below. Thanks to Sriram Krishnan for help preparing for this episode.
***
MATT MULLENWEG: Howdy, everyone and welcome to the Distributed podcast. Today’s guest does not need much in the way of introduction. He is the co-founder and CEO of Twitter and also the Founder and CEO of Square. In addition to creating three iconic products, Twitter, Square and Cash App, he has been a philanthropist and a world traveler. And what we’re going to focus on today is he has recently issued an invitation to all Twitter and Square employees to work from home forever if they want. So everyone please welcome Jack Dorsey. Jack, thank you so much for being here.
JACK DORSEY: Thanks for having me and making the time.
MATT: Now I know that you like to live your life intentionally and I’m curious about the intentions that you have set currently for those three things we talked about, those three iconic products – Twitter, Square and Cash App.
JACK: For Twitter, our intention is to serve the public conversation. It is our purpose and we believe global public conversation is just so important in that it elevates and amplifies some of the common problems we are all facing as a global community. Never has it been more true and a better manifestation than what we’ve seen with Covid and how the world was focused on one thing at the same time, which was pretty incredible to think about. And I think we’ll have a lot more of those.
So, having a place for global public conversation that is valuable and is not just built around and encouraging more people to spend time with it but actually you can walk away from it and you learn something is ultimately the intention to learn from it, not be distracted by it.
With Square, we have two ecosystems. And I call them ecosystems because they are this suite of tools that I think positively reinforce one another. And one is focused on sellers and the other is focused on individuals. So the little white reader was our beginning and it was a very simple tool to empower people into the economy, which was the company’s broader purpose, economic empowerment.
And it has grown into a series of tools that not just help you take a credit card but actually understand your business or understand your customers and all of the goal of helping you grow if you make informed decisions about the data you have around you. So that business has done very well and we have helped sellers around the world, mainly offline sellers, physical sellers.
And then Cash App, its intention – and this is broader for Square as well – is we see more and more people who don’t have a need for a traditional bank and being able to go to the app store, download something that you can store your money in, that you get a Visa card to spend that money around, you can go to an ATM and get actual paper cash or you can do things you couldn’t do at a traditional bank branch, like buy bitcoin or buy stocks, or fractions of stocks – if you can’t afford one share of a company that you love, you can buy five dollar’s worth of it.
And all these things ultimately lead to empowering people into the economy in a way they didn’t have access to in the past. Like the stock thing is a great example. There’s a lot of people that love Disney, a lot of people can’t afford one share of Disney. But I can spend five bucks on it and I can see that five bucks grow over time. And if I don’t like the stock market, the crazy weirdness that is Bit Coin has had similar performance or greater performance.
So that’s the intention for both, one, empowering public conversation because we just believe it’s so important to understanding our common problems that we’re facing, which we think there’ll be a lot more. And then Square and Cash App have an economic empowerment, just simple tools to empower people into the economy around them, which is very conversational and has a lot of parallels between the two.
MATT: You mentioned the fractional thing. I’m surprised by how many people tell me they can’t afford to buy Bitcoin. I’m like, you don’t need to.
JACK: Exactly. Yeah.
MATT: You can get one Satoshi worth and…
JACK: Yeah, exactly.
MATT: Related, what’s your intention for coming on this podcast about distributed work?
JACK: Anytime I go on a podcast I get feedback and I always have an opportunity to learn from the feedback. So hopefully I’m gonna learn from the conversation with you because you’ve been doing this for quite some time. But also I imagine our conversation will result in some feedback that I see on Twitter or in my email inbox about how I’m thinking and how it might be better evolved in this direction or if I consider something new. So it’s really to learn.
MATT: Well I’m excited about it. Thank you so much for coming by. I know that distributed work is not a new practice for you. Can you talk a little bit about your history with it?
JACK: The only reason I’m in this space, in technology, is because I benefited so deeply from open source early on. I was a kid growing up in St. Louis, Missouri and was active in the BBS community and when the BBSs finally got access to the internet through Washington University, it just opened the door to so much.
And for me it demystified a lot of how computers and networks work because I could actually see the source code based on this extreme generosity by others to share their work and to, I think more importantly, be okay with failing in public and being open in public. And it resonated with me a lot because I was in the punk scene, which is very much a pick up a guitar, be horrible at it for a while and then eventually you get better and better as you play in front of people and you do that uncomfortable yet courageous thing to put yourself out there.
And I saw a lot of the same patterns with open source. And these people were not in any one location. They happened to be all around the world. I mean, obviously (Linus?) [00:06:33.15] started in Finland and had a community across the internet that was helping him build something of immense complexity that had incredible value and it was all visible. And not just the source code that made the operating system work but the way they worked together was visible. The way they disagreed was visible, the way they slowed each other down was visible.
So I guess I’ve been a student of these models for quite some time but they have been fairly limited in my direct experience to open source (rather than?) companies. And when we were starting our companies, we followed the giants who came before us, especially in Silicon Valley and most notably Google. There’s so many practices that we borrowed from Google to start both Twitter and Square, culturally, process wise, tools. Obviously we are entirely on a stack created by them for their own work and now is benefiting others.
But one of the things I wish we would have questioned earlier is do we all need to be in one city, do we all need to be in an office, is that really required to make our work and to make our work valuable and to continue the urgency? I think open source is seen as inherently distributed but also I think slow, yet deliberate. And I think that deliberateness is undervalued and the focus on slow is overvalued.
And I think you can go into the patterns and still have all the benefits of having something that is more distributed, that is more global that could be fast and could maybe not be as deliberate so that we’re working mistakes much faster than we’re learning from at scale. When we were starting these companies, we just drafted off a bunch of assumptions that this was how you build a company, rather than questioning some of the fundamentals.
And I’m really happy now in that most of the entrepreneurs that I meet today are starting out questioning all that and starting out with an intention of not having an office, being fully distributed. And that’s meeting the expectations that I experience when I go to recruiting conferences of kids who are coming out of university and asking, as a first question, do I have to move to San Francisco? Can I work from home? Whereas like five years ago, that was not the first question but now predominantly it is. And I think that signal is interesting, especially as we have to consider bringing new people into the work force.
MATT: Yeah and it’s an interesting thought experiment to imagine if you had been able to start these from St. Louis and the impact that would have had on the local community.
JACK: A hundred percent. And now we have 1,000 people in St. Louis for Square and we want to hire even more there and get back to my hometown but I wish we were able to do that on day one. But we’ve learned more importantly why it’s important now and how to unwind some other things. And coronavirus certainly accelerated a bunch of our plans to the positive I think, generally.
MATT: Were there any other practices that you had copy and pasted from Google that you would look back at now as being particularly valuable or, like distributed work, you wish you had not brought over?
JACK: Yeah, tens of.. [laughter] I’m trying to think of the right ranking in terms of impact here. But I think because we were in San Francisco, because we were in Silicon Valley, we let ourselves be in that bubble of ‘this is how you build a company here.’ And it certainly removed ideas that would have benefitted us internally.
But also, like, even in other cities like Seattle and Amazon has this practice that we take on right now, which is phenomenal for distributed work, which is writing a document before a meeting and adding comments to the document in the meeting and then having a discussion based on those comments. And what that does is a few things – one, for people who tend to be a little bit more reserved or quiet or shy, they have no problem writing their feedback in a document so you see a lot more feedback and a lot more ideas.
Second, it records interest in where the meeting should go and it’s not just within the meeting, it goes beyond that. So when the notes are shared or when that document is shared, the whole history is preserved. And third, I think it gets people out of a presentation mode and into a discussion and debate mode much, much faster.
And we kind of just ignored the Amazon culture, what that meant, because we’re so in the bubble of what Google created. So I think it’s more of a wish that we were able to break out of the bubble a bit more and see things in a different way. And there were so many incentives to stay in that bubble, like the VCs that we took money from were in Silicon Valley and they had success indicators like Google and would suggest similar things. So it was hard to see outside of that isolation of concentrated ideas around what success meant and what it looked like.
MATT: How about OKRs?
JACK: Yeah, yeah we use OKRs, there you go, that’s one example.
MATT: Do you like them?
JACK: I have mixed feelings. I think they are good in terms of allowing us to articulate why we’re doing something and what we expect to see out of it but it just feels like there has to be a better method of that that I certainly haven’t discovered. The main benefit is there is a greater understanding of what they are, so there’s less ramp up time for most people coming into our company because they are part of the industry. What are your feelings?
MATT: We have some teams that use them but we don’t do them company wide. I don’t know if I love the structure. And I think where I chafe at it a little bit is in that the metrics might need to change more frequently than I have typically seen OKR update processes go.
JACK: Yes.
MATT: So it doesn’t always survive that contact with the problem. And so where I see it or where I feel like it was a negative for teams that have tried it have been when they stick to it for too long. But at the same time, it’s also a negative if your teams are always changing their priorities. So we have some teams that have.. I think there’s one called Gist that I liked a little bit better. It was like goals.. gosh, I don’t remember what it stands for but I resonated with that one a little more.
How about meetings? Even today I feel like my friends at Google are in meetings all day long. And they were distributed, they’re in offices all over the world, but lots of these meetings are usually on video. What’s your thoughts on meetings? How were they early and how are you doing them now?
JACK: I know a lot of people in our organization and certainly around the world are definitely fatigued by the camera. I mean, look at us doing this podcast, we’re doing it on Zoom right now but the camera is off and I know that’s to save bandwidth but.. There is a fatigue that develops in just being on camera every single hour of the day and I think it’s real.
And I think it points to a general issue with meetings, that a lot of our work is optimized around synchronous points of collaboration instead of asynchronous. And I think if we don’t focus more on the asynchronous problems and how to solve for asynchronous work we’re missing a bunch of opportunities. And that is one of the things I appreciate so much about the open source community.
And most recently, in just studying how Bitcoin has developed, which is.. a lot of what I got excited about in Linux development is now in Bitcoin development – it is global, it is complicated, it is impactful, it is asynchronous, it is slow and it is deliberate. I think there’s just so many lessons there that I think can be applied. But I think generally the meeting forces.. meetings force a way of working. I would rather have answers around how to do similar.. how to perform similar sorts of use cases but in an asynchronous way.
I think meetings are great for when a debate really needs to happen and certainly text mediums are not. But I think it’s kind of enumerating the list of like what is the job of a meeting, why are we having this in-person meeting? What do we expect out of it? Just to borrow Clay Christianson’s Jobs To Be Done framework, like, why (do we hire in?) in-person meeting? And what are the hiring criteria and what are the firing criteria?
I don’t think we have done enough of that work. We are certainly doing it at both companies right now just to further unlock our work so that we can be more asynchronous, which frees us up to hire more people in different time zones, which I think is the important goal and making sure that if someone happens to be happy in a particular area that they can stay there because they feel really creative there and they can still have as much impact as someone who might happen to be in San Francisco.
I don’t know, it goes.. it just asks the broader question, whenever I have to have a meeting, of is this necessary to be synchronous right now? And what is the asynchronous equivalent and why didn’t we do that?
MATT: And even people living in time zones, we find a lot that people like to work in different times regardless of where they live. Some folks really like starting super early in the morning, some folks might want to break up their day to pick up their kids or do different things. And even if an office culture said they were cool with that, it could feel against the social mores of an office to leave for two hours from two to four PM or something.
Have you seen my post on the five levels of distributed autonomy?
JACK: I did.
MATT: Oh cool.
JACK: I think, Matt, I mean, you’re one of the teachers in this space because you have been doing it for so long and have had so many experiences and incredible experiments with it. So I definitely am a student of your work in this space.
MATT: Well we have messed it up for 15 years so if we can share the things that we have learned from those mistakes I hope it helps other people accelerate. I had heard that you, a few years ago, started doing where a day of the week you worked from home. Can you tell me a little bit about the context of that?
JACK: Yeah, about two years ago I started doing a day a week. And then a year ago, before this Covid year, I was doing two days a week. So every Tuesday and Thursday I would work from home. And the reason I structured it that way is Monday at both companies we have our direction setting meetings, so we review everything that’s going on at the companies – and they are four hour meetings – and the goal is to get as much of that out in the beginning of the week so we don’t have to be dependent upon meetings during the rest of the wee, we can focus the majority of our work on the work and not scheduling this time together and however that manifests.
And then we would have Wednesday –
MATT: Are these big meetings? How big are the Monday ones?
JACK: It depends. It’s with my direct team and then we bring in folks from their direct teams and beyond to review some work or have a discussion or a debate. But it is generally meant to like.. let’s get everything on the table that is important for this week, let’s tie it as much as we can to previous weeks or previous months or previous years if the context merits that, and then well have a 30 minute check-in on Wednesday and Friday.
So we always know we have a lot of time together on Monday and we have a consistent and predictable check in point on Wednesday and Friday. And I found that that really creates an ability for us to not have to feel like we have to schedule the together randomly. We know that something might be able to wait until Wednesday or until Friday. So it sets a higher bar on when we do meet or when we don’t.
And that structure works pretty well. And I was finding on Tuesdays and Thursdays that I was more or less free to work on more strategic stuff and really spend some time thinking and having broader conversations, not meetings, but actually conversations around ideas. And I didn’t need to be in an office to do that. And I felt very focused at home because there was no other noise or people walking by every now and then and snacks and all these distractions within the office that come to occur were gone. And I really got more focused and I felt even more creative and even more productive. And then Covid happened and it became every day. [laughter]
MATT: Would you encourage your executives to also work from home on those days or the whole company?
JACK: I believe in showing and not telling. So I certainly talked about the fact that I worked from home and the reason I did is because I felt more creative and more focused. And if you’re on a role that enables that you should consider it, maybe. I didn’t ever say that word, I would just assume that people would. And if you’re in a role that doesn’t enable that maybe we should figure out how to enable it for people as well.
And that is not a reality for everyone, like the folks in our data center have to go into the data center every day . But for a lot of our folks there is something there that may be worth exploring. And again, Covid really forced the issue immediately. And it was one thing when school was still open and something completely different when schools closed and your whole family was suddenly in the same room as you every hour of every day.
MATT: Yeah, we’ve seen definitely a bifurcation of people’s experience in Covid. I think you mentioned that you consider yourself an introvert, is that true?
JACK: Yes, meaning that I get my energy from being alone. That’s where I draw my energy, it’s not from groups of people that energize me, it’s from being alone, being in nature, having some space to think and be present.
MATT: And you’re running companies with I think 4,000 – 5,000 people each, right?
JACK: Yes, I think we are up to about 6,000 at each company.
MATT: What was the experience, again, pre-Covid, of walking through the office?
JACK: In terms of being an introvert and walking through the office?
MATT: Yes, would you feel that people’s eyes were on you? If you’re in an elevator with someone, are they nervous?
JACK: Yes, I do also appreciate the fact that I am going to.. I want to have a mindset that every experience I have or every person I meet is going to be a teacher if I decide to let them be. And when I’m in the office and I’m walking around, there’s all these moments of serendipity, all these people that I don’t encounter on a daily basis, all of them have something to teach me. So I do try to at least go out of my way to say hi or ask questions and also if there is any opportunity to take the edge of a bit when we are having a stressful week, that I think is also important and great.
So yes, when I was walking around the office.. as much as I can to learn as much as I can. And that worked. And that is one thing I have missed. Because you can’t just.. You don’t have serendipity on all these video calls that we’re doing. Every now and then you do but it’s very rare. I think that is what has been lacking. And they haven’t found a replacement for, in distributed work, I would love any insight you have on it, but the randomness and what the randomness creates can be quite powerful. And I haven’t found a good way of creating that digitally and virtually.
MATT: I ask partially personally because I tend towards getting my energy alone or in smaller groups. But usually one week a year we’d bring the whole company together and that week was both my favorite week, cause I love my colleagues, I love spending time with them, but also my most exhausting.
JACK: Yes.
MATT: And I really felt that.. I don’t know if maybe I became more introverted since I’ve been working from home for so long but I kind of felt just.. a little self-conscious. Normally I’m able to walk around quite anonymously and just that presence or I would find that people would get a little nervous. And I have heard this from other leaders in the company as well – as you might move up in the org chart at our company, your day feels very flat and egalitarian but then sometimes how people act, especially if they haven’t interacted with you directly before, can change based on your perceived position.
We have found some serendipity with these donut chats, which is a Slack-bot that randomly pairs people. Have you tried that?
JACK: No.
MATT: Oh, it’s literally just a Slack-bot.
JACK: That’s a great idea.
MATT: There’s different channels that I’m part of and it will randomly pair two people in there and the bot kind of pings you both to schedule it, checks in if you’ve scheduled it, it just has some nice, built in.. I think it even has a thing where it will find a free spot on both your calendars.
And I’m part of a few of these, one for leaders in the company where we do talk more about professional stuff, our work contacts but random pairings, and then one that’s randomly paired with anyone in the company who joins the channel and that tends to be more personal where I try to.. I do my best to not talk about work and just try to learn about them as a person, which used to happen a little more organically in those in-between, liminal spaces, like waiting in line for coffee or at the bar after or something like that.
And the other thing is just when there’s lots of internal spaces for other stuff. We have a lot of what we call water cooler channels, like Slack channels about Magic the Gathering or gaming or P2s about it and people self-organize among us and stuff like that and those can be nice, particularly some of these remote games, which can really connect people for people that like them.
JACK: Yes, those are great points, good idea with the donut chat. I’ll look into that.
MATT: Gitlab also is a fascinating company to follow if you don’t already.
JACK: Yeah I definitely do.
MATT: And they have been sharing some fun things they’ve been trying. I’m curious to see this. You mentioned being on video all day being tiring, which yes, we started saying hi on video and then we turned it off to relax a little bit. I’m also curious.. I love the concept.. it is so much more intimate now that we’re all in each other’s homes all the time, right?
JACK: Yes.
MATT: I found that people would start at Automattic.. or when we actually had a team, the Tumblr Team, which was in an office and then had to go home unexpectedly and wasn’t really set up for work from home, particularly in Manhattan where they might have roommates or a small place. And at the beginning, folks would often have a virtual background probably because they didn’t feel like they had a very professional background. But over time, when they could rearrange their desk in the room or often sometimes move, we’ve had a lot of people that have moved, they designed their background to be part of their personality, almost like you might decorate your locker in high school or something.
JACK: Oh that’s cool.
MATT: The virtual backgrounds I see that too but I don’t know why we can’t do that for the foreground, some equivalent of Apple’s Memoji or Bitmoji or something, which would then remove the pressure that people feel to appear a certain way.
JACK: Hmm. Yes, you can do that on group FaceTime, which we have used as a team pretty effectively.
MATT: Ah.
JACK: Which makes it a little bit more fun too.
MATT: I like that. It is a feedback I get from some colleagues that they worry about their appearance. When we do an on-demand thing, it’s almost never a video because it feels so rude to unexpectedly video someone, they might not feel like their room is set up or something. But audio is usually pretty clean.
JACK: I will say one benefit and one moment of serendipity that video does enable is that when people come to an office you only see what they choose to share and to bring up and make manifest. So you hear about their kids, you hear about their pets and their life outside of work. But to your point, when you’re inside their home and the camera is on, you see their kids and you see their pets and you see more dimensions of your coworkers, which I think creates a lot more empathy for who they are and what they go through on a regular basis.
So that has been one positive element of being on the video is that I know my colleagues in a very different way that I don’t think would happen in an office environment because it’s just so challenging to bring the kids in or the pets in or whatnot. And we certainly have events around that but they are more staged and synchronized. And this, a kid just randomly appears on the call, everyone’s kind of disarmed and taken aback in the right way. And that has been very positive.
MATT: It’s really beautiful how quickly that shifted from people being mortified, usually the person who it happened to, to seeing the reaction and it being such a positive reinforcement of that humanity.
JACK: Yes, exactly. It’s like the BBC News anchor who has their child storm in and he’s absolutely mortified.
MATT: You’d mentioned some moments of serendipity even in this.. everyone on video. when did they pop up?
JACK: Maybe as we start using these technologies more we get less wrapped around the axel around the precision of their use and we allow for me messiness. When we all went back to work from home because of Covid, I think there was a lot of angling of the cameras and backgrounds and making sure everything was just right but now people just don’t care. Just.. you’re gonna se the bottom of my chin and that’s what it is for a while because I’m tired of holding this phone in front of me and I don’t have my laptop working. I think that’s when all this emerges.
And I think that’s true of how we use the documents to organize our meetings and our debates. Running a board meeting in this environment has been interesting and different, especially for our board members, which tend to be a little bit older, more traditional. Having them read a doc and comment in a Google Doc about what they are curious about has done such amazing things for helping us steer the conversation and make it so much more productive than if we were in person.
And we have boards that are (comprised of?) people all around the world and when you have someone flying from London or Nigeria to come to San Francisco, it puts a lot of weight on the value of that meeting and how much time you inherently spend. Like, you’re just incentivized to spend more time because wow, this person came from all the way all around the world to spend time with us.
MATT: A high transaction cost, yeah.
JACK: Yes, you can have greater impact if you focus the time more. And I think the in-person meetings hid that. And I would say our board meetings now at both companies are just so much more effective, so much more impactful. And I don’t want to go back. I mean, I do think we should meet at least once a year, again, just to build that empathy up and to have dinner with one another and drink together and just get to know each other in a different way and be present, but the conversations we’re having right now are just not the same as they were in these forced, in person meetings.
MATT: And you feel like it has gotten deeper, more relevant to the topic or more helpful to the company?
JACK: Yes. Because even with our board members, I mean, they are at home, they’re thinking from home, they are comfortable because they have full control over their whole environment so they’re not worried about not having the right tea or coffee or the lunch was terrible. They are fully in control of everything. And I do think that gets us a better mindset from meeting start.
And then because we are so aware of the time we are spending together and we are focused on making it effective and impactful, we put a lot of work into these documents so that we can really have a productive conversation. And we give these documents to our board members a week ahead of time and they have plenty of time to read and put questions in and as they are putting questions in, we get live notifications so we can see how they’re thinking in real time. And yes, it’s just been great. Whereas we couldn’t do that in the past.
MATT: It sounds like you’re rehiring your board meetings.
JACK: A hundred percent. Yes. Like, why do we hire the board, why do we have these meetings and how might we make them solve the problems we are identifying in a better way.
MATT: And do you still have slides or is it all prose?
JACK: It’s mainly prose. I mean it is mainly a written Google doc. We do have demos every now and then. There are things that just need to be on slides just because of the flow. But generally it’s a lot of paragraphs. And when you look at it in the meeting, there’s highlights on certain pieces and discussion around it and we zoom in on that. And we also get a sense of like was this document robust enough based on the question that was asked here. So it’s just a lot of really good signal in terms of how to make our meetings better and better every quarter.
MATT: I remember I was at actually a Gitlab board meeting and there was a bajillion slides at the time but it was like hey, go through them beforehand and then we’ll talk about the questions. And I think I heard that but I didn’t entirely hear that and I was amazed and it sort of taught everyone the lesson that they did not go through any of the slides, they only would jump to the ones that people had put questions in the document about. So it was actually jumping around a lot. So if you hadn’t already studied them, you were a little bit lost. And it was maybe rough the very first time but now I do, I block out on my calendar three, four, five hours before every one of their meetings to make sure I go really deep on all the documents. It taught the lesson.
JACK: That was one of the greatest lessons that we learned from Amazon is having these documents be read not beforehand but in the meeting, silently, and commenting on them silently for the first 15 minutes of the meeting before we get into discussion. The greatest thing it does is everyone is on the same page.
MATT: Literally.
JACK: Yes and there’s no excuses in terms of I didn’t have time to do the pre-read or whatnot, it’s all right there and everyone has the same information at the same time. There is a lot of value in that that I think we benefit from.
MATT: Do you think you (are at a place?) where people do it beforehand?
JACK: Yes, there’s certain information in certain meetings that probably need more consideration than the start of a meeting allows and the board meeting is one of those. We haven’t – although we may have tried it once. Actually, we have gone through a few sections of the board meeting where we encourage board members to read at the start of the section and we are then on the same page and that is often when it’s fairly nuanced in terms of like, we all need to be.. we don’t want to waste time here so we all want to have the same understanding at once. So generally we need to balance that with how efficient we are with the discussion itself.
MATT: One thing I love about pre-reads or asynchronous versus in-meeting reads is you don’t just get people’s reactions, you get after they have walked around the block with it, taken a shower, slept on it, had time to really develop their thoughts over time.
JACK: Yes, it’s a great point. There’s definitely positives and negatives. But I do think the more asynchronous work we have to do, obviously it doesn’t allow for that. We need to optimize for more of that.
MATT: Yes. You’d mentioned those four hours, which is five percent of a normal work week at least in this e-team meeting both at Square and at Twitter. Why are you rehiring those every week it sounds like? What is done in those that can’t be done asynchronously?
JACK: Yes, that is exactly what I’m trying to figure out right now is like do we need to restructure that even more. I think right now I’m just trying to observe what is the criteria for spending so much time together at the beginning of the week. And I think the biggest value we get is that we feel like we have this incredible touchpoint of shared understanding on very complicated topics that we all experienced at the same time live. And I think there is value to that because it makes the conversation so tangible. But I don’t know if it’s necessary. I think it’s additive but I don’t know if it’s critical. So we are going to experiment more with why we hire that meeting and why it has to be synchronous and what we lose if we shift it. That’s probably a start of next year thing.
MATT: Do you do anything at these meetings to have social ice breakers in the beginning?
JACK: It kind of naturally happens. We get on the call and someone brings something up that feels a little bit random and we give space for that because it does enable people to see different dynamics and different dimensions of each other so we definitely give space for that. And there is a lot of laughing at the beginning of the meeting usually, which also sets a tone that we can have laughter in the rest of the meeting too if we find an opportunity for it because it de-stresses so much.
MATT: Reed Hoffman has a really good anecdote on that in his new book “No Rules Rules” where I guess it was.. And Automatic was guilty of this as well. We made the meetings like ultra work-focused I think because I had been burned by bad meetings, we mad them way too focused and there was no space for that more social side.
And he talks about it in the context of expanding internationally. As they had more Brazilians come into the company, they saw this as very impersonal. Or during their interview day they left them alone at lunch instead of taking the guy to lunch. And how they started to incorporate what he terms as Brazilian but I actually think of it as just a personality type, like, more of that warmth and personal side at the beginning of things. And now it’s their new policy that they do this at all their meetings. So I found that interesting.
JACK: Wow, wow.
MATT: I think you’d enjoy that book too if you check it out. Netflix has some interesting heterodox ways of working.
JACK: I’ll definitely look at it. I’ve been trying to avoid books that have anything to do with our industry or society or technology at all recently. So the last book I read was this book entitled “Surf” by Gerry Lopez who is a legendary big wave surfer and wow it was refreshing. It was just so beautifully written and its distracting in all the right ways.
MATT: Do you surf?
JACK: I try. I’m not great at it. I’m really good at paddle boarding, which is much easier for everyone but I would like to become better at it because it’s so pure. I used to wind surf a bit and I love sailing but just the purity of understanding a wave such that you can be in the same flow with and be in the same power of it is a pretty incredible adrenaline rush and a reminder of what flow feels like, literally.
MATT: The ocean is so humbling.
JACK: And that, and that. Just how powerful it is.
MATT: I think I’m in the same space. I’ve been learning more – particularly this year I’ve been able to make it out a bit more. Yeah, my dad was actually a surfer but he had long stopped that by the time I was born and so after he passed few years ago, I began to do a lesson on his birthday as a way of remembering him. Just this year I was able to get a few days in a row and get a few times. It was so nice to be disconnected. I have also felt that with diving, if you’ve ever done scuba diving.
JACK: Yeah.
MATT: Because it’s so connected to the breath.
JACK: I really want to do free diving because it freaks me out. It feels so scary and that’s exactly why I want to do it because I just learn so much when I put myself in uncomfortable situations.
MATT: Speaking of uncomfortable situations and scary things, you had talked about going from I guess two days working from home to actually working from Africa and India where you’re going to do two or..?
JACK: Yes.
MATT: What was the plan there before everything in the world happened?
JACK: This year before Covid really emerged, I spent November of last year in Africa going between Nigeria, Ghana, Ethiopia, I mainly focused my time there. And the reason why.. I had never been to the continent, I had never been to those countries and never really immersed myself in the culture and the people, and I wanted to do that personally but I also see Africa as an incredible opportunity from a entrepreneurial standpoint and also from our businesses, both Twitter and Square.
So I wanted to go and in November I met with entrepreneurs, I met with schools, high schools, and colleges, and that was it. I didn’t talk with anyone in the media or the government and that was the intention. And the goal was to learn enough that I could go back and send four or five months there and my goal in that four or five months was number one, to understand the countries more because it will impact our business and our opportunities in the future.
And in that dimension, also how to work from halfway around the world, from our headquarters in San Francisco, how do we figure out a structure where we can truly force ourselves to be asynchronous because the time zones demand it. And if I could do that, then we could probably scale it to a bigger majority of the company. And then the second goal was to hire and to have partnerships with local companies there for both companies.
And then the third was to help entrepreneurs that I met in whatever way that I could. And I was all set to spend four or five months and then Covid happened and changed everything. So, it is still my intention. Maybe it’s next year, although it doesn’t seem tingly probable. Maybe the year after that. But I definitely tend to spend a significant amount of time there to really understand it and to build and to support in any way that I can the phenomenal entrepreneurs that I found there. And there’s just so many solving extremely tangible problems in very creative ways.
MATT: I love that. The altruistic side is also really good and laudable. But I think even just purely for your business it would be huge.
JACK: Yes.
MATT: Were you planning to continue all these standing meetings, the Monday, Wednesday, Fridays while you were there?
JACK: No, we were going to figure something out with that. But I wanted to use that time zone change as a forcing function because obviously it would not work, I would not be able to sleep in a healthy way if that were the case so we would have to change a lot. And that was the intention is if we can run the company without missing a beat in such a distributed, asynchronous way it really opens up the door for a lot and especially our ability to hire anywhere as we.
MATT: Yeah, I found I can get by.. I did one month where I was actually taking some writing classes in Paris and I just kept my normal schedule. So I’d work.. it would be like 2PM to 10PM. So I guess you could still do your.. if your meeting is in the morning, you could still do it.. Oh, but you must have two because you’ve got the Twitter and a Square one.
JACK: Yes.
MATT: So that full eight hours…
JACK: Spread it between two days but..
MATT: But when I’m in Asia or even Hawaii, that gets so much harder because it’s the middle of the night when you try to keep the time of those meetings. And it’s one of the biggest I think fair criticisms Automattic gets is that a lot of our meetings are optimized for morning west coast, early evening Europe to cover the most people and we don’t do time zones or things as friendly, like town halls as friendly to Asia-Pacific time zones. and our executive team, even though we have the ability to hire people almost anywhere – we’re in 77 countries and we try to be very open there – the folks who are at the very top of the company tend to be more North American based.
JACK: Yeah, last year we did this thing called a (tweet?) tour where I visited every single one of our offices around the world and I just took a whole year to do it and we spread it out throughout the year and I was able to.. It was a Twitter initiated effort but I would also visit the Square offices around the world. We don’t have as many as Twitter but there are still some.
And the first thing you notice, the first thing I noticed, I should say, was how much of the company runs on the San Francisco clock and just how immediately unfair that feels and how much friction there is and how much friction that creates. You can assume that that’s the case and when you’re in San Francisco, you don’t think about it as like, oh, we really need to change it. But when you’re actually on the other side of it, it just puts such a weight on the need ultimately to change that. For serving a global audience, which is our intention, and we’re building a company that is in service to one time zone, it just feels so out of synch and so ridiculous.
And again, pointing back to open source, it’s a solved problem and I just don’t think we’ve gone deep enough in really understanding how to take all those benefits that we receive from open source and how it is structured and add a little bit more prioritization and urgency around it. Because I think again that is a thing that people tend to put open source down for is the slowness of the development cycle. And I don’t think we need to rest there. I think there is a lot of goodness there that can also be done in an urgent, quick way. It’s just a function of how deliberate it is or not.
MATT: That’s funny, I actually don’t think of the speed as much, I think because our release cycle for WordPress is a lot faster than most of our competitors. But I think a lot about that most successful open source projects are more developer facing or more back end and there’s only a handful, Chromium, some of the file sharing tools, WordPress, that are more consumer facing.
Something I’d be curious your thoughts on.. how they evolve over time, or if you have some now, are engineers working asynchronously versus designers, product managers, all the other people who make great consumer facing products working that way?
JACK: That feels like a great unlock. And just in my own personal experience.. Let’s take Bitcoin, Square funded this thing we call Square Crypto, which is an independent organization of five developers, and the intention was to have one or two designers as well whose goal was just to do whatever it took, whatever they thought was important to help Bitcoin be better every single day.
So they had nothing to do with Square’s goals, they don’t have a manager at Square, they don’t take direction from anything that Square is doing, we can’t tell them what to work on or what not to work on. They are completely independent but they’re working on something that ultimately will benefit our company just.. it’s unpredictable as.. at this point how that manifests.
And we found developers right away but one of the big problems with Bitcoin I believe right now is that there’s a lot of design problems that have not been solved. (Key entrant?) is a great example of this. I think it pushes more incentive towards these custodial wallets and.. which is more or less against the ideals of Bitcoin and having this concept of self-sovereignty and being completely independent of a custodial, like a corporation like Square.
But there’s a lot of design problems. And we were searching and searching and searching for designers who did their work in an open source model and ultimately didn’t find any and struggled with it a bit and ultimately decided that we would kick off a project to fund a bunch of designers and a community, to build a community up first, so that people would have a foundation with which to share best practices around designing in an open source way and designing for open source and designing for consumers in that open source model.
And it’s early but it manifests as like a Slack channel and a group of designers showing off work and commenting and critiquing on it. But I think there is ultimately something there. And if we do figure that out, I think it will point to expanding those ideas to other disinclines as well. And that is our intention. But I think the problem.. the immediate problem that I think will bear a lot of fruit for us is solving his open source designer problem.
MATT: Two things there. One, we have something in WordPress called Five for the Future, which is the idea that whatever you are benefitting from in the WordPress ecosystem, if you could take five percent and put it back into core, kind of like you had those engineers just working on core Bitcoin and things, that will avoid the tragedy of the commons. For some people, maybe that’s two hours a week as a freelancer or for some, like at Automattic, now it’s 60-65 people essentially working on the dot org side of things.
Often companies will come to me and say okay, who should we hire? And their first inclination is to find someone already contributing to WordPress and hire them. And I was like, okay, well that will get you the points but it won’t actually add anything to WordPress, that’s just changing where someone’s paycheck is coming from. So I really started to encourage them to hire folks who we don’t already have a representation inside of WordPress and more other roles. So, product managers, project managers, designers, researchers. And it has been kind of fun.
And actually, this has been another place I’ve been inspired by Gitlab, who actually streams their product review meetings. Actually, Steven Wolfram does that too. Check out his Distributed interview, it’s kind of funny because he’s been doing this for like 30 years. Yeah, we just started doing user tests and then posting the videos on our P2. We would of course have to get extra permission for that.
Yeah, just radically opening that has had a pretty good impact so far and also changed the people contributing. We actually just had WordPress 5.6, named for Nina Simone, was the very first in our project and maybe in [00:54:20.17] open source, all women release squad. So 36,37 women led that entire release from start to finish.
JACK: Wow. You said it was named Nina Simone?
MATT: Oh yeah, we name every WordPress release in honor of a jazz musician.
JACK: Oh, that’s excellent, Nina is one of my favorites. That is an excellent choice. It must be an incredible release.
MATT: A lot of people focus on that you’re the CEO of two companies. And my bugaboo there is they don’t ask Tim Cook how he runs a hardware business and a services business. If you look at any of these larger entities, they typically do some very different things, you just have a structure where you can have independent shareholders in each. How much do you try to run them in the same way or share best practices or even cadence of how things work or hire between the two?
JACK: So to answer that question, I would go back to what to what I believe my job is. And I think I have three jobs, I think there are three reasons why the company hires me every day in my role. And the number one is to create a healthy team dynamic. That’s the interconnection between the members of the team. It’s the ‘how we work together’ it’s the purpose that aligns us, it’s the values or the principles that guide our work to serve that purpose better.
I am not as concerned with the individual nodes or individual people on this big graph of the company. I’m more concerned with what connects them and how they connect and making sure that we have something that is healthy. And to me, that means it’s positively reinforcing, always. So any contrast in the team is a positive reinforcement that increases our creativity, (why not??) So that’s job number one is building and actively building that dynamic and there are multiple tools I use to do that.
And job number two is to insure that decisions are being made. I see a signal and if I have to make a decision that ultimately there is something I can, I’ll say debug in the organization, and I think it’s more important that I insure that the organization is making decisions and not just that they are making decisions but they are making decisions in context of our purpose, in context of our customers who are serving, in context of the technology trends that are emergent, in context of societal or cultural trends that are emergent and they are showing that context as they make these decisions.
Because what that ultimately does is it removes single points of failure. And it builds a framework and a system that can expand and that can outlive myself or anyone that is currently in the company. So I pay a lot of attention to those frameworks of decision making and I’m constantly looking for opportunities to help them.
And then third is I believe my third job is to raise the bar on what we thought was possible. As we get older as individuals and as companies, as we grow, we tend to take things for granted, we tend to stop asking questions around various aspects of who we are and what we are, what we’ve built, we tend to take less risk because we are more precious about what we have built up and what we have and we don’t want to lose it.
We are less likely as individuals in our late twenties, thirties or forties to jump on skateboard as we were when we were a teenager or four years old. And in that risk taking, in that appetite for risk, there is learning and if you remove that, we remove some potential for that learning. So I think injecting some risk every now and then, injecting uncomfortable situations or questions with the goal of raising the bar is important.
So I say all that because I perform those three jobs at both companies in the same way. But the outcomes are different at both companies. And the outcomes are different because they inherently are working on different canvases, we have different people, we have different problems that we are trying to solve and raising the bar on one problem is very different from raising.. in terms of how it manifests, raising the bar in another problem.
For instance, at Square, one of the things I believed fully was that we must understand.. the biggest societal and technology trend that is affecting us as a financial company are crypto currencies and namely Bitcoin. We need to do everything we can to learn about it. And the only way I know how to learn about it is to build it. We’re going to build it into our Cash App. And that was very scary because Bitcoin is seen as kind of an unknown thing and seen as a scary thing by a lot of people, and we were a public company. There have been no other public companies that talk to the SEC about Bitcoin so we had to do that for the first time.
And all those firsts that we had to do to secure all this Bitcoin to introduce it to our customers in way that they are not going to be financially unhealthy with it, which was a big concern for people, to do all that for the first time really upped our game and really reminded us of what we’re capable of and what is newly possible.
So applying those three jobs to two very different companies.. sometimes I see parallels. Like they are both very supportive companies, they have amazing cultures, they’re both working in spaces that I think are inherently foundationally conversational and I see commerce and transactions as conversational as conversations are, [laughs] as social aspects are.
There is a lot in the culture of Twitter that the product was trying to do in bringing more transparency to the world that the company became. We became very transparent internally. And I took that when I started Square because we were going into an industry that was very obtuse and it actually profited from the fact that there was very little transparency. And we also wanted to bring more transparency to the financial industry so we had to be a transparent culture, a transparent company, because we needed to know what it felt like every single day.
So it’s just really sticking to my understanding of what my job is and applying it in the exact same way and knowing that these principles will lead to the right outcomes for each company because it’s putting the focus in the work and its focusing the work around who we are serving ultimately. And that is how I designed them and what I want to make sure I’m holding myself accountable to.
MATT: How do you choose when to do the same best practice at both? I felt like around the same time, although it might have been a week or two apart, you announced that at each company people could work from home forever versus allowing one side to do one.. one company to do it and not the other company?
JACK: Yeah, that becomes tricky. Just given my particular situation, I think there’s some ideas that are just good for companies. And if I have weight in two incredible populations that we can change the outcome at the same time for, I’m going to take the opportunity. So our reaction to Covid and encouraging people to go home in early March and then you never really have to come back was a discussion that we had at both companies and a push at both companies and something that was accepted equally at both companies. It wasn’t difficult.
There are other things, like let’s say Square’s investment of $50 million Bitcoin, that makes absolute sense for Square because we are building for this financial future and you could also argue, as other companies have, that we should put some of our balance sheet, Twitter should put some of its balance sheet, into Bitcoin as well. But the connection is not as apparent and ultimately you’re becoming more of a currency trader rather than what the intention is. And that investment that Square made is only one part of what we have done I believe to the benefit of the broader Bitcoin community, including opening up our patents and creating a non-profit to enable other companies to join in and help defend the open source nature of Bitcoin and crypto currency against patent trolls to the five developers that we hired to work on Bitcoin.
I think there are certain ideas that may benefit both companies but are much more important for one and I’m not going to force it. I think it has to be adopted if it was meant to be adopted. But there’s some that I do want to force because I just think we need.. it’s a step to move forward.
MATT: And you open sourced that treasury management stuff, right? I’m sort of remembering a document that came out..?
JACK: Yes, we did. Yeah.
MATT: Is that with the intention that other companies.. obviously with the intention that the companies adopt it, so with the intention that the relevant folks at Twitter might see that and start to explore it as well with it out [01:04:51.06] to be top down?
JACK: Just to make.. that wasn’t necessarily the intention for Twitter. We didn’t have Twitter in mind, I didn’t come up with the idea to open source the process behind it, it was actually our CFO and her team. I love that because it gets more of what felt sacred in the past in terms of a company and how it did things as proprietary. Now, we’re going to open this up and we’re going to share all of our learnings and if it’s useful to inform a decision that you have questions around or are considering, great. And we’re putting an artifact out there that hopefully will be built upon in the same way that you would with open source software.
And I think our companies have taken so much from open source and from that culture specifically. It’s anything that we can do to give back to it in a meaningful way we should take. And when we set up Square Crypto, this nonprofit, external group of Bitcoin developers, Steve, who runs it, decided that he was gonna write everything down and he wanted to share that playbook with other companies who are considering the same in the hopes that they would do the same.
And now we have seen more and more crypto focused companies start funding developers and engineers just to work not on what they’re doing but on Bitcoin and ideas in the crypto space. So I think it has worked. And if we can contribute more to those ideas of like just being open and sharing, not just our code but our practices so that others can follow and make it better, that’s important to me because that will come back to us. If they make it better, it comes back to us.
MATT: Kudos to that. I hope you do a lot, lot more of it.
JACK: Yes.
MATT: Do employees ever drive something across the company, so whether that’s large things like hey there’s this HR policy at one but not another or trivial things like Twitter employees being like oh the Square office looks so cool, why can’t our office look cooler?
JACK: They do a little bit. I think they tend to be smaller but there’s a lot of conversation between folks at both companies in terms of best practices. And I think a lot more coordination, especially around Covid, because we.. because the companies are so close in terms of ultimate leadership there is a desire just to make sure that we are sharing as much information as possible so that we can both get on the same page as quickly as we can.
MATT: How much coordination – I mean, you have the benefit of building hem both – how much is the head of HR or [01:07:42.05] or folks talking to their counterparts at the other company?
JACK: Between these two companies specifically?
MATT: Yeah, just sharing?
JACK: I don’t know actually. I don’t know. We do have one time a year where both my leadership teams and myself get together from both companies, which is always fun and usually involves roasting me in some way. And I love when they do get together because I just see so many similarities in the people. I love who I work with and really I’m so grateful and so appreciative that I’m at a point in my life where I can say that I fundamentally love the people I work with and I learn from them. And when I see them see each other through that lens as well it just makes me so, so happy. So I imagine that’s happening elsewhere in the company as well, I’m just not really all that aware of it.
MATT: It sounds like you really want people to experiment within the companies as well. You framed it as learning even as you get older. Are there any temporary autonomous zones or some equivalent within the companies where you allow people to do something really different?
JACK: I love the concept of a temporary autonomous zone, I used to read (Hackerbay?) as well. I think we have had some of those. Some of them have been more top down enforced. Like Cash App came out of exactly that where we had a very small kernel of an idea and we tapped three people just to.. and shielded them from the rest of the company.. and it ended up being a great idea and it ended up requiring a shield for four years because the rest of the company effectively wanted to kill Cash App.
Our company was started to serve the needs of underdogs, small businesses, this is not that. We had some people who had experience with PayPal and they said that has been won. There is no value in peer to peer so let’s stop doing this thing. It costs too much right now so let’s stop doing this thing. And I think a big part of my job became just defending Cash App’s existence (as it grew?) and people. And ultimately it worked out because we believed in it so much. And there are other things that we protected for a little bit and then didn’t and they died.
MATT: Anything that long, that you protected for four years?
JACK: Not that long, not that long. We had a number of things in Square. This product called Card Case, which was a phenomenal experience and really cool which kept it around. But I don’t have any regrets because we have a better path with Cash App against the same sort of experience. So Cash App was definitely the greatest test of my patience and my ability to defend.
Because every time you do something like this – and you know this – you lose credibility. Every day I was defending Cash App, for a lot of the company I was losing credibility. And it’s taking a lot of that credibility out of the bank constantly and eventually you earn it back. And I feel like if I’m not losing credibility to someone in the company I’m probably not doing something interesting because I think it is a constant cost benefit analysis of like I am going to lose credibility for this move and that is okay because of X, Y and Z. And we have had many experiences in both companies around that.
MATT: I think about that a lot because I feel like it is a responsibility. As a cofounder or CEO, you get some extra of that credibility in the bank that you can spend down on things. But I think a lot about how to allow others who aren’t a cofounder or have that sacred place in the founding of the company to be able to make those same bets. Because I’m not going to have all the good ideas.
JACK: Yes, exactly.
MATT: So, how to set up that structure. We’re basically out of time. I feel like we covered a lot. I did want to end on one quick thing. I know mindfulness is important to you. How has that influenced the organization structures or how do you encourage mindfulness throughout the organizations that you have weight in?
JACK: I don’t know if it’s affected the structure as much as it has our reaction to what’s ahead of us and what we are presently experiencing. Because the greatest tool I learned in meditation is observing my reaction to something and ideally observing it to the point where I can make a different decision and not just blindly react but decide to go in a direction based on this thing that is in front of me.
I think for me it’s just made me a lot more observant around what we inherently react to, what natural, organic incentives are in a company, where those incentives ultimately lead. And you know this is a big one with Wall Street, obviously, it incentivizes a very different thing if you don’t pay attention versus the intention when you start the company. There is an inherent incentive in the stock price and it being a thermometer every single day for how people might feel about their work with us or their value or our value as a company.
And being able to show that that is an output, it’s a very emotional one usually especially on a day by day basis and it’s affected by so many variables outside of our control. And it’s a reminder of what do we control? Well, the only thing we truly control is how we’re spending our time, what we’re spending our time on, and what we do with this minute in front of us. And if we let the minute dictate what we do versus what we intend to do with a minute, we get to very, very different outcomes.
So I guess the meditation practice and mindfulness has really just taught me so much about observation, understanding, self-awareness, organizational self-awareness, and then most importantly recognizing reaction and deciding to accept it or go a different way, if that makes sense?
MATT: Yes, that’s beautiful. I think that is a good place to end. I really appreciate – I want to be respectful of your time – I really appreciate your time. You are @jack on Twitter, is that the best place to follow you?
JACK: That’s the best, yes. Thank you so much, Matt, for the time. I always love having a conversation with you and I’d love to do it more, it doesn’t have to be on a podcast. But I love that too.
MATT: I appreciate that. You’ve been listening to the Distributed podcast. Thank you so much, Jack, thanks for tuning in. See you next time.
End.
Episode 25: Davit Baghdasaryan on the Science of Sound in a Distributed Work World
Oct 15, 2020
Trying to sound your best as you work away from an office more than ever before?
As audio and video conferencing surge worldwide, Matt talks about the science of sound with Davit Baghdasaryan, the CEO of Krisp, a fast-growing company offering an AI-powered noise cancellation app for removing background noise on any conferencing platform. Krisp’s technology, including its proprietary deep neural network krispNet DNN, processes audio securely on the user’s computer.
Find out how Krisp started, why Davit foresees his company returning to a hybrid work model, and what it means to Work from Forest.
With employees in the United States and Armenia that shifted to working from home in 2020, Krisp surged this challenging year, announcing a $5M Series A round in August and growing to 600 Enterprise customers despite continuing to focus on consumer users. Check out this demo of how Krisp works in meeting room.)
A native of Armenia, Davit spends time in both countries leading Krisp. Prior to co-founding Krisp, Davit was a Security Product Lead at Twilio in San Francisco, among other security-focused technology leadership roles.
The full episode transcript is below.
***
(Intro Music)
MATT MULLENWEG: Howdy everybody. Today we are going to talk to the Co-founder and CEO of a company whose technology makes it easier for those of us working from home to hear each other, even with all of life’s noisy distractions going on in the background behind us.
At Automattic we say, “Communication is oxygen.” We are advocates of anything that makes communication easier and more effective. And one of the tools I find myself recommending over and over again is Krisp, which is an app that uses machine learning to mute background noise in just about any communication apps you use.
For Krisp’s Davit Baghdasaryan, there is even more to the story. He is leading a young and fast-growing company through the challenges and opportunities of this year, balancing his own company’s transition to a remote workforce and a surge in demand for Krisp. He is a native of Armenia and also a global citizen and experienced technology leader at great companies Twilio and he has made his own adjustments to working and leading from a distributed point of view. So today we are going to chat. And thank you so much for being here.
DAVIT BAGHDASARYAN: Thank you, Matt. Thanks for the intro. Hi, everyone. I’m Davit, CEO and Cofounder at Krisp, as Matt mentioned. I’m so happy to join this podcast.
MATT: Was there any key biographical detail that was missed that you’d love to share, things that people usually don’t know?
DAVIT: Absolutely. I think that was a great introduction. I was born in Armenia, I’ve lived in ten years in the U.S. Right now I’m back in Armenia. I’m sure we will go deeper on my background and biography. I’m happy to share as much as needed.
MATT: In 2018, when you started Krisp, what was the thing that you were seeing? Because people weren’t on calls or Zoom nearly as much back then. What was the need you were seeing?
DAVIT: Yes, absolutely. Well the story behind Krisp is very personal. I was actually working at Twilio, which is a big communication platform, and actually at Squadcast. I just figured that Squadcast is powered by Twilio. But because my family and my friends were in Armenia, I was traveling a lot to Armenia at every chance, I guess.
And because of the time difference, almost 12 hours of difference, when I was connecting to meetings, it was evening time here. And in the evenings you want to go out with friends and family but that was the time that I needed to join meetings, like my daily meetings. I was heading the Product Security at Twilio so that means I have many meetings with different teams. And I always wished there was a button I clicked and get some privacy, like people don’t know where I am, [laughs] they don’t know that I’m joining from bars. Not necessarily bars of course, but still.
MATT: So almost like a virtual Zoom background but for audio.
DAVIT: Exactly. So I had the need but I had no idea how to build the technology. And I knew it must be done with machine learning. I knew about voice but not machine learning. But I mean that’s where I met my cofounder and that’s how things have started.
MATT: I think I first came across Krisp actually on the NVIDIA machine learning blog. It was very early on, it felt like the company was.. I think it was all still free at that time.
DAVIT: Yes. Well actually Krisp wasn’t released at that time yet, or maybe just launched. And then that blog post was very important for us. We worked on it for a very long time and that was the first exposure that our company received. And the blog post got actually a lot of visibility. So it was at some point I believe the most shared and visited blog post on NVIDIA developer AI section. So yeah, it brought us a lot of visibility.
MATT: I actually made a mistake early on when I was advocating for Krisp. I told people it was from NVIDIA, or spun out of NVIDIA, I was so.. Because the post had seemed so great I couldn’t imagine that it was a guest post.
DAVIT: Yeah. Well there is a fun story actually behind that. When we did that post and it was successful, we thought that we needed to put that post on Hacker News. And we put a title which sort of implied that it was from NVIDIA so that people open it more. It was a small hack from us and it worked out because Krisp, that blog post was in the top five of Hacker News that day. Yeah, exciting times.
MATT: That might’ve been where I saw it too. [laughter] I don’t recall exactly but that would certainly be plausible. So I imagine you’re able to kind of turn Krisp on and off on your set up right now. Can you demonstrate how it works?
DAVIT: Yes, absolutely. So Krisp is on right now. I’m going to clap. I’m clapping right now. And when I do this with video it’s much more impressive. And now I’m going to go, it’s a single button, when I turn it off and then I clap [clapping] you hear the clap. Right?
MATT: Yeah.
DAVIT: Yeah, that’s the easiest way to demonstrate it. But Krisp is.. with Covid and with everything that happened lately, people moving to home, Krisp was very handy with kids at home, with dogs barking at home. So it does a great job at removing noise. And I’m happy to actually dig more into how that works and where Krisp is going.
MATT: It reminds me of the Zen Koan, what’s the sound of one hand clapping. I guess it’s like Krisp. [laughter] Oh, one reason I have been advocating for it a lot is that for a good meeting you don’t need video, you could turn video off its not working, we’re not using any video now obviously, but if audio doesn’t work, the meeting stops. A meeting with video.. unless I guess you’re really good at American Sign Language or something, you really do need great audio.
And I find it so distracting when folks have just a ton going on in the background. But I also feel for them because we are all home, we have kids working from home, all sorts of things. What sort of Covid boost have you all seen?
DAVIT: Yes, absolutely. Well voice is, we believe that voice is going to continue being a key means of communication and it’s going to grow, actually, way bigger than it is now. With Covid we saw a very large boost in increased downloads and usage. I believe it’s now like.. It’s been 7X growth for Krisp.
MATT: Wow.
DAVIT: Because – yeah – there was no technology like this in the world. And when we were just starting, people didn’t really.. Every person that was seeing the download, they could relate so much to the app, to the problem. But they didn’t really know that the problem existed because we are so used to what we have. So it took us a while to market this. And early on, we were having a lot of struggles to explain that there is actually a pain here.
But with Covid things have changed because all of a sudden this has become a big problem because everyone is home and their kids are crying and there is just a lot of noise coming from the kitchen and everything. So yeah, people have gradually started spreading the word and most of the growth has been done by word of mouth. So yeah, from a business perspective there was a lot of growth during this time.
MATT: Let’s dive a little bit into how Krisp works. It uses machine learning and what sort of a learning technique does it use?
DAVIT: Let me do a short intro into noise cancellation in general, the state of the art before machine learning. People usually use multiple microphones to try to remove or cancel noise. Our phones have multiple microphones on them. One of the microphones is close to your mouth, the way you hold the phone, and the other microphones are very far from that microphone, from your mouth.
MATT: Like there’s one on the back of most phones, right?
DAVIT: Which ones?
MATT: There is usually a microphone on the back, like where the camera is.
DAVIT: Yes, exactly, exactly. It must be as far as possible so that you can.. by subtracting the two audios from each other, I’m just simplifying it, you can isolate the human voice. And this technology is deployed on every phone out there, I guess, like more or less expensive phone. And that technology also exists on our laptops but it just doesn’t work because your mouth, the person is very far from the laptop.
So it has two problems. One problem is that it requires multipole microphones, so it requires specific hardware. And the second is it has limitations on how much noise it can remove. Usually it’s great with removing stationary noise, like static noise, but when the noise comes and goes, like clapping, barking, it’s just not possible to adopt to these sort of noises.
And then in the last five years, as machine learning has started to grow, people have started, like in academia they started machine learning for noise cancelation. And we were very early on in this problem. So when I met my to be co-founder and we started talking about this, we knew that we needed to solve this with machine learning just by intuition, right? And we started looking at this, what’s out there.
As a technology company, we were the first to actually design and implement such technology which purely uses machine learning for this problem. So the way it works is we have a very large data set of background noises, which we had to find from somewhere. It was tough to do that. [laughter] But we were clever I think with that.
We tried some interesting.. we found the right sources for that. And these are very different types of noises, like 10,000+ type of noises. And then we also have collected a lot of clean studio recordings where there is no noise at all, so we have a lot of such data. And when we mix them together with different sound to noise ratios, we get pretty much an infinite data set of noisy speech for which we have the clean speech because we used that data set.
And then what we do, we have designed this special neural net for which during the training we say well this is a noisy space, this is a clean space, noisy space, clean space, noisy space, clean and we do it for all these artificially generated noises page. And then it starts to learn what is human speech, what’s clean speech, what’s noise. And then doing the inference, like when you start using it, even if it sees noise types that it never saw before, it is able to recognize them and separate them from each other.
So this is a very simplified explanation of how it works. Obviously there is a lot of IP. Audio is very difficult, it turned out. If we knew what.. I mean we were not audio experts. Our team is very strong at math but we didn’t have any experience in audio. And I would say, I always say, if we knew how difficult audio is we would be just scared of it and we wouldn’t start this. And yeah, we were lucky that we didn’t know that because many teams who have prior audio experience, they are still struggling with this.
MATT: What do you think it was about not knowing audio that allowed you to take a different approach or succeed where others haven’t been able to yet?
DAVIT: This is sort of the classical approach to the audio problems, like to digital signal processing problems. Like, DSP, digital signal processing, the theory and like everything is there for three years or three or four years, it has been out there. And if you are a DSP engineer or audio engineer, building microphones and speakers, you are trained to think from those constrained perspectives, from this classical theory perspective, from this classical algorithm perspective. If you need to solve something, that’s where your brain goes by default.
And from our team perspective, like when we started the company we were seven people and six of them have PhDs in math and physics, I am the only one who doesn’t hold that. So we have a lot of experience in math. We understand the math required for dealing with audio and machine learning, but we didn’t know the existing theories. So that was easier for us to start doing new things, which was required because when you do.. with a machine learning approach, you don’t necessarily need to use a lot of the old stuff that has been developed for four years. And I think that was a key difference.
MATT: It sounds like you’re compressing the audio a bit and maybe doing some low pass filter?
DAVIT: We are not. What we do in Krisp is.. Well, even today, yes, Krisp is only working with wide band audio, up to wide band audio, which means like 16 kilohertz of sampling. Great. That’s great for.. Well, I am currently using a Bluetooth headset.
MATT: And Bluetooth compresses a ton, right?
DAVIT: Yes, exactly. So it does it by default. But even if I use a full band microphone, Krisp today would down sample to wide band before doing the processing. And the reason for that is we have spent a lot of time on optimizing our technology for CPUs. There is no such technology running on CPUs. People can (run those algorithms?) on GPUs easily but for CPU it’s very hard to squeeze that. So we have spent a lot of time on doing this. That’s one of the reasons why we decided to stick with wide band.
At the same time though we are in a week –
MATT: Stick with wide band as opposed to what?
DAVIT: To full band. So, down sample to wide band. In a week’s time frame we are going to.. I believe it’s in a week.. we are shipping a new version of Krisp that is going to support full band as well. That has been a very long effort for us to squeeze these neural nets to understand the higher frequencies of voice as well and then but at the same time be able to run on CPU.
MATT: Do you use a GPU if it’s available?
DAVIT: No, we only support CPUs.
MATT: Why is that?
DAVIT: Well, two reasons. We could support in video GPUs and they are very powerful, it’s very easy to run neural nets for instance on these GPUs. And when you do that, the CPU is off loaded, that’s great. But Krisp is used in enterprise by a lot of professional users who don’t have GPUs. So most of our population of users, they have just CPUs. And the GPUs they have, like the [00:17:22.06] GPUs I have on my Mac, is just not capable of running this neural net. It’s just too small for that. So we decided to spend this extra effort, a lot of effort actually to support everything out there rather than just focus on one type of hardware deployment.
MATT: And to also be clear when you’re talking about squeezing the neural nets, Krisp all runs locally on your computer, right?
DAVIT: Yes, absolutely.
MATT: Which is awesome so there’s not the latency of going to the network and the audio data is not being sent anywhere else, it’s all happening locally. What does it mean to squeeze itdown? Are you worried about download size or the runtime or how much GPU it’s going to use…?
DAVIT: Privacy has been very important for us and we are very, very happy that we were able to actually run this locally. We don’t think the audio should through a server, especially in this world, privacy is very important.
So to explain what it means, this quiz for the CPU, like as Krisp is a virtual microphone, it sits between the actual microphone and the app. In this case, it’s the browser app running Squadcast. So Krisp is between them. And it needs to run its neural net on every other frame in real time and without introducing too much latency, so that means that it keeps receiving these frames and it needs to not only not look too much forward in the audio so that it doesn’t introduce this artificial latency but also not spend too much CPU power so that it can keep up with our speech.
So that is very constraining from an engineering perspective. And that means that you need to squeeze and make your neural net smaller and more efficient and use, I don’t know, the right library that fits best for this kind of mathematical problem so that it runs properly on the target CPU. Does that make sense?
MATT: Yes. And it’s only about 70 megabytes now. When it has this new full band neural network will the download get larger?
DAVIT: Yes, it will get a bit larger. Even in the 70 megabytes we have multiple neural nets. So we have neural nets that work for like the eight kilohertz sampling grade, we have neural net that supports larger. And then you know that with Krisp, Krisp works directionally, so if I have Krisp, I can remove the noise coming from you and that has a different neural net.
So there’s a lot of engineering actually in this simple app. I believe we have like there or four models, like neural net model shipped today and with this new version we are going to have, like, six or seven models shipped. So a lot of… yeah.
MATT: Wow, that’s actually a fun feature a lot of people don’t know about Krisp is that if someone is annoying you with bad audio, you can actually filter them as well so it sounds good and you would never even know that they have a dog barking in the background or something.
DAVIT: Yes.
MATT: Was that in the original version or did that come up when you were talking to people who weren’t using Krisp yet?
DAVIT: No, that was in the original version. And in the very original version, one of the challenges we had, we didn’t know how to structure Krisp. We didn’t know whether they will be using more of this inbound noise cancellation or outbound. Like, what is more important for people? And that was such an interesting question. Like, do you worry more about your noise or do you.. are you willing to pay for canceling your noise or are you just.. you don’t care about that and you are willing to pay for other’s noise.
So when we shipped in the very original version, inbound was entirely free and then the outbound was a pro feature. [laughter] But then we changed. Now it’s a freemium product. Krisp comes with two hours free every week and then if you go to pro it becomes unlimited. And the pro is going to get some more very cool things very soon.
MATT: It is such a good deal. What is the latest pricing on it?
DAVIT: Right now the pricing is $40 a year. That’s going to change soon because this was a Covid pricing. When Covid started we started a program with which all the students (in universities work?), universities, garment workers, hospital workers, would get Krisp for free for six months. And we also dropped the price by 20 percent, 30 percent. Actually we went with that for like seven months now and we are bringing back the price, it’s going to be $60 per year.
MATT: Even at $60, when you look at how much money I’ve had to spend to make the room quieter.. you’re basically getting a full studio and a really great microphone and everything.
DAVIT: Yeah, absolutely. We plan to keep that price but we are going to add some very cool things in the near future around virtual backgrounds and more even greater noise cancellation. So yeah, we are working hard on this.
MATT: Cool. I can’t wait. I will be a top customer. How much latency does that introduce right now?
DAVIT: On the algorithmic side the latency is between 20 and 30 milliseconds. On the app side, the application introduces an additional 20 to 30 milliseconds. So overall it’s around 60 milliseconds.
MATT: I did do a video where I posted.. I think I recorded just using QuickTime video and used Krisp to take out some background noise and people could tell that my mouth was just a little bit off. So if you had a way to also introduce the delay to the video so it synched up, I think that would be pretty nice.
DAVIT: I’m not sure that was Krisp. Usually with Krisp you wouldn’t notice the difference. Video is doing a lot of things which might contribute to that. Like, we are using Krisp everyday with video, obviously, with Zoom, we have never noticed that. There are a lot of reasons why you might have latency but I.. I mean, everything adds up, obviously, and this 50 to 60 milliseconds might contribute at the end if there is enough latency but that is just not enough to be noticeable.
MATT: Yeah, on Zoom I’ve never noticed it, it was only when I was recording this video. So you’re right, there might have been something else maybe in the HTMI conversion or something where it just felt a little bit out of synch.
DAVIT: Yes.
MATT: I actually didn’t notice it at all and then I started getting some comments about it and I was like, ohh I kind of see it. Kind of like when you use a sound bar with a TV, sometimes it can be just a little bit off.
DAVIT: Yeah, yeah, it’s interesting. We won’t see that, like our eyes usually are.. get adopted. But for example, when you use a virtual background in Zoom or Microsoft, you start noticing it. It’s there. You start seeing that. And even when you move there is latency, yeah.
MATT: What’s the latest going on with hardware? So for example, I know that old MacBooks had a terrible, terrible built in microphone and the latest 16 actually sounds pretty good. I think John Gruber on Daring Fireball posted an audio file just straight off the Mac 16 microphone and it sounds like they’re doing something that’s better. So what are they changing and what do you think about it?
DAVIT: You mean from an audio perspective?
MATT: Yes.
DAVIT: Oh, I’m not really sure. I think Mac is a high end, like usually using a high end microphone and speaker, although we are not.. I don’t think people are very happy with what that high end means. So yeah, I’m actually using it.. I mean, I don’t do podcasts, obviously, that’s a more important question when you do podcasts, but yeah, for everyday communication what they have works great. But I’m not really following what’s happening on the platform.
MATT: Check it out, I’m kind of curious. And I’m also curious more broadly how much do you think some of this gets built in by the phone makers, the laptop makers versus [00:26:52.07] software?
DAVIT: Yeah, I have no doubt that this kind of technology is going to be there in every device in the next three to four years. Typically phone venders, they don’t like to make changes like these kind of changes, they are a bit slow on that. Because as you can imagine, they already know how to build these multi-microphone systems on the phone and they have everything, like the lines set up for that, they know what the yield is and everything. So any change there is going to take time.
But I have no doubt it’s going to happen. So but it also depends what is that that’s going to happen. Like noise cancellation, even today, Krisp is not perfect. So we are spending a lot of time on improving what’s out there and we.. In the next year, hopefully in the next six months, we are going to shift something inside Krisp that is going to be just revolutionary in terms of noise cancellation because it’s just going to take this to the next level. And I don’t think something like that is going to come to hardware soon enough. It’s going to take some more time.
But in terms of when these devices will have noise cancelation, I have no doubt that in the next two or three years everyone is going to have some version of noise.. like ML based, machine learning based, noise cancellation, no doubt.
MATT: And how do beam forming mics work? I know some of the new headphones, like the Bose and also the Facebook Portal and or the Alexa devices have these mics that seem to be able to pick you up from all the way across the room.
DAVIT: Yeah, the way they work, they have multiple microphones on the device. And when you turn on the device and you start talking to the device, it starts to calibrate and it starts to sort of.. given that these microphones are far from each other, they start to understand where the direction is coming from, where the voice direction is coming from, and they start to focus only on that direction. And again, like using the same technique that I explained, they are trying to ignore anything else that is not coming from that direction. That’s beam forming.
The problem with that is when you keep moving around, it needs to recalibrate again and again and I’m not sure that it’s.. the technology is able to fix this problem just by its own. It might be very useful for far field, like for Portal or Alexa, which is in a big room and they need to fix the noise problem, but I’m not sure how efficient it is. We are not dealing with this problem. Actually we are not dealing with far field as well, that is a very, very different problem. Although it might be similar but in audio every problem is so unique and we are not dealing with that.
MATT: That’s interesting. And one more technical question. You had mentioned full band and wide band, how should people think about their Bluetooth headset versus a USB headset versus other things and what type of audio is being captured by the computer that Krisp is receiving?
DAVIT: Yeah.. By the way, I am not an audio expert, I should.. [laughs] I should say that.
MATT: Oh, sorry.
DAVIT: We have a lot of audio experts in the company. But I know as much as I know. In terms of Krsip, Krisp doesn’t really matter where the audio is coming from and that’s one of the beauties of these machine learning based algorithms. You can even, what we have, you can even run it in the cloud because it really has no hardware dependency.
Let me give the example of inbound. So imagine I have Krisp here, you talk and I can cancel the noise coming from your audio. So when you talk there is so much transformation happening to your voice starting from the microphone, that the microphone has its own transformations, including noise cancellation and then the browser gets it and sends it over webRTC with all the codec and everything. And then it receives here on [00:32:09.24] and gives to Krisp and then Krisp runs its technology on it.
So pretty much it doesn’t matter where you run. You could easily run it in the cloud. So from that perspective it doesn’t matter whether it’s a USB microphone or a Bluetooth microphone or just a wired microphone, the (ordinary?) microphones. It doesn’t matter. Obviously we have to add the support for all of these but from an audio perspective it doesn’t matter.
Usually Bluetooth audio has more latency, it’s just there with the Bluetooth transport. You might notice that with Air Pods. If you have Air Pods usually the.. I don’t know why but something doesn’t work very well with them when it comes to latency. Sometimes it’s just too much latency with Air Pods and without Krisp.
MATT: Maybe because they have to connect to each other as well as.. as far as [00:33:17.27].
DAVIT: Yeah, I mean, the connection is one time. You connect and then there is a connection. But sometimes the latency adds up. I don’t know what they did wrong there but I hope they will fix it. But with USB, it’s usually more powerful, less convenient. But yeah, I mean, in general that’s the.. Krisp doesn’t care really where the audio is coming from.
There is one more thing, when you use a Bluetooth headset, if you just listen to music, it’s using its highest frequency, like it uses all the frequencies possible –
MATT: Yes, a higher codec, right?
DAVIT: Exactly, yes. But when you turn on, when you start a call, when you start using the microphone off your headset, it brings everything down to wide band typically. Like some –
MATT: Wide band is 16 kilohertz?
DAVIT: Yes, like 16 kilohertz, exactly. And the prior version of these Bluetooth headsets, they would bring your voice to eight kilohertz. You know, that’s not great. But –
MATT: And it’s kind of like using fewer colors to paint a picture, right?
DAVIT: Yeah, yeah, exactly.
MATT: So it doesn’t build sound as full or as natural.
DAVIT: Yeah, yeah. Every time we use a telephone, when you call a phone number, most of the world is still using eight kilohertz codec because they just.. to transmit less data. So that’s, we are used to that. Bu t when you hear full band and then narrow band, which is eight kilohertz, you will see the difference. It’s a big difference.
But so if you are using a Bluetooth headset, there is a big, big chance that it will down sample it to wide band in the calls. And this is because they need to use.. from an energy perspective, from a processing power perspective, they need to keep it efficient.
MATT: It’s actually amazing. I recommend folks.. If you have an iPhone, try calling a friend who also has an iPhone using FaceTime audio versus just a normal phone call. It is astounding how much better you can hear them and understand them. It actually makes phone calls pleasant again.
DAVIT: Yeah, yeah, yeah. Obviously it’s using VoIP and like the best codecs out there. I mean telephony still wins I think because of the network, like the service providers, like the AT&Ts of the world, they dedicate the bandwidth to voice channels, like telephony voice channel, and then the rest is used by everyone else, like the data channels. So your VoIP is going to impact it if the signal is not strong enough but the telephony voice will still be there.
So I guess that’s more important than the higher frequencies of the voice because you can at least hear each other. But that’s going to fix, it will be fixed with 5G. So once 5G is deployed, I’m sure those problems will go away. And everyone will switch to VoIP.
MATT: Cool. Actually I think even now they use voice over LTE by default for a lot of.. by default on the new iPhones.
DAVIT: Do they? I don’t know if that technology is even live. I don’t know if there has been any VoLTE deployment. Maybe I’m wrong but I thought…
MATT: It definitely is on like AT&T and Verizon here in the U.S. but probably not internationally.
DAVIT: Oh, okay.
MATT: It does sound a lot better if both sides are on it. But well I feel like cell phone calls drop so much anyway…
DAVIT: Yes.
MATT: It’s funny, when I was a kid, I remember spending lots of time, hours on the phone. And then your parents would pick up the phone and you’re like, Mom, I’m on the phone. But now I feel like people don’t do phone calls as much anymore partially because the quality is so bad, it’s very frustrating.
DAVIT: Yes, I think it depends on which part of the world you are in. As I know, like in Japan and South Korea, like, I guess nobody is using telephony anymore. Everyone is on VoIP. And it also depends on the network connection. That’s why like if 5G is there, if there is enough bandwidth, why would people use the telephony.
There is one use case though that I really believe is going to still thrive is phone numbers. Phone numbers are such a cool concept. We don’t appreciate them that much but they are the most deployed, known, understood, like handles that we have. And everyone can reach out to you, although it’s spam of course with the promo, spam. But I think that technology is not going to go away. I thought about that a very long time. And I think it’s going to stay around. I think there’s a lot of things that you can build on top of phone numbers and it’s going to thrive.
MATT: I can tell some of your Twilio days coming through.
DAVIT: I know, I know it’s definitely coming from there. [laughs] Yes.
MATT: I really love that we’re able to do a deep dive into Krisp. I can’t wait to see what you’re launching in a week or two. I’m looking forward to the update. I’m going to do a ton of audio tests and record things with different mics and try it all out. So thank you so much.
You are also running a company. And I know that you all were mostly in person I think in Armenia before. How have you adapted and how has it been and what are you planning to do once we can be safely in offices again?
DAVIT: So our company is distributed between the U.S. and Armenia and we have a team member in Germany as well. So we are distributed. We have a big presence in Armenia. I spend a lot of time in Armenia and my co-founder as well. So before Covid, we were spending a lot of time in the Armenia office, although everyone else was remote. And after Covid obviously we are working remotely.
And right after I think Covid started, I guess two weeks in, we decided that Krisp must become a remote-first company. And it’s not because of Covid, we always had that idea because it just makes so much sense especially for us because we are focused on building a tool that helps remote folks. So we always had that idea but Covid catalyzed that.
And yeah so I think at the end we are going to become a hybrid company because we have the office and a lot of people actually enjoy being in the office a couple days a week. They might not have the right set up in the house, they might have kids. And so just like I personally like to come sometimes to the office because that’s how my brain works, it needs that environment.
But at the end of the day, 80-85 percent of our workforce today just doesn’t come to the office because they enjoy working from home. And actually one fun fact – we also have a program called Work From Forest. So every week [laughing] we have 10-15 people taken to some nice place outside, you know, countryside, and they have internet, power, and they do hikes. And they actually work as well and it’s very efficient and productive work happening.
MATT: That’s so cool.
DAVIT: Yes, I’m in love with this program. So yeah, so like –
MATT: So this is happening right now? You just are able to do it in a distanced fashion, Work From Forest?
DAVIT: Yeah, yeah, yeah.
MATT: Well that’s a new one for us, I haven’t heard that one before. I think it’s a great idea.
DAVIT: Yeah, I highly recommend that. It’s quite popular now in our office. And I think it’s going to evolve. One problem with that is the weather, if the weather is good or not. But I think we will find a solution for that as well. It’s a great way for people to still gather together and see.. when you see each other in person, and that’s a very important part of building a culture and relationships, but they don’t have to come and sit in the office for that.
And yeah, we are determined to continue growing as a remote force, global company. So we are very excited about that.
MATT: Awesome. Well I can’t wait to see what’s next. Davit, thank you so much for coming on. If you’re listening, please get Krisp.ai as soon as possible so your calls sound better. If you get in soon, you can get their $40 pricing but it’s a good deal even at $60. And yeah, as you go distributed, make sure to check out the other episodes of the Distributed Podcast, there might be some good tips for you or your managers there. So thank you again for coming on.
DAVIT: Thanks a lot, Matt.
MATT: All right, you have been listening to Distributed with Matt Mullenweg. Please subscribe or tell your friends or rate it and we’ll keep doing this. See you next time. Bye-bye.
Episode 23: Lara Hogan on the Secret to Being a Successful Manager
Jul 24, 2020
Are companies setting up their managers for success? What are BICEPS? How do you assemble your colleagues like a management Voltron?
Lara Hogan is the founder of Wherewithall, a firm that specializes in management and leadership training — a company that Automattic has worked with in the past. She’s the author of Resilient Management, a must-read for anyone who is a manager, wants to become one, or generally just wants to learn how to be a better teammate.
Lara spent a decade growing emerging leaders as the VP of Engineering at Kickstarter and an Engineering Director at Etsy.
MATT MULLENWEG: Hello everybody, this is Matt Mullenweg with the Distributed Podcast. I cannot think of another time in my entire work career when we’ve been so faced with so much dramatic change in so little time. How we come together, how we listen to each other, and even how we understand ourselves can define the future of our companies right now in this pivotal time. What does it mean to be a good manager or leader in this moment?
Today we’re going to chat with Lara Hogan, she is the founder of Wherewithall, a firm which specializes in management and leadership training and that Automattic has worked with in the past. She is also the author of a book called Resilient Management, which is a must-read for anyone who is a manager, wants to become one or generally just wants to learn how to be a better teammate.
She spent a decade growing emerging leaders as the VP of engineering at Kickstarter and an engineering director at Etsy, both companies known for their excellent engineering and execution. So thank you so much for being here.
LARA HOGAN: Thank you so much, what a lovely introduction.
MATT: We’ll make it easy with a one-sentence question. What’s the secret to being a good manager?
LARA: [laughs] Oh, this is going to be such an annoying answer of mine, but it’s listening. It’s so obvious to me how this all boils down to how we as humans are not really trained to listen. We are trained to share our knowledge, we are trained often to teach, we are trained to set direction, but we are so rarely trained to listen and that seems to be the crux of most things.
MATT: How did you learn that?
LARA: I’m going to say the hard way by… [laughs] by not listening. I think that especially in engineering land so much of the value is placed on the information that we can provide to others, what we can build, what we can create, again what we can teach. And the act of listening is not really I’m going to say valued in an obvious way.
So for me, when I became a leader or a manager, I just kind of assumed that everybody was functioning the same way that I was, needed the same things, valued the same things, liked the same kind of feedback or recognition. And I’m going to say I learned the hard way that that is not the case. We are all pretty unique and special.
MATT: How would you describe how you like feedback and communication and everything?
LARA: I have started to hone how I ask for feedback in terms of after I give a workshop or a talk. I much prefer for people to read it first and digest it before I talk about it. I was a public speaker before I was a coach or a trainer, just giving talks. And I found especially at lots of tech conferences I was receiving a lot of unsolicited feedback, a lot of which was gendered, and it was really hard to be able to distinguish the stuff that was really valuable from the stuff that was this one person’s opinion and perspective and not actually valuable to me getting better as a public speaker.
And I started to realize if I could read it first and digest it first I wouldn’t get so amygdala-hijacked, my fight-or-flight mode wouldn’t kick in. So now these days I always try to ask for feedback written first, that way I can digest it and then talk about it afterwards. Because still, digesting it with somebody is also equally important. But for me I need my prefrontal cortex, the rational, logical part of my brain to be online before I can really have a healthy conversation about feedback.
MATT: One of my favorite things about distributed work is how the asynchronous nature allows for you to catch that amygdala hijack.
LARA: Yeah, yeah. It’s funny though, a lot of people think that when you’re distributed you can’t notice it as much in the other person. You can’t notice when someone is amygdala hijacked. And I don’t think that’s true at all.
MATT: You don’t even notice it.
LARA: You don’t notice it if you’re not listening, I guess I’ll put it that way. But if you’re watching for it, if you’re sensitive to this other person’s body language or voice, if you’re on over video, or obviously if they’re on the phone with you, if you can only hear their voice, you can still tell if someone is not themselves.
And via text, when someone’s text-based communication changes from their normal pattern, either more long-winded if they are more terse usually or more terse if they are long-winded usually, these are all… If you’re looking for it, if you’re paying attention to it, it’s so easy to tell, I think. I don’t know. How has it been in your experience?
MATT: That’s very interesting that you mention people becoming more long-winded. In my experience you can pick up clues for sure in how people are showing up or their responsiveness or the timing. There is lots of metadata in how we communicate that and we can have clues, but I don’t know if it’s a perfect signal the same way that reading someone’s face might be.
LARA: Totally.
MATT: Not that that’s a perfect signal but maybe it feels better.
LARA: Yes it feels like we can get more data usually when we have the extra sensory experience, absolutely.
MATT: And we’re wired to pick up on lots of those things, even if subconsciously around physical presence that we might not get from text.
LARA: Totally.
MATT: That’s why, yes, text is definitely I think one of the superpowers but also one of the weaknesses of distributed organizations, or at least ours. You mentioned listening, do you mean that for listening to others or listening to yourself and what is the relationship there?
LARA: When you asked the question, I was talking about listening to others but I think when it comes to the feedback question I needed to get to know myself first before I could be able to direct others and how I would much prefer to receive feedback. One thing that I’ve learned is that I’m really bad at listening to my own body. I have a chronic illness and it flares up whenever I’m stressed out, which I learned when I was in my early twenties was a thing, and until then I just didn’t pay attention at all to what my body was telling me.
MATT: Wow.
LARA: You know? So it’s one of those things that once you start to realize that you need to pay attention to those extra signals, you start to pick it up elsewhere in the world too. Like about the long-winded thing, I can tell when someone is over explaining when they’re normally pretty succinct, I’m like, oh, something is going on for this person.
There’s these five common forms of resistance in humans that — again it’s not a perfect system but it’s a nice framework to think about. If we notice one of these and it’s unusual in the person that we’re talking to, one of these five forms of resistance, it’s pretty likely that their amygdala has been hijacked.
Again, that lizard brain, that fight-or-flight response has kicked in and they are all about fighting, verbally fighting, questioning, or doubting, like playing devil’s advocate, avoidance behavior, just being really checked out, looking for an escape route, trying to leave the team or leave the project, leave the company. Or, my personal favorite, which is bonding, which is when you go and try to talk to other people to either process, verbally process what you’re feeling, or just try to find comrades who might agree with you on it. But once you start to pick up on these five common forms of resistance you start to see it everywhere.
MATT: Is there a fun acronym for remembering those?
LARA: I wish, I really wish. This is the longest one it took me to memorize just because I haven’t found a good acronym yet. [laughs]
MATT: You have a book called Resilient Management, which is a fantastic guide to understanding management as a practice.
LARA: Thank you.
MATT: So many people get promoted into management as a next step in their career or whatever feels like an upgrade, but they are not always given a playbook.
LARA: No.
MATT: Maybe there isn’t even a playbook for how to do that. What should organizations do when they promote people to set them up for success?
LARA: Even that word promotion is so unique to organizations. Some organizations do view it and treat it like a promotion, like you’ve now got this new level of responsibility and power and title and then that’s true. Some organizations say that but then there actually isn’t that much of a change in power, responsibility and title. And others treat it more like it’s a role change, which is actually my preferred way of thinking about it just because these skills don’t come naturally to most folks, just like any discipline.
So for me I think a lot about it as this is a new rule with a new set of skills, a new set of responsibilities, often more power, but that doesn’t necessarily mean it’s a level up from what you were doing before. It just means that there is a new heaviness than what you were doing before. So I like to think about it in terms of okay, what are the skills that someone might need to be successful at this new kind of role that they haven’t really done before.
MATT: Yes, we’ve tried to decouple some of that by when someone starts managing people they don’t get a compensation change.
LARA: Yes.
MATT: And vice versa if they ever want to stop that wouldn’t be a downgrade. But yes, I did use the word promotion. [laughter] So you mentioned that there’s skills needed.
LARA: Yes.
MATT: In your book you had something that did have a cool acronym called the BICEPS model?
LARA: Yes, I love talking about this, thank you so much for bringing it up.
MATT: Let’s dive in.
LARA: It’s funny, I also… Right now we’re in quaran-times and I talk about the BICEPS model more now than I ever have done before. So this acronym, BICEPS, was coined by Paloma Medina. And she helped us come up with this handy acronym so that we could easily remember what are the six core needs that humans have at work. And I think that managers are not the only ones that need to pay attention to these things because all humans have these six core needs in different amounts.
So I’ll really quickly run through the acronym. The B stands for belonging. So it’s how do we belong to a group? Any time we feel othered or left behind this core need is going to feel threatened. And just like all of the six core needs, this comes from evolution. We needed to belong to a group in order to survive, so any time we feel like oh, everybody’s going out to lunch without me, that’s your amygdala trying to keep you safe. So just keep that in mind, even though a lot of these might feel very like non-events, our amygdala… they are not trivial to our amygdala.
The I is for improvement and progress. We need to feel some kind of forward motion in our work or in our careers, in our life. We need to see change and improvement in the things that matter to us. Any time things feel stagnant or it doesn’t feel like we’re learning, those core needs might feel threatened.
The C stands for choice, which is effectively autonomy. This is a funny one where we all have a different amount of choice that feels comfortable. Paloma, who coined this acronym, she needs like 98 percent choice in her work-life but that would stress me out so much. I need a solid 80 percent. We are all different. And we need just the right amount, not too much or not too little.
E stands for equality and fairness. We are seeing this so much right now come up not just with the pandemic and how members of minority groups are more heavily impacted by COVID, but also with the Black Lives Matter movement. When humans perceive a lack of fairness we will take to the streets, we will riot, and this is equally true in the workplace. Any time there is a perception of a lack of fairness, organization psychologists see teams ripped apart, companies destroyed, usership decline.
MATT: I have actually seen research as well that shows that it occurs in primates as well, the perception of unfairness. It seems like very, very deep inside us.
LARA: Oh yes. All of this.. There is that great video of the two monkeys.. [laughter]
MATT: Yes.
LARA: All of these things, we see all of these things in animals because, again, this is how we evolved. Our amygdala really… This is not pseudoscience, this is neurology of our limbic system.
So the P stands for predictability. We all want to have some sense of certainty and understanding what’s going to happen in the future. Just like choices, we need a balance, too much predictability and things will get really stagnant and we’ll get demotivated and de-energized and totally bored. But too much unpredictability and we will also freak out a bunch.
And the last one is significance, which is effectively status. We want to know where we sit in the informal or formal hierarchical structures and how we relate to the power around us.
So yes, BICEPS. If I think about this over time, significance used to be the one that would come up most often for me. My amygdala, if it felt like my status was threatened, my amygdala would lose it a little bit. But honestly, since April 2020 predictability is the number one thing I need. Just the volume of change.
And everybody is so different. So when we think about mask-wearing, we can actually track back why someone might not wear a face mask to any of these six core needs because they show up super differently in all of us and the same stimulus can threaten any of them.
MATT: Could you do that for me just so I understand? Would that be choice?
LARA: Absolutely. Yes, choice is absolutely one of them. I want to have autonomy over my body. I want to have autonomy and control. Don’t tell me what to do. So you can see how choice might come up. Fairness, it’s unfair that I have to do this, it’s unfair that in order for everybody… I need to get mine. We could do belonging, we don’t want to feel like the uncool kids, we don’t want to feel like we are… we want to feel like part of the in-crowd and who we are surrounded by.
I mean, I know this is true where I live. Like the more and more I see people not wearing masks I’m like, oh, if everybody else is not doing it, what am I doing? Now obviously my core need is going to be different there — predictability, I need to have… And choice for me too. I want to have control over my own health and I want to have some semblance of what the future will hold so I’m going to choose to wear it. But yes, you can see how the same stimulus can threaten…
Which my normal thing I like to talk about is desk moves. I don’t know if you’ve ever worked for a company where desks were assigned or where people were told to move where they sat every day, but it absolutely caused the most emotional reactions in folks. I talk about it with re-orgs too. Every time there’s a re-org it could threaten any of the six BICEPS core needs.
MATT: Acquisition?
LARA: Oh, absolutely, right. Precisely. Literally anything. It’s so relevant.
MATT: The desk move resonates a lot for me because when I moved to San Francisco I worked at a company called CNET Networks. And I started with this really cool corner office and then a VP saw it and I got moved into an interior office. And then there was a re-org and I got moved to the basement and I felt like… oh gosh, who’s that guy from Office Space with the stapler?
LARA: Yes, absolutely. [laughs]
MATT: That character. Don’t take my red stapler. And then I started Automattic. I thought, oh, okay. I probably overcompensated for the lack of office moves.
LARA: I’m curious, if you think about those six core needs in that example, which ones stood out for you?
LARA: Yes. [laughs] Yes, it can absolutely threaten multiple, which is why this stuff is so hard because you can’t guess, you really have to think about it and process it. And we are really bad at guessing other people’s… Like when you were telling that story and you mentioned the corner office, I was like it’s going to be significance for Matt. But you didn’t start with significance. You listed it eventually in your list but it was choice first.
We are really good at projecting our own onto other people but again, coming back to the listening thing, we’ve got to start asking lots of genuinely curious open questions and listening to people’s answers and preparing to be surprised by what we hear and not just assuming.
MATT: One of the other ones that stands out is fairness. Again, at this moment in time we’re at where there is so much going on is people’s perception of fairness to a third party might be unfair. So there’s almost a point of view to fairness.
LARA: Absolutely. And we all are our first person —
MATT: How do we navigate that? What did you say, we’re all our own..?
LARA: Our own first person. We are all the protagonist of our own story, things are happening to us. And so any perception of fairness from where I’m sitting is going to be very different from where you’re sitting.
Which is why as managers I think it is so important to develop some of those empathy muscles, but mostly just to do this act of reflecting back what you’re hearing the other person say to make sure you have it right. Like, okay, what I’m hearing you say is blah and then just asking “is that right? Do I have that wrong?” and waiting for them to respond is so powerful. And triple-checking that again you’re not just projecting or assuming, that you don’t have it wrong.
MATT: And by these being amygdala lizard brain reactions, is it also fair to say they are not always rational?
LARA: Yes, they’re almost never…
MATT: Like your rational mind might disagree with it?
LARA: Well it’s funny, so your amygdala, its whole job is to be looking out into your environment for threats, threats and rewards, that is the only thing it’s categorizing. And if it gets a sense that a threat is headed your way, if the threat feels significant enough it actually tells your prefrontal cortex, the rational, logical part of you, to go on standby.
Because your amygdala is a lot faster than your PFC and your amygdala can actually make sure it can keep you safe. It can tell you to run and jump and duck and hide to avoid danger. If split-second decisions were left up to your prefrontal cortex we would never have survived the many wooly-mammoth attacks that got us to where we are today.
So when we are amygdala-hijacked our rational, logical brain is nowhere to be found. And on average it takes about 30 minutes after you have removed the threat from your environment for your PFC to come back online, and that’s if you’re not still stewing on it. If you’re still stewing on it, your brain is still releasing these chemicals into your body from your amygdala, it’s just like nope, still in threat mode. So it can take a long time for your rational, logical brain to come back online.
MATT: Do we just live in an era of these always being activated?
LARA: With the pandemic I am seeing it all around me. And our PFC is a finite resource anyway. Usually by 3 or 4PM in our workday it’s shot. No more decisions should be made. The eight-hour workday is an absolute lie when it comes to this.
So it is already a finite resource and the fact that our amygdalas are just constantly on overdrive, every single thing right now is a threat, physically, emotionally. I think about all the parents who are struggling also with figuring out… everybody in their household, all their amygdalas and their core needs, it’s just… Our poor prefrontal cortexes are overloaded at the moment.
MATT: Well knowing this how do we not become victims in this story?
LARA: The number one thing I recommend to folks is to figure out what’s your number one core need right now. Like I said, it’s usually significance for me and then after about a month of not figuring out what I needed, like, really having a hard time, I started to think about okay, what’s mine? If it’s not significance right now, what’s mine? Feeling this bad right now is a clue to me that I’ve got to do some more thinking and research.
So once I put my finger on the fact that it was predictability, I put a little sticky note on my laptop, I still have it here actually with a little star next to it that just says ‘predictability,’ as a reminder to myself the I need to optimize everything in my life for creating this. Because I can’t get it in the outside world. I don’t know when a vaccine is going to hit, I don’t understand what the next few months are going to look like, so I need to take every opportunity I can to create more predictability.
In my case, I had… the vast majority of my income for Q2 and Q3 were coming from in-person workshops, so me talking to a room of 40 managers. Obviously those could no longer happen. So how do I take this complete lack of predictability — and obviously compounded with other things, lack of choice, lack of fairness, yada yada yada — but really try to say okay what is one thing I can do today to create more predictability?
And again, predictability might not be your core need right now but it’s really important for everybody to take a look at this list of six core needs and say, okay, what is my number one and how can I make sure I’m reminded every single day to get one new thing to happen to nourish this core need? Or, if I have to choose between two things, as yourself which one is going to get me more of that core need right now? Use it as a north star to help you out of this season that we’re in.
MATT: I want to dive into knowing this for others. But first, a quick sidebar since again a lot of the people listening to this work at distributed companies. Have you developed any thoughts yet on virtual or non-in-person versions of what you do and what could be effective?
LARA: Yes. So I almost exclusively now do this virtually. I’ve been able to, thank goodness, within about three weeks of everything changing, create a bunch of new workshops that are more ad hoc so people can sign up for the individual workshops, one-on-one, or, it’s so easy, I’ve always brought them into distributed companies anyway, I’ve just made it much more of a clear offering.
Just last month I had this opportunity to do this leadership program for a distributed company’s employee resource group for marginalized genders. So it was a four-week global program all over video and it has just been… who knew that a pandemic could really bring to the surface some really important business decisions for me going forward.
MATT: Wow.
LARA: Yes.
MATT: And also for anyone listening, they can get in touch with your website, right, Wherewithall?
LARA: Yes, Wherewithall.com, two Ls. Thanks, Matt.
MATT: Perfect. Well no, I think obviously we’ve been a customer in the past and hope to be one again in the future.
So we’ve talked a lot about the self-awareness version of the BICEPS and asking the questions. You refer to some of these questions for asking others. So if I’m a manager and it feels like someone I work with is really having a reaction that doesn’t seem rational or that’s not moving things forward, what should be my first thing to do? Because normally telling someone to calm down or something would be counterproductive.
LARA: Yes. Any time someone has told me to calm down I think it has had the opposite…
MATT: Right? [laughter]
LARA: My amygdala is like, oh yeah? See this?
MATT: Just relax.
LARA: Yes. [laughter] So when I’m a manager my choice here will be dependent upon my relationship with this person. Either we have worked together a bunch in which case they are familiar with the BICEPS core needs list or they are someone who I think would be cool talking this through.
I find that handing them this list, showing them the website, or showing them a handy link, it actually does this beautiful job of bringing someone’s prefrontal cortex back on line because what you’re doing is asking them for a second to do a little bit of a problem-solving exercise, like it’s a puzzle. Like, okay, which of these six things is it? It’s a beautiful practice in getting your prefrontal cortex back online.
So if they are already familiar, if I think they’re going to be interested in the brain science stuff, I will describe these core needs and just have a very frank conversation. I will say let’s read through these together and as we do this start to think about which one or maybe multiple of these might feel really true for you right now?
But let’s say I don’t know them that well or it doesn’t feel like this is a time to go into the brain science part or to walk through this acronym together because sometimes that can feel a little cheesy, like here’s this management framework. So in the other case I’m just going to ask them one of these really short, open ended questions that starts with the word ‘what.’
Okay, let’s just take a step back. What feels really motivating to you right now? Or, cool, I just want to at a high level start to think about what’s the number one most important thing on your list? What’s your north star right now? What are you optimizing for? I will pick maybe max two of these questions and ask them after giving them lots and lots of space to unload and process out loud.
Usually from that I will start to then reflect back what I’m hearing, like, okay, so it sounds like if you had had more choice here or if you could have made this decision yourself, that would have felt better. Do I have that right? And then they’ll say yes or no and we’ll go from there. That’s me pinpointing what this might be. And hopefully down the road we can actually have a more fun chat about BICEPS core needs but even if we never get there at least I can figure out okay, let’s creatively address this core need for this person.
Because they can’t get it.. In the corner office example, you were moving into the basement eventually. You couldn’t have controlled that. But as your manager I might have said, okay, where can we get you some more choice here, or where can we create some more significance for you here?
MATT: It seems like the interrupt there is almost like that pause and question and reflection.
LARA: Mhm, yes. It’s pretty magical. One of the things that I learned in coach training that I would have never realized was happening until I saw it firsthand was the act of giving someone space to share what they are thinking and not responding with what it means to you, not responding with ‘oh yes, and also this.’
And not coming up with the next thing you want to say while they’re still speaking but actively listening, actively hearing them, and then reflecting back what you just heard them say is this really bizarre, beautiful thing that happens. It is just so rare that we have someone actually listen to what we are saying and then triple check that they have it right. Yes. I can’t describe how powerful it is.
MATT: I feel like I can do the more often than not if I’m in real time with the person having a conversation. But often with asynchronous work, I arrive at the scene hours or maybe even days later. What would be a way to apply that in an asynchronous manner?
LARA: That is a great question. I think that a lot of this too is going to be dependent upon what you’re optimizing for, what your core need is. If my amygdala is hijacked there is no amount of intention I can put into it to be a good active listener.
So I think from a distributed community perspective, checking in with yourself and making sure that your prefrontal cortex is active as you’re reading through messages or as you’re getting ready for whatever your next thing is, triple-checking that your amygdala isn’t super active and online but rather you’re feeling pretty chilled out can help to be a centering moment before your start to read these messages.
Now it is a super natural thing to read a message and say okay, how does this relate to me? Okay, how does this impact the thing that I want to do? Or, what are they trying to ask of me right now? Those are all very ‘me’ focused, which is by the way normal. That is a normal human thing that I think is appropriate. It’s just about what is the impact that you want to have.
If the impact that you want to have is to move a project forward then it’s totally okay to have your own perspective and to be thinking about how it relates to you and the project. If your intention is to make this person feel really supported or really help them grow, that’s when it’s really important to have that reflecting back, make sure that you’re actively hearing what they are saying and not thinking about how it relates to you.
MATT: Is there a version of this that could improve Twitter?
LARA: [laughter] I can’t imagine. Because Twitter is all about the one-to-many voice. It’s not about active listening. I find that with Twitter the thing that helps me a lot is tweeting questions instead of statements. I found this especially when I try to enact some change. Because then it’s like I’m trying to communicate a statement via a question, not a leading one, not saying what if we tried blah, blah, blah. But rather saying okay, in this moment…
Let’s pretend what I’m trying to do is get everybody to start to think about their BICEPS core needs. Instead of saying, hey, here is this really cool framework, here is how it has worked for me, you should all check it out, I might say, hey, what is most motivating to you right now? Just a rhetorical question. Just take two minutes and think what is most motivating to you right now or what is terrifying for you right now? Then compare and contrast to this link and see what you think. It’s actively asking a question that prompts an introspective response that I think can be real valuable.
But yeah, I don’t think that Twitter is usually the medium for enacting huge amounts of change. That’s my opinion.
MATT: What’s interesting is our internal blogging system, or email, often has elements which are public, it might be public to a smaller audience, but… I find that people can… When you have that amygdala reaction and that becomes memorialized in a written thing there starts to be an identity that you end up defending it a bit more or being attached to it than you might if it were just part of a conversation.
LARA: Absolutely. And the creators of the character The Hulk really tapped into this. Bruce Banner and The Hulk are the same person but we know more about The Hulk. We can associate The Hulk, we think about that character so much more I think than most of us think about Bruce Banner.
So if all that’s documented is your Hulk version… And by the way, The Hulk is just literally Bruce Banner’s amygdala growing three sizes. When we get amygdala-hijacked we turn into different versions of ourselves, versions that we’re not proud of. So if what’s documented about us is our Hulk version that’s what we’re going to be known for.
And honestly, any time that stuff is memorialized, you’re totally right, I’ve got amygdala triggers, I know what they are. If anybody brings up the hills that I’m going to die on, my Hulk version of myself is going to be right near the surface.
MATT: Hmm, I definitely have got to think about that. I have heard myself in recent months, in conversations, where I was trying to be open and vulnerable but the person on the other side of the tweet screen I felt like was the opposite.
LARA: Yes.
MATT: And that can be challenging. And probably the best thing then is just to walk away, or at least what I’ve tried to do.
LARA: Yes. A lot of my workshops and coaching sessions that are focused on these things are all about developing a back-pocket script for yourself. To end a conversation with a promise to return to it once everybody’s amygdalas are chilled out but to end it in a way that doesn’t escalate it, to actually end it in a way that feels safe and can help everybody chill out.
I like to have something really short that feels natural to say and then a really quick, like, here’s the next time we can check in about this. Mine, because I work with so many people who I talk about this stuff with, mine is literally I’m so sorry, my amygdala is really hijacked right now, can we talk about this at our next one-on-one, would that be okay?
And for people who know me those are real, natural words that I would say. And so it’s easy for me to pull that out of my back pocket and it’s a signal to everybody, like, oh, one or both of our amygdalas is on fire right now, you’re right, let’s chill out for a bit.
MATT: You have a great moment in the book where you talk about tapping into the best qualities of your colleagues like a management Voltron.
LARA: Yes, yes.
MATT: I’m liking a little bit of a comic book theme here.
LARA: [laughter] Yes. It harkens back to the 1980s television show, Voltron, where you have a group of super heroes that come together and form a giant super robot, à la Captain Planet or any number of television shows.
MATT: Power Rangers?
LARA: Yes, Power Rangers, exactly, they come together and form a giant thing. So the idea here is we as individuals, we often rely on our manager for their support and their coaching and their mentorship to learn and grow but that manager is just one person. We all are just one person that has a particular set of skills and experiences and ways that we can help each other. So your manager can’t be your everything. I think to the managers of my past and how each of them always had some things I could learn from but not all the things that I needed. [laughs]
So the Voltron idea is that you shouldn’t just lean on this one person to support you as you grow but you should amass a Voltron of different kinds of people each of whom have a different set of experiences and perspectives and skillsets who can come together and be your ideal manager. And that’s going to be custom to the individual.
Like what I need from my manager is probably very different than what you would need from a manager. So it’s important to think about what are the things that I need in order to grow or based on where I am in my career or the kind of company that I worked for. When I left Kickstarter and started doing more consulting work, I got to experience so many other kinds of companies that were not primarily public benefit corporations or mission-driven organizations but totally different kinds, different ages, different sizes.
And so to have a perspective from someone else who understands those kinds of organizations, who can share with me their ways of operating or their opinions or their frameworks, has been invaluable. And that list of people needs continue to grow as you grow.
MATT: How do you walk the line between realizing when other people’s amygdalas might be hijacked and trying to deescalate or come back to the conversation with something like a tone policing, or something you would normally encourage people not to do?
LARA: Absolutely. I think it is really important to state your goal. Because without stating a goal, people might perceive your action as shutting them down. So saying something like…
Like, in the feedback example, now when someone comes up to me after I give a talk, if it’s in person, which who knows when that will happen again… [laughter] But in the past if someone came up to me after a talk I gave and was like, “Hey, great presentation, can I give you some feedback?” I have learned to say, “I would really love to hear your feedback, I just know I can’t right now, do you mind sending me an email?” Which is my way of stating the goal — I am interested in hearing this feedback or I am interested in continuing this conversation, I can’t.
You don’t have to say my amygdala is hijacked. And you don’t have to say that the other person’s amygdala is hijacked. You can just say hey, I really deeply care about us coming to a good solution here, or I really want to make sure both of our needs are met in this one.. It feels like now is not the right time for our brains. It’s so important to me though, when can we chat about this next, maybe when we have had some time to chew on it?
MATT: And how has that gone?
LARA: Oh, so well. Who is going to be like, no? [laugther]
MATT: I need it to be written. Well, probably not someone who you want to hear from.
LARA: Right. It’s actually been really funny because I had this one person come up to me after a presentation and ask me that question, I said… I didn’t actually say even you can talk to me later, in this case I just said “no thanks,” because there was something about the situation that just didn’t feel right, didn’t smell right.
And he took a step back and he was like, “whoa, I was always taught to say that but I’ve never actually had someone say no before.” And I was like, “cool. What else do you want to talk about?” And so we started talking about something else and then maybe five minutes later he was like, “oh, whoa, I see why you said no.” As in like, “we needed to chat first.” It was almost like the act of me saying no opened up this whole new world of possibilities for him about the way that these conversations could go. [laughs] It was really cool.
MATT: Really beautiful. I’m glad that went that way.
LARA: Yes. But contrast that… I was playing a video game the other night with a group of people and two people got really amygdala-hijacked and one person tried to wrap it up, tried to be like, okay, let’s reconvene, let’s do this raid later, we shouldn’t be doing this right now. And they were both in such an amygdala-hijacked state that neither of them could hear it.
And so I think in those situations, no matter how polite you are, how clear you are, how whatever you are, sometimes our Hulk moments will continue to play out. In that case, I tell people to take the space that you need, do what you need to be safe, to keep your brain and your body safe. Exit that situation.
MATT: It seems like video games are also where you’re going to be riled up.
LARA: Always. It’s amazing to me.
MATT: That’s kind of the purpose in some of them.
LARA: Yes. Well, there’s a lot of studies about it. And coming back to the core needs at work, there’s this brilliant study about belonging where they ran this experiment where some people weren’t chosen as players in a video game and the same parts of their brains lit up as if they were experiencing physical pain. Again, belonging. All of these core needs are core to how we have evolved. Like any time we feel left out… So yes, video games are absolutely… Just all of these things can totally threaten our amygdala.
MATT: What video game should all managers play?
LARA: I think every manager should get practice leading a raid group or leading a guild of some sort and trying to corral a group of six people around a section of a video game. It teaches people so many management skills, it’s amazing to me. [laughter]
MATT: That’s cool.
LARA: Yes.
MATT: Which ones do you like? I’m not as into… or current on video games. What do you recommend?
LARA: I can’t say that I can safely recommend them but the ones that I am currently playing, the one in particular is called Destiny. It’s just lots of aliens… keeping the solar system safe from some aliens. It’s nice to be able to be vegetable-mode after my amygdala and prefrontal cortex have had a long day, to just check out. Video games have definitely been a safe place for me to recuperate.
MATT: That sounds like a lot of fun and I will take that as some homework as well and try to make some time for that.
LARA: Amazing.
MATT: Thank you so much for this conversation. I learned a lot and I really appreciated that you’re taking the time to share your experience and your learnings with a wider audience.
LARA: Thank you so much for having me. It has been a pleasure.
MATT: All righty. This has been Distributed with Matt Mullenweg. And Lara, where can people find out more about you, Twitter, websites, etcetera?
LARA: People can come find me at @Lara_Hogan on Twitter or on Wherewithall.com.
MATT: That sounds good. I encourage everyone to do so. We will also include links to these questions that you mentioned and more in the show notes. So check that out at Distributed.blog.
Episode 22: Raj Choudhury Sees a Future Where You Don’t Have to Move Your Family for a Job
Jul 03, 2020
“We have introduced so many frictions to people’s lives by forcing them to move.”
Prithwiraj (Raj) Choudhury, the Lumry Family Associate Professor at Harvard Business School, studies the future of work — specifically the changing geography of work. What happens to cities, to immigration policies, and to issues around gender equity when more companies let people work from anywhere?
Choudhury earned his doctorate from Harvard, has a bachelor’s degree in computer science from the Indian Institute of Technology, and an MBA from the Indian Institute of Management. Prior to academia, he worked at McKinsey & Company, Microsoft, and IBM.
MATT MULLENWEG: So here we are. It’s been more than three months into this global transition to remote work. And let’s be honest, a lot of this has been difficult and exhausting and even for folks at Automattic, who have been doing distributed work for 15 years, it’s quite different when there is a global pandemic and economic uncertainty everywhere.
But there have been a ton of positives too. I’ve heard from many friends who are working in knowledge-worker roles and they’re saying “I never want to go back into a full time office,” particularly with the restrictions that these physical offices are probably going to have. So they’re seeing benefits in their productivity, their lifestyle, and their connection with their families and their life. So there is uncertainty but there is also opportunity.
Today I am excited to speak with Raj Choudhury, a professor at Harvard Business School, who is focused on questions around the geography of work and the outcomes of mobility on productivity. He has studied this question very closely and I was excited to find out what he has learned. So welcome, Raj.
RAJ CHOUDURY: Hi Matt, thanks for having me.
MATT: Oh it’s a real pleasure. What brought you to study all this?
RAJ: So I’ve been studying essentially the future of work, but the topic I have been studying for a long time is geographic mobility. So that includes studying both cross-border migration but also what happens to productivity when people move within the same country.
And as I was doing that research for the past eight, nine years, I discovered that there are lots of reasons why people do not move. So yes, there’s productivity benefits when they move but there are tons of reasons we have immobility. So the obvious reason would be immigration, but dual careers, even the cost of living, which might be super expensive in a place like Silicon Valley, might constrain geographic moves.
So as I was doing that research, I was thinking of solutions to that problem. And then I stumbled upon that U.S. Patent Office experiment with letting people work from anywhere, which would presumably solve this problem of trying to move people to Alexandria, Virginia. So that’s how I arrived at this topic.
MATT: And people moving for work in the U.S., I have heard it’s gone down actually over the past 20 years or so.
RAJ: That is correct. So we are in this era of not only people moving less within the country but also internationally. We just have all these constraints on immigration not only in the U.S. but it’s tightening in many parts of the world. So the other great example would be what’s happening with Brexit and what it means for the talent coming from continental Europe. Yes, so I think we are in this phase of immobility on the rise.
MATT: So here’s where I say something random I’ve heard and you can tell me whether it’s correct or not. I’ve heard part of the, one of the hypotheses for why in the U.S. mobility was going down was double-income houses. So it was harder to find two new jobs in one city versus one new job.
RAJ: That’s true. And there is also research done by other colleagues, not me, which has shown that in those dual-career situations, Matt, it’s typically the wife who is the trailing spouse. So women have made disproportionately greater sacrifices in dual-career situations. And that’s among many of the reasons why I am super excited about working from anywhere.
MATT: Because even if one spouse can get that flexibility, they can maintain. If one spouse has it and one spouse doesn’t, they can still move, because one of the jobs is not geographically constrained.
RAJ: That’s true. And one of the subpopulations that I’ve been working closely with for whom this is a huge deal is military spouses, because they just have to constantly be on the move. And now they don’t have to experience a break in their careers. So I think that group and many other groups have been tremendously benefited with work from anywhere.
MATT: That’s awesome to hear. Because if we get this right it benefits so many people’s lives.
RAJ: Correct, yes.
MATT: These past three months I don’t think any of us would have predicted, but it must be a boon for your data collection and research. So what has happened that you found surprising or unusual or heterodox?
RAJ: Actually I would argue that these three months are such an anomaly. This is not normal work in any way. Even under normal, remote work, you are not having to homeschool kids, you’re not prohibited from going to the gym, you’re not stressed out because of people being sick in your family. So I feel that this will be less relevant for research in terms of driving generalizable findings.
So what I’ve been doing is I’ve been studying work from anywhere years before the pandemic and I feel once we come back to a more, quote/unquote, “normal” situation it will be, again, fun to see what happens with which companies and which workers stick with remote work. I think that is something I’m super excited to study going ahead.
MATT: Yes, there have been a ton of announcements already — Stripe, Shopify, Facebook, Square, Twitter. Is there anything coming out of that? Are we seeing more mobility from their employees or any early indications? I know it’s too early to see big data but…
RAJ: Yes. I think there’s been tons of very exciting announcements. And I can tell you about one project which I am personally working on very closely and that relates to TCS, which as you would know is the largest IT service company headquartered in India. I hesitate to call them an Indian company because they are truly global. They have 500,000 employees, they have three campuses in China, they have campuses in the U.S., they have a campus in Hungary and of course tons of campuses in India.
And what they did in the past six weeks was the CEO made an announcement saying that 75 percent of their workforce would become remote in three years. So that is one situation I am working closely with because this… It’s probably four to five times of Facebook and they have built all these campuses and for them now to go 75 percent remote, I thought that was super interesting in terms of the challenges they have to overcome and the change in the processes and the culture and whatnot.
MATT: One thing I heard from other companies when they worked with partners in India that had offices, it was harder for people to work from home because they might not have the home setup which is as productive as the office, meaning literally internet, power, etcetera. Have you come across anything like that?
RAJ: So I feel that’s still true in parts of not only India but parts of emerging markets. But I feel with now better fiberoptic connectivity and all the transitions… In the case of India, just this one single Reliance Jio sort of proliferation has increased internet penetration and speeds tremendously. So I feel that is less of a concern now.
And just given the tradeoffs. So I was speaking to a group of TCS employees and many of them said they will now leave large cities, like Chennai, and move back to their native villages because that’s where their family lives, that’s where they really want to live, given a choice.
MATT: We ran into this in South Africa. We bought a company based there and a lot of people would want to go into the office, it was just much harder to get fast internet at home, like it was maxed out at DSL. I even had a colleague outside of Austin that ended up having to put a tower on his property because he’s a little more in the country and there wasn’t a good wired service. So he had to move to some point to point wireless.
When you think of the hierarchy of distributed work, internet is probably the base. It’s like the oxygen in the room for getting that.
RAJ: Sure.
MATT: I’m curious if wireless will be able to support mass people doing high bandwidth things at the same time. It’s definitely scaled far beyond what I would have imagined. But we shall see.
RAJ: Yes, you’re right. But the way I think about this, Matt, is not only internet and wireless but it’s also the host of other services that remote workers would need, including schooling, good quality schools, healthcare. But I feel it’s a chicken and egg. So my conjecture, my belief at least is if large numbers of people experience a reverse brain drain and move back to middle America or move back to smaller towns in emerging markets, those services will follow.
So the other project I’m working on right now is with Tulsa Remote. So Tulsa Remote, as you might know, has been —
MATT: Yes, I just blogged about that.
RAJ: Yes, so I’ve been working with them and it’s been a super interesting situation to study from many, many perspectives for me.
MATT: Do you want to talk about it really quick for the podcast listeners?
RAJ: Sure. So Tulsa Remote started about two and a half years back and the intent was to bring remote workers to live in Tulsa, Oklahoma. So they offered, as an incentive, $10,000 to each person moving. And these were people moving from the coasts, from Houston, Texas, and they would be all working remotely. And what they keep saying…
So, as I did all this work over the past few months, they keep saying that $10,000 is just the starting point for the discussion to begin. So no one would move their family and their lives for $10,000, they would move for other reasons. And one of the reasons might be it’s cheaper to raise a young family in Tulsa, Oklahoma. Or you are the kind of person who wants to really contribute to a city which desperately needs to think about diversity.
So they have been extremely successful. They moved I want to say about 200 to 250 people in the past. And this is all pre-pandemic. But they got like thousands of applications.
MATT: Wow.
RAJ: And the applications were extremely diverse. They were people from all parts of America, all races, and a large number of women who moved. And the wonderful thing that it did was in choosing who should come they involved the Tulsa local community. So there was actually a wonderful event that they organized where community members voted with Post-Its on applications just to make sure that these guys coming in would feel welcomed by the community.
MATT: That is pretty cool, although I don’t know why you’re taking people from Texas. [laughter] I’m in Houston right now, actually.
RAJ: Yeah.
MATT: One of the big fears that people have for distributed or remote work is that people will not be as productive, like if they’re not in the office how do I know they’re working. What have you found there so far?
RAJ: I think that’s one of the fears. So I feel the setting that I studied extremely carefully was the U.S. Patent Office setting. So there actually the benefit was that productivity was extremely objectively measurable. You knew to almost the day how many patents were being examined by each patent examiner, so shirking was less of a concern. But I can see that to be a general concern in many settings that people will just shirk and there will be free riders on teams.
The other concern I have… and I don’t think people will explicitly state this… but managers seem to have this expectation in many cases that their questions… they’ll tap a shoulder, ask a question, and people will respond in the minute. And I feel the change in mindset, which is critical, so as I studied there all-remote companies such as Gitlab and Zapier, the realization I had again and again was you will not get an answer right away because people might be in a different time zone.
So you need to move towards asynchronous communication, put your stuff on Slack, and then just trust that people will wake up and answer your question. But I don’t think that’s an easy habit to change. And you might have a perspective on that given your experiences. But I feel the fear of shirking and giving up that freedom or that flexibility of letting people answer two hours after I posed the question would be the two biggest changes in habit.
MATT: Yes. I think that if you can unlock that asynchronicity it’s really, really powerful for organizations. But it is an adjustment, particularly for managers. Shirking, I think that you have the problem that people could do less work but then it’s easier to see because you have solvedthe problem for people who would do everything that looks like work in the office — they look professional, they show up at meetings, they ask questions but weren’t actually producing anything.
RAJ: Correct.
MATT: Which I think is maybe a larger epidemic in the professional world.
RAJ: Yes.
MATT: Where a lot of people do the things that look like work but aren’t actually contributing to your bottom line.
RAJ: Yes, yes, you’re totally right. I feel especially… If the productivity measures are objectively defined, I am sort of like… You know, many people have asked me in the past few weeks what do you think about surveillance, putting automated software on computers. And I keep thinking that is a horrible idea, that has to backfire. I feel yes, you need some productivity measures that are objectively defined but you totally need to trust people, your colleagues, your subordinates. That trust is going to be a key part of the culture of being a remote organization.
MATT: Do you yourself work distributed with your team?
RAJ: I do, yes. So I have been doing this even before the crisis and I still have to be physically at Harvard while teaching but who knows, maybe in a decade that will change as well.
MATT: Yes, are classes going to be reopening there?
RAJ: We don’t know yet. I think there will be some hybrid form is my expectation but I don’t know. I’m going to teach in the spring, which might be different from the fall, so who knows.
MATT: That will be interesting to see. So much of the value it seems like from these higher institutions, especially the super prestigious ones, comes from people being together.
RAJ: Correct. But I think the general principle… And that collocation argument can be made for any organization, right?
MATT: Mhm.
RAJ: And before I stepped into the world of Gitlab and Zapier and Seek, my prior, like many others, was that this can work for certain rules, so maybe if the person is working independently, for coders and designers this might work, but then working with Zapier and working with Gitlab and working with Seek, I have come to realize that this can work for any role, any level of the hierarchy, as long as you have the supporting organizational processes and the culture baked in to support this.
MATT: What do you think the macro economic implications are for this new way of working?
RAJ: I think about that all the time. And especially, as you probably would have realized by now, the form of remote work I am most excited about is work from anywhere. So it’s not the work from home that is being forced on us right now. So in work from anywhere once again you can choose where to live. So you can relocate to a smaller town or to your country, back to your country, or even to a rural area.
And you might work from home there or you may actually work from a co-working space. So the Tulsa Remote people are actually offered a co-working space in this facility in Tulsa that is called 36 Degrees North. So you could choose to work at home, that’s totally cool, but you don’t have to.
So when I think of work from anywhere, I feel there are lots of very, very interesting macroeconomic implications. First, you will experience a reverse brain drain coming back to the smaller towns of middle America and back to the emerging markets. We will see urban decongestion. So we’ve been predicting two and a half to three billion people to live in the cities, maybe we will actually see half of that. And once the white collar folks move back, there has to be blue collar folks who are incentivized to move back too because there’ll be more construction in these smaller towns, there will be more services in the smaller towns.
So the climate outcomes, the urban congestion outcomes, you can just think about all the second-, third-order effects. And I feel that is the thing that really excites me about the phenomenon.
MATT: Yes, the blue collar work moving seems to make sense, right? I imagine it’s not called trickle-down economics but is there an academic term for when people move back and start injecting their salary back into the local economy?
RAJ: Yes, it’s a classic multiplier effect. So once enough white collar people move back there’ll be construction, there’ll be all kinds of needs for restaurants, and healthcare workers and everyone else. And then what might happen is that this urban mass migration that we have seen with… not only in the U.S. but worldwide… and some of the cities in the emerging markets are really, literally breaking at the seams.
So if you go back to my home town of Calcutta or Taka or Bangalore, it takes three hours to get from point A to point B, which is ridiculous, right?
MATT: Wow.
RAJ: And with all kinds of negative externalities on climate outcomes and whatnot. Water — water resources are just like completely out of proportion in those locations. So I feel once enough people, the white collar force, moves back, the blue collar force will not have to leave those smaller towns or the hinterlands of those smaller towns.
MATT: And is that because these towns, or these cities in emerging markets, grew up too quickly versus where in the U.S. they were able to grow over hundreds of years and build more infrastructure along the way?
RAJ: That’s partly one. But I also feel, just given the dynamics of what I would call agglomeration economy, something that Ed Glazer and Enrico Moretti at Berkeley and others have studied, there was almost a gravity pull towards these extremely large global cities. So Bangalore got identified with the IT service industry, Delhi with the NCR region, with call centers. The same thing happened in Manila, the same thing happened in multiple Chinese cities.
So I feel once we now let people choose where to live, especially if a large number of millennials start not moving to the cities… And the other interesting thing about millennials is this global… the globe-trotting that goes on with the digital nomads. So if we see enough of these complementary phenomena, then we’ll see less congestion in the cities and then the blue collar work doesn’t have to move to the city and live in terrible conditions in the slums.
MATT: Sometimes I wonder as well if we’re seeing a homogenization of cities where cities are starting to look more like each other than they do the more rural areas even surrounding them.
RAJ: Correct.
MATT: Because there is this kind of like global culture that much of the economic growth has been concentrated in. I have heard it called the Airbnb aesthetic, [laughter] the exposed brick, the Edison lightbulbs, the open plan seating. But that was all in an environment that really rewarded people being physically proximate as one of the benefits.
RAJ: Yes.
MATT: And that was already under I feel like attack from an academic point of view, meaning that open plan offices appear to be less productive than when people had privacy, or private doors, and now it’s under attack from a biological point of view, where now that has an increased risk from something like a coronavirus.
RAJ: Correct, yes.
MATT: Interesting, interesting. You mentioned Ed Glazer?
RAJ: Yes.
MATT: Who are either your colleagues or people doing research in the field that you think everyone in remote work or distributed should know about that they don’t?
RAJ: So I guess the thing is remote work was so out of the paradigm of mainstream prior to this crisis. There has been research of course, so Batia Wiesenfeld at NYU has been studying remote work, Ravi Gajendran at the University of Florida has studied remote work. There is a very, very good paper by Nick Boom and colleagues at Stanford where they looked at this Chinese call center. There was an actual experiment there where they measured productivity before and after working from home. And then we, I did the work with the U.S. Patent Office.
But I feel the field academically is probably still at very, very early days. And now I see tons of people joining the field, which is great, so I’m super excited about that.
MATT: What would be most helpful to your work? You probably have dozens of CEOs listening to this as distributed companies.
RAJ: I guess what I’m super interested about is whether this crisis… I will tell you what I’m not excited about, Matt, and then I’ll tell you what I’m excited about. I know a lot of academic energy is being spent trying to understand whether productivity will dip or not dip in these three, four, six months. And I feel that is an exercise which is not very helpful because once the crisis is hopefully behind us soon, we will not be in a crisis anymore, so why do we want to generalize the findings from a crisis? And just my prior productivity is going to dip.
And academically the thing is studying remote work now is confounded, as we say in economic parlance, by the stress and the lack of child care and the lack of separation between the work life and the family life. What I am much more interested about and excited to study with anyone who is interested is whether this crisis acts as a turning point for remote work and especially work from anywhere to move from an HR discussion to a CEO discussion.
And with others like the TCS CEO, like Facebook, like the companies you mentioned, whether CEOs start thinking of work from anywhere and remote work as a device to hire talent globally… So now I could hire folks from Iran who will never get a visa to come and work in the U.S., or this might be a great way to engage Chinese talent, which is going to get a lot of pressure from immigration going ahead. Whether this would be a great way to bring more women back into the workforce or make them more productive. So I feel those discussions are really, really cool and I am happy to engage with anyone who wants to have that discussion.
MATT: I am also really excited about that. Also for Automattic we are doing it with global pay equity. So we’re not discriminating on the basis of geography and the pay, which I think also opens up a lot of opportunities for all of those places you just mentioned. Although I think Iran and China are.. happen to be places where it’s difficult for us to hire because of the firewall in China blocks most of our services, and I think there’s some sanctions in Iran.
But we have folks in 77 countries otherwise and we try to keep people in the same ranges regardless of what geography in the U.S. or internationally, we think same pay for same work. And that could inject a ton of economic opportunity into places where there’s been less with the way the economy has developed so far.
RAJ: No you’re totally right. So I’ll make three quick points. So the first thing I’ll say is that I’m seeing a lot of opportunities and business models development where Canadian startups, and I am actually working very closely with one of them, they are trying to arbitrage this current impasse with the U.S. immigration system. Because what you can do in a near shore center in Vancouver or Calgary or Halifax is essentially take the people who are getting rejected for U.S. H1B [visas] or a green card, put them in Canada, and they get expedited visa processing there and then they can just work remotely for whichever tech company they used to work for in the U.S. So that’s the first thing.
The second thing is, of course as you said, now it’s not only Canada and the western coast of Canada, now you have the ability to hire talent in Kenya, in northern Scotland, in Bangladesh.
So actually I’ll tell you about Bangladesh. I visited that country last year and I asked a group of CEOs, god forbid if the textile sector collapses, which is happening right now, what would be your next industry? And the answer was it’s going to be software because they have a very large chunk of independent developers who are all on GitHub, they’re all on Stack Overflow, they are incredibly talented, but there is no software firm there to hire them.
So I think work from anywhere is just a gold mine for any global software company to find these pockets of talent in Bangladesh or Kenya or wherever this talent exists. So I guess that’s the discussion. And the gender issue as well. I keep coming back to that because I feel this is such a wonderful device to ensure equity on gender, based on everything I have seen with trailing spouses and the sacrifices women are forced to make.
MATT: What is your take on the pay equity? I have actually had executives in other countries, like India, tell me we’re going to mess it up because the market, the local market won’t support that sort of thing or if it does it will totally distort it and people will have issues with their families and… I don’t know, they seemed to be pretty against it.
RAJ: So let me understand your question. You’re saying that when a company does work from anywhere should you keep the wages at an equitable level or should you play around with the wages? Is that the…?
MATT: Yeah, if the average wage in a different country is 30K versus 60K or something, should you be proportional to that?
RAJ: And I’ve been asked that question a lot recently given what I think the Facebook announcement mentioned that they will allow 50 percent workers to work from anywhere but there might be wage consequences. The way I think about this, Matt, is at least the context I studied super deeply, the U.S. Patent Office, they did not cut wages. So this was actually more money in the pockets of people when they moved to cheaper locations. And more than half of the people in the Patent Office moved to cheaper locations.
I feel if a company adjusts wages downwards, it just immediately creates the potential for a competitor to say, hey we’re going to do work from anywhere but no wage deduction. Right? So I don’t know why the equilibrium will be wage deduction. Just putting my economist hat on, I feel the equilibrium will be some company arbitraging this and saying we are going to skim the talent on the right tail of the distribution by not reducing wages downwards.
MATT: That’s what we’ve been doing, so… But I have also heard on the other side, folks in the wealthier countries, worry that this will bring down the average. Like if there is a global minimum wage it’s probably not $15 an hour like they’re moving to in the U.S. So what’s the answer there? I’ve seen people say that people are worried about robot automation but actually global… equality opportunity to global jobs will probably have a bigger impact on the middle class in America than almost anything else.
RAJ: Yes but the flip side of that argument is that even if I’m in America, I don’t now have to live in Silicon Valley and support Silicon Valley cost of living. So if indeed that happens, like hypothetically that happens, then the option available to the Silicon Valley worker is to move to Tulsa where it is way cheaper to live and it’s probably an order of magnitude closer to what the emerging market cost of living is in many parts of the emerging markets.
So I feel that is the equilibrium that might emerge. Yes, if the wages on average get depressed but it’s still equitable, then the expectation would be that in the U.S. people would leave the super expensive cities and move to places which are cheaper to live.
MATT: But like you mentioned, they might not have the infrastructure for things like education yet. One thing I’ve heard from Bay Area friends is they want to move but their kids are in a school that they really, really like and there is no equivalent of it in some of these… in a place like Tulsa or Houston yet.
RAJ: That’s true. And that might change very dramatically. But also that might change because the schools themselves might go partly remote, right? So I feel there are lots of opportunities to innovate on business models for everything, including schools.
So I was actually with a group of 1,000 principals from India a couple of weekends back. And they have amazing teachers and I told them look, you have amazing teachers teaching this class of 50 people while there’s an ocean of students all over the world, especially in emerging markets, so why don’t you think about remote business models where you can leverage the human capital you have? I feel remote work now will extend across all the layers of our society, including all kinds of services.
MATT: That makes a lot of sense and it’d be powerful if it could happen. I know the distributed education experiments haven’t been as successful, at least the ones that I’ve seen yet. But it feels like if we can do work really well and be even more productive from a work point of view, learning should be part of that.
RAJ: Yes. And just one random thought. You mentioned what would be an interesting thing for CEOs to think about? I feel, just like the academic research in remote work is in its nascency, I feel the one area where we are still in nascency, and that’s just my view, is how we do our virtual communication. So be it Zoom or Google Hangouts or Microsoft Teams. So I feel there can be lots of imagination in how we organize our… how we conduct our virtual communication using VR, ER.
So I feel that is one area where I would imagine there would be a lot of interesting things to work on and customize technology to the business models. A school might need different kinds of communication technology compared to a software company, compared to a manufacturing company.
MATT: And the software does make a huge different. It’s funny how… Automattic actually had very few meetings before we adopted Zoom because there were just… they weren’t very good.
RAJ: Yes, yeah.
MATT: People would talk over each other, it wasn’t very high quality, it would be laggy. And I don’t think it was fully a positive thing. I think the pendulum swung where we started doing too many meetings and we had to walk that back a little bit just because the tool afforded it.
RAJ: Yes.
MATT: I think a lot of folks are experiencing that right now where they’re on eight or ten hours of Zoom calls a day and that is not the same as being in a conference room for eight hours. It’s exhausting in a different fashion.
RAJ: Yes. And you’re totally right. So you know… and we talked about asynchronous, that just makes me feel that we need to celebrate asynchronous, we need to have… So Slack is a great tool, it’s a great improvement at least in my opinion. But it’s not the end of the world. I think we can put a lot of imagination in how to do asynchronous communication, but also synchronous communication. And I feel that is one area where I would urge people to think harder and be extremely creative.
MATT: Check out my “Five Levels of Distributed Autonomy” post. I really try to push to asynchronicity as the ultimate level.
RAJ: Yes.
MATT: One thing I have also been trying to get people to do is to change the terminology, which I will introduce for your consideration. Which is remote implies that you are away from something and that there is a central. So I’m really trying to get people to move towards either distributed or decentralized as a way to describe this new form of work because you really want every node in the network to be at equal footing, not that there is a hub and spoke, like I think offshoring or near shoring or remote work has traditionally been tried.
RAJ: I like that. Yeah, no, you’re totally right. I think the thing I keep thinking about is of course we have had all these all-remote models, now we are having some large companies…
So Dell is the other large company we didn’t talk about. They, as you probably know, they have been aggressively pushing distributed or remote work, whatever you may call it. But once we have a critical mass of companies being majority-remote, then we probably need a complete change in terminology because that will be the common paradigm and then the office might be the exception, right?
MATT: Yes, we need a word that says the office is the remote thing, not the… yeah. [laughter] You had mentioned… I actually didn’t know Dell was doing a ton of distributed work. That’s good to know because that’s kind of in my backyard, in Texas. You mentioned the H1B visas. I think some of the companies you mentioned, like TCS and Accenture, are the majority of those, right?
RAJ: That is true. But you know, we just got hold of this amazing data set on the I129 applications for the H1B. So there’s a completely, in my opinion, unscientific cap to the H1B visas. It’s 65,000 plus 20,000 every year. There’s no scientific basis for why it’s not 66,000 or 100,000 or why there should be any cap. And we have looked at the I129 applications, which is an order of magnitude more than 65,000.
MATT: Can you define what that is really quick?
RAJ: So it’s an application to participation in the lottery. So there is a lottery. You have to pay $460, file this application, and then you are part of this annual lottery that the USCIS runs.
MATT: Is that the Green Card lottery or is it different?
RAJ: No, this is the H1B visa lottery.
MATT: Ohh gotcha, gotcha.
RAJ: They only give 65,000 H1B visas and additionally give 20,000 visas for people with a U.S. masters. But the number of applications to participate in the lottery is way more than 85,000. And if you look at the distribution of the company —
MATT: What’s the number of total people who ––
RAJ: I want to say it’s upwards of 300,000 at least.
MATT: Wow, yeah.
RAJ: And you’d be surprised at how many manufacturing companies, U.S. manufacturing companies participate. There’s healthcare with lots of applications from the Philippines, so they try to… there is a large contingent of nurses coming in from Philippines. So it is not just these IT service companies.
And I feel no one has done this study before and we are trying to do it now, no one has calculated the loss to American startups for not getting an H1B visa. Because you are participating in the lottery, if you really wanted a talented engineer and couldn’t get that person, you don’t have a subsidiary, like Microsoft or IBM, so you lost that person forever. What is the loss to a startup for losing out on the lottery? There is no study. And I think it’ll be a very interesting thing to at least document.
MATT: Politically what do you think will happen there, especially in an environment when unemployment in the U.S. is at historic highs?
RAJ: Your guess is as good as mine. [laughter]
MATT: What would you like to happen, I guess is a good question.
RAJ: I can tell you at least what is happening. So I feel that the Canada arbitrage model is happening. And you might call that arbitrage, you might call that being just super smart, but they have figured this out.
So in the U.S., the data, if you look at the data, the bulk of the immigrants who come into the country are coming in on a family reunification visa. And I have nothing against that, I think that is wonderful. But Canada, as a proportion of total visas, gives out a much larger share of work visas. And they have now found these ways to grant work visas in a super expedited way, even as quickly as two weeks.
And there are startups which have negotiated special deals with the Canadian government saying we will find the best talent in the U.S. which is being asked to go home and we’ll move them to Canada, just give that person a visa within two weeks. So they receive the person in an airport, they do the exact same job as before, nothing has changed, but now they are paying property taxes and local taxes in Canada and not in the U.S. So that’s what’s going on right now. So I feel some… We need to pay attention to that from a policy perspective, the local economy perspective of the spillovers that we talked about in the U.S.
MATT: I think I saw that of the cities in North America that are growing, most of them are Canadian, which is funny because Canada itself is only like 38 million people.
RAJ: Yes.
MATT: But if these people are going to cities but cities are also desegregating a little bit because there’s more reasons to live in the suburbs, what happens to the benefits of cities as well? You hear about the creativity born of collisions or the environmental factors that make cities more efficient than when everybody is in the suburbs?
RAJ: That is an interesting question and I can speculate. I feel two things might happen. We might have more livable cities if a chunk of people move to the suburbs or even farther away. We might have much more livable and much more desirable cities.
The cities might still act as a location for temporary collocated events, so even if everyone is spread out all over the country, or all over the world, you might want to do an event every quarter or every year where people come together and then you are not only showcasing new technologies, you are also very actively socializing. You may want to do that event in Hawaii as well, that’s totally understandable. [laughter]
But I think there will also be an upgrade at least in the context of emerging markets on the physical infrastructure and the social infrastructure for the smaller towns, which is wonderful. Because you cannot move, in the case of India, one billion people to the cities, and in the case of large African countries, like Kenya or Nigeria, they have similar problems. So I feel the infrastructure and the quality of life will become better in the smaller towns. So you’ll see that and the cities might become more livable. So it might be a win-win for both cities and towns.
MATT: I have heard even in Manhattan and San Francisco, just with the people who left the cities because of the pandemic, to get out of the city, it has made everything a lot… It’s just taken a little bit of the pressure off the infrastructure.
RAJ: Sure, yes.
MATT: And for San Francisco, even, 50,000 people or 20,000 people would be pretty significant as a percentage.
RAJ: Yes, yes, exactly.
MATT: I guess we are also getting into one of the hardest problems of politics and morality, which is how big of a tent do you talk about? If someone is getting wage pressure on a downward level in San Francisco, yes, they can move within America but it’s helping these smaller cities all over the world. What is the moral compass and calculus there?
RAJ: It’s an incredibly important question to think about but I feel geography can be a great leveler in terms of creating opportunities and wages because there are lots of people… First of all, there’s decades of research on migration, which is documented that not everyone can move given tons of reasons. And we talked about decreasing mobility in the U.S. even in the past few decades. And even if you move your living conditions are probably much worse than if you had not moved. Right?
MATT: Why is that?
RAJ: Think about the international migration that happens from all over South Asia into the Gulf. So these guys are going to work as construction workers or as restaurant workers, and they are probably making a decent wage, that’s why they’re going, but they’re sharing four people to a room. If you read some of the stories that have been documented about these migrants, it’s just terrible, right?
MATT: Yeah.
RAJ: Or the construction workers who move to cities to build these buildings and then move onto the next city and the next building. So I feel if they’re closer to home they not only have a better quality of life, they also have better social networks. So in places where there’s no insurance, social insurance safety net it’s much better to be closer to home because that is where your community or your friends are, your family is. And I feel geography can be a huge leveler in terms of improving economic outcomes and quality of life outcomes.
MATT: What should an enlightened government do there? Because, like you said, some of these stories of the migration, or the immigrant workers the Middle East, sound horrific. And they have I think in some countries even a majority of non-citizens in the country but conditions which sound like modern-day slavery.
RAJ: Yes, it’s a complex problem which doesn’t have one good answer for all sectors and all countries. So of course the construction workers have to move but if more construction work is moving back to other parts of the world, then they probably don’t have to move in the numbers they are moving right now. But in some sectors, you don’t need people to move if work becomes more distributed or what I call work from anywhere.
And I feel it cannot be a subsidy solution that the government is taking care of everything. I feel the economic geography itself needs to correct for many of these frictions. And if the economic geography corrects for these frictions, then, on average, lives and quality of life will improve.
MATT: And like you said, they could be closer to their families or social networks. And typically these visas are generally for solo people.
RAJ: That’s true, that’s exactly true. And so I’ll just give you one example. In China, I just finished this project, there is actually a visa, they don’t call it a visa, but there is an administrative document called a hukou, which needs to be transferred if you are moving from a small town to Beijing or Shanghai. So every person in China gets a hukou at birth and it’s tied to the location of birth and if you are not able to move that hukou to a large city then you don’t get healthcare in the large city and your kids can’t go to school there.
So what the Chinese economy has done for several decades now has leveraged, actually, the hukou to make sure that these migrant workers come and work for a few months. So they come in July to these coastal cities and they stay till mid-January, just before the Chinese New Year and then they clear out, they all go back because they have no incentive to live permanently.
So the kids are all left behind, the kids are being taken care of by the grandparents, and there is actually a whole generation of kids which has got into tremendous problems. And I read somewhere Jack Ma talking about this generation of left-behind kids, fixing their lives is going to be one of his priorities going ahead for the rest of his career.
So I feel we have introduced so many frictions to people’s lives by forcing them to move. And now, if work from anywhere becomes truly a phenomena these Chinese workers don’t have to come every July to the coastal cities, then they can stay where they are, the kids are benefited, they are benefitted, the local economy is benefitted, I think it’s going to be an awesome thing over all.
MATT: What else is going on globally that you’re excited about? Should every city in the U.S. be doing something like the Tulsa experiment or if everyone does it does that negate Tulsa’s ability to attract better talent there?
RAJ: No, I feel we are far away from the equilibrium. So I know Vermont did something similar two years back. The Tulsa experiment was actually done by the George Kaiser Foundation. So it was a private initiative. And my understanding is there’s some discussions going on with the government now to say that if indeed the remote workers come and stay for a period of time there will be some sort of compensation that the government will pay because it’s getting taxes.
But the state of Vermont did something very similar. And I’m just excited about this, Matt. I feel we need experiments to try to get people back to Detroit, you name your favorite small town in the U.S. I feel we need both government as well as private-capital enthusiasm to make this a bigger movement. The equilibrium is decades ahead of us, I think.
MATT: What do you think it will do to the tax base in places like California?
RAJ: Sure, so there will be changes but I’m sure like… And I’ll tell you one thing that I’m studying right now in India, it’s a very interesting story. So in India, they don’t have a hukou, they don’t need a document to move from one place to the other, but there is something called a ration card and the ration card essentially entitles you to subsidized food, which is a huge deal for these migrant workers.
And it has not been possible for several years now to make ration cards portable across India. So ration cards are given based on where you are born and if you move to a different city or a different state you don’t get subsidized food because the ration card is not portable. And the main reason it’s not portable is that fiscal transfers between states — so the state that is experiencing a migrant, or receiving the migrant, is saying why should we pay that migrants subsidized food? That state, the home state should pay us a fiscal transfer. So taxes would be a similar thing.
But I feel if there’s enough private companies doing this there will be government action following it and that’s what’s happening in Tulsa. They have been successful for two years and now the state of Oklahoma, and just given what’s happening with the oil economy there, they are now talking. So I feel policy makers will only engage if there is enough private companies engaging in these initiatives.
MATT: Do we end up in a place where cities really have to compete on quality of life?
RAJ: That would be a good thing, right? So I feel if people have more choice and on average if the quality of life is improving across cities… So one of the books that I got hooked on years back was Hillbilly Elegy. It just opened my eyes to what middle America is. And it broke my heart, like many others. So I feel we need… and now with work from anywhere we have a mechanism, which is elegant and it’s a win-win for the company and the worker, which has an impact on society and smaller towns. So I’m personally super excited about this.
MATT: Cool. If there is an executive listening to this who agrees with you or is seeing that productivity is down in this pandemic, work from pandemic environment, versus work from anywhere, what would you encourage them to look for as things open back up? It sounds like you would encourage them to stick with it anyway.
RAJ: Yes. And I would actually encourage them to think really hard not as an HR policy but think about what remote work, or let’s call it distributed work or work from anywhere, could do for the company’s strategy. And what I mean by that tangibly is what does it mean for having a better hiring policy where you can now hire globally, what does it mean for if you are a CFO, what does it mean for staring at an empty office for three months and what it tells you about the value of that incremental marginal office campus you were planning to build, what does it mean for women in the workforce, what does it mean for career continuity of people? So I feel it’s a great opportunity for us to engage in these conversations and have these conversations at the C Suite and not at the HR manager level.
MATT: Well I think that’s a really powerful place to wrap things up. Raj, thank you so, so, so much. If people, as I expect they will, want to hear more from you, where can they find you?
RAJ: So I have my HBS website and my twitter handle is @prithwic.
MATT: Cool. Well, you’ve got a new follower here. And I can’t wait to see what other research you’ve found. And if myself or Automattic can ever be of help there, please let me know.
RAJ: Absolutely, Matt, I look forward to staying in touch.
Episode 21: Morra Aarons-Mele on Introversion and Anxiety in Remote Work
Jun 19, 2020
Is working from home a breakthrough for introverts?
The answer, of course, is not so simple. Matt Mullenweg’s latest Distributed conversation is with Morra Aarons-Mele, host of The Anxious Achiever podcast for HBR Presents from Harvard Business Review, and founder of award-winning social impact agency Women Online and its database of women influencers, The Mission List.
MATT MULLENWEG: You are listening to Distributed with me, Matt Mullenweg. Today’s guest is Morra Aarons-Mele. Morra is the founder of Women Online, an award-winning social impact agency, and she is also the author of “Hiding In the Bathroom: How to Get Out There When You’d Rather Stay At Home.” A title I love. [laughs] It’s a book that rethinks introversion in the workplace. Interested to hear about her experiences so I can learn more about how Automattic can better serve the many introverts on distributed teams and talk about the theory that maybe distributed is better for introverts. So, welcome, Morra.
MORRA AARONS-MELE: Hi, Matt. How are you?
MATT: Thank you so much for joining. And where are you joining from today just out of curiosity?
MORRA: Right outside Boston.
MATT: Cool. I’m in Houston, Texas.
MORRA: All right.
MATT: I celebrated 100 days here yesterday which is my longest I’ve been here in a long time.
MORRA: Oh my gosh. [laughter]
MATT: So we had a very brief introduction there but what brought you to this topic?
MORRA: Uh, life. [laughter] I didn’t know that I was an introvert with social anxiety, I think that’s an important piece of it, which we can talk about as well, until I was about 35 years old. I would never have wanted to be an introvert when I was younger because I didn’t really know what being an introvert meant. I was really ambitious and I worked in sales and marketing and I talk a lot, I’m not shy. And so I remember even taking a Myers-Briggs once in graduate school and sort of gaming it so that I could be as extroverted as possible because I felt like I should be extroverted, you know?
MATT: How did you game it? What answers did you change?
MORRA: All the answers that are about… This is 16 years ago so I’m… but you know, the answers that are leading you to the E about your interaction style and do you like to be in big groups and all that.
Anyway, so it never occurred to me. But what did happen to me was I was just often really, really unhappy at all my jobs. And I had a lot of jobs. I quit a lot of jobs. I hated office politics. I would get really good jobs but because I was sort of preferring to not be in the ring I would get layered over real quick.
And then I finally quit my last job for good and started freelancing. And it’s like this lightbulb went off when I was sitting at my kitchen table doing the same work I had always done but by myself on my own time, in my own lighting. I was like, “ohhh this is for me.” And as I spent more time working for myself and learning about work styles and workplace flexibility, I began to read up and realized I am really introverted and I have really intense social anxiety and I have been working in an entirely wrong way for many years.
MATT: If it’s worth it, do you mind defining what an introvert is for people and maybe what social anxiety is just so we’re working from the same set of assumptions?
MORRA: Yes. The thing about being an introvert is there is no blood test. So you could probably talk to a bunch of different people and they would say different things. And it’s funny because over the years I’ve had people email me and say you’re not an introvert, you’re a highly sensitive person. You’re not an introvert, you have ADHD. This all may be true but the thing about being an introvert is it’s actually not about whether you are shy, whether you’re quiet, whether you are… some people think you’re socially awkward if you’re an introvert.
It’s really about how you manage your energy and what kind of situations fill you with energy versus drain you. So this is… I think a lot of people know being… engaging with a lot of people, giving a lot of output all day, getting a lot of stimulus back can be really hard for introverts. It’s hard for most people frankly, but introverts just do not get energy from that constant being on with the people in collaboration.
And we are also usually very sensitive to other kinds of stimuli, so lights, noise. If you walk into any modern hotel and it’s full of bright lights and a million different cable channels as well as music piped over the loudspeaker and you want to close your eyes and hide in a dark closet, you might be an introvert.
MATT: The energy part has always been hard for me because I… Like, I love seeing people so much but sometimes I do feel really worn out at the end of the day, but I’m not sure if that’s because it was a great day or that was draining my energy.
MORRA: I mean that’s the thing, right? I think that even extroverts probably at the end of a long day with a lot of people are drained but they would choose to go back the next day whereas most introverts probably wouldn’t. When we gear ourselves up for something like that it tends to be more performative, it’s something that we have to prepare for, something that we have to get ready for, something that we have to rehearse.
And a lot of introverts are performers. Some of our most famous performers, like Oprah and Lady Gaga and people who get up and literally own a stadium are hugely introverted. And this means that when they’re out there, they are giving it their all, they love it, but it is very much about gathering the energy and performing. It may not be a natural switch. You’ll also talk to a lot of introverts and they’ll say, you know, I can go give a speech in front of 3,000 people, no problem, but if I have to mingle afterwards that’s it, I instantly feel drained.
MATT: Did you just say that Oprah and Lady Gaga are introverts?
MORRA: Mhm.
MATT: Wow.
MORRA: Yeah, yeah.
MATT: Mind blown. Today I learned. [laughter]
MORRA: Oprah actually likes to hide in the bathroom to get away from people.
MATT: Wow. You mentioned social anxiety. Do you mind defining that for us?
MORRA: Social anxiety is a learned trait. So introversion is something that we’re naturally born probably one way or the other, although I think it ebbs and flows given your life experience and your life stage. But people might naturally be introverted if they prefer quiet, if they like to be by themselves, if a great day for them involves being with fewer people versus being with more people.
Society anxiety is a learned behavior and it is when you actually fear social interaction and that could be with one other person or it could be a group. It is that experience of walking into a room and feeling like you don’t belong there, everyone hates you, you’re going to make a fool of yourself, it’s really about shame.
Ellen Hendrickson, who is one of my favorite psychologists on this subject, calls it the fear of the reveal. So if you’re listening and you think about a time when you walked into — back when we had networking events — a networking event and you felt like you were a total fraud and that you were scared to open your mouth and talk to people because you definitely did not belong in that room, that’s social anxiety. It can come from being ashamed when you’re a kid, it can come from being criticized if you are a quiet introvert for not talking enough. There’s a lot of reasons why we become socially anxious but it’s really about shame.
MATT: I didn’t realize that one was learned and one you were kind of born with.
MORRA: I mean, I’m not a scientist, but most of the literature would say that introversion is more of a character trait. And the same way that some people really love music and love to work to music and some people need quiet, I think of it like that. You know? It’s just who you are. Whereas social anxiety… Of course there are some people who are more genetically anxious, etcetera, it could be epigenetic, but it tends to stem from learned behavior over time.
MATT: What would you say is the prevalence in society, do we know a percentage for introversion or social anxiety?
MORRA: You’ll hear it all over the map. Anxiety is very, very prevalent. Up to about a third of adults have some sort of anxiety disorder at some point. Introversion, I’ve heard 40% of the population, I’ve heard 30%. Again, it’s on a continuum. So I would think it’s probably between 30% and 40%. But of course a lot of people convince themselves they’re not introverts so they would never admit or they wouldn’t even know they were.
MATT: And that was you at some point, right?
MORRA: Mhm.
MATT: So if 30% of the population — let’s just go with the lowest — is introverted, why are offices designed like they are?
MORRA: Where do we start? [laughter] I think work sucks, the way that most knowledge work places… Actually, the way that most workplaces are set up… Even I see my kids in school, there is such an emphasis on team and collaboration and performance from an early age, it’s really, really ingrained. I think it’s a very western thing. It’s very American.
We have a very old-fashioned view of leadership. It is still based on command and control and usually a white guy in front of the room telling us all what to do. And one thing that I think all the white guys who used to run the world — no offense, Matt — is they liked their people close, they liked proximity so that they could work hierarchically and tell people what to do and then gather everyone together and rally the troops. I’m using a lot of quasi-military language, I realize, but I think that’s intentional.
And so the office really comes out of that model. It is this hierarchical leadership model where being present means you are committed, you are going to go and report to whoever is in charge, be at their beck and call, which they think means just seeing you, it’s not really that they are engaged, it’s just that they are there. And a lot of leaders over time got to be lazy and think ehh, I just want my people here so I can get them to do what I want. I really think it’s just the old models are really slow to die.
MATT: Well there’s probably a lot of CEOs listening that don’t relate to what you just described and I can speak personally that I’ve had impostor syndrome sometimes over the years being like, well, why don’t I travel with an entourage everywhere I go [laughs] like some of these other CEOs I know? And it’s like uhh.. I think there’s some very different models that can be successful.
MORRA: 100%, 100%. And again, a lot of the workforce, even before the pandemic, was distributed. I think though that it is the stereotypes, the reality is different but I think that the stereotypes die hard. I think you see it especially in sales and marketing cultures where there is this sense of being present and being on as a sign of being committed.
And I think also that it’s all down to communication. Communication is not most managers’ strong suit because we’re not taught how to be effective communicators and to be in touch with our feelings and other people’s feelings.
And I’d love to hear your thoughts. I think when your team is distributed and you can’t just gather them in a room, you have to communicate better. Right? You have to rely on different models. And that’s hard work and so a lot of people just don’t want to do that.
MATT: Yes, I’ve been thinking a lot about that it’s… It’s not even being distributed or not or centralized or not but the way meetings, the structure of a meeting tends to reward people who do well in meetings. And a meeting is usually a means to an end. Right? It’s to solve a problem for a customer or it’s a… it’s to have some outcome. And there are other ways to get that same outcome.
MORRA: 100%.
MATT: I think meetings encourage a lot of reaction, so we’re responding in real time versus considering something, thinking about it, editing it. And there is a ton of research already about who speaks up or who is most present in meetings.
MORRA: Well and I’ve seen research, and I think this is true, that introverts, we are not as good on the fly. We actually prefer the time to digest and sit with our thoughts. And social anxiety, which a lot of introverts have, is also a real hindrance to performing, what did you say? Doing well in a meeting, being good at meetings.
And so yes, the way that meetings are set up, the way that a lot of work is set up is really hard on people who think differently. And I always tell introverts who are in a lot of meetings speak early, just say something, it doesn’t have to be earth-shattering, because then you have registered your presence and you are not going to get that look at the end of the meeting of “hmm, Julie, you haven’t said anything, do you have anything to add?” Which is totally, you know…
MATT: Which, by the way, is taught as a best practice.
MORRA: Yes.
MATT: So I do try to… If I feel like someone is really hanging back in the meeting or it’s being dominated by a few people I try to make a space for the folks who might be quieter. But that probably also might be a little terrifying, you know?
MORRA: I don’t like it. I think it’s a team thing, it’s an individual thing, and it’s… I think also if your folks know that you’re introverted they might respond differently if you ask them to talk because they’re like “oh, he gets it.” I think often though it can make people feel like they are being treated like a child and it turns the whole spotlight onto you at the end of the meeting and really can set all those shame bombs, like “why didn’t I say anything, oh my god, they’re going to think I’m dumb, I’m definitely not getting that promotion.” It can really set the ruminating in motion. So I am in general not a fan. It is hard to shut people down though who take up a lot of room.
MATT: Yes. What do you recommend then? Because I have definitely seen it as well where there might be gender differences. Often men talk a lot more in these meetings. And so just trying to make room for maybe the not even introverts but just people who don’t have as much room to speak if you just let the meeting dynamic continue uninterrupted.
MORRA: I think it’s better to keep it general. Like you said, you could say, “You know, let’s hear from some folks who haven’t talked,” because that also shuts down the talkers rather than picking on people individually.
But I also think it’s always worth a one-on-one check-in afterwards because one of the other things that I have learned in my journey is that if you have social anxiety you might talk and blurt out a lot of things that you may regret and that’s your anxiety talking. And so it’s really good for everyone to get meeting feedback from a trusted boss, colleague, you know? Meetings are so essential in so many workplaces, and we’re never taught how to be good in a meeting, that I think it’s worth it to say you know, I loved your ideas but maybe make room for other people. Again, that’s hard to say.
MATT: It’s been one of the things… I’ve been speaking a lot to executives who have unexpectedly moved to distributed. And I have this framework where I talk about the different levels and the highest levels when you can move to be asynchronous. And what has resonated a lot with these typically very extroverted executives is that you can unlock the genius of the introverts in your company. There’s 30% or 40% of your people who aren’t served by your environments or by the meeting structures and there’s a lot of wisdom and intelligence in that 30% or 40%. And in some companies, tech companies, I would argue it’s maybe even higher.
MORRA: That’s right. So what do good CEOs do?
MATT: I think a lot about the structures. So we just had actually a really interesting conversation that I found very tactically useful about how to compensate to make a meeting a little better and if that’s something I thought was maybe helping might have been worse for some people. So, a good example of that. But maybe it’s the concept of the meeting existing in the first place which is the problem.
MORRA: I think that introverts like to prepare and so if you feel like you have talent that is locked up… And so much talent is locked up not even because of introversion but, like you said, because of race, because of gender, because of frankly men who have always just BS’d their way through life and gotten rewarded for it — and women too — who just think that if they talk a lot that’s them being smart. And so thinking about how to unlock people who aren’t getting a word in is really important.
And I do think that a lot of introverts are really great at presenting, they just need to be given the platform and time to prepare. A lot of it is about our obsession with brain storming and being spontaneous. So you can try write-storming instead of brainstorming because brainstorming and big conversation favors people who are comfortable at just jumping in and taking a lot of space.
MATT: It can be fun when it goes well.
MORRA: Oh yeah.
MATT: But it’s a skill which is orthogonal from actual wisdom or intelligence about whatever the problem set is. So I guess our solution there is trying to make it asynchronous. Most of our collaboration happens on internal blogging systems where people can respond. And the design of these systems tries to put the words first. It’s really about the writing, not about the avatar who is saying it or things like that. That still is there so it doesn’t remove it but… And we even take this all the way back to our hiring process. So we will do most hiring just on chat.
MORRA: Wow.
MATT: There will be no audio or video real-time communication.
MORRA: That is super interesting to me. Yes, that’s interesting.
MATT: Well you probably have a lot of folks… Well, most people are not working in companies that are asynchronous, including parts of Automattic are not asynchronous. What’s your advice for them? And you yourself, you have some podcasts, you’re a public speaker, there’s probably a lot of introverts hearing you share your story and being like, wow, I wish I could be more like her because she seems such a natural to all this.
MORRA: Yes, no one ever believes I’m an introvert. I mean for me, I just say it’s just practice and it’s building in structure and boundaries. I think coming back to the Oprah example, Oprah for many years would come into our lives every day at 4PM and carry us in a way that was a gift. You’d never think that this is someone who is happiest on her own and needs to hide in the bathroom to get space.
So I think what’s really important to remember is that introversion is about energy and managing your boundaries. And everything, every work should be about that, frankly. I think we should treat everybody like they are introverts, especially now, because remote work is draining in a whole other way that we can talk about.
Understand what people need in terms of preparation to give it their best, understand the space that they need — if they need you to say, “you know what, Matt is going to take ten minutes now and share some thoughts.” Understand how their day flows and so don’t book a ton of back-to-back meetings so that people can catch a breath and get some alone time in between. Understand their boundaries, like video calling might be really, really hard for a lot of introverts so maybe mix it up with asynchronous stuff, text-based, phone with no video and video.
MATT: You mentioned the challenges of remote work. I’d love to hear your thoughts there.
MORRA: Well I have a lot of thoughts. [laughs]
MATT: What would be the categories that you think —
MORRA: I’m sure you do too. I’ve run my… I had a small company of ten people but we have always been remote as well. So I have been working remotely since 2006, so for many years. And I think that you’ve obviously invested years and years of thought and infrastructure and systems to creating a successful remote workplace, right? As have I.
You can’t just approach remote work the way that you might approach that present office system. I think that again we’re sort of lazy in that we just take one schedule and slap it onto remote so we think, well, if we had the 2PM meetings on Wednesdays back then we’re going to have the 2PM meeting on Wednesdays now and it’s going to be Zoom. Right?
MATT: Yes and it will always be video and it will always… yes.
MORRA: Why? It will always be video. And again, the same things happen but the problem with video and remote meetings is that you… Even the biggest introvert is going to get some kind of buzz by being with people. We’re human, that’s who we are, we pick up on other people. And so we get none of the good stuff in remote meetings and all the bad stuff. We have all the anxiety, we have all the talking over, we have all the stressors to people who don’t like that environment and yet none of the comfort of sitting near your friend or having a donut or getting people’s energy.
MATT: Yes. Sometimes I wonder, and I have felt this, where if you had said, “oh, you get to stay home for a while,” I would’ve been, like, “great!” And now I’m wondering if I’m getting too much of a good thing and maybe losing some of the practice of being around people.
MORRA: Exactly. [laughs] I always call it chunking, chunking your time or pacing your work. I think that the introverts that I know who do it really well have a really good sense of their ideal pace. And they build in a lot of infrastructure and a lot of downtime. And so I think that’s what we’re all responding to is that now we are all separate and we’re all trying to figure out the new rules of work and we don’t have any of the comforts of coming together.
And so if it’s possible and you’re listening to take a step back and think about jeez, what is that cadence? Do I want to see people twice a week, ideally, and then have three days where I’m just working remotely? Do I want to have one day where I’m not accountable to anybody else, I have no meetings, I have no Zooms, I can just work? And then do I want to have one day where I am in meetings with everybody all day and we do have a big collaborative, fun meeting? It’s awesome to be able to take a step back, if you can, and really think about the pace of your interactions and the types of interactions.
MATT: It seems like a precondition for a lot of the things you’re describing is a level of self-awareness.
MORRA: Yes.
MATT: How do you cultivate that self-awareness? I think certainly in the past I’m just not aware of my energy, whether it’s high or low, and I kind of realize after I crash or too late.
MORRA: You play detective. [laughs] I have a friend, Rebecca Harley, who is a psychologist at Mass General Hospital here in Boston and she calls it playing detective, really starting to tune in. And this is what I believe so deeply and why I also believe that any of the best-selling self-optimization or leadership bibles in the world won’t do you a lick of good until you have that self-awareness.
Because so many of us spend our entire work lives reacting, getting triggered by things we don’t know are triggering us, and then reacting in ways that we don’t know, whether it’s pushing ourselves too hard and then crashing, or getting extremely anxious about something, reacting in a negative way, and then wondering why things went wrong. So until you understand what makes you tick in terms of your energy, in terms of your anxieties, in terms of your dark thoughts and demons and fears and insecurities, I don’t think you can be your best work self. And it start with tuning in, it starts with actually going through your day and thinking, Wow, why after that conversation do I feel like I need to take a nap? God, that conversation really made me feel like I want to cry and I want to take a nap. Or, why am I over work is a really common, anxious reaction. We think it’s a good thing because again we get rewarded for it but why is there always that one boss or that one client who you just work, work, work, work for even though they don’t need it? What’s triggering you? Start paying attention. When does your neck ache? Why does your jaw ache? When does your breathing get tight? If you see a certain person’s name in your inbox and all of a sudden… We’ve all had that feeling, right?
MATT: Yes. We did an interesting hack where we… Next to the posting box on our internal blogging system, which is called P2, it shows a random oblique strategy. It’s one of the things from Brian Eno. But on Reddit I heard they started to put a message that said ‘relax your jaw’ which actually… I hadn’t really thought about it but it is so nice that if you relax your jaw… So much of this experiences somatically in the body.
MORRA: 100%.
MATT: But we are very turned off to that. Have you heard of the HALT acronym?
MORRA: No.
MATT: Oh, I like this one a lot. HALT stands for hunger, anger, loneliness, and tiredness. Just if you find yourself feeling bad or reacting a certain way just ask yourself those four questions — am I hungry? No? Am I angry, am I lonely, am I tired? Just going through it as a check-in. And I’m sure there’s a million different versions of this, including meditation and others, that allow that check-in. In engineering we say you have to profile before you can optimize, which just means you have to see where the bottlenecks are in the system before you start trying to fix them.
MORRA: See, now there you go because again Alice Boyes, who is a great psychologist, who does a lot of work on anxiety and tool kits says every person who tends toward a bit of anxiety has anxiety bottlenecks. And this could be the same for anything, you could have introversion bottlenecks where…
For me, because I am in client services, there’s many times where I’ll fly to a city and I’ll have just days of meetings and I’ll reach that point at 5:00 where I’m just so done but I still have to go to dinner with someone. And that’s my bottleneck and I need a solution. And so yes, you have to understand the cause and then the reaction and the space between is meditation, that’s all meditation is, is having awareness in the space between the cause and reaction.
And so what Reddit is doing basically is actually a little bit of a meditation, of mindfulness. It’s saying oh, are you clenching your jaw? Relax it. But then the next question is why am I clenching my jaw?
MATT: Totally. And has some form of meditation or mindfulness been a part of your journey?
MORRA: Yes. I’m not a good meditator, I’m not a formal… I don’t do a lot of long meditations or anything like that. I think for me it’s really about the mindfulness and trying to spot my reactions. What was most powerful for me as a small business owner was understanding how much money triggered anxiety in me. And I mean talk about jaw clenching, I would get migraines if I got stressful financial news because I would clench. Or being in a negotiation with a client.
I was so triggered by money because money is an issue for me, it’s an anxiety for me, that I was making bad decisions, I was reacting in bad ways. I’d get migraines. And so even just understanding, to be a little mindful. Like, okay, Morra, you know what, there is a pandemic and you’re going to go look at your forecast and instead of going down a spiral of anxiety, like “we’re going broke, we’re never going to survive, everything is coming to an end,” breathe, do it with your colleagues so you’re not feeling so alone. Just building a technique, that kind of mindfulness has been life changing for me.
MATT: Thank you for sharing that because, well, one, that’s an interesting one to share and two, I think money is actually a big one for a lot of people.
MORRA: Oh yes.
MATT: I’ve seen it in people I know who are actually quite wealthy.
MORRA: Oh yes.
MATT: And then you get both an anxiety around money and a guilt around that you shouldn’t be anxious around money because logically they are past that point.
MORRA: It’s not rational. It’s not rational. And I think also just the space of saying it’s not rational [laughs] is really good. Getting distance. But again, it all comes back to self-awareness. I mean that’s why I think every leader should be in therapy as well. I think it’s so key to your leadership.
MATT: Is there a type of therapy people should be in, or leaders should be in?
MORRA: Well, there’s so many different kinds of therapy but I think talk therapy, not coaching. I think coaching is incredible but I think a lot of leaders really need to go to the fundamentals of what’s driving them down deep. And people tend to want to solve things, we are all about solving and optimizing, but there has to be a little bit of time to un-peel the mess.
MATT: Actually even in my question I was solving things because I was like, well what type? [laughter] And really probably almost anything is better than nothing if you’re just dealing with self-inquiry.
MORRA: Well that’s right. And a lot of people will say well I’m going to sign up for ten sessions of cognitive behavioral therapy because my health plan covers it and it’s useful. And some people might say I’m at a place in my life where I’m going to go do analysis three times a week and I’m finally going to work on some big stuff. So it’s very personal. But I guess what I would say is it’s really about feeling your feelings, which is not something that we get taught much at work.
MATT: Before we get too much into anxiety, I did want to ask a little bit more about introverts and extroverts.
MORRA: Yes.
MATT: This is kind of a two-sided question. What is something that you really wish that extroverts understood about introverts and then on the other side what’s something you wish introverts had empathy for in extroverts?
MORRA: Well I’m married to an extrovert so I have had so much practice. [laughs]
MATT: Perfect answer.
MORRA: Oh my god. So I would say that there is a lot of judgment on either side. And a couple is actually a great way to think about this because an introvert/extrovert couple might have the same argument every once in a while which is the extrovert says, “you never want to see anyone, I’m bored. Why can’t we have people over? Why can’t we go out? You never want to do this. Every weekend you just want to stay home and watch Netflix.” And then they are frustrated, they’re not getting what they want. And the introvert is saying “why are you always making me see people? I’m tired, I am with people all week long, all I want to do is stay in and watch Netflix and hang out with you.” And neither person is getting what they want.
So I think it’s really understanding what the other person needs and it’s not a personal judgement. It’s not about you. It doesn’t mean that I don’t like you because I don’t want to talk on the phone, it’s because I really cherish my quiet time and my alone time and I don’t get a lot of it. So can we meet in the middle and find a place or a time where we can connect that it’s meaningful for both of us?
Or, can I have a deal with my husband where we get to go out twice a month and the other two weekends we’re home. Or I have a 90-minute rule when we used to go out to dinner where he loves to go out to dinner, he loves to be with people, and I was allowed to leave after 90 minutes and he could find his own way home. [laughs] So again, you have to be willing to compromise and just talk things through.
MATT: Ahh. Those are again some very practical tips. I like it.
MORRA: Thanks.
MATT: You mentioned on your podcast page that anxiety is normal. Why do you think that needs to be said?
MORRA: First of all, of course anxiety is normal because anxiety is good. Anxiety is what kept our species going and now keeps us performing and keeps us working hard and trying and getting jazzed with energy before we give a talk. So anxiety at a normal, healthy, manageable level is really good.
I think that we think… again we, who is we? In success culture, in this culture that many of us who have come up in business subscribe to, we think that anything that has to do with mental health is bad and weak. And so we don’t want to let weakness show. And so admitting we are anxious many people would think is akin to saying I’m not in control, I am weak, and I can’t do this, or you’re going to think I can’t do this and that’s dangerous. And so people shy away from it.
MATT: One thing I have heard from colleagues is that they don’t want to be perceived as other people need to walk on eggshells around them.
MORRA: Mhm.
MATT: I don’t know if that resonates with you, or there’s maybe a reason they are scared to share it or when they shared it they regretted it a little bit.
MORRA: You know, it’s funny, I hear that a lot and I’m reflecting now because my husband and I, one of our fights as a couple is he will say to me, “well I didn’t want to tell you because of your anxiety.” And I’ll say, “my anxiety doesn’t make me unable to hear bad news or not be able to help you when you’re in a crisis. My anxiety is something that I am in conversation with and I can manage, it’s not your responsibility to hide things from me.”
And so yes, I think there is that perception but that’s why it’s important to say that anxiety is normal because anxiety doesn’t make us weak, anxiety is a human reaction. And if we can understand it and be in conversation with it and manage it there’s nothing bad about it. It’s when we aren’t in touch that we are acting out of control.
MATT: When you said that, I thought of my relationship with my mom.
MORRA: Oh, why?
MATT: Well sometimes I’m hesitant to tell her things because I feel like she will worry about it more than I will. So for me it might last an hour, for her it might last several days. And I feel like it’s putting an undue burden on her.
MORRA: Have you ever asked her?
MATT: Yes. [laughs]
MORRA: Oh okay, well maybe it is.
MATT: Well she likes to know though, just like you said.
MORRA: Yeah, yeah.
MATT: She of course loves me and wants to be supportive.
MORRA: And she’s your mom.
MATT: And she’s my mom. [laughs] That too. So what can companies do either in one-to-one relationships, like manages and colleagues, or maybe structurally?
MORRA: I think structurally the good news about what’s happening now is that companies have to look at what’s working and what’s not working, and so that’s really good. I pray that many companies will achieve some sort of hybrid model that gives introverts and people who frankly just don’t want to commute for hours a day, etcetera, space to work at home if they can, or work wherever they want that isn’t going into an office.
But also understand that a lot of people do value human connection. There is a way to do it. Really, again, it’s about mindfulness. I think companies can be mindful about how they program work, right? What the company model is for scheduling calls, what the mandatory office hours are, what a meeting culture looks like.
I think that starting with meetings could be so powerful for so many organizations — how do we run a good meeting, what does this look like, who talks when, what are the criteria for scheduling a meeting? You hear a lot about Amazon, of course, and their process, but I think there is something to that. It’s just about being more mindful.
I wish that every team would sit together and talk about their work styles and their boundaries and, you know, when you email me on Saturday morning it really freaks me out and I wish that we could have a policy where we wouldn’t send emails on the weekend unless it was super urgent, is that possible? Where people can ask for what they need and organizations can respond mindfully.
MATT: It sounds like what you’re saying is that if we do these things it should help everyone, not just the anxious people, who might not know or not whether someone’s anxious.
MORRA: And not just the introverts. There is a classic, classic example that Leslie Perlow, who is a professor at Harvard Business School, who has studied time use and always-on culture, talks about, which is… And this has nothing to do with anxiety or personality at all.
Think about… I love to clear out emails on Saturday mornings. It’s just a really great time for me. So think about me feeling awesome, having her coffee, clearing out emails on a Saturday morning and on the receiving end is my colleague who is at his kid’s soccer game and who picks up his phone and all the sudden has 10 emails from his boss. And he feels like crap. You have just ruined his soccer game. Because you just haven’t thought… right?
MATT: Hmm. Yeah. I wish every messaging platform had time shifting. It’s one of my biggest wishes for Slack.
MORRA: Honestly I think Slack is really, really dangerous because there aren’t boundaries built in. At least with most email these days you can schedule. Slack creates such an always-on expectation that I worry, I do worry because it erodes our mental health to have to always, always be watched by that little message app.
MATT: The good news is that’s not technically difficult. They have a lot of the things in there and they try to make the controls I think more on the receiving end where you don’t get notifications. But…
MORRA: But it’s a cultural thing. Because if no one else on your team uses them, well, you’re not going to be the only one.
MATT: Well and I also found that, particularly as an executive or if you’re an executive listening to this, it doesn’t matter how many times they say you don’t need a response after hours, if people get the message they do and they feel like they should. And so I have really… I actually just started keeping a text file where… On some platforms, like Telegram, I can schedule the message to go out next day, during normal hours, but otherwise I just keep a text file and Iput it all in the text file and try to get to it the next day. Although in an asynchronous organization you don’t always know when people are working or what their normal hours are.
MORRA: Well that’s right, and you have people all over the world, right?
MATT: 24-7, yes. So I’m receiving messages actually 24 hours a day.
MORRA: Well how do you keep those boundaries for yourself?
MATT: I just don’t look at it. But I’m also the boss, so…
MORRA: But you’re the boss, yeah.
MATT: So I think that that is a way to… I feel more comfortable doing that. But I will say, even as the boss, I consider myself at service to everyone in the organization. So if I see an unread message from someone who I know is going through a tough time or something, or a difficult situation, I am probably going to open it, even if it’s after hours or I shouldn’t, because I think well maybe I can just do a quick response that will unblock something. So there is a pressure that comes to leaders as well who want to be empathetic or don’t want to be a bottleneck.
MORRA: I mean, that’s the thing, we are human and we’re trying to master all these different kinds of communication that just want more from us. But I think a good place to start, if you’re listening, is just to think about… It’s sort of like tuning in and playing detective… is to think about that feeling of a boundary being crossed. You may answer that email from a colleague and it may make you feel really good, even if it’s Saturday night at 11:00, because you care for that colleague, you’re reaching out, you feel like a good leader. That’s great, right? You’re not crossing a boundary for yourself.
The Saturday morning on the soccer field is crossing a boundary for him because all of a sudden he is sent into a state of anxiety — my boss needs me, why am I out on the soccer field when she is working, am I not doing a good enough job, is that what…? He is sent into a very heightened state of uncomfortable arousal. So I think that is a very good place to start is what is my team, what is my boss, what are my colleagues, what are we doing that makes me have that Spidey sense that this is a little too far for me and I’m not comfortable with it.
MATT: So we are in a very unique situation right now — the first global pandemic I have lived through. And depending on how you feel about it, there is a virus, there is a silent killer moving through our midst and a lot of people are experiencing anxiety that maybe weren’t aware of it before or maybe hadn’t felt it before. So as someone who covers this area, what would be your advice to folks who are feeling maybe new to anxiety, what would you recommend for them?
MORRA: To say I’m anxious, this is hard, and to not try to shut down the feeling. It is so tempting to, especially if this is your first time or it’s something that you don’t want to feel, to just try to move on. But I think right now it is really important to say okay, yes, there is a global pandemic, I am anxious, here is why, and then to understand that A, that is completely normal, who isn’t anxious right now? The world is… whoa. And I am not alone, my peers feel this way, the people I respect most in the world feel this way, the people who work for me feel this way. And so what do I need to do? What do I need to do? What especially is driving me?
And there is a great exercise that I have written about and I have talked about this on the podcast but it’s a real instant calmer-downer if you are having a bout of anxiety, right away. It’s from Jerry Colonna and he calls it “the possible versus the probable.” So oh my gosh, there’s a virus, it’s a silent killer, everyone I love is going to die. Is that possible? That’s possible. It is possible. Is it probable? No. The statistics are very limited, here is how I’m keeping my family safe, here is how we’re safe, here is how we are going to continue to stay safe.
You can do this with your business if you are worried about going out of business and all these fears that we have now. But this is where we are at but we can’t stuff these feelings under the rug.
MATT: I love that framework of possible versus probable.
MORRA: Yes.
MATT: What I use sometimes is, is the anxiety serving me?
MORRA: Mmm.
MATT: Is it helping me find a solution or is it revisiting something that maybe there is already a solution to or I’ve already made a decision on. …You said earlier don’t push it down, don’t ignore it, don’t try to suppress it. But we also have been talking about strategies for getting past anxiety. So what is the difference between those two? How can I tell if I’m doing the bad version of getting rid of it versus the good version of getting rid of it?
MORRA: Right. Well the bad version of getting rid of it might be drinking a bottle of vodka. So I think we could all agree that probably drinking a bottle of vodka is not great. Right? Having a martini, love it, having a whole bottle of vodka? Meh. So it’s really about your reactions. Sometimes you might react in a really good way. You might be anxious and you might think I’m going to go for a run, that’s going to really help me. Great. Right?
So I think it’s really sometimes flat-out “is this bad for me.” A lot of times we get anxious and we eat, we drink, we take drugs, we spend money, we avoid work, we procrastinate, we overwork, we over-compensate, we try to control our team and drive them crazy. I could go on. I think again it’s about thinking how am I reacting? Is this a reaction that is hurting me?
And sometimes you just have to get through the day. So if you’re anxious in the middle of the day but you have to go lead a meeting, go for a walk, breathe, try to do something in the moment and save it for later. But if you’re finding that this is happening over and over again, take a step back and think, “I think I need to think about the root of this, what is causing this and how am I reacting and can I work on trying to react in a different way because this is not serving anybody.”
MATT: How deep do you go on those causes? So earlier you said it’s caused by money, do you need to keep going levels down to find the root of these things?
MORRA: It’s a personal choice. You can learn techniques that will help you manage it more quickly or you can go deep into your parents, like I did, your parents got divorced and your father stopped paying the bills and da da da and on she goes. So that’s a personal choice and that is about where you are in your life. There’s no easy answers.
MATT: What are your favorite in the moments, getting back to that place of positivity or avoiding the anxiety?
MORRA: I talk to myself. [laughs] Like it sounds like you do. And I will say, you know what, anxiety, not now, it’s not a good time. Or, this is a really old trope, the money thing. If there is something that is a recurring anxiety I will just say you know what, this is my anxiety talking, this isn’t the truth. I need to deal with this, I need to be a grown-up here. I will give myself a tough love pep talk.
And I actually like to get up and stretch and move a little bit, try to physically shift. Those are some things that work. And sometimes… Sometimes it doesn’t go away and that is really hard, especially right now. And I think many of us just gritting our teeth and getting through some days and that’s okay too right now.
MATT: Thank you for saying that’s okay. That’s a powerful message right there. I’ve really appreciated and enjoyed this conversation. So, thank you. Is there anything we haven’t covered that you think is important for the managers, leaders, CEOs, people listening to this?
MORRA: I think again it’s just… Well, if you are listening to this, I think you want to ask questions. But I do think that checking in with people is really important right now. And I don’t think that that’s necessarily a great thing to do on Slack or via text because it can be read the wrong way. So that is a moment when, even though I hate talking on the phone because I’m an introvert with social anxiety, there is something to be said about just checking in in a more casual way. Even a text, sending them a text on their cell phone versus an email or a Slack, or you could use lots of emojis if you must use text. But the power of one-on-one checking in is really important right now.
MATT: Do you have a pretty strong emoji game?
MORRA: No, I am bad at emojis. [laughs]
MATT: I always admire people who are really good at them because, I don’t know… [inaudible] the emoticons where you just have the colon and the parenthesis, so I feel like I’m not as expressive as I could be on emojis. But I’m working on it because I do think in our text-mediated world it does help.
MORRA: It really does. Just throw a smiley and a heart in there and some flowers and… Maybe not a heart. That’s inappropriate. But just throw a smiley in there and you’re good.
MATT: I hope we can get to a place where the heart isn’t inappropriate.
MORRA: Me too.
MATT: But I could see where it could be misread. I’m sure people are going to want to hear more from you. You have a book, you have a podcast. Tell us all about it.
MORRA: Well, I have a book called “Hiding In the Bathroom” which is literally a manual for getting out there when you’d rather stay home. It’s not about physically getting out there, so it’s still really useful, all kinds of online networking tips and things, ways to think about building your presence when you are an introvert or you have social anxiety. But I really love my podcast. It’s called The Anxious Achiever. And I encourage people to listen to it.
MATT: That is awesome. How about on social or a website?
MORRA: I have a website. It’s womenandwork.org. Or you can go to hidinginthebathroom.com. And you can follow me on Twitter at @morraam. Or on LinkedIn. I really love LinkedIn. You can look for me on LinkedIn.
MATT: Awesome, I’ve never heard someone say that. [laughs]
MORRA: I do, I love LinkedIn.
MATT: That’s great to hear. Well, Morra, thank you so, so, so, so much. I really appreciate it.
MORRA: Oh, thank you, Matt.
MATT: Thank you for joining. I’m looking forward to learning more and checking out your podcast.
MORRA: Thanks. Be well.
Episode 20: Adam Gazzaley on the Distracted Mind During a Crisis
Apr 29, 2020
Matt Mullenweg speaks with neuroscientist Dr. Adam Gazzaley, co-author of the 2016 book The Distracted Mind: Ancient Brains in a High-Tech World, about how our brains work, particularly during times like the current pandemic. How does the brain handle internal and external stimuli, and what do we know about the effect of practices like meditation, exercise, nutrition, and sleep?
Gazzaley obtained an M.D. and Ph.D. in Neuroscience at the Mount Sinai School of Medicine in New York, completed Neurology residency at the University of Pennsylvania, and postdoctoral training in cognitive neuroscience at University of California, Berkeley. He is currently the David Dolby Distinguished Professor of Neurology, Physiology and Psychiatry at University of California, San Francisco, and the Founder & Executive Director of Neuroscape, a translational neuroscience center at UCSF.
Gazzaley co-authored The Distracted Mind with Larry D. Rosen, and he’s a scientist who enjoys seeing his work solve real-world problems. He’s also founded startups, including Akili Interactive and Sensync, to build technology products that enhance learning, mindfulness, and well-being. More can be found at his website, gazzaley.com.
A full transcript of the episode is below.
***
(Intro Music)
MATT MULLENWEG: Hello everybody and welcome back to the Distributed Podcast. We’ve all had to make so many adjustments in recent weeks and some of them quite radical. I hope that wherever you are and wherever you might be tuning in from this process has been going smoothly for you, or at least as painlessly as one might hope under these circumstances.
In conversations with my colleagues at Automattic and with people at many other companies, both distributed and not, one common thread I keep seeing is how difficult it has been to stay focused in recent weeks. I have been struggling with this as well. We’ve been dealing with non-stop bad news. Many of us have either been directly affected by Covid 19 or know people who have, either health-wise, financially, or socially. Even more of us have had to learn how to work from a new or dramatically changed environment.
So for this episode, I wanted to talk to someone who knows a lot about focus, distraction, and changing our work habits. I couldn’t think of any person more fitting than neuroscientist — and my friend — Adam Gazzaley.
[music]
MATT: Welcome, Adam.
ADAM GAZZALEY: Thank you, great to be here, Matt.
MATT: Just to set the stage a little bit for listeners who might not be familiar with your work, you have written.. is it over 130 academic papers?
ADAM: Yes, yes. Peer reviewed, more scientific-style papers, correct.
MATT: Even some on the cover of Nature, which is like Sports Illustrated for scientists.
ADAM: [laugher] Yes. My musician friends would say it’s my Rolling Stone cover. But yes, that was several years ago, but it was an exciting one.
MATT: How would you describe the area of your passion that you’ve devoted your life’s work to?
ADAM: It has migrated, maybe evolved, as I like to think of it, over the last 30 years, but yes, it’s been pretty much exactly… I would say 2020 is 30 years since I’ve been in the neuroscience world. I started grad school in 1990 in New York City at Mt. Sinai. I was trained as both a neuroscientist and a neurologist, so both the clinical and the scientific side.
And my research has always had some common elements, a focus on plasticity of the brain, or the ability of our brain to remodel and optimize its function in response to the environment. I focused on neural networks, which is the phenomena that our brain doesn’t work as just these isolated islands but really as an interconnected network of communication that’s constantly and dynamically changing all the time. And aging has been a main aspect of my research.
And I preserved those focus areas through the last 30 years although I’ve moved from animal research, looking under a microscope at the beginning days, all the way to today where I focus on human research using functional brain imaging and tools to understand how the human brain interacts with the environment around us.
MATT: Was there any particular personal experience that brought you to attention and focus?
ADAM: My research focus when I was a graduate student was more on memory systems and how they change with aging. After I finished my residency in neurology and moved to San Francisco to work at Berkeley and study human neuroscience, I became very interested in what I can do as a scientist that was most relevant to people, not just what was relevant to other neuroscientists or was following an iterative path across the field, but what did people actually care about in their lives.
So this was like mid-2000s, like say 2003-2004, when I was moving my research into cognitive neuroscience, using tools such as functional brain imaging, non-invasive brain stimulation. And I became very fascinated by how people interacted with their environment in ways that were positive for their performance and their mental health and ways that were negative.
And at that time there wasn’t a lot of understanding about the impact of interference in our performance, things like distraction and multitasking weren’t really in the zeitgeist yet of how they may impair our abilities. At that time it was considered a badge of honor if you were a good multitasker, whatever that may mean.
And so I was really fascinated by the idea of doing research on a topic that spoke to people so directly about things that were relevant to their lives. And so around 2005, I really turned my own sites full time into studying attention in the brain, specifically how we manage interference successfully and unsuccessfully.
MATT: At a physical level what happens when we pay attention to something?
ADAM: Well attention is such a fascinating concept and one that is worthy of an hour just to unpack it. But just to not go off on an incredibly long tangent as I try to answer that question, I’ll be very specific by what I mean by attention because attention has many, many different aspects to it.
What I assume you meant by that is what we call top-down attention, goal-directed attention. We also have this amazing ability to pay attention to things that are not in our goals. We call that bottom-up attention. It’s how we survived is that you could pick up a very subtle trace, even if you didn’t intend to, of a threat or food or a mate in the environment. This is largely what drives other animals’ attentional processing.
MATT: Do those signals make it all the way to the frontal lobe or are they handled some place lower?
ADAM: A lot of those signals are just handled even at the brainstem, some of them even in the spinal cord. You could prick your finger and withdraw without it even going into your brain, a lot of that can happen very local, very reflexive, input-output circuits.
The frontal lobe, which you mentioned, is the most evolved part of the human brain and it is really the seat of the top-down attention. And other animals have it to some degree but most of what we might look at an animal as goal-directed behavior, many of it is not, it’s really this complex but very reflexive response to environmental stimuli.
But the top-down attention, that very human-based attention, is the one where we decided based upon our goals and decisions that we make about what we pay attention to and what we ignore. And when we do that, you’re right, it is a process that is driven by neural networks that really involve the prefrontal cortex. And when we look at it inside an MRI scanner with EEG — and this is what I’ve been doing for almost 15 years now, 15 years actually just this year — is that we see that there is communication between brain areas that involve the prefrontal cortex and whatever other areas are involved in the operation.
So, for example, if your attentional focus is a visual one, or maybe a visual and auditory one, then we see a network that involves the prefrontal cortex, which allows you to maintain that focus with visual cortical areas and auditory cortical areas. But it may also involve connections with the hippocampus if it involves memory, which it almost certainly does, or the amygdala if it has emotional content.
And so that’s how we pay attention is that we activate these networks that have all the different component systems associated with whatever you’re engaged in. And what we find is that that network is maintained unless you are distracted or you multitask. But that is essentially what happens physically or neurally, which is a chemical and physical and physiological process in your brain.
MATT: This is a place where I was saying that you have a whole book on this called The Distracted Mind. And one of the things I found fascinating in the book was not just that your prefrontal lobe can activate different parts of your brain that might be associated with what you’re paying attention to, but it quiets the other parts. Can you talk about that?
ADAM: Yeah so we… It is impossible for us to take in all of the elaborate and extensive and diverse inputs that are available around us, even within one sensory modality, even visually you couldn’t, never less the fact that we have olfactory scent information and auditory information. And so we need to selectively process information that’s relevant to us. In this case we’re talking relevant to us based on our goals.
And so in order to accomplish that, our brain doesn’t just focus our limited resources on whatever you consider relevant but it actually actively suppresses the information that has been deemed irrelevant. It’s sort of like a filter system.
This was a lot of my early work. A lot of scientists thought that maybe the filter was a passive filter, like the active process was focus and then everything else was passively suppressed just because it wasn’t getting the spotlight. What my research in like 2005 to 2008 and 2009 was showing was that the process of ignoring is as active as the process of attending.
And you could imagine that it creates greater contrast, right? So if you were to be standing on the floor and the floor is your baseline and you jump up, you may add two feet, let’s say, or three feet if you’re really good at jumping. But if the floor also dropped down at the same time you jumped you could imagine that you would be jumping six feet off the floor.
And so that’s how I picture it. It’s not that the baseline stays the same, the irreverent information actually drops down and becomes muffled and that’s what allows us to create even more precise processing of information that’s relevant.
MATT: So when with things that can help you improve your ability to focus or not be distracted, like meditation, which part of that is meditation activating? Is it different for different types of meditation, like a mindfulness [meditation] versus a body scan?
ADAM: Yeah, meditation is such a wonderful topic and a complex one. At its core meditation really is attention-training no matter how you slice it, even across all the different types of meditation. I tend to think of meditation in two general categories — open-monitoring meditation and then concentrative, focused meditation. And they are quite different.
Focused meditation has many, many different practices within it. So the most I would say common and traditional in many ways is breath-focused meditation, but focusing on a mantra, so a word or a phrase in your mind, focusing on a mental image or scanning your body would all fall into that category of concentrative meditation. And then open-awareness meditation is where there isn’t a predetermined focal point but rather you keep awareness to whatever arises and then let it move on and move to something else as that arises.
And they are both forms of attention that involve maintenance and switching but the concentrative meditation is I would view as the clearest practice that would allow you to fine-tune your ability to control where your attention is because that’s essentially the nature of that practice.
As a matter of fact, when I talk to meditation thought leaders, like Jack Kornfield, who is a good friend and a collaborator on many of our projects at UCSF, he would say that’s why most meditation, no matter where you wind up, whether it’s meta, like loving kindness and compassion meditation or some type of open-awareness meditation, it often starts with breath-focused meditation because that allows you to have control of where your attention is, and beyond control, it’s awareness of where your attention is. So I’d say that’s a twofold process.
MATT: I wonder if there’s a difference between when you’re focusing on something maybe abstract, like a mantra, versus the type of meditation where I’m trying to focus on a bodily sensation like the feeling of breath or a body scan, like how the top of your head feels, how you face feels? Because that seems more like sensations that are coming in that I was ignoring that I’m trying to pay attention to or be aware of.
ADAM: Yeah, it’s a great question and I have found very little scientific data on that. It’s something that Jack and I talk about and it’s really a great question because it’s an experiment that we’re planning on running.
We just ran a five-year study and project to build a meditation closed loop experience — and we can break that down a little bit if you’re interested — but essentially a meditation practice that’s very different than people have done previously but one delivered by technology, which makes it more accessible, but also baby-steps you into the focus of breath meditation. And what we found, we actually just had a paper accepted today, I just found out this morning —
MATT: Awesome.
ADAM: — to a nature journal, yeah, Translational Psychiatry, and we had a paper accepted maybe six months ago to another nature journal, Human Behavior. The previous paper was on healthy 20-year-olds and the paper accepted today was on children, actually adolescents from India with adverse life events, really traumatic events that had attentional problems. And in both populations we showed that six weeks of this breath-focused meditation game improves their ability to focus their attention in a goal-directed way and in the children we showed benefits even a year later.
And to bring this around to the question you asked, one of the really interesting future studies that we’re planning now is how would the benefits that we achieved with the breath-focused version compare to a different focal point? And I would go so far as to say how about if that focal point is not even a body sensation but an externally delivered sensory input?
For example, our game is played on an iPad or a phone where you close your eyes and you focus internally on your breath, you monitor your awareness of where your breath is, if your focus deviates from your breath, you return it. We can have the same exact type of method but now you’re focused on a flame that you’re looking at on your device — would that improve attention the same way? Might it have the same advantages for your attention but maybe a different advantage or disadvantage in terms of your stress reductions which is another benefit that we have also determined?
So it’s a great question. We do not know all the different positive benefits that might come from different focal points during a meditative practice but it’s something we are very interested in.
MATT: Awesome. And Neuroscape is the name of your lab at UCSF, correct?
ADAM: Correct. So my lab used to, as most professors, used to be named after me, Gazzaley Lab. And I started that 15 years ago at UCSF. And it’s become so big really with our Nature cover that we talked about before, and other activities that now we’re a center at UCSF. So instead of a lab being pretty much defined by having a single PI, principal investigator, now we have multiple faculty members and we’re almost 40 people.
So Neuroscape is a not-for-profit research center at University of California San Francisco. And it did evolve from my lab. And what we do is focus on how we can use technology to improve brain function and also assess brain function but in a more real world way than we have accomplished previously.
MATT: You had four categories of — I don’t want to mess up the terminology — but there was internal, external…?
ADAM: Back in 2005, when I started studying interference, I was frustrated when I read the scientific literature because there was no conceptual framework for how to think about interference. Some people call distraction one thing and other people refer to distraction as something else.
And I was like, it’s okay, there’s no right or wrong, but we need to just have a common language, semantics, that we use so that we know that we’re talking about the same thing. So I created this taxonomy of interference that I use and I think others have used it since then and that is thinking about interference in two main categories.
One is what I call distraction and the other is what I call multitasking. And I define them differently based upon your goals. And they both have an internal and an external component. But let’s just start with distraction and multitasking.
So distraction is when you have a singular goal. Like your goal as a listener might be right now to listen to what Matt and I are talking about and that’s your primary goal. And that means that everything that falls outside of that is technically a distraction. So since you’re working from home, if your children are running by, that’s a distraction, if your vacuum cleaner is going off in the next room, that’s a distraction. And your goal is to filter all that information and maintain sole focus on what you’re listening to. So anything outside of the goal of focus is a distraction.
Now on the other side of the interference coin is multitasking. Now you have more than one goal. So maybe one of your goals is to listen to this podcast but your other goal, which would be, I think, a foolish goal, is to check your email, right?
So we know very well that you can’t actually accomplish both of those goals at the same time. And the reason people would say multitasking is a myth is because from a behavioral point of view, sure, you’re multitasking, you’re listening to the podcast, you’re going through the email, but if you look at what happens in the brain during this type of dual activity is that you’re not multitasking in the true parallel-processing sense that a computer might be able to run two different processing streams simultaneously without interference.
What’s happening in your brain is that the network involved in listening to this podcast, involving the prefrontal cortex, your auditory cortex, other regions, when you switch over to reading that email, this network is essentially disabled and a new network is activated. And then when you come back to the podcast you have to deactivate that network and come back again.
What we do not see in our studies and other research shows is that those two networks that both demand attention can be maintained with high fidelity simultaneously. And so that’s why I and others will sometimes say multitasking is a myth because when it comes down to what occurs in your brain, we are showing that you’re not capable of maintaining them in parallel.
So what happens is you switch between these networks and with each switch there is what we call a cost. There is a loss of some of the high-resolution information that has to be reactivated. And you can feel that in something obvious like listening to this and doing an email, you know that you can’t do both of them at the same time. You could just empirically assess it in your own behavior. But for other things it’s more subtle. You may not realize that you actually have a performance cost, but you do. We see it all the time.
So those are the two types of interference — distraction and multitasking. And they are different in how they occur in the brain. And we have published multiple papers showing that.
And then for each of them they can occur internally or externally. So just to quickly summarize what that would be… So, a distraction, you’re listening to this podcast, you could have an external distraction, which is what I mentioned, your child running by, a vacuum cleaner going off, if the TV is on something dramatic might happen that pulls you away. That is an external distraction.
But you could have an internal distraction too. Like I said, your stomach may grumble and you’re like, “oh I’m hungry,” and now you’ve been distracted from your task by something that essentially arose internally. Or, you may just have a memory of something, like a bad event that happened yesterday.
For multitasking that could happen externally or internally too. So the example I’ve described about listening to the podcast and multitasking by doing your emails are two external forces. But you could be listening to the podcast and also planning your day. So then you have an external focus but also an internal focus going simultaneously.
And so that just gives you a little flavor of how complex the world of interference is, is that it occurs across these two different domains but has both internal and external variance.
MATT: What does it mean or why do some people think that they are able to better focus if they’re in a cafe or have some background noise or something like that?
ADAM: Mm, that is a great question that has very little data in the scientific literature. We published one paper on that topic about why do people seek out environments that would almost universally be described as distraction-inducing environments as opposed to low-distraction environments to do something that they need to focus on. I call it the coffee shop effect. I don’t think that’s a name but that’s how we talk about it internally.
It just makes sense that if you were doing something that involved focus you should go to a quiet library rather than a busy coffee shop if you’re just thinking about the brain in terms of interference, what I just described. But humans are complicated and there are several [factors] that I hypothesize are involved there.
One is the arousal aspect, that being in an environment that is stimulating can help maintain your focus just by maintaining your arousal. So arousal and attention are not the same thing. One is a wakefulness measure, which is arousal and drowsiness and the other is where your resources are directed, which is attention. But they intersect with each other. So if you’re drowsy, it’s harder to maintain attention. So if you’re in a stimulating environment you can have better attention just because your arousal level is higher and it could also affect your mood. Like, you’re in a better mood and that can also have intersects with attention abilities.
The other thing that’s interesting, and this is what we have started investigating, is that it is possible, and this is still a hypothesis although we’re starting to show evidence, that having external distractions may help you decrease internal distractions. In other words, you’re in a coffee shop and the act of suppressing some of the cacophony that’s around you is also helping you suppress your internal mind wandering, which is the internal distraction.
In other words, you’ve engaged your suppression system and that’s quieting down your own internal mind wandering and allowing you to focus. So if you’re in a library you don’t have that external need to suppress your environment and so now you may find it harder to focus on… let’s say you’re writing an article or reading an article… you have a harder time doing it because your mind keeps wandering. That’s a hypothesis but it’s one that I think is true and we’re trying to maintain, to get some evidence for that now.
MATT: And do I remember correctly that most internal distractions or interference tend to be negative?
ADAM: Yes.
MATT: So would having positive (external) interference, maybe keep those internal negative from bobbing up?
ADAM: Yes, that may be. That would be an interesting hypothesis. And that could be done in an experiment by presenting both positive and negative external stimuli and seeing how it regulates your attentional focus, which is something that we’re actually planning on doing. I’ll come back to that in one moment.
But that study was not done by us. It was actually published in Science. I’m unfortunately forgetting the last author’s name right now. But what it showed was that if you experience sample, meaning that you have a device — I think it was done by phone — that periodically just pings you and says hey, where is your focus right now, it finds that most people are mind-wandering most of the time and that when they are it’s usually on something negative, which was a really fascinating finding, that that’s where people tend to travel to in their mind-wandering.
And some of that is occurring even while they should be doing something else, or they’re trying to do something else, like have a conversation with a significant other or have sex or other things that you think should be absorbing their attention completely. So yes, most mind-wandering does fall on the negative side, it seems.
MATT: To me that’s the most interesting part of meta, or loving kindness meditations. And as you expand that sort of circle of loving kindness, I guess some people put yourself in the beginning and some people put it at the end as it gets harder.
ADAM: Yes. And some people even remove that part of it for beginners because it is in many ways the most complicated. It’s something that I talk about with Jack. We are actually building a meta loving kindness version of Meta Train, which is the app that I described that we just had our second paper published, so moving from beyond breath focus to focusing on words of love and kindness and compassion and empathy. And I think we’re actually not including a self-focus because it is incredibly complicated for all these interesting reasons. It doesn’t mean it should be avoided always but it is really interesting to understand how the act of being kind to yourself is as complicated as it is.
MATT: So much resistance.
ADAM: Yes.
MATT: And for listeners who want to learn more, Jack Kornfield, that’s Kornfield with K, right?
ADAM: Correct.
MATT: And Sharon Salzberg is another great proponent of loving kindness meditation.
ADAM: Yes, she has some great books as well.
MATT: One of the things I’ve noticed for myself is that sometimes these bottom-up interference distractions are mixed up. So sometimes I’ll think I’m hungry or I have the feeling of being hungry, but actually I’m anxious or I’m procrastinating or things like that.
ADAM: Mhm.
MATT: So what’s going on there?
ADAM: I think that what you’re describing is just like what I always think of as the tip of the iceberg. We have the 90% bulk of the iceberg, like a whole internal milieu, which is a combination of the sensory inputs, our own memories and reflections that exist below awareness. And then what we experience as our consciousness is really that tip where it bubbles up into our ability to be introspective about it.
And because it’s not singular, it’s not like it’s just 100% anxiety, 100% hunger, 100% joy, it’s complicated, it’s really difficult to understand what is the content of our consciousness at any moment. I think a lot of what comes from a meditation practice is a better ability to be able to make sense of that, that internal space that is now in your conscious awareness.
So the act of being meta, not the same meta that we were just talking about, or loving kindness, but the meta in terms of awareness of your own awareness, right? The understanding of your own world, of your own understanding, is a complicated one. It’s one that I think we take for granted. It’s like, oh, it’s my brain, I know what’s going on. But it’s really not very easy and it takes years of practice to be able to distinguish between things that may have very similar physiological responses, like anxiety and hunger. They are very ancient forces, like fear, that really are trying to capture your bottom-up attention because there is a survival advantage in your attention being drawn to them.
But the way that they do it is not necessarily so sophisticated. So there’s lots of overlap. It’s not like there is a perfectly discrete signal for fear that has no overlap with that signal for hunger or even excitement. So yes, it takes time to be able to distill out all the components of what may be the subject of your awareness at any moment.
MATT: And the more you think of something does it strengthen those neural pathways, make it easier to think of it in the future or more likely to?
ADAM: It does so through memory. So there is this really amazing description of memory that you only have one perceptual event, which is when it occurs. And everything after is just a reactivation of the memory, which is why memories change all the time. You’re really not remembering the original perceptual event but every subsequent memory is the memory of the memory. There was only one chance for the perceptual event to be sort of laid into your brain as an event.
So yes, if you keep returning to them… And this happens for good things and it happens for bad things, right? It’s part of what post-traumatic stress disorder is and why it is so debilitating is that very, very salient events that have high emotional content get repeatedly embedded in your networks and then they return both when you want them to and when you don’t want them to. So yes, that is both a positive and negative aspect of how perception and attention and memory intersect.
MATT: What do we think is the evolutionary reason for emotions? I think I can guess it for attention and goal-setting and everything but what about emotions?
ADAM: Emotions is the tagging of both memories and perceptual events that gives our attentional abilities some sort of rationale for its direction. If you imagine interacting with the world without any emotional content, all of your decisions would be based completely on… I guess I’m going to use a term here that is not devoid of emotion… but based on intellectual decisions — right — based on pure logic, like the Star Trek, Vulcan way. And the emotional elements of it definitely give it a different flavor, they may override some of the more logical decisions in a way that has survival advantages.
So all of these aspects of our internal space and consciousness that we currently experience all had at some point some evolutionarily driven advantage. And you can imagine before we maybe even had sophisticated logic processing, I’m not saying that it’s sufficient right now, but the emotional content is what drove our decision making. Things that led to stronger fear responses led to a more consistent behavioral response of not engaging in whatever caused that fear and things that led to great joy and pleasure and happiness become reinforced and allow you to pursue it again.
So it’s a very ancient process that tags different perceptual events as being either positive or negative and allows you to engage in them repetitively or avoid them.
MATT: It would be amazing to understand that better as well, like why meditation can provide that very pleasant feeling or sensation.
ADAM: Yeah. I mean, emotion and its intersection with other aspects of cognition, like attention and memory and perception and decision making, is what gets me so excited about modern-day neuroscience.
I think that it’s true for all of science, in my perspective, is that us humans, we really like to put things in categories and study them, in like this chapter and that book. It just doesn’t work like that in the real world and in the brain.
These phenomena are incredibly dynamically interactive. There is no such thing as emotion devoid from attention and perception and memory and decision making and all these other aspects. And I feel like neuroscience is reaching that stage now where we have accepted that the isolated focus approach is not really helping us understand the brain in the real world. And so it’s more complicated and it takes a whole different type of multivariate analytical approaches to understand complex systems in that way but that’s where I think neuroscience is arriving. And I think a lot of good will come from us thinking about the brain and cognition and behavior in that manner.
MATT: Well you are a scientist but you also run an organization. What professionally has changed for you since COVID-19 started?
ADAM: Well it’s been quite complicated, as it is for everyone. I mean we all have our own stories and they are all important and fascinating in their own ways. And we have multiple stories. We have our personal story, how are you interacting with your family or your co-shelter-er or by yourself, with yourself, if you are… certainly if you are sheltering alone.
And then there’s the professional story — how are you still engaging in your work if your work even exists during this phase? And these stories obviously intersect more than they ever did now — holding meetings with your baby on your lap would be an example.
In my particular case I am sheltering with one other person, my wife, who I also happen to work with, so that helps. So my story is already interwoven between professional and personal.
I’m in a situation that I find very challenging because we have almost 48 employees at my research center, at Neuroscape, and I feel a personal… I don’t know, burden is not the right word… a personal responsibility, although sometimes it does feel burdensome, to make sure that everyone is okay, that they are safe and that they are happy and of course that they are productive. And that is a weight that I guess was always there but didn’t feel quite so in my face or in my brain as it does right now.
So personally that has been a really challenging journey over the last… now we’re in our sixth week… of really making sure that every one of these human beings and their families are as safe, in all the ways that we think of as safe, as they can be. So that’s a lot of my burden.
From being the director of this center I also have an obligation to make sure that not only are we safe and healthy and happy but that we are productive, that we are meeting the obligations and the mission that we’ve set to understand the brain and help people, that we are meeting the obligations that we have to our funders, whether they are philanthropists or the government, like the NIH, and that we are doing the type of work that gives us satisfaction and feel a sense of personal growth, not just productivity.
And so that’s the world that I have been in is trying to both maintain my own personal self-care and make sure that I’m feeling both happy and capable of being a leader and then making sure that my team is and that we are also still doing research in this really challenging time.
MATT: Let’s start with you. So, being one of the world experts, having read probably thousands of papers about the brain and everything, what have you found are the most important things that you do to bring your best to your work?
ADAM: I think I keep having this mental image, because I haven’t flown in a long time, but I fly a lot, I know you fly a lot too, Matt, and I wrap around the world pretty continuously largely giving lectures in various countries for the last decade.
And, you know, you go on the plane and you try to ignore that message about how to fly because you’ve heard it thousands of times. But this one part of it that has stuck in my brain now, which is the part where they describe that you put on your mask before you put on the mask for your child, which feels so counterintuitive but obviously they tell it every time because you can’t protect your child if you haven’t made sure that you’re going to survive enough to do so. And I feel that that is sort of the message that I try to embody right now, that if I don’t have my own self-care and make sure that I’m physically, mentally, emotionally healthy I can’t help my team at all.
And so I do pay a lot of attention to make sure that I am maintaining the routines, even enhancing the routines that I have taken from my own self-maintenance, through this period. So my diet, my exercise, my sleep, my quality time with my significant other and friends, even if it has to be done virtually, those are super important for me now. They don’t feel superficial or frivolous or that I’m not doing my work or that I’m not taking care of my team. Because if I fall in any of those capacities, I’m not going to be able to function at the level that I think my team needs me to.
So I would say that’s the first message, is like self-care has never been more important than it is right now.
MATT: Wow. And do you have anything specific around food, sleep, exercise that you find works really well for you, that you would recommend?
ADAM: Oh yeah, I have too much for us to cover in this one podcast. [laughter] It’s like my obsession right now. So okay, I’ll just tell you a couple from my own life. These are not necessarily recommendations for anyone. I haven’t vetted these with careful research.
But I schedule in my calendar my workout times. I have found… and I did this actually beforehand but now I even do it more… I find that these are the things that disappear if they’re not there. My assistant, who does a lot of my scheduling, will just… She will literally fill any unoccupied space. And so I put these in there as important as any podcast that I’m doing or any research or any important meeting.
So I think that it is very important to make sure that you treat your exercise as prioritized as anything else. So I put them in there and I never miss them.
MATT: What effect does exercise have on the mind?
ADAM: Oh, exercise has more data for preserving the health of our mind, especially with aging, than I would say any other intervention that we have ever studied. And some of that is because it happens to be very well studied, not that nutrition is not important but it’s a lot harder to do the type of randomized control blinded studies on nutritional interventions as it is on physical exercise. But physical exercise, both in terms of resistance training and aerobic training has a plethora of really, really convincing data throughout the lifespan, especially on children and older adults, but it’s there throughout.
And so it has benefits both acutely on your mental functioning and chronically, so long term. So it is incredibly important both in the moment and the sustained benefits in terms of how your brain functions, even in terms of how it intersects with things like the onset of dementia. So it’s incredibly important for older adults that may not have the ability to do heavy weight training or running, even walking in the neighborhood has shown to be beneficial.
I know it’s all complicated now in terms of what’s appropriate to do outside and what isn’t and it depends on where you’re living. But as much as possible using physical exercise to help your mental state and the function of your brain I would give almost the highest checkmarks to.
MATT: You mentioned nutrition. Any strong connections there?
ADAM: Yeah, the best data for nutrition and the brain really is around a diet known as the Mediterranean Diet. And many of your listeners may be familiar with it. I would say it’s not because it is the perfect diet necessarily, I think it has a lot of great things, but I think it has been the best studied diet in terms of the brain, especially related to aging. And you’re probably familiar with it, it’s fish and olive oil, nuts and legumes, vegetables, red wine falls in the diet, which makes a lot of people happy. Yeah, so that’s how I try to eat most of the time.
I would say that some of the unique COVID challenges are the fact that you’re now a lot closer to your refrigerator than you ever have been before and using food as a stress reliever or as something to do when you’re bored is not the best idea. I think just like we schedule our workouts, I think food and eating should also be quite diligently scheduled.
MATT: And finally sleep was one you mentioned.
ADAM: Yes, sleep is an amazing, amazing field of research. It has become more in the awareness and fortunately the public zeitgeist than ever before. A good friend of mine, Matthew Walker, wrote an amazing book, Why We Sleep. I actually wrote a recommendation for it on the back of that book because I really enjoyed and felt that the message is so critical.
We know that sleep is important for all of our functioning but when it comes to the brain, our memory consolidation and our ability to maintain focus, it’s critical. So finding the right conditions that lead to both time of sleep, being seven hours plus, as well as the quality of sleep, is also critical. And this intersects with technology, like not necessarily engaging in technology late at night.
I would add again another COVID-specific piece of advice is that I don’t think it’s healthy to listen to the news all day. I’m not saying that you should be uninformed but just like all other distractions, like in the context of the Distracted Mind, I think that there is a diminishing return in having a cluttered workspace and having a cluttered mind. And that this act of being attached to a news source is likely not going to help any of the things that you need to stay healthy, especially doing it right before you go to sleep.
So at least personally I have set, just like I have scheduled times for exercise and eating, I also schedule time for news consumption. It is not something that I do all day long and it is not something that I use as a break. Breaks are really important but breaks are not all created equal. So the break of going on social media or listening to the news I would say is not a great break. It leads to a lot of emotional distress, it could take you through a wormhole where it pulls you away from your goals.
I would say much better breaks are looking at nature, even if you can’t see nature from your window, but looking at even a screensaver of nature. I would say meditation, maybe doing some light physical exercise, some pushups or some squats, these are the type of breaks that are better to take to give you some restoration when you’re working rather than going on to news or social media.
MATT: Like I mentioned, there’s a lot of people struggling with this environment right now. Is there any other practical advice you would give for others or that you have given to your teammates for how to operate in this very stressful and anxiety-inducing time?
ADAM: Yeah, those are a lot of them. I think that… I mentioned this before but I’ll mention it again… is clutter. In the context of the Distracted Mind and the concepts that we talked about, that our brain has an inability to take in everything at the same time, decisions have to be made on where we direct our limited resources, it helps to have a clean workspace externally.
I have a lot of things around me right now. I use an iPad, a desktop, I have my headset that has its own interface, I have a camera. But I also have flowers and candles around me, things that help maintain a mood that feels very positive to me. And then pretty much everything else I get off the table and outside of my visual space. I think that that’s important for the external environment and definitely a challenge for people at home but it’s important, I think, to try to keep a clean environment when you’re engaged in a focused activity.
I would also say it’s important to try to reduce the clutter in your mind. And that’s where the breaks come in. There’s only so long that we can really go before you fatigue mentally. Like, we know a lot about fatigue and there is so much research on fatigue in the physical world, right? Muscle fatigue, even Olympic athletes and professional athletes have embraced the fact that although they are the best in the world they fatigue and they need to restore in order to be able to re-engage at the top of their abilities.
It’s the same thing for the brain and the mind. We will fatigue and it’s not a sign of weakness to recognize that. It’s a sign of good-quality introspective abilities to know that you have now reached a point where your productivity has declined and you are more vulnerable for all of these types of interference where you’re just going through the motions of working. So keeping your mind clutter-free involves having the insights to know when you need a break and have an appropriate break, as we talked about, in order to allow for you to re-engage again.
So I would say clutter both internally and externally, being aware of it, is really important. And just like meditation, how you become better at maintaining focus over time, this is also a skill, this idea of introspection, of knowing your emotional and focus-oriented space in your brain, is something that can only come with practice. But I think that it’s always critical and it’s more so now than ever before.
MATT: Yeah, the environment makes such a big difference. One thing I have found is that when I get a little stuck, when I’m feeling unproductive, sometimes just moving. I have a laptop, I might go to the couch or against a wall or outside or something. It can help unblock me, get me past whatever the productivity version of writers’ block is.
ADAM: I agree. I do that as well. And it can be something really, really easy. Like sometimes I will just do some pushups. It may be more awkward to do it in an office, this might be the ideal time to do those type of things, but yeah, ya know, just ten pushups, ten sit ups, a couple squats, just really reorients your whole brain and that’s a nice simple way of just taking a restorative moment.
I think that it’s really going to be interesting how… I am always fascinated, you know this Matt, by how technology that has entertained us and allowed us to communicate in certain ways may be used to unlock new potential in our brain, to elevate us, not just when we’re impaired and have a clinical diagnosis of depression or anxiety but just everyone that suffers from many types of roadblocks in terms of their thinking. And so I’m always exploring technological tools that allow us to connect more deeply both with ourselves and others and also restore. So I think that’s an area that the COVID crisis right now will help accelerate hopefully is to think about technology in that way.
MATT: We’ve talked a lot about meditation but what are some other trainings that people can do to strengthen their mind muscle?
ADAM: Meditation is such a good one because it is just pure attentional focus but it is very hard for people to do at the beginning because the signal that we’re focusing on, like your breath, is very subtle. It’s one of the reasons why we’re working on — especially for children — we’re working on other types of meditation and mindfulness using technologies where you focus on sounds as opposed to your breath. Because we could regulate the sound volume depending on how well you’re maintaining it. So I think there is a real great potential to be able to use technology to unlock new types of meditative processes that are more accessible to some people than traditional meditation has been.
The other big type of attentional training is physical exercise. We did talk about that but I do want to connect those things directly. The data is quite convincing both acutely and in the long term that physical exercise helps attentional abilities.
I would say another one that helps with attention is this aspect of introspection that we’ve been talking about. It’s not enough to be introspective. You actually have to find a way of using the data that you gather about your own internal space and making it actionable, but it starts with some awareness, right? So in other words, knowing that smoking is bad for you is really not enough to quit but it’s a good starting point because if you don’t know it, you’re unlikely to do any of the things that are difficult in order to get there.
It’s the same thing with the distracted mind. Once you realize how susceptible you are to be pulled by these influences, whether it’s just quickly jumping on social media all the time, it gives you then the building blocks to make decisions about how to modify your behavior, not that it’s going to be easy, but at least you now have a little bit of motivation.
And then it comes down to routines. We are really great at habit-forming. Not that habit-forming is easy, it takes a certain amount of exposure, but a lot of what we’re doing with our behaviors are really forming new habits. Hopefully those habits that you’re forming are healthy ones and hopefully they are based on your goals and not just based on your environment. Because a lot of the habits we form are not healthy and they’re not based on our goals, right? That is a very common way to form a habit.
But I think that if you’re thinking about exercises for attention it’s to start understanding what it takes for you to form a new habit and then try to do those habits and to understand how hard it is to form them. But once you form them it’s really interesting to follow that in an introspective way.
Like, for example, I decided that I wanted to use moisturizer, [laughs] because I don’t. And especially when I go outside in the sun, I’m like, really, should I not put on a moisturizer that has some sunblock? And what I was struck… So I say okay, I’m going to do that in the morning. Like I brush my teeth every morning, I’m just going to add that on. And it was amazing how difficult it was to just add that one practice on to my morning routine, so much so that I literally would have to put the moisturizer right by the toothpaste, which was part of my routine, and risk the problematic issue of brushing my teeth with moisturizer, which actually happened one unfortunate time. [laughter] Yes.
But it’s really fascinating to follow yourself through a simple aspect of creating a new habit and then realize that it is not trivial but once it happens, it’s in there. And that is a good thing and a bad thing because a bad habit is just as hard to remove as it is to create. So that’s another thing that I would mention.
MATT: For someone listening to this who might be like, “Hey Adam, I’m an old dog, you can’t teach me new tricks,” do we have neuroplasticity even when we’re in our thirties, forties, fifties, sixties?
ADAM: Undoubtedly. That was the first research that I did as a graduate student. As a matter of fact, some of my papers in the ‘90s are on that topic, and that topic is aging and plasticity. For a long time, I mean like hundreds of years, neuroscientists really thought that after critical stages of development the brain was basically static and the only changes it made was degradation. [laughs]
Now we do change in a lot of negative ways as we age, and it’s true for every organ system. Our hair changes colors, the calcium in our bones changes, the elasticity in our muscles, but our brain changes in a lot of ways as well. But one thing that it retains throughout our life is plasticity, which is the ability of our brain to remodel itself at every level, the structure, function, chemistry of the brain, all in response to experiences. It is not gone.
And we have many, many papers. If you go on Neuroscape you’ll see our publications. For me they go back 30 years showing that the brain is capable of really amazing plasticity throughout our lives and that is something that we should embrace. And it may decline with aging, I have some data that suggests that, but it is there and finding new ways to unlock and harness plasticity with aging is one of my main research focuses.
MATT: Well I’m glad you’re working on that and that is a beautiful and hopeful I think place to end this up. Adam, thank you. Where can people find you? I heard you have an awesome WordPress site.
ADAM: So, yes, so Gazzaley.com is the website that acts as a source of all my aspects of my life from my photography to Neuroscape to some companies that I started to bring the tools that we created into the real world. So that’s a really beautiful place for you to visit to see the scope of activities that I’ve been engaged in.
MATT: Awesome. And that is Gazzaley. Adam Gazzaley, thank you again for taking the time to speak with us today.
ADAM: Thanks so much.
Matt Mullenweg with Sam Harris on Distributed Work’s Five Levels of Autonomy
Apr 15, 2020
Distributed host Matt Mullenweg recently appeared on Sam Harris’s excellent podcast, Making Sense, sharing the “five levels of autonomy” when it comes to distributed work. Listen to their wide-ranging conversation on how companies transition to remote work in the wake of the COVID-19 pandemic. We love Sam’s podcast, Making Sense, so for more go to samharris.org/podcast/ and you can also subscribe to get his premium content, which is totally worth it.
The world has dramatically changed in just a few weeks. As companies around the world shift to remote work, how do we navigate this crisis? Distributed host Matt Mullenweg talks to Vanessa Van Edwards, bestselling author, speaker, and founder of Science of People, about how we communicate with our friends, family, and coworkers during a time when Zoom and Slack are our primary tools for understanding each other.
MATT MULLENWEG: Howdy, everyone. Welcome back to the Distributed Podcast. This is our first episode since, well, everything has changed for our lives, for our family and friends and for the way we work. A lot of folks have been using Distributed.blog as a resource for remote work and best practices, so we wanted to do everything we can to help folks out in the weeks and months to come and look for lots of updates to the website that are already happening.
Today we are going to speak with Vanessa Van Edwards, an expert on public speaking who had to change the way she thought about her own work. And she also has some great tips for how we present ourselves in remote work as well. So without further ado, here is my chat with Vanessa.
Welcome, Vanessa Van Edwards.
VANESSA VAN EDWARDS: Thank you so much for having me.
MATT: I’m very excited. And also, thank you for.. you were one of our featured speakers at the Grand Meetup.
VANESSA: [laughs] Yes.
MATT: So just to give some background to the listeners, once a year, Automattic would bring everyone together and we invite very few awesome speakers and Vanessa was one of them last year.
VANESSA: It was such a lovely audience, too. I remember they actually gave me a standing ovation, which made me cry on stage.
MATT: Well, thank you very much. And it was I think one of the earlier talks we had in the week so it ended up being fairly influential. Just to give a little bit of background for you though.. Now my understanding is you actually started off doing more online teaching?
VANESSA: Yeah, I did. I actually stumbled into the online course arena before I even realized that was a thing. I was also on YouTube back in 2007, if you can believe that, when people thought that YouTube was a joke and a fad.
And then online courses, I started my first online course in 2011-2012, and thank goodness, because at the time I was teaching a lot of engineers, programmers, accountants people skills. As you know, Matt, I like to joke, I’m a recovering awkward person. And so I was teaching soft skills in a very science-backed way. And so there was a platform called Udemy, where a lot of engineers were taking courses on programming and software, and so I thought well, let me put my “Charisma for Engineers” course on there and see what happens. And little did I know it would totally explode and change my life.
MATT: Wow. So YouTube at the time was I guess pictures of dogs on skateboards. What were you putting on there at the time?
VANESSA: [laughs] Yes. You know what was really hot when I first got on there? Does anyone remember fingerboarding? Do you remember that craze?
MATT: Ohh, miniature skateboards that you would do with your fingers?
VANESSA: Yes! Yes, so I remember –
MATT: Wow, I haven’t thought about that in a long time.
VANESSA: Okay, so I remember I was competing with fingerboarding videos. That was a thing that I was competing against. And in the beginning I was just doing very casual, on-my-phone communication tips, conversation tricks. And the funny part is because it was so casual, YouTube in the beginning was very, very casual, I was doing them from my bedroom and in a weird way that actually endeared me to people and I think got me to really make long-time students.
MATT: It probably felt a lot more authentic, which people now do on purpose. And you, I guess you grew through this and published a book in 2017 called Captivate. Can you just give us a quick rundown so people can check that out?
VANESSA: Yes, for sure. So I always would walk into rooms in college and interviews and I always felt like everyone had this written rulebook of social interaction that I was just missing. And I quickly picked up every book I could find on social skills and relationships and friendships, Dale Carnegie and Cialdini, everything I could find.
And one thing I figured out very early was that most social-skills books were written by extroverts. And I am an ambivert, so I am somewhere in between. I lean towards introversion and I also have a lot of social anxiety and awkwardness. And if you are trying to learn people skills from an extrovert who is naturally very good with people, they say very well-meaning things to you, like just be yourself, or be more authentic, or smile more, or be more outgoing. Telling an introvert or an awkward person to be more outgoing is like telling them to not be themselves. So I really wanted to —
MATT: Hmm. It reminds me of that advice where sometimes people are freaking out and you’re like, “just relax,” which is probably the least helpful thing to say to someone.
VANESSA: Amen. I’m also a high neurotic, I mean, I feel bad sharing all my dirty laundry already, it’s only the first five minutes, but never in the history of “calm down” has “calm down” ever calmed anyone down. It’s exactly the same thing with ambiverts and introverts.
So I thought what if there was a way for me to study people like you study for chemistry or math with formulas and vocabulary words and maps of networking events and specific tips on what to do with your hands? And that is what Captivate ended up being. But I had no idea that this book would reach as many people as it did. It’s in 16 languages now, which is shocking, and I had no idea there were so many people who were also struggling with awkwardness.
MATT: How did that turn into a speaking career? Did the speaking come first or did the book come first?
VANESSA: The speaking came first actually. Speaking came even before online courses. I started doing group speaking. And in the beginning, because I was, in the beginning I had a niche. In a business they always say niche, niche, niche.
And I had taken a weekend passive income course when I was 17 years old — thank you, Mom — my mom is a lawyer and she said, I never want you to be paid for your hours, I want you to create this thing, this magical thing, called passive income. So she sent me to a seminar in a big ballroom in Los Angeles and I learned about this concept called passive income. And one of the things on there was creating a website or a blog, writing books and then doing speaking. Now speaking is active income, but it, quote/unquote, “can sell books.”
So in the beginning I was told to pick a niche and at the time I was 17, so I picked parenting and teens. And so I was speaking to —
MATT: [laughs]
VANESSA: I know, I know. It’s just funny how my business has grown out of that. But I was speaking to PTAs, I was speaking to student groups, I was speaking to some companies, parents, lunch-and-learns. And that is what got my feet wet in the corporate world, realizing “oh, you can reach a lot of people at the same time.” And so slowly I started to grow my corporate speaking and I have been doing that probably since 2008.
MATT: And so just to set the stage a little bit, we’re recording this at the beginning of April, everyone is affected by this COVID-19 pandemic, where in the world are you located?
VANESSA: I’m in Austin, Texas.
MATT: And as a fellow Texan, I’m glad you’re here, but things… We’re probably a little bit behind other places but it will probably get bad here this month.
VANESSA: Mhm.
MATT: What have you found so far in your own work as you’ve had to shift in this self-isolation world?
VANESSA: Yes. We saw massive shifts almost from day one. And I think on the personal side, this crisis is having everyone face their personal demons — people’s fear of being alone, people’s fear of being out of control, people’s fear of germs.
And one of my fears, definitely, is being out of control. And so in our business we have grown very, very organically specifically on keywords. I bet you didn’t expect me to go to that answer with that question. [laughter] But let me try to explain how this goes.
So I didn’t realize this literally until three or four weeks ago — so we have never had to buy traffic or buy ads or pay for traffic. Our first ad campaign was last May, so less than a year ago, everything has grown organically. And I live, our entire business feeds off of keywords. So even down to communication speaker, keynote speaker, conference speaker, Austin, and then all of our blog content. So we track… Every morning I would say I wake up and I look at my keywords, and they are quite predictable. And predictability, I didn’t notice until this pandemic, is incredibly important for my sense of calm, my well-being.
And so the first day they announced social distancing in the U.S., I saw all of our keywords, which have been very predictable for the last ten years, immediately decline because our top keywords are things like conferences, networking events, keynote speaker, conversation starters, ice breakers, body language.
MATT: Wow.
VANESSA: It was like my business became immediately irrelevant. My life’s work became immediately irrelevant in a day. And that was — is — terrifying.
Now, [laughs] I think it has taken me a couple weeks to realize there’s opportunity there because, while our top 50 keywords dropped to no traffic, very significantly lowered, keywords I didn’t ever pay attention to have started to climb back up. For example, and this warms my heart, the number-one performing post right now, which is by the way paying the bills with ad revenue, is our post on 36 deep questions to ask your partner.
MATT: Wow.
VANESSA: And that makes me so hopeful, because it means that in this crisis people are still connecting, they are still wanting deep conversations, and thank goodness we have some content to be able to help them. And so from that day we pivoted, we started pivoting all of our content.
MATT: Wow. A lot of things you just said really resonated with me. [laughs] Do you feel like some of your background in online teaching is coming back?
VANESSA: Yes and thank goodness. So interestingly I think there are different kinds of online courses — there are online courses, there are online programs. And I had created a lot of them — from 2012 to 2017 was course-creation time. In 2017, Captivate came out, totally changed my business because wow, it was working and it was a book and I had never done that before and it was driving so much corporate speaking and so I stopped making courses.
Now we have one big course, it’s our flagship course, it’s called “People School,” and that was selling great. So I took down all of my courses, literally, I took all of my courses off my website. We were also seeing, when we did split testing on the website, that too many choices made no purchases at all. Classic choice paralysis. So I was like okay, we’re going to sell one course, take down all of our other courses, and the book, and I’ll speak.
Well, now people want all those old courses again and they want new courses and different courses. And so for the first time I’m thinking you know what, maybe it’s time to dust off the old camera and the old teleprompter and get to it.
MATT: I will say one thing we have observed is that people are looking for online education more than ever. I think people just have a lot more time and so they are very open. And we’re also, all over the country and the world, being thrust into new work situations.
So the same way that maybe I was going to a conference and nervous about meeting people before, I might google things that ended up on your website, now I’ve actually been thinking a ton about just how do I show up better for my colleagues that I’m not going to probably see at all this year. Because although Automattic is fully distributed, we were really, a big part of our culture was these meetups. So we would build a lot of the trust and bonding in those in-person times and then kind of draw on it the rest of the year.
A question I’m also getting a ton is: how do you build culture when you’re not physically together? So I’m curious. Why don’t you start there — how do you build culture if you’re not physically together? How do you build that trust with each other?
VANESSA: Yeah, so one of my favorite things to do is to look at the psychology of change and exactly what we’re talking about here is we already had a lot of companies who were remote, who were virtual, who were working from home, but right now we are looking at people who are being forced into that situation and trying to create culture and connection.
And when I think about connection, I go to the chemicals. And I don’t know if this is a weird way to look at it but it helps me break it down into something we can actually produce. So when you’re looking at connection there are —
MATT: And do I remember..? I think I saw one of your videos. Do you actually have some of the chemicals behind you in a video?
VANESSA: [laughs] Yes! Right now I do. I’m gazing lovingly at them. I have literally my three favorite chemicals on my wall, yes.
MATT: Which are?
VANESSA: Which are.. okay. So these are the three chemicals that are essential for connection. They are serotonin — and by the way, this is a little bit of a simplified explanation of these chemicals but it gives you a basic idea. Serotonin is the first one. Serotonin is the sense of calm and belonging. It has never been more important than it is right now. It is that feeling that you get when you’re on a video call and everyone laughs together and you go, ah, these are my people. That is serotonin that’s coursing through everyone’s bloodstream at the same time.
The next one is oxytocin. Oxytocin, again, a little simplified, is the connection hormone. It’s nicknamed the cuddle hormone because it happens when we touch. Well, what happens when we can’t touch, when we can’t shake hands or high five or fist bump? Well, the good news is they are finding that there are lots of ways we produce oxytocin, because oxytocin is the feeling of the warm and fuzzies. This is when you are on a phone call with someone and they share a vulnerability, like they’re scared or they are not sleeping at night, and you say, [sigh] yeah, me too, and you feel like wow, we are in the same place. That’s oxytocin, that’s the warm and fuzzies.
And the last one is really important for how we combat dread. And this is what I’ve been thinking a lot about in the last few weeks is how do we stay productive on these video calls where we are having family members that are sick, where we are worried about making ends meet? And dopamine is actually a critical part of that. Dopamine is the pleasure chemical, it helps us feel excited, it helps us feel motivated, it is an active chemical, it makes us want to take action and it is how we fight dread, malaise, feeling listless. So in a really exciting interaction, you have dopamine.
So what I’ve been thinking about, and I’m so excited, I’m going to be doing a webinar for Automattic in the next few weeks, which I’m so excited about, is how do we create those three chemicals in a virtual workplace for our self in self-care and as shared rituals?
MATT: There’s something that we talked about a lot at the GM. You said when hands are visible we’re more trusting and if it’s in pockets, we’re less so. So maybe share that really quickly and then we’ll talk about that.
VANESSA: Oh yes, this is one of my favorite pieces of science. The best part about this science is it seems to be very sticky. Whenever I teach it in a webinar or from stage it seems like it infiltrates culture so much so that.. Automattic has been helping with my website, I have my entire company built on WordPress… and on our video calls, they always start with a big wave and they always have their hands visible even months and months later.
And the reason for this is because when we first meet someone the very first place we think we look is eyes or face, but actually when you look at eye tracking studies they find that the very, very first place we look is someone’s hands. And they think that this is a leftover survival mechanism that somehow, back in our caveman days, if we were approached by a stranger caveman the very first place we looked was their hands to see if they were carrying a rock or a spear.
We also look to hands to see is someone going to touch us, are they going to hand shake with us. And so we are always a little bit aware of the hands. And this is such an easy scientific tip to bring into our real life because it’s basically leading hands-first. The moment your video call turns on, having that waving hello to everyone, can immediately subconsciously take down anxiety when they see it.
MATT: Okay. Now I have been on a lot of video calls in my life and recently. I have started noticing that most webcams are not positioned to have your hands in there.
VANESSA: Yes. So I have two tips for video calls. One is make sure that you scoot the camera or your screen back or get an external camera so that they can see the tops of your hands, basically your upper torso and your head. It does so many things. One, it allows you to see hands easier, two it also allows you to gauge someone’s confidence easier.
A really easy confidence cue is the distance between someone’s earlobe and the top of their shoulder. And this makes sense if you think about it logically. If you are tense or anxious, you tense your shoulders up toward your ears. I’m doing it right now, you might even be able to hear it in my voice. When I tense my shoulders up and then I turtle my mouth down, it really decreases the amount of oxygen I can take in because I am tense. And then the moment I put my shoulders down, it gives me more oxygen, it gives me more space, and I hit my what’s called a maximum resonance point. So to be able to see hands and shoulders, it’s extremely helpful.
MATT: Hmm. It’s tough because to me the most important thing on these calls is the audio quality and sometimes the further people get away from their – if they don’t have some sort of microphone – the further they get away from the computer, which is their camera, the harder it is to hear them or the more background noise that comes in. And I heard you talk a lot about body language, what is the vocal or aural input that influences our trust and acceptance in those three chemicals?
VANESSA: Yes, okay. And by the way, I totally agree with you that the further away your computer is, the worse it is. So you can easily.. if you get earbuds your microphone is as close to your mouth as possible and the camera can be farther away. So that’s a little easy tip, it also helps with background noise and kids playing and all kinds of background things. So that’s my go-to with my teams.
Okay vocal power, Matt, this is my favorite topic. We don’t realize that we are constantly making vocal impressions and that a lot of our charisma is being signaled through our vocal power. And this is one of the most interesting studies that I have ever read. It was done with doctors and what they did is they had doctors record ten second voice tone clips. And in these clips they had them say their name, their specialty and where they worked.
So it sounded something like this, “Hi, my name is Dr. Edwards, I specialize in oncology and I work at Children’s Presbyterian Hospital.” Something very basic like that. They took these clips and they warbled the words. They made it so you could hear the volume, the pace, the cadence, but not the actual words being said. So it sounded something like this. [warbling, nonsense words]
MATT: Wow, that was a really good warbling impression.
VANESSA: Well, thank you, thank you very much. Thank you. And they asked participants to rate these clips on things like competence and warmth. So imagine this for a second, you’re given a clip of gobbledygook and you’re asked how smart is this person, how friendly is this person?
And so participants did it and they found that the doctors who had the lowest rating in warmth and competence had the highest rate of malpractice lawsuits. That is an incredible finding because it indicates that we don’t just sue doctors based on their skills, we sue doctors based on our perception of their skills.
And so in voice tone, and they looked at patterns, why some doctors across the board rated as highly warm, highly competent, whereas other doctors were seen over and over again as not dependable, not smart. And they found all kinds of patterns. And these are very tied to our body language. Our body affects our voice and our emotion affects our body. So it is this one big circle.
And so I’ll give just one easy example here. We know that confidence is contagious. So if someone feels calm and competent and confident in what they are presenting in a meeting, that means they are high in serotonin and that means we feel calmer, confident and more capable in their message, so then we get more serotonin.
So the way that we do that is the more space that we have in our body, the better our voice, the closer our voice is to our maximum resonance point. So when you think about voice, we all have a range. Right now I am working very hard to stay in the lowest end of my natural range. When I get excited or I’m talking to my daughter, I talk a little bit higher, like this, [demonstrating] and when I’m like oh hey baby, how are you, it’s so good to see you, I miss you, I love you.
Now if I did the entire podcast like that, it would drive you crazy. You couldn’t listen to it. [laughs] And that is because those are both natural to me but one of them shows less space, it’s higher up, versus now, I’m hitting the lower end of my range. Now we know that people who are relaxed, they have low shoulders, high head, space between their torso and their arms, in other words they are using hand gestures, that actually translates into lower, more resonant voices.
MATT: If I were going to put up a post-it note by my webcam of some things to think of and do before I go on a meeting with colleagues, what would you put on that post-it note?
VANESSA: Lower your shoulders. [laughs] And that’s, I know that sounds really weird. My second choice would maybe be “breathe,” but that’s… We always breathe so that one is not as good.
But I’ll give you an example. So a lot of the times people answer the phone or get on a video call or start their speech or their presentation on the highest end of their breath. So they take in a deep breath and they go [inhale, in a high-pitched voice] hello? And they are at the very highest end of their breath. That sounds tense. Your shoulders also go up when you do that.
When you speak on the out breath.. So that sounds like [demonstrating] hello, your voice immediately goes down, your shoulders immediately go down and then it’s a much lower resonance point. So if your shoulders are down it’s not only that you are probably breathing, but it’s probably that you are [out breath] speaking on the out breath.
MATT: Anything else on the post-it, number three? So we’ve got lower your shoulders, breathe, and maybe room for one or two more.
VANESSA: Hand gestures. So there’s two aspects of hand gestures here. First, visible hands, yay, bonus points, love when your hands are visible, wave hello, keep them visible when you’re talking. The second aspect is competence. And that is that we tend to look for hands for further or deeper comprehension.
And this also touches very closely to honesty. And the reason for that is because it’s very easy for a liar to lie with their words, it’s very hard for them to lie with their hands. And so we look to gestures to look for congruence. We are looking to see if someone’s hands match their words.
And we did a huge TED Talk experiment in our lab where we looked at the most popular TED speakers based on view count and we saw there was a clear, clear difference between the most viewed TED Talks and the least viewed TED Talks. The most viewed TED talkers use very explanatory gestures. When they are talking about three things, they hold up tree fingers. When they are talking about a small idea, they hold it small, like a little tiny jewelry box. When they’re talking about a big idea, they literally act like they are holding a beach ball.
This is incredibly important even if you’re on the phone, even if you’re not on video. Researcher Susan Goldwin Meadow found that our hand gestures contribute to our vocal charisma. So right now I’m using tons of hand gestures. You can’t see but they are just moving and moving and moving. If I were to sit on my hands that would actually translate into two things.
One, we recall less and are less vocally fluent without hand gestures. So hand gestures actually help you be more interesting. By the way, I’m sitting on my hands and I couldn’t even think of the word. Your hand gestures help you be more charismatic. I’m bringing them back out. And they help add depth, personality to your voice, even if you’re just on the phone.
MATT: I have heard that when you’re virtual versus when you’re in person, you should try to amp up your energy a bit more. Do you find yourself doing that when you’re doing online courses versus in person?
VANESSA: Ooh. Okay. So I do not believe in fake it till you make it. I do not believe in faking energy if you don’t have it. I also think that there is something naturally human and beautiful that happens when you match the energy of the person you’re with as much as that feels good to you.
So if you have a lot of energy because you’re passionate about your topic, yes, keep it as high as it feels good for you. If you don’t feel energetic — you’ve gotten bad news, you’ve had a long day — the worst thing you can do is be forced happy. And we all know what this sounds like, right? It sounds like this. [demonstrates] Hi everyone, it’s soooo good to see you, so today.. Ugh. Like, ugh. I just.. We just can’t do it. So what I would say is first, try to honor where you naturally are.
The other thing I would say is, Matt, you have a very calm, peaceful way of speaking. When I met you in person, you have a very calm, peaceful presence as well. What I like to do is actually try to match and mirror your energy as much as possible. So I’m actually speaking at a lower volume, at a lower energy than maybe I would with someone who is a fast talker and super high energy and pelting me with questions, because I actually want to be on the same energetic page as you.
MATT: Interesting. I always think about trying to get folks who are a little more amped up to compensate for my more normally dulcet tones. [laughter] One thing I’ve noticed as well is group dynamics. I recently blogged about this, that I don’t love Zoom calls where everyone ismuted. Have you ever run into that where it’s like you’re not getting any auditory feedback on things you say?
VANESSA: Oh, yes. Actually it’s really a subtle thing that you picked up on that’s really important. So, oh my goodness, if I could remember this research… I’m going to paraphrase this research because I haven’t read it recently but I believe it was by a researcher, Monica Moore. And she found that in a conversation when a man says more mmm, ahh, ohh, in a conversation, when they’re listening, just when they’re listening, the woman finds them more attractive.
MATT: Hmm.
VANESSA: And that when women say mmm, ahh, ohh, the woman also likes the conversation more and the man feels like he’s being better listened to. So there is something very important about that feedback loop.
So a couple of things here — one, if you have a small enough group I do highly recommend keeping people off of mute unless they have a cat sitting next to them and they’re typing on the keyboard or kids in the background. But two, if it’s too big of a group, give time where you want people to come off of mute. So, for example, if someone is presenting and you want to say, “oh let’s give them some feedback, everyone unmute themselves, give them a round of applause” —
MATT: Ahh.
VANESSA: — Or, okay everyone, we’re going to do a little intro here, everyone unmute themselves, say hi. Unmute. Hi, hi, hi, hi, hi, hi. Thank you. You can actually have group, even with Zoom calls of 50+ people, his, applause, byes, thank yous, it’s really the next best thing.
MATT: That is a really interesting tip. We have started to do more jazz hands instead of applause as a visual way to applaud and I guess I actually learned it’s the American Sign Language for clapping.
VANESSA: Yes.
MATT: But I’ll try the unmute thing. We do a monthly town hall, which is where generally anyone can ask anyone any questions and I try to answer them or other people jump in to answer them. But it is typically only one or two people unmuted and then many, many hundreds watching.
Have you picked up anything else on Zoom that we should be leveraging that the software might help make things a little friendlier or a little better?
VANESSA: Well, you know I love a good filter. So if you have not discovered the filter yet on Zoom it really lightens you up, makes you look like you’re sleeping really great. Do you use the filter, Matt?
MATT: Oh this is the one that smooths you out, right?
VANESSA: Yes.
MATT: Yes, let me see exactly what it’s called. That one is kind of neat. It’s under Video and it says “Touch up my appearance.” And I do not have it on right now but maybe I should turn it on.
VANESSA: I’m going to change your life, Matt. You’re going to look so young and so well-rested, it’s going to be amazing.
MATT: Have you tried the Snap camera yet?
VANESSA: I have not tried it yet, what is it?
MATT: So Snap, as in Snapchat, released a computer utility that lets you do Snapchat-like filters, so more fun ones or irreverent ones, in real time through your web cam.
VANESSA: What..?
MATT: I know.
VANESSA: Oh that’s real cool. Okay so that’s really cool. So filters, Snaps. I was just talking to your team about this, most people also don’t realize that you can have multiple co-hosts. So if you’re running a meeting, like a smaller meeting, and you need help with muting people or posting things in chat or recording, I always recommend double- or if not triple-recording. You can make as many people as you want co-host and they have controls to help you. Because as a meeting manager it can be a lot to do it all yourself.
MATT: I’m also going to throw in one of my favorites and cheapest improvements is just a lamp or positioning yourself where you’re facing a window rather than being backlit. The lighting can make such a huge difference, especially as the days start to get shorter or you’re on meetings at odd hours. You don’t want to look like you’re in a horror movie or badly lit otherwise.
VANESSA: Oh my goodness, lighting from the front, game changer, probably even better than that filter I just told you about. I’ll also give you one more. So it’s really helpful if you look…
The tendency for the eye is to look at the person speaking, which is actually underneath the camera, or to the side of the camera, depending on where your camera is. What I do is I actually shrink my Zoom screen down into a very small video and put it right below where my camera is so that when I’m looking at the camera, I am also looking at people’s faces and it doesn’t feel like it’s that different.
MATT: That is so cool, I do the exact same thing. [laughs] It’s neat that we both independently arrived at that. And my dream is for the camera to be able to be on this screen a little better.
VANESSA: Oh yes. Yes, exactly. I do try when I’m speaking to speak directly to the dot.
MATT: Yeah, that is really hard. I also sometimes make the Zoom full screen so I don’t have any distractions but then I end up turning my head, because I have a really wide monitor, when different people are speaking. I don’t know if that looks like I’m looking at something else or whether they have some sense that maybe I’m turning to look at their face.
VANESSA: I say that to people. Like if I know that I have… I have a couple of external screens, I will literally say hey, I’m actually looking at you on the other screen even though you don’t realize it, just because you don’t want people to assume that you’re checking email or something.
I also have a master-level tip. If you really want to get good at video call, if you really want to get good at video call, I would highly recommend learning the seven universal facial expressions. Dr. Paul Ekman is an amazing researcher, he’s where I got my training, and he discovered something called the micro expression, which is a universal facial expression. It’s a very quick one, it’s less than a second, and it’s our natural reaction to emotions. And he has discovered across cultures and genders and races there are seven universal facial expressions.
I will tell you, learning those facial expressions was like suddenly seeing the world in HD. I was seeing emotions behind words, I was seeing how my words were being heard. And so I would highly recommend, and I have these all for free on my website, I think this is a universal skill, I think everyone should have it, so just go ahead, you can look at it all for free. We have video demos and photos on there.
Once you learn how to spot the universal expressions you no longer have miscommunications about emotion. You are able to skip a lot of the “what is she feeling, what is she thinking,” with knowing wow, that was sadness or hmm, that made her nervous, that was fear, or whoops, just saw some contempt, I better back up and explain again. If you really want to be a dynamic presenter or meeting coordinator, I highly recommend learning those seven.
MATT: What should we google to find that on your site?
VANESSA: Its scienceofpeople.com/face and you’ll see lots of me making funny faces for your benefit.
MATT: That is awesome. Did you have any acting in your background?
VANESSA: [laughs] No, no, not at all. I’m actually honored that you asked because it means I’m doing a decent job.
Although I will say I have always wanted to be funny and I used to think of myself as funny, now it’s just an accident when I’m funny and people are laughing. So I have tried to take improv. And when I was seven years old, I carried around a bunch of jokes in my pocket because I had no friends and so what I would do on the playground is when anyone sat next to me I would pull out my book and I would tell a joke. So I have tried it a little bit in comedy.
MATT: I kind of love that. On these facial expressions, do they ever steer you wrong? Because sometimes I can see myself on the webcam and maybe the lunch I ate wasn’t sitting with me well and I feel like my face is not expressing my inner emotional state, or it’s expressing something that has nothing to do with what the person is saying.
VANESSA: Yes. Yes, absolutely. I’ll give you a really real example. I was hiring a new person on the team and loved her resume, we had a great phone interview, brought her in to do an in-person interview and she kept making these really negative facial expressions, specifically she kept making contempt. And I thought my gosh, this is not what I expected. And it kept throwing me off.
And I was like god, that interview did not go well. And so I kept looking for more candidates, I didn’t find anyone as good as her, and I called her and I was really honest, I said, Listen, you were my first choice but when we met in person, I had the feeling that you were worried about something or something was wrong. And she said, You know, I wanted to wear a pair of heels to the interview and I borrowed my roommate’s pair of heels and they were too small. And I didn’t expect us to walk to coffee and as we were walking around and standing at the coffee bar, I was in a lot of pain.
MATT: Ohh…
VANESSA: And so it had absolutely nothing to do with me or the interview but it did steer me wrong. So since that experience, that was about four years ago, since that experience I have developed just a rule of thumb, which is the rule of three. If you see a negative or positive facial expression, before you do anything about it, before you take it seriously, you want to look for three other pieces of evidence. And this could be non-verbal or verbal.
So let’s say that you see contempt. Contempt I’ll teach you even though we’re audio, it’s the simplest of the micro expressions. It’s a one-sided mouth raise, so like a smirk. So if you try it with me, if you just smirk one side, you’ll kind of feel better than, like a little bit scornful. It’s like a hm, hm. Don’t do it for too long.
So contempt is a very powerful expression because it is very simple and people often mistake it for apathy or even half-happiness, like a smirk. So if I see contempt on someone’s face, like I did on her face that day, I should have been looking for two other cues that she actually felt contemptuous.
That could have been verbal, like a disparaging comment or a difficult question or a non-verbal cue like pulling away, distancing behavior, blocking behavior, a shame gesture. The universal shame gesture is when someone touches the side of their forehead with their hand. So I would be looking for two other cues to say okay, there really is something negative happening here.
MATT: Huh. In trying to get my hands visible, even though my camera isn’t well positioned for it, I found myself trying to cross my hands a little bit. I’m trying to describe it, like if you crossed your fingers and then rested your elbows on the table, maybe you can imagine that.
VANESSA: Yes, yes.
MATT: So that my hands were visible. And I also find myself leaning, having one hand that my head leans on a little bit, which I also feel a little bad about because we’re not supposed to touch our faces, but I’m home so I do. Is there anything there that we should keep in mind, anything with those particular gestures which is good or bad?
VANESSA: Yes, great, great point. Remember that there is kind of a hierarchy when it comes to non-verbal. So I would rather see your hands even if they’re touching your face. I would rather see your hands even if they’re in a blocking gesture, like in front of your body, because on video camera that’s pretty much the only place they can be. They can either be typing, they can be resting lightly in front of you or you can be holding your head. You’re not just going to hold your hands up in the you’re arrested position, right?
So yes, I would say resting them lightly in front of you, as long as they’re not tightly gripped. Any kind of fist or tension in our hands typically signals tension in the body. So nice and loosely at rest, I love it. Lightly touching your face or keeping your hand on your face is better than picking at your face or playing with jewelry or playing with hair.
My personal favorite actually is I almost always have a pen in my hand and my Moleskin notebook next to my computer and so almost always I’ll be holding my pen, which keeps it visible and kind of poised. It’s more of an active response, and it’s also very authentic because I’m usually taking notes.
MATT: There is one other thing which I wanted to bring up, which I think I got from some of my HR colleagues here at Automattic, is that there are so many ways to misinterpret things when you’re in lower-bandwidth communication, so when you’re not in person. We talk about API, or assuming positive intent. Is there anything in your teachings that goes around that?
VANESSA: I love that. I love that different definition of API. I think that there is something really interesting that directly ties into this and it’s the idea that we tend to think that our positive cues are overly obvious and our negative cues are not as obvious. And this is a really big aspect of likability.
We typically think that people know that we like them, but actually it takes far more for someone to be sure that we like them than we realize. And so not only do you have to assume positive intent, I think we also have to be incredibly clear with who we like and what we like.
You might assume that you have told a colleague or a teammate that they have done great work, but it takes three to four times — and I am making up that number because it very much varies based on romantic settings, professional settings, and friendship settings. But I think in a professional setting you can tell yourself that it takes three to four times of telling someone that you appreciate them, that you like their work, that they did great work, that you enjoy working with them on a team for them to actually believe that’s true.
Whereas one small what’s called a micro negative, one small negative gesture, like an eye roll or a [loud sigh] that they hear at the beginning of a video call, or one short, terse email that you sent because your kid was yelling and you had to get the email out as quickly as possible, that one email can negate three to four positive sentiments. So what I would say here is be absolutely sure the people on your team know what you enjoy about them — that you enjoy working with them, talking about them, talking to them, that they are productive, that you appreciate their skills, that they have helped you in some way.
There is something called the positive impact test and recently I have been doing this every night. So at the beginning of this crisis, I was having a really hard time sleeping. I was worried about business, worried about traffic, worried about family, and I just couldn’t fall asleep at night. And I realized it was because I was in these worry cycles where I was just worrying about the same things over and over again. And so I decided that every night I wanted to do the positive impact test. This was a test that was developed by Tom Rath and I just shortened it into three questions.
And this is what I ask myself every night at 9:00. And if the answers are not yes, I try to fix it. So they are, in the last 24 hours, have I helped someone? In the last 24 hours, have I praised someone? In the last 24 hours have I told someone that I cared about them or appreciated them? They are three questions that ground me on what matters. Revenue doesn’t matter, traffic doesn’t matter, but me feeling like I’m doing my very best in this crisis does matter.
And so what I would say is maybe you could invite yourself to ask yourself at the end of a workday or the end of a night that you should be able to very clearly answer those at least at the end of a week.
MATT: I love that. So thank you for sharing. We mentioned a few times that you’re going to be giving a talk at Automattic soon. I would highly encourage every person and every company listening to this. Do not stop your internal education and helping people get better just because everyone is working from home. If anything, it’s even more important now because people… I think it helps them feel agency if they are able to learn new skills or get better at what they’re doing, which is a very unusual and challenging work environment for all of us.
So Vanessa, where can people find out more about you? Where can they reach you, where can they see you on YouTube, Twitter, etcetera?
MATT: Vanessa, thank you again, you bring together so much great information, you synthesize so much, saving people a ton of time. They can listen to you for an hour instead of reading 20 different books. And I do really appreciate your wisdom and thought that you bring to this. So thanks for coming on and hopefully we can get you on again sometime in the future.
VANESSA: Yes, I would love it. Thank you so much for having me. I hope everyone stays well.
Episode 18: Jason Fried on Treating Workers Like Adults
Jan 09, 2020
For our first episode of the year, host Matt Mullenweg talks to Jason Fried, the CEO of Basecamp. Jason runs a semi-distributed company that’s been making project management software for 20 years. He’s accumulated a wealth of wisdom about how trusting employees and treating them with respect can yield long-term success.
The full episode transcript is below.
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MATT MULLENWEG: Howdy, howdy, and welcome to the Distributed podcast. I am your host, Matt Mullenweg, and I’m here with our first episode of 2020. Today’s guest is Jason Fried, the CEO of Basecamp, a semi-distributed company that’s been making project management tools for about 20 years now. Back in 2013, Jason wrote a book called Remote, which was an early manifesto for remote and distributed work models. I’m excited to catch up with him to hear about what he’s learned in the six years since that book came out and how Basecamp operates today.
All righty. Let’s get started.
MATT: Jason, I am so glad to connect today.
JASON FRIED: Likewise.
MATT: Basecamp, formerly known as 37signals, has been in so many ways an inspiration for Automattic over the years, and I’m sure countless other distributed companies, so thank you for that, first and foremost.
JASON: Of course. And I would say likewise. I mean, you guys are even more distributed than us, so I feel like you’re the ideal situation where we’re getting there because we still have about 15 people in Chicago and we have an office that we’re maybe getting rid of, so we’re going to be following in your footsteps.
MATT: Ah. So we had zero offices but then with the acquisition of Tumblr we’ve now got a space in New York again, so we’ve gone in the opposite direction.
JASON: Ahh, right. That’s funny how we keep trading. Yeah. We’re not sure what we’re going to do but our lease ends in August so we’re thinking about moving on, as in moving on to nothing and then trying to do that for a while and see what happens. And if that works out, we’ll do that. If not, we can always go back to getting an office again. But we’ll see.
MATT: Just for our listeners who might not be familiar with Basecamp, what do you publicly share about the scale of the company, customers, number of employees, that sort of thing?
JASON: Well we have about 56 people who work at Basecamp and we have close to 100,000 paying customers all-in across all of our different products. Although, Basecamp is the primary product, but we have Basecamp, we have Highrise, we have a few others, but basically it’s Basecamp in all three generations. Some have Classic, Basecamp 2, and Basecamp 3.
This is as specific as we’ll be, but we generate tens of millions in annual revenues and annual profits. And we’ve been around for 20 years. This is our 20th year in business, and we have been profitable since the start. That’s a big thing for us, is to always be profitable. So that’s the only KPI, we don’t really use those terms, but that’s the only one we have, which is, let’s make sure we make more money than we spend every year, and other than that, whatever happens, happens.
MATT: How do you think about investing more or not?
JASON: We don’t have an investment shortfall kind of thing. It’s not like if we only had an extra — I’m just making up rough numbers here — an extra million bucks, we would do X or Y. We have everything that we need to do and we don’t want more people because we want to keep the company as small as we possibly can. So we have, not a dilemma really but it kind of is, in a sense, because I feel like we’re doing everything we could do and having more wouldn’t help us.
In fact, I think in some ways it would probably hurt us. We’d be a little bit slower, we’d be probably doing too much work at the same time, which I think can often dilute what you’re really trying to do. We might take on more stuff than we really want to. We might just find work, invent work, to keep people busy. There’s always of course more work to do, but we believe in doing it at a certain pace, and I think having more people, or fewer people, at this point would kind of mess up that pace.
MATT: When you say as small as possible do you mean by customers or by colleagues and employees?
JASON: I mean employees. I mean the number of people who work here. We have always wanted to stay at 50 or less but we’re about 56 right now and that feels like a really good place to be, so we’re very comfortable with that. The thing is that we could have considerably more people, but again, we’re just not really — maybe we’re just not good at it. I’ll just take the blame for that. I’m probably not good at running a much larger company than this and I don’t think David is either. I don’t think we want to.
I think it also keeps you a bit more honest in terms of the experiments you’re willing to do, which — and in some places more and more and more experiments is a good thing. I think a few are a good thing but I think too many — people can get stuck doing things that never ship over and over and I think that can be a bit demoralizing.
So we think we’ve got a good enough feeling here right now at least. But then again, we’re the largest we’ve ever been, and I’m sure when we were 30 people we said 30 is enough. So we’re here at 56, that feels like enough right now. A lot of it probably has to do with the success of this other product we’re going to launch next year.
Because the one part of our company that does have to continue to grow is customer service. Product development doesn’t have to grow, we have enough people there, but as we have more and more customers, of course, we have to make sure we support them at the highest level. So that is one place where growth does continue to happen even if we don’t want it to.
MATT: Yeah, for Automattic that’s been pretty large. It’s been at points that half of our company was customer service just because we wanted to maintain a certain level there. And as the customers went up, it just got — it goes linearly.
JASON: Yeah.
MATT: It’s one of those things that — of course you want to invest in making the product easier and documentation and self-help and everything like that, but at some level if you want a person talking to a person you need some more of them.
JASON: Yeah. You know, you want to do documentation and make things easier and everything, but I’ve also come to change my mind a little bit on it. Earlier on, when we had fewer people, we were focused on the self-help side of things and making sure our documentation was really good and our answers were great online and people could find their own answers.
And we want to make sure that that’s true too, but I also see customer service interactions as a competitive advantage. Most companies are pretty terrible at it and the larger the company is, it seems like the worse they get. Try to email Google and get help. It’s like — forget it. Or Amazon, sometimes, but not always that great, although quite good sometimes also. It’s one of these things where the larger you get, the more customers you have, the harder it is to maintain that level of standard.
MATT: Have you tried out a live chat for customer support yet?
JASON: Yeah we do that sometimes. And it depends on availability. And then we also use Twitter as well for that. Those things all work out really well. It just depends. We want to meet people essentially where they are, with the exception of we don’t have a published phone number, but if you want us to call you, we will.
MATT: Yeah. Live chat was a big step function for us. Both in terms of agent and customer happiness, because you can resolve things on the spot.
JASON: Yes.
MATT: We do a support rotation where everyone at the company does customer service for at least one week a year. Mine is actually coming up in a couple of weeks.
JASON: Your turn, you mean?
MATT: Yes. So if you contact us in the third week of December, you might get me.
JASON: Ha! We do the same thing, we call everyone on support one day every roughly six weeks or eight weeks… So we’ll each do support for a few days a year throughout the year. It’s great and I’m glad you guys do that too.
I think it’s one of the most valuable things you can do for a variety of reasons — camaraderie, hearing from customers and understanding the language they’re using, sensing their frustrations or their happiness or whatever it might be. And then also just having a lot of respect for customer service as a job and as a career.
In a lot of places, customer service is treated as almost a part-time job, a stepping stone to somewhere else. But I think it can be a wonderful career and it’s just really nice to see the people who’ve dedicated their time here — and this is my only experience of course — to working in customer service for five, six, seven, eight-plus years and really see the work that they do and see how important it is. It’s our front door, it’s our front line, it’s really important to experience that.
MATT: What is your company breakdown now in terms of roles in the 50-ish?
JASON: I’ll give you some rough numbers because some people are multiple things, so you can’t really…
MATT: Sure.
JASON: I’ll give you the counts, it just might not add up to 56. But so we have currently, I believe 16 people in customer support, and that also includes, I believe — this might make it 17 or still 16 — the team lead. So all of our managers or team leads are working managers in that they do the work too. So 16-ish on customer service.
We have seven-ish on technical operations, all the server work and that kind of stuff, all the low-level infrastructure work. And then we have four people on what we call the SIP team, which is Security, Infrastructure, and Performance. We have about seven full-time designers, we have around 15 developers. Actually a few fewer than that because some of them are now on SIP, but around that number.
We have two people who do our podcast work, we have one data analyst, we have an office manager/bookkeeper. We have a Head of People Ops. And then we have David, who is CTO, and me, I’m CEO. We have a Head of Strategy and a Head of Marketing.
MATT: And did I hear it right that you seem to have a two-to-one or a three-to-one developer to designer ratio?
JASON: Yes. Close. Depending on — in some companies you’d consider ops programmers. It just depends on how you all add it up. But yeah, we have probably a two-to-one programmer to designer ratio. Or I should say product development programmers, because we have programmers who do other things. But on the product side of things, basically two-to-one.
The way a typical team is structured here at Basecamp is there’s three people working on something — three or two — never more than three at a time and when there’s three it’s usually two programmers and one designer and when it’s two, it’s one programmer, one designer. And then of course sometimes there’s some things that a designer can do on their own and sometimes there’s some stuff that a programmer is going to do on their own.
MATT: I’m going to toot your horn a little bit in that in your latest book, It Doesn’t Have to be Crazy at Work, there is an excellent chapter on the three-person teams.
JASON: Oh yeah.
MATT: I do think something that’s interesting. A lot of the listeners here get obsessed about the 1,000+ person distributed companies, and people sleep on Basecamp a little bit. But I think that would be incorrect, because you all are an amazing example because of your culture, your retention, everything, where you move really fast and do quite a bit for your size. And that’s where I think there’s a lot of learnings for companies of all sizes.
JASON: Thanks, we try. I think one of the reasons we’re maybe able to do that is because we don’t do a lot of other things that most companies do. We don’t have a lot of meetings, we don’t share calendars. It seems like a simple thing but it has such a huge influence.
When nobody can take anyone else’s time through a system, people end up with more time to themselves. When you have more time to yourself, you end up doing better work and more work. You can get a lot more stuff done in a given day than maybe you could in another organization that has six times as many people but 20 times as many meetings, 30 times less time during the day to yourself.
So we try to avoid anything that breaks days into smaller and smaller chunks. So we are pretty anti-chat for work. We use chat internally in Basecamp for mostly social stuff. But any time there’s anything going on at work we write it up in longform and we post comments and we let people discuss it over a matter of days on dedicated pages inside Basecamp. So that’s the kind of stuff that we’re able to do, and it gives people a lot of their time back.
MATT: What are your favorite meetings? What do you look forward to? What’s a meeting you love?
JASON: Two or three people might get together in a room — typically it’s two — or on a Zoom call or something like that, to work something out, hash something out. That, I enjoy.
I enjoy really working on a problem, like a design challenge or “God, how are we going to figure this out?” or “This seems complicated, how could we simplify this?” Or “What’s the best way to write this sentence? This headline just isn’t quite there.” That, those productive moments when we are actually making something versus talking about making something.
I don’t like talking about making things, I like the making of things. So whenever I’m together with somebody and we’re working on something real, [I] love those all the time. And I’ll do that many times a week. But just to sit around a table and have people go around a table and talk about stuff that isn’t actually the work — I think it’s important to have those discussions, but I don’t think they need to be happening in person or via video.
I think most of that stuff is better off written down. It allows people to really present themselves, a full idea. We call it “forcing the floor.” The idea being that if you’re standing up or sitting down, or whatever, in front of a bunch of people, and you’re talking for a while, there is a good chance someone is going to interrupt you and ask you a question or whatever. And there is nothing wrong with questions.
And this is especially bad in chat rooms. You can’t possibly own a chat room for a while while you make a case. You just simply can’t. People will chime in and that’s a problem. Now, I’m not a big fan of chat, but there should be a pause button when you chat. You should be able to hit pause, which would prevent anyone else from saying anything while you’re talking.
The reason that should exist is because you need to have the floor. You need to make your point. That allows you to work your thoughts out yourself, get your thoughts together and put them out there in the world as a single unit. And that allows other people to read that single unit uninterrupted and take their time to respond back to you.
If you’ve taken three days to think about something and you say it in a meeting and people start just throwing stuff right back at you — in some ways you’re asking them to because you’re sitting at a table, what else are they going to do? But it seems unfair to them, in fact, for them to have to react to this thing that you have thought about for three days or three weeks or three months, for them to have 30 seconds to say something back seems unfair.
By writing things down in longform and publishing them and giving people a chance to get back to you on their own schedule, I think you end up with much deeper and fairer discussions and better discussions. So that’s why we do have, quote, “meetings,” in a sense, but they’re not meetings in time, like around a room physically or even on video, they are written down and people respond over a number of days, on their own schedule, and those conversations are much richer.
MATT: Well that emphasis on writing and the well-written word, how does that influence your hiring process?
JASON: It plays a big role. Aside from somebody being able to do the job — obviously, the fundamental job — beyond that you’ve got to be a great writer. If you’re not a great writer, you will not get the job.
The first thing we look at whenever someone applies for a job is the cover letter. We don’t look at the resume first, we look at the cover letter first. And the cover letter is the first filter. Can this person explain themselves well? Are they clear-minded? Are they clear writers? Are they clear thinkers? Do they want this job, or are they just applying for any job?
Typically a resume is going to be sent to every job the same way, for the most part. You’d hope that cover letters are not. You’d hope that cover letters are customized for the job.
MATT: You would hope. [laughs]
JASON: You would hope. I can tell you’ve done a bunch of hiring yourself. Yeah. So most of them are not. And those are immediate no-gos for us. If you want to work here and if you want to work at any job, I would say you need to write down why you want to work here, not just why you want a job. And from that, you can derive a lot of things as a hiring manager, as someone who is involved in the process, you can really tell where someone’s head is.
So writing is very important, and then we often give a lot of writing exercises through the job hiring process, depending on what it is, and continue to double down on that. And every time we’ve been hesitant about someone, their skills have been great but they weren’t great writers, it turned out that we probably shouldn’t have hired them. And the main reason why here is because most of our communication is written, almost. I’d say 95% of it is written.
MATT: Let’s say I was a colleague of yours at Basecamp and you were going to coach me or give me pointers to resources or something to become a better writer, how would you do that?
JASON: My favorite book on writing is a book called Revising Prose, and the cover — I think it’s in the fifth edition now — the fifth edition cover is horrible. It’s a CD-ROM. It’s a picture of a CD-ROM, it’s the strangest cover of a writing book. But Richard Lanham is the author of Revising Prose, fifth edition.
It’s outstanding because it’s a book about writing sentences. It’s not about grammar really, it’s not about elements of style or rules, it’s about how to hone a sentence, how to get a sentence right, how to make a point. It’s a very, very good book. I’d recommend reading that first off and then I would write and write and write and write.
And I would work with you to review your writing, your headlines, your sentences, whatever you’re going to do and talk about, like, “We could say it this way or maybe you could say it this way. And if you said it this way, it would feel like this. And if you said it this way, it would feel like that.” I like to talk about feeling when it comes down to writing, so how does this come across, what does it make the reader feel, what does it elicit in them — that kind of stuff.
But it’s the process of whittling something down and not losing any detail as you go, maybe even picking up detail as you go, until of course you hit a certain point and then it’s more of an academic, fun exercise to whittle it down to one sentence and one word.
MATT: Basecamp has a pretty unique structure. Do you look to any other tech companies or outside of tech or companies in general that have inspired you to the structure of how you do things there?
JASON: I tend not to look at tech companies mostly because I think it’s healthier to look outside your own industry most of the time. We’re inspired by what you guys are doing at Automattic because you’re fully remote and you’ve been around for a long time. In broad strokes, I like to look at people who have been around for a long time because I feel like if you’ve been around for a long time, it’s not a fluke.
MATT: I know you follow the watch world and I know you like… I think you like Cucinelli, actually. Are there any examples in that realm that you like?
JASON: Yeah, Brunello Cucinelli, I don’t know him but I admire his ethos and how he runs his business. I consider him a mentor because of the way he runs his business and how he’s all about integrity and dignity. And there is a lot you can learn from that. You don’t need to talk to anybody to learn that from him. So I think there’s a lot of really wonderful examples.
In the watch world, the mechanical watch world, which I am a bit too absorbed in these days, there’s a lot of old businesses. I mean some of them are hundreds of years old, many of them are family-owned and have been passed down through generations. I just find it fascinating. To see how different generations do different things is fascinating to me. And to see how something can last beyond a generation.
I always often think, well we’ve been in business 20 years, I’m 45 now. If we’re going to last another 20 years — which I hope we can, I’d love to — I’d be 65, I probably shouldn’t be running a software company at 65, it’s probably not the right thing to do. So what’s going to happen? Who is going to take over? How are we going to do that?
We haven’t really thought about succession planning but at some point you have to. It would be sort of a shame for a business to die with its founders just because they didn’t think about who else could do the work or anything like that. So it is interesting to think about how something can last beyond you, beyond your own generation, and also how it should change or shouldn’t change.
For example, in the watch world — the watch world is a very traditional world with arts and crafts and science passed down through generations, and a lot of that is very traditional, it doesn’t change very much. But then you have these upstart independents, and they are the ones who actually change things for the most part. And sometimes it takes someone brand new to change something.
Other times, you don’t want to change things. You’ve got to figure out “Can a software company not change?” Probably not. A restaurant probably could not change.
MATT: I get super fascinated with companies or businesses that are able to do that multigenerational.
JASON: Yes.
MATT: So where there’s different leaders over time. Because that gets even harder, right? It’s one thing to have this passion yourself but to be able to pass that on and have it maintained or hopefully improve is really, really hard. All great companies I think are fractal. So how do I make a division at Automattic have what was great about Automattic when we were 30 or 40 people and that division can operate just like we were at that point.
So that’s one way I think about scaling as well. The whole thing doesn’t have to be big because most people don’t have to keep the whole thing in their head, they just really work with their team or division or area.
JASON: Yes, it’s so true. And the other thing that’s great about the fractal viewpoint is that you don’t have to change an entire organization to have an effect on it. You can change a corner of it, an edge of it, a branch of it, and then those other branches and those other corners and those other edges can look back at that change and go “Ohh, I want some of that too.” And that can carry through. It can sort of bleed into the rest of the business, which is great.
MATT: And there was a point when we started to scale a little bit in terms of number of people, and also breadth and depth of what we were covering — that’s when I started to think about it a lot. It’s amazing how many companies will experiment and do a ton of A/B tests with their product or their customers but never really test internally how they work.
JASON: Yeah.
MATT: You know? Have two teams have the autonomy to work completely differently and then just judge it by the results. We even had a division which tried holacracy once.
JASON: Oh yeah.
MATT: Which was kind of the rage at the time. And I’d read about it and I’m like, “Hmm, I don’t know if I buy all this but I don’t know…”[laughs]
JASON: Maybe, yeah.
MATT: Let’s try it. They had to maintain their interface to the rest of the company, which is fine, because they were relatively self-contained, but internally they did a pretty substantial, maybe six or nine month experiment with holacracy, and it was actually really cool because coming out of it, they decided not to continue it, but they said “but this really worked well,” and “this is what we’re actually going to bring back,” kind of cherry-picking what they found to be the most effective part of it.
JASON: What was that part?
MATT: Part of it, that we’ve adopted pretty much throughout the organization, is this idea of a DRI, or a Directly Responsible Individual. Someone owns everything, but people wear different hats but those hats are clear. I think it can be tough when those hats are not clear, or when someone has too much, they’re not explicit about what they’re doing, they take on too much and then become a bottleneck. So when you can be more explicit and transparent about those things, you can generally avoid those problems. Not always but at least it’s apparent where it is.
JASON: We’ve even struggled with that. For a long time, we didn’t have titles here. We thought titles were what you do at big companies, you had titles. And then for a while we allowed everyone to make their own title, which was stupid, but we thought it was cool.
MATT: [laughs] We still do the own title thing.
JASON: Okay. [laughs] Well, stupid maybe is unfair. But let me say the reason we discovered that titles matter is actually, people have careers after Basecamp, and it’s tough when you don’t have a title that matches up with the rest of the world, in a sense, when someone else can look at your title and go, “Oh, I know where they are and what they have done and what position they’re in and where they’ve come from and the whole thing.”
So we decided to get extremely boring with titles. It’s like: junior programmer, programmer, lead programmer, senior programmer — boring titles. We also made sure everyone has one or had one. For a while people were like, “Oh I’m just a designer.” Well, no, you’re actually not. You’re a senior or principal designer. Other people should know where you are in the organization as well.
MATT: Well it sounds like you’ve combined leveling with titles as well.
JASON: We did.
MATT: Did the leveling process always line up with where people thought they were?
JASON: No. And that was the other thing is that when we ended up switching to standardized salaries across levels and across roles, we had to make a lot of things clear for everybody, so everyone knew where they stand and what salaries attach to each level and each role. So there’s no salary negotiations at Basecamp. If you’re a senior programmer, you get paid X. If you’re a lead designer, you get paid X. And that way you know that everyone else who’s a lead designer who does the exact same work you do — same skills, same experience — gets paid the exact same.
MATT: And that’s regardless of geography?
JASON: Regardless of geography. So we pay everybody 90th percentile San Francisco rates, even though we have nobody who lives in San Francisco. We basically want to pay the highest salaries in the industry. Of course 90% means there’s 10% that might be higher than you but that’s pretty high.
So that way you never have to wonder, you never have to hear — because things leak — “Why does Bill get paid $172,000 when I get paid $164,000? I thought we were both senior designers.” That stuff happens, people talk, and that’s where discontent begins to foment and it gets dangerous because people then don’t want to talk about it, and they hold resentments.
And also, the other thing is that there is no reason why you have to be a great negotiator to get what you’re worth. It’s hard enough to be good at your job, and then to also be an ace negotiator doesn’t seem fair. People don’t like to negotiate for their cars, for their houses. I mean some people love it but —
MATT: And it’s asymmetric too because you know everyone’s salary and you do this all the time where they’re going to only do it once every time they change jobs or once a year or something.
JASON: Bingo.
MATT: Yeah.
JASON: Yeah, and think about a manager who manages 12 direct reports. Well this manager gets to practice a lot of salary negotiations while each individual person barely ever does, once every couple years, whatever it might be? And they’re going to be nervous and you’re going into someone else’s office. It’s hard.
We wanted to eliminate all that and with all that — this is kind of a bigger systemic change, which is unified salaries, leveling, and titles were all tied together — [we] just eliminated a whole bunch of questions and unease and — dis-ease, I should say. A few people didn’t like it because a few people thought they were worth more than the role or the level that they were at and I understand that.
MATT: Did some people get adjusted down?
JASON: No. So our policy was, nobody got adjusted down. What would happen was if anyone’s salary was above the level that they were placed in, their salary would be higher than everybody else’s, but they would never get a raise until everyone else caught up to them, basically.
So it was like, here’s your number, here’s where you’re at, maybe you’re $6000 more than someone — I’m making up numbers here — but $6000 more than someone else. You’re at 156 and everyone else is at 150. Other people are going to get raises as the industry moves and as the standard of living increases. You will not until they catch up to you and then you’ll all move in unison again. If the industry moves down, we will not move anybody down, we have made that promise as well. So you might not get a raise for many years until the industry catches back up again but that’s how we’ve set that up. So no one ever loses salary.
MATT: How do you deal with foreign exchange? Because you must have people outside of USD.
JASON: It depends on the role and — I should say the country, not the role, the country. Since exchange rates do fluctuate, basically they submit invoices every few weeks and some of that is adjusted based on if there is a significant fluctuation.
And the other thing that’s tricky is benefits. Because in some countries, for example, in most countries, pretty much every country, healthcare is included essentially. Here it’s not. So we pay people’s healthcare, or most of it. We pay 75%. So we do basically a cash-equivalency benefit to people who live in Canada or who live in Spain or something like that. So the numbers can’t be exact but they are really, really, really close and we do our best to make them as close as is reasonably possible.
MATT: As we wrap up, we’re coming up on ten years since Remote was published.
JASON: Yeah. Wow.
MATT: Which is kind of wild. Now there’s a ton of companies doing remote too, so I would say it’s not “mission accomplished,” but it’s really shifted now where there’s a lot of companies. I’m hearing now from my investor friends that it’s actually the default now, even in the Bay Area. New companies are being built this way.
JASON: That’s great.
MATT: What do you feel like has changed the most and what do you really want to see change for companies operating in a remote or a distributed fashion?
JASON: I’d like to say it’s technology and whatnot but I really actually don’t think it is. I think what ended up happening is that cost of living got so high in San Francisco and continues to get so high in San Francisco that it just doesn’t make a lot of sense for a lot of people to live there anymore. And so at some point if you want to find great talent, you’re going to have to look outside the walls of that city, and that region, because a lot of people just simply can’t afford to live there. And so you begin to realize that hey, there’s great people everywhere, all over the world. Amazing people.
And I think it just takes a few companies, like Stripe is a good example now. They’re opening up the remote HQ or whatever they’re calling it. Companies that are widely respected. Of course Automattic is widely respected, but you’ve always been this way so it’s more about the companies that have been all about [how] everyone’s got to be together. Those are the ones I think that people are looking to and [saying] “Oh wow, they are even considering going remote, that’s interesting.”
Meanwhile, I think what you guys are doing is incredibly interesting, but you’ve been doing it for so long that things don’t become interesting anymore after you’re like, “This is what we do.” [laughter]
But yeah, to see someone like Stripe and other companies doing that, that gives other companies cover and investors cover to go “You know what, if they can do it, if they think it’s okay, if they’re going in the opposite direction of what they believed five, six years ago, then maybe this is okay. And you know what? We can find some great people. And guess what, there are great people. And wow, they’re finding great people, there is a whole world of great people, there is a lot less competition out there for great people when you can look at the whole world.”
So I think all those things are finally beginning to happen. Like, video conferencing has been around forever, text messaging has been around forever. It’s not like some new tech came out. It’s really I think just an economic reality. And then of course just people getting more used to things and a new generation coming up that feels very comfortable with it, and some of the people who were very opposed to it are just going away, in a sense. They’re realizing, well other people can do it, and let’s give it a shot.
So I hope to see it more and more and more. I think it’s wonderful for everybody involved. It’s, to me, the most respectful way to work. I have always found it borderline offensive that someone would have to lose their job because their partner that they live with had to go somewhere else to get a job.
So you’re living with someone and they have to go move to Madison, Wisconsin, because that’s where the work is. And you’re working for a company in Chicago but you’ve got to move because your partner has to move, and all the sudden you have to lose your job. Why? That seems so horrible for everybody.
It’s bad for the employer, because now they lost someone who was great and now they have to find someone new and train someone new and all that institutional knowledge is gone. And it’s bad for the employee who feels like they have to be chained to a city. And/or things far outside their control can cause them to lose a job that they might absolutely love, they might have spent their whole life trying to find this job and they got it and now they have to leave because someone else in their family has to go somewhere else. It feels so unfair.
So I think remote is so fair. I think it’s important, really important, and I’m glad to see things changing.
MATT: Jason, thank you so much.
JASON: Thanks so much. Great to hear from you again and catch up in this way and hope to do it again soon.
MATT: That was Basecamp’s Jason Fried. You can find him on Twitter at @jasonfried. That’s Jason F-R-I-E-D. He’s on Instagram at the same, but I believe he’s trying to quit both networks. So probably Basecamp’s website and the Rework and Remote podcast are the best places to find him.
Basecamp has been building productivity tools for 20 years, which makes it pretty advanced for an independent tech company. In a world where many startups race to make it to the next funding round, sale, or IPO, it’s refreshing to see leadership that see themselves as long-term stewards of a company, mission, and most importantly, their users. I’m grateful to learn from folks like Jason who’ve been at it a lot longer than I have.
On the next episode of the Distributed podcast, I’ll be talking to Merritt Anderson, an HR veteran who advises companies about distributed work, among other things. She spent over four years in HR at GitHub, helping to build out their distributed teams and the policies that facilitated that work, and a really interesting hybrid model with a ton of success from both a user point of view and of course an outcome point of view.
Thank you for listening, and see you next time.
Episode 17: Matt Mullenweg Reflects on Distributed Work in 2019
Dec 26, 2019
To close out the year, our host Matt Mullenweg is joined once again by Automattic’s Mark Armstrong to discuss the state of distributed work as we transition into a new decade. Matt discusses his key takeaways from his 2019 conversations on the podcast, and reflects on his year as the CEO of a growing distributed company.
The full episode transcript is below.
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MATT MULLENWEG: Howdy, howdy. Here we are. We made it: the last episode of 2019. The finale of our first season of the Distributed podcast, with me, Matt Mullenweg.
We’re currently in the thick of planning a fresh slate of episodes for next year. We’ve got the first female 4-star general in the U.S. Army, a guy who grew up in a family of Argentinian sheep ranchers and now runs a distributed blockchain company. Business leaders, thinkers… I’m really excited for next year overall.
But December is also a great time to reflect. So that’s what we’re going to do now — reflect on some of the great conversations we had in 2019 and talk about where we think distributed work is headed in 2020.
Today I’m joined once again by my colleague Mark Armstrong, who works on a bunch of editorial things at Automattic. He’s been very involved in developing this podcast from day one.
MARK ARMSTRONG: Hey Matt, how’s it going?
MATT: Pretty good, pretty good. It is the end of the year so it’s exciting. I’m actually on my support rotation this week so if anyone contacts WordPress.com support they might get me.
MARK: Yeah, feel free to take a break from this interview to do some live chats if you need to jump in there. [laughter]
Well, Matt, thanks again for having me on. I have been enjoying the podcast all year and I am curious to understand some of your takeaways from the interviews on this podcast. And also, it’s been a big year for Automattic itself, so [I’d like] to understand a little bit about how the changes at Automattic have changed how we work as well.
But first I want to go all the way back. I want you to tell me a little bit why you wanted to do this podcast in the first place.
MATT: As we were scaling Automattic — and continue to scale — I meet and interview a lot of really fantastic leaders — in technology, outside of technology — who don’t know how the distributed thing works. And they have a ton of experience leading teams, running products, etcetera, but not in a distributed manner.
And so it’s combined with two things happening. One, there are more and more distributed companies than ever, all over the world, many who we’ve had on the podcast already, a lot who are coming up, that were showing that it works and that you could create a world-changing, ultra-competitive company without even a single central office.
And two, there weren’t as many materials or information for how to run something larger than a small team or a freelancer but smaller than the whole thing. I guess the target audience for me for this [podcast] is really managers. People who are managing maybe for the first time, maybe for a long time, distributed teams. Just having that point of reference for how other companies do it and what are the best practices they can take away from it.
I also hope that people at Automattic are listening to this. [laughs] Many of our colleagues are people who are in this very situation. And the first line of our creed is “I’ll always be learning,” and so I hope that people have been learning from this because I know I certainly have been.
MARK: I think it helps clarify what we think and what we believe about how we work, day in and day out, just hearing the other perspectives from the other companies and the other executives or product people within those teams on how they work similarly or differently from us has been hugely helpful.
I think you hit on another point too, which is a lot of the remote work materials that are out there right now are very much about selling the lifestyle versus looking at the reality of what’s happening inside. Do you find that’s the case?
MATT: The lifestyle is definitely part of what I think attracts people to it. But it’s not the lifestyle people expect. It’s more about autonomy, control. I think sometimes people get this idea of Remote Year or something where people are in a different city every other day or every week or every month. And very, very few people who do remote work actually work that way, which is interesting.
MARK: Yeah. Now you very intentionally avoid using the term remote work in favor of distributed work. Can you explain why that is?
MATT: Well, “remote” is appropriate sometimes. It’s also a little bit — it rolls off the tongue a little easier than “distributed.” But I think what we are trying to build at Automattic and many other companies we talk to, is a truly distributed organization. So “remote,” even the word itself, implies that there is a “central” — a bunch of people in one place and there’s a few people who are remote.
When you’re building a truly distributed company, you want to have all nodes on the graph to be equal. So for no one to be remote, for everyone to be equally participating. I would say even if you have an office, and technically you could describe people who aren’t there as remote, you don’t want them to feel remote, right? Almost no one has ever said “Oh, I hope I feel more remote today.” They want to feel connected, they want that equality of interaction and inclusion.
So that’s really, really important for everyone who’s working with anyone not physicallywith them to make them feel included. And I think the more we can get away from the term “remote” the more we can help people feel included.
Another thing that has really changed for Automattic is we have gone from around 800 people to closer to 1200 people, so it has been a year of big growth. And of course with the acquisition of Tumblr, we acquired a company which had a very strong presence in New York City, and in fact we now have a pretty substantial office in New York City.
If you listen over the course of the year, before and after that, I started asking a lot more questions about hybrid organizations where they’re partially distributed and partially in-office, and what the best practices are for that. And something fun for me in the podcast is just being able to ask really, really smart, experienced people what’s on my mind and what challenges we’re facing. And that is something that’s been a new challenge and new learning for Automattic this year.
MARK: Yeah, I think it’s been fascinating. So this was an acquisition that went through in September, Tumblr joining Automattic, and close to 200 plus employees joining Automattic. So that is a big influx of employees that even within a fully distributed organization can change the culture. But now, on top of that, you’ve got an actual office in New York City in which they’re working in that culture.
It has only been a couple months so far but what have you learned about the merging or not merging of those cultures?
MATT: It has definitely taught me that we can’t take anything for granted. It actually made me think how much more important the Distributed blog and this podcast are because things that I haven’t thought about for years are — like how best to do calls or conference calls or meetings or things like that, that are inclusive of remote folks and people who are in the room, are not always widely known and might not even be widely agreed on. This is why in the episode with Anil Dash this came up pretty well, it also came up pretty well in an episode with Merritt from GitHub. So these topics that you’ll hear throughout some of the different episodes, both past and future.
It made me also realize that culture is so much more than what goes on in an office. It’s really the sum of what everyone does all the time — all those little decisions, the way people communicate, the way people text, expectations for how you reply to things, how meetings happen. Meetings are such a huge part of it. It’s what people are doing when no one else is looking that really makes up culture.
And it’s something I’ve always subconsciously missed is thinking that there’s more culture in an office. I wouldn’t say there’s more, there is just a different culture in an office. It’s a culture of that ambient intimacy, a very different type of connection that develops between colleagues when you’re in person versus when you’re not. And it has been so long since I’ve closely interacted with an in-person team that I hadn’t really thought about a lot of those things in a while.
MARK: Are you doing that now with the Tumblr team? Do you pay many visits to the office? What is your plan around that?
MATT: Yeah, I’ve been trying to make it into their office really whenever I’m in New York City. And that has been really great to be able to make one of those connections. I have also realized that they were a hybrid organization even before they joined Automattic. So they have some great colleagues in Dulles, in Richmond, in LA, in Seattle, and some folks just kind of sprinkled all over the country and the world, so that’s also been really great.
I feel like those people have taken extremely quickly to some of the things that Automattic does, including things like P2, and that’s been pretty exciting to watch. Some of our closest integrations have been so far on just the systems side because we’re migrating all the data from Tumblr. It’s billions and billions, maybe hundreds of billions or trillions of posts, and users and things like that that are all coming over. So our systems teams have been working pretty closely together. And I would say systems is also a field or a role where people tend to be very comfortable communicating online.
MARK: Yeah, a couple big ceremonial moments that I have witnessed from Tumblr joining Automattic is the first P2 post and the entire company joining Slack and the point at which we decided, like, oh these divisions should all be on the same Slack together. I’m sure there were a lot of meetings around that, correct?
MATT: It actually ended up being a technically driven decision as much as anything where I guess they had maintained their own Slack in the past, and that was a good thing, but it turned out it was going to be hard or even impossible to migrate most of that data, so we were like, “Well the data, the archives can’t come over, we might as well just get everyone on the same thing.” Because we had a lot of overlap already.
MARK: One of the other things you mentioned in the Anil Dash episode that I found fascinating was the concept that when they’re working together in a physical office they’re not really supposed to talk about work. [laughs] Is that something that you think there is a takeaway from that can be applied within Automattic?
MATT: My big takeaway — and we haven’t tried this yet with Tumblr but perhaps we will at some point — is that idea which you’ll hear in the Merritt episode. One face, one voice, the idea that if you’re on a call, if you’re on a Zoom, wherever it is, if you can have each little box, there would be one face and one voice versus a conference room or something like that, it really does make the conversation flow a lot better.
MARK: Yeah, that makes a huge difference when you’re on a Zoom, and there is also a little bit of FOMO that happens on the Zooms that I’ve been on where there’s a group of people having a good time together, and you’re watching from your silo and feeling like, “Oh that looks like a fun party, I wish I was there.”
MATT: [laughs] But I do think that Anil was very articulate on the importance of building those non-work connections as well. It’s something we try to do. At Automattic teams do meetups a few times per year and once a year we bring a lot of the company, the majority of the company together, [and figure out] how to leverage that in-person time for that connection.
A number of people who weren’t part of the Tumblr team but part of Automattic have been rotating to work on Tumblr, both to help integrate the systems and also just accelerate hiring things.
MARK: Now in a lot of the conversations you’ve had this season you’ve spoken to what I would call strong founders or people who had the control and the power within the company to shape it into whatever culture they deem best. I think a lot about how distributed work expands beyond very specific companies into this broader movement growing among mid-size and large companies and how exactly does this work when it comes to bringing distributed into a company where maybe it’s a 50-year old company on its tenth CEO? How do you get to a place where those companies really start to get into this?
MATT: It’s funny because companies that old typically have multiple offices so they have a version of the distributed problem already, you know?
MARK: Mhm.
MATT: What I see is probably the most important thing to unlock is this idea of getting everyone around the table [being] the best way to solve a problem. That assumes being in person and being synchronous is definitely a way to solve a problem, but I see many companies, particularly older companies or managers with experience in older-style companies, see that as the only way to solve those problems.
I do think that there are asynchronous ways and of course non-physically collocated ways that can actually be far superior in many situations to solve many or most problems that businesses face. I don’t consider it my personal mission to switch all companies to be able to do this but partially that’s because I feel that companies that don’t do this will die off. [laughs] So there will be a Darwinian process where companies who are able to tap into the global talent market and work asynchronously and efficiently all over the world.
That’s where business is going to be and that’s how things are going to expand. Even if you have a coffee shop, if you have any ambitions to have multiple of them, you’ll need to start to expand your culture, expand the way you work, expand the way you collaborate, expand the way that insights move from customers to process to design, to innovation in a distributed fashion. I would be astounded, completely astounded, if five, ten years from now Google, Microsoft, Apple, Facebook, Netflix, the tech giants that we think of, didn’t have distributed work as a major, if not the major, part of the way their employees work together.
MARK: It’s interesting. Also the broader movement of companies, if they are spreading out beyond the bigger urban centers. There’s this tipping point that has to occur as well, and this goes back to another thing from Anil’s episode. We have always compared Automattic’s distributed model to — maybe it’s a Silicon Valley company with a big campus in a boring suburban area of Mountain View or Menlo Park.
And he’s saying, “Here you get to live in New York City and people want to live in New York City and that’s exciting!” So cost of living aside, there is this gravitational pull of the big, exciting, urban centers bringing people in. So it feels like maybe there has to be a tipping point still for these companies to take that plunge and to get those workers to want to spread out in other places.
MARK: I think that trend and that story will be so fascinating to see play out over the 2020s as well. Because there’s a lot of data that shows pretty much all the job growth, all the economic activity that has happened in America through this incredible bull run has been really concentrated in urban centers. And if you correlate that with things that are happening politically or frustration or — there’s all sorts of things that could be correlated with that economic activity.
When you start to spread that economic opportunity throughout America, throughout the world, [think about] how that changes those centers. Part of the reason New York is one of the best cities in the world is it’s a center for so many different industries. There’s great jobs there that support great quality-of-life things — great arts, great restaurants, great everything.
As you start to get more of that economic abundance flowing to other places, guess what, that supports other jobs, other restaurants, other arts, other things that people will consider part of a great quality of life — schools, parks, etcetera — in other places as well. And in fact, places where you might not have the problem of San Francisco being on a small peninsula, Manhattan being an island, you know, the kind of geographic constraints that you do in some of these urban centers.
MARK: Thinking about this on the broader scale, should there be a government role in promoting distributed work? I feel like we see some novelty initiatives, like Vermont’s remote worker program, where they’ll give people $10,000 to move there. Have you thought about what city, states, and government should be doing?
MATT: They absolutely, crucially should be doing programs like Vermont’s. If you think of the brain drain problem, where some of the smartest, most successful people leave where they grew up, which has also economic implications and everything, anything you can do to bring those people back is huge. Economic incentives are definitely one way. I think that there’s also streamlined regulation. And then finally, just incredible broadband [laughter] and normal things you would invest in, in a city, to make quality of life good, like great schools, I think are really, really powerful.
And we see it so much with our colleagues — people like to move back to where they’re from and where their family is, and that can be such a powerful thing. I don’t know if I were coming from scratch to America and looking at the top 20 cities if Houston would be at the top of my list to live in. [laughs] But because I’m from there I have such a connection to the place. I grew up there, it’s a formative part of my history. My oldest friends and family are there. It kind of beats out every other place in the world because of those things.
Because I can get cool music, cool food, cool other things that you can get in New York, San Francisco, etcetera, I can get that in Houston but I can’t get those people [elsewhere]. So I think that draw of where you’re from could be great to reverse the brain drain that happens very naturally all over the world and all over America.
MARK: Are there moments from this season and in conversations with other companies and with our own Automatticians where you think to yourself, “Wow, we are doing this part all wrong?”
MATT: [laughs] That’s a good question. I’ve definitely been challenged and learned new things every episode. We could almost go through them one by one. But even some of the more out there stuff, like John Vechey talking about how they’re collaborating over VR. That just got mereally, really excited about how much better than the gold standard today — which is probably Zoom — we could have, to connect and feel presence with each other.
I really enjoyed our episode, episode four, where we dove into some of the history. Leo Widrich, talking about the downsides, the isolation of distributed work. His and Arianna’s episode, talking about the downsides [of distributed work], I really like those as well, and I hope to have some more of those in the next season where we talk about people who do not agree with this. Because I think that that actually sharpens the ideas quite a bit.
Stephen Wolfram kind of blew my mind. I don’t know if you remember that one?
MARK: Oh yeah. He has been doing this for almost, what, 30 years plus? What were some of the lessons from that conversation?
MATT: One of the things I took away from that is the investment — making the internal tools, which also makes me think there is an incredible business opportunity to create tools which natively incorporate remote people and distributed people much, much better, because a lot of the stuff for running companies currently doesn’t. Even things like Google Calendar, which still has meeting rooms built in, and things like that. You could imagine the next generation of this being so much nicer for getting people together.
If you’re in an office, you could walk around and pull five people into a meeting. The distributed version of that is kind of tricky. You end up Slacking each other and trying to pick a time and things like that. And Automattic is not too bad because people aren’t in too many meetings, so sometimes they can hop on things with a short notice.
But it would be nice to have a way that pops something up and you can raise your hand — I’m available, I’m not available. And then when you reach some quorum of people who need to be at this thing, you can all just immediately hop on a call or something. And making that a little more ad hoc and on demand versus everything having to be so pre-scheduled, which sometimes can be tricky.
I think a lot about speed of iteration and anything that introduces any lag time into particularly decision-making slows companies down. And you really start to look at places that are moving slower than they need to, you often find these little things, these little one-day, two-day delays that just add up to be weeks and months and then eventually years of things moving slower than a more agile team would be able to.
MARK: I recall you’ve called that chess by mail in the past.
MATT: Yes. Now in an office you can get the opposite problem where it is so interrupt-driven that people can’t get real work done, that deep work that Cal Newport talks about, who actually would be a cool person to get on the podcast now that we mention it. When you have too many interruptions, it’s really, really difficult to get things done.
MARK: Yeah, it seems like Slack is still the main place where an impromptu discussion can happen, but again, it’s got some pros and cons there. This year was probably the first time I started to feel personally some real tension around time zones in Slack, and it became apparent to me that Slack is not the best on the time zone front. What’s your take on how to move beyond that?
MATT: It’s an interesting question because I also feel like 2019 was the year where I felt like for — at least for us — Slack went from being a net contributor to our productivity, to a net detractor. We probably need to do a reset around our norms, around not being signed into Slack all the time, do not disturb notifications, not needing to reply. That just resets that a little bit more for us.
One idea we’ve toyed around with and discussed before is just every person, regardless of your role, not signing into these real-time communications for the first couple hours of their day. So you’re still working but staying off email, Slack, other things that are more communication-driven and really looking at, “What’s the most important thing for me to get done today?” and really checking that off the list.
MARK: It’s interesting when you talk about cultural norms. Cate Huston from Automattic talks a little bit about autonomy, and the choose-your-own-adventure nature of some of this work, or how different teams work. And I wondered, should we be asserting ourselves more to new employees when people come in pushing the Automattic Way? I think it has been great in terms of people coming in and being able to define what works best for them and their team, but I also wonder whether some of the things that have previously been proven to work have been maybe not completely bought into.
MATT: One hundred percent. And that is something — we’re going to make a lot of changes to Distributed.blog next year, and I’d like to get some — almost like some free manager courses. Maybe we can use the Sensei plugin for WordPress.
Also, Automattic could be 100 times better at this. I was really impressed with some of the stories of how Glitch, how InVision, how others do onboarding, for both new employees or periodically bringing existing people through things.
Training is an area where we’ve only scratched the surface. And actually one of the hires I’m most excited about that we made in 2019 at Automattic was our new Head of Learning and Development, Michael Norman, whose learning and development is looking at this problem around onboarding, feedback, skill-sharing — everything to do with knowledge, which in a knowledge-worker company is something that I think we could be a lot more deliberate on.
And, of course, in Automattic fashion, whatever we figure out we will try to open source.
MARK: Excellent. One other big thing with Automattic was Automattic raised $300 million this year from Salesforce Ventures. And I’m curious what fundraising is like when you’re a company with no central headquarters.
MATT: [laughs] I think it throws some people off.
MARK: Those coffee shop meetings are a little difficult?
MATT: Yes, yes. So it is nice to have a dedicated space where you can go — you can bring people into. The reality is also a lot of these things, you’re going to their office. [laughs] But it is nice. There was a time maybe in previous Automattic fundraising when we did have an office, people would come into this empty office and you could almost see it run through their head, “Hey, is this a real company? Is this a pyramid scheme or something? There’s no one here.” So that’s all gone. That doesn’t really pop up as much anymore.
But for me, I would say the distributed aspect can make it a little more challenging. I spent a lot of time on planes this year, going to those meetings. It also drew me away from the product and engineering work that is my native talent, or thing I’m drawn to, certainly my history with WordPress and Automattic, and it took me away from that a little more than I would like for the year.
But it was super, super important. This fundraising really sets up Automatic’s independence for the foreseeable future and allows us to invest in what I think the opportunity is, and other people agree, is a really, really huge tens-of-billions-of-dollars opportunity out there. It allows us to go for it but the actual fundraising process is one which is, well, just incredibly inefficient in so many ways. And I hope to see things change there more in the future, particularly for private companies.
MARK: With the fundraising process, did you have a period in the past where you had to spend a lot of that time rationalizing the distributed model compared to this time where it’s more, “Of course, of course you have a distributed team, now let’s talk about the business,” kind of thing?
MATT: It’s completely changed. So I think both at the high end and the low end. At the high end you have companies, like many of the ones that we had this season — InVision, GitLab, GitHub, Toptal — there’s so many out there that really show — Upwork — an incredible scale.So you’re getting to thousands of employees, billions in revenue often, with the distributed team. So people aren’t really worried at that end anymore.
But the other thing that I think has changed is that folks who work also at the seed level — so invest in seed and series A — and a lot of these investors look at companies both large and small, I’m hearing from investors at that end that almost every company is, if not doing a distributed model, then a hybrid model. So maybe the founders are in San Francisco.
And by the way, if you’re a founder or a CEO, I do think you need to be where the other companies in your space are, or where the funders are going to be or things like that. So there is going to be a lot of time in those clusters of those things — technology clusters in our industry that you’ll need to beat. But they are not hiring in the Bay Area anymore and they’re not even trying to.
If you draw that line out a few years, there’s going to be 10 or 100 times as many fully distributed, ultra-successful, large-scale companies five years from now than there are today. And that is exciting.
And one of the things I wanted to do on Distributed.blog is have a company directory that talks about a few public stats about the scale and approach that some of these companies we have mentioned and had on the podcast have taken, and then of course if they have been on the podcast we can link to it. That I think will be dozens of companies today. And at some point we’re probably going to need to retire it over the coming years, it will just be too many.
I also like it as an idea, though, as kind of a no-fee jobs board. There are some jobs boards dedicated to the distributed work, but I think just the links to the companies, because all companies have hiring pages, could be kind of a nice thing for people who are looking to switch to work in one of these. And then to the extent that the founder or CEO or HR person or someone from the company has been on the podcast, what a great way to learn about the culture and approach of the company.
MARK: Speaking of jobs, what are some tips, what’s a script for people to use if they want to, if they are out job hunting, and they want to make sure they’re building in remote work as a piece of their job? I feel like a lot of distributed work in the future is going to be driven by worker demand, which is insisting that remote work is a piece of what’s available to them, or flexible work. What are some tips that you have to bring this up in the hiring process?
MATT: One tip I do give, sometimes we see people for whom the bulk of their application is that they want to be remote. And that’s not really compelling on the other side of the table. [laughs] This is just general advice for applying for anything. But if you can make your application about why you’re excited about the mission of the company — the products, what you feel is your unique contribution to the products, and the mission and the vision for where the company is going, your experience with a technology stack or their products, or you’re a user, how you supported it. Those sorts of things.
So if you can really personalize the application — I hate to say it, but that would put you ahead of 95% of applicants. You’d be surprised how much of applying for a job is very much spray and pray, where people are obviously just sending out their application to dozens, if not hundreds, of people or companies without much personalization.
Some of my favorites for applying for Automattic is when people actually make a WordPress website and they make a little mini website about their application or about wanting the job. In fact, we had a colleague of ours, Dave, who was previously a designer at Automattic and then reapplied, and I think he must have known that because he made a website for his reapplication. So in addition to his going to the top of the list because he was an awesome colleague before, it showed that he wanted the job. And that really means a lot.
There’s some advice, if you’re in an in-office job and you’d like to have some more flexibility, that I might have first read in Tim Ferriss’s The 4-Hour Work Week, which was forever ago. But first, be amazing at your job. [laughs] If you’re clearly one of the highest performing people on your team, I think that gives you a lot of built-in credibility and currency.
And then talk to your boss, your manager, about maybe taking a day a week. And once you get that permission, make sure that day you work even harder than the days you’re in the office, so that it’s really, really clear that there is no downside to the company. If you’re not really respecting the work part of remote work, it can ruin it for your team or the whole company, where people start to associate it with slacking off.
So if you can set a good example there, and make sure to hold any colleagues accountable — that if they aren’t going to be in the office, they need to contribute just as much if not more — that helps a lot for warming up organizations to be more inclusive of that non-in-office approach.
MARK: I want to go to InVision CEO Clark Valberg and your episode with him, talking about the mental models that we build of the people we interact with and how face time helps us increase the fidelity of those mental models. Have you ever been in a situation where you’re having a conversation with someone, text, audio, or even video, [when] you thought they felt a certain way and then, once you meet with them face to face, realized you had the totally wrong impression?
MATT: A hundred percent. Although, I will say that that comes more from text than audio or video. Audio is actually — particularly when it’s high fidelity, like you’re not on “Can you hear me now, can you hear me now,” it’s a good connection, good microphone like we’re using — you can get so much from someone’s tone of voice, their approach, etcetera. It’s really much higher bandwidth.
[With] text, even the best emoji users don’t always communicate as well, and it’s very easy to bring your own point of view or your own view of how things are going into the conversation. So you might view something as being annoyed or short or curt when it’s not.
So the ability to hop quickly onto an audio call or a video call is really key for compensating for that misreading, which is very natural in text communication.
MARK: I think this is the second time we’ve hit on something where it’s like there is a need for an impromptu call or an impromptu video conversation that is not so rigid in these scheduled Google calendar slots. Whoever solves this will be in good shape.
Going back to Leo Widrich, formerly of Buffer. He talks a bit about isolation, and for me that’s one of those things I read about but I feel like I wouldn’t know if it’s actually impacting me in a negative way because it is such a slow creep when it’s happening. Do you grapple with isolation in your own work and life?
MATT: I am 16 years into working with people remotely from the start of WordPress, maybe even a little bit before that. So I feel like for me, I have a lot of experience now both developing online relationships — the kind of chatter and back and forth that can help deepen that — but also having a strong social network outside of that. I think that’s very much key.
One thing that can happen really nicely if you’re around people you work with every day and you like them, is that also turns into your friendships and your social network. I think that can be really positive, it can also be a mixed bag. It can make it more difficult to give critical performance feedback or if someone gets a promotion, that can change the dynamics of people who used to be peers, now being managers or responsible for compensation, or whatever it might be.
It’s really nice to have friendships that are just friendships. Neither of you is economically entangled with the other or reporting to the other or any of those other things that introduce a layer of complexity into human relationships.
So I encourage everyone, even if you really love the people you collocate with every day, to have that. It’s actually one of the cool things I think about co-working is because you can be physically present with people who aren’t at the same company as you, you can have that, get thebest of both worlds, get the people who you like going to lunch with a few times a week, and learn from different companies, but not actually overlap in your work-work.
Now, the one thing I do miss — it’s almost like the opposite of what Anil suggested where he said no talking about work at office lunches. I do feel like the catch-up over a meal with a colleague does get you something in terms of the zeitgeist of what’s going on in their part of the company or the world, which is hard to recreate any other way, part of the reason I find it so valuable to have a less formal catch-up with colleagues.
MARK: To that same point — Automattic: too many in-person meetups or not enough in-person meetups?
MATT: I might have to look at the data to see exactly how many we’re doing. I know that we got to a point where we might have had too many a few years ago and we decided to start dialing it back a little bit. Not in a super explicit way but maybe moving teams from every nine months, from every six months, or even greater cadences than a year to balance out the total amount of travel time that people are doing. But I don’t know, I don’t think it’s the amount of meetups, it’s how you use the time.
MARK: Yes. Several of your guests talk quite a bit about that, in which thinking about the time as a very specific thing, and only addressing the things that can only happen in person versus trying to get a lot of work done, or a specific project that you probably could have done on your own, from your own homes.
MATT: Where I see teams get negative feedback on their meetups is often where [there] was a mismatch of expectations. If your goal in the meetup is to bond as people and get to know each other better, make that the intention going in, and then everyone is expecting that. I get sometimes that we’re, some people were expecting to have a hackathon meetup and some people were expecting to have a team bonding meetup and the distance between whatever actually happens ends up being dissatisfaction for folks.
I think that you also need to be explicit about the goals and what you’re going to try, because people, rightly, are taking [time] away from their family and their home, so they want to feel like there is something that they’re getting out of it that they couldn’t have done in a distributed manner. So by being explicit about those goals ahead of time, you also have that conversation about other ways you can solve that problem, things you can do before the meetup to try to address it.
And I think it’s still okay if you try something and it doesn’t work in a meetup. I actually find that people have a lot of open-mindedness to an agreed-upon goal, trying something new, and it’s not going to work 100% of the time, you know? We definitely do this at our Grand Meetups. I tell people, “Hey, we’re going to try a bunch of new stuff this year, it’s not all going to work, that’s okay, that’s how we’re going to find the things that do work and we’ll do them again.” And the things that don’t work, now we’ve eliminated that from the possible solution space and next time we can say “Alright we tried that, it didn’t work, we’re going to try something different to solve this problem.”
So it’s okay if things don’t work if you have the shared expectation about something being an experiment and what the actual goal was going in.
MARK: Great. Matt, thanks again for sharing your experiences with us.
MATT: This has been very exciting. I also want to take this opportunity to thank you and the team that has made the Distributed.blog website, the podcast just a really, really rich resource. I love reading the posts that Cole and others do for each episode. I get something out of it that actually wasn’t in the audio, which I think is a real testament to [how] we’re trying to make the learnings available to as many people as possible and hopefully shift how work is done all over the world, which I think will be a positive impact on the globe.
MARK: So there is a lot more coming from the podcast in 2020. Matt will be speaking with author Morra Aarons-Mele about what distributed work means for introverted people, Merritt Anderson from GitHub on how distributed work can empower people with non-traditional backgrounds, Ann Dunwoody, the U.S. Army’s first female four-star general on running logistics on what might be the world’s largest distributed organization, Xapo CEO Wences Casares on the future of work on the blockchain, and many more.
MATT: Thank you to Mark Armstrong for joining me today, and for the folks at Automattic and Charts & Leisure who make this podcast happen. Most of all, thanks to you, the listeners, for spending your time with us every couple of weeks. It’s been a joy for me personally to hear our guests’ stories, and I’m honored you’ve chosen to invite us into your device to share them with you.
We’re going to hear a lot more great stories about the future of work in 2020, and it’s going to be pretty awesome. On the next episode I’ll be speaking with Basecamp CEO Jason Fried about the frantic pace that defines life at many startups, and whether or not it has to be that way, and how distributed work might help to alleviate that pressure. Basecamp, formerly known as 37signals, was one of the pioneers of distributed work and their book, Remote, is still one of the best ones out there.
I’d like to wish a happy, happy holidays to everybody celebrating this time of year. Thank you for listening, and see you in the next decade.
Episode 16: Glitch CEO Anil Dash on Strengthening Values in a Distributed Startup
Dec 12, 2019
Anil Dash didn’t like the direction the web was going, so he joined a tech company that promised to take web development back to its indie roots. That company became Glitch, a semi-distributed company based in New York City. In this episode, Matt and Anil talk about the good old days of blogging and how the ideals of those pioneers inform the way Glitch treats its employees and its product.
The full episode transcript is below.
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MATT MULLENWEG: A lot of tech companies talk about prizing “people over profits,” but Glitch is a startup that is serious about these ideals, and holds itself publicly accountable for sustaining this commitment as the company grows.
That’s partially because Glitch’s CEO is Anil Dash. Anil’s an old acquaintance of mine — he’s one of the early pioneers of blogging. Over the last twenty years he’s developed a reputation as something of a tech prophet — not just for predicting what’s going to happen next, but for holding the industry’s feet to the fire.
Glitch is a partially-distributed company that runs a social platform for building and sharing web applications. To do that, they’ve developed a workplace environment that centers around employees’ well-being. I’m interested to hear from him how his company has aimed to go beyond platitudes and create a genuinely equitable and respectful workplace, and to learn where their semi-distributed structure fits into that goal.
Alright, let’s get started.
MATT: Anil, you have been blogging forever.
ANIL DASH: [laughs] Roughly, yes. In geological time, it’s short, but in human years it’s 20 years.
MATT: How did you start and what keeps you going?
ANIL: People in my life were tired of hearing me rant about things. So they were like, “Go put it somewhere else.” [laughs] And at the time I had a really long commute. I was commuting by train an hour and a half each way. I mean it was really — it was like three hours a day on a train and I was going nuts.
MATT: Wow.
ANIL: You didn’t have Wi-Fi back then. So I had a giant Dell laptop and I was like, “I’ve got to learn how to do more with HTML.” I knew the basics but I wanted to do it. I would do it, literally just practicing on local on my laptop, on Internet Explorer 5 or something, whatever it was at the time, and I thought “Oh, I could take these rants in my head and put them out here onto the internet.”
Right about the time that I had that idea in maybe summer of ’99, I saw the first couple sites. I was like, “Oh, this is what I could do. I could organize it this way.” I saw Peter Merholz’s site, PeterMe, and then very quickly discovered a couple of others. And so these pioneers were doing it, and I thought, I don’t think I can write like them but I think I’ve got something to say.
It really felt like it was the right time too because I had started in maybe July and by September the Pyra team had built Blogger and the Danga team had built LiveJournal. Even just the fact that there was software to me meant “OK, this is legit.”
MATT: So 20 years later?
ANIL: 20 years later.
MATT: Dashes.com.
ANIL: Yes.
MATT: Why do you blog now?
ANIL: One, it’s part of how I think. My wife will always say, “You’re staring off into space like you’re writing something.” She just knows that it’s this thing where I’m collecting my thoughts. Certainly one of the most important things to me is, I think better and organize my thoughts better and share my ideas better when I write it, and it introduces a rigor to what I’m sharing. I love that push to accuracy and push to quality. It makes my thinking stronger.
Some of it’s just, I like to write. For a long time, I had no other place to do it. I was lucky, after I had written a million words online people asked me to write for things. [laughter] You know? I got a column in Wired and I was like, “Where were you all ten years ago?”
MATT: Cool.
ANIL: But nobody was trying to hire me to write so I might as well put it out there. And that’s still true.
MATT: What would make you stop blogging?
ANIL: Well I’ve slowed down. So I would say the thing that slows me down is, well, life, right? So I’ve got to spend time with my child and I’ve got a company to run and I’ve got — the priorities have shifted. I can’t just say I’m going to stay up all night and finish this 3,000-word piece like I used to.
But at the same time, the biggest thing chipping away at it is having other venues and other platforms. I resisted doing a podcast for the first 15 years of the medium. [laughs] I think the week podcasts were invented somebody was like, “You should go do one,” and I was like, “Ah, I don’t know.”
MATT: And now you have your own little studio.
ANIL: Yeah, exactly. Then I started thinking about the craft that… The same is true actually of other social media. Like Twitter in particular I spend a lot of time on. And this is a strange thing to say but I think you’re probably one of the few people who can appreciate it — I care about being good at it. I think people are like, “That’s an absurd thing to say,” like, “Isn’t this disposable, isn’t this ephemeral?” I don’t feel that way at all. I have Twitter threads that have been going for six years. I am very mindful of how I use my audience, who I retweet and who I amplify.
So I think very much of that as a body of work too. I never delete tweets. Again, same thing, I am certain somebody is going to go back and be like, “You said this thing that’s terrible,” and hopefully I’ve learned since then. But I very much want there to be a body of work between all the things I’ve done that I look at on a years — and now decades — timescale. I don’t think very many people look at their YouTube channel or their Snapchats [that] are like “Yeah, how is this going to age in 20 years?” But I have that luxury so I try to do what I do with that in mind.
MATT: As you mentioned, you’re running a company now — Glitch.
ANIL: Yes.
MATT: How is that culture of blogging or writing part of Glitch’s culture?
ANIL: So Glitch is the latest name and current incarnation of a company that started as Fog Creek Software in the year 2000, founded by Joel Spolsky and Michael Pryor. Joel is, to me, one of the all-time legends of blogging, one of the greatest people to ever do it. Joel started Joel on Software in ’98, I think.
MATT: Super early, yes.
ANIL: Yes. I would read Joel’s blog and he would talk about a company where they cared about the software they made, cared about how they treated their people, were very thoughtful about the work that they did. They did not want to be just another dot-com, which at the time that was what was in vogue. I thought, “Wow, that would be an amazing place to work.” And also, “I would never pass their coding test.” That was the other thing I thought about the company.
And in late ’99 — December ’99 — they had a blogger’s dinner in New York City, which is a funny thing to say because the premise was —
MATT: Of all the bloggers.
ANIL: All the bloggers, right. And we fit around two tables in a Mexican restaurant. You fast forward over the next 10 years and they had built some products and really established a culture, and Joel reached out and it was just like, “We’ve got something to show you.”
I saw the prototype of what became Glitch. You could have live-in-your-browser code. And as you coded and typed your code out, it would live-deploy without you having to run anything, do anything, touch anything. You didn’t have to ask somebody down the hall for the access to the AWS account. It just worked. I still have the notes from that first meeting, and we were looking at them not long ago, we had had some folks join and I wanted to show them where it all came from.
That first meeting that we had of the demo of it was — we talked about, well, we need to have a social network wrapped around this so you can find the apps, and you need to be able to remix the apps so you can redo it, and we need to have multiplayer editing, so more than one person can edit at the same time. And we had this list, and we made these bullet points in the first hour, all of which we did, all of which are the heart of the Glitch experience.
It was really like few moments in my career. It actually felt a lot like when we first saw blogs. I first saw the blogging tools and it was like, “Oh, this is going to be it. This is… I don’t know if what we’re building is going to be the way it happens, but this way of creating the web is going to be how we make the web.” It was really, really clear.
I remember really early on, when I was talking to Mena Trott, who had led the creation of Moveable Type, and was one of the bloggers that influenced me most, with her voice and her tone. I had said, “Someday there’s going to be a million blogs.” And she just looks at me and she’s like, “You dumb ass, there’s going to be like a hundred million,” you know? [laughter] And it was just such a great, both affirmation, and also “This is so much bigger than we can imagine.”
I had that feeling with Glitch, which was — I think a lot of us had lamented the web we make. That we have apps on our phones, and what I always experienced with the apps on my phone. Everybody complains about [how] the algorithms aren’t fair, and there’s all kinds of awful content being shared, and misinformation and these things. What I miss most is, I look at my phone and I look at the apps and I don’t know who made any of them.
MATT: Hmm.
ANIL: It used to be [that for] every website I went to, I knew the person, and I knew what they liked, and I knew why they made it the way they made it, and what their peccadillos were. I mean, I still go to Daring Fireball and I’m like, “Damn it, John Gruber, the font is still too small. [laughter] I mean we are so much older now, just nudge the type size a little bit bigger,” you know? I’m sure he’s been finessing the font for 17 years to find exactly the right size but he’s not ready to commit yet. [laughter]
But ultimately I come away and I’m like “That’s fine, I know exactly why it is what it is, I know his personality is captured in every pixel on that screen.” And then the stuff I spend my time tapping on, on my phone, has none of that. It doesn’t have people behind it, I don’t know the peccadilloes.
I always use the analogy of food. Every meal I remember in my life was made by people I love who were — maybe it was a part of a tradition, like our culture. I know where the ingredients came from, I certainly know who was in the kitchen. And in none of my great digital experiences do I know who made it and can I thank them.
You and I both have had this experience where we see an app or a tech that meant something to us, or a website that meant something to us, and we get to meet the creator.
MATT: It’s so exciting.
ANIL: Yes. So I felt that all like a flash the first time I saw the prototype of Glitch. Then we spent a year and a half, almost two years, really remaking the company in that vein. So I joined, which was incredibly intimidating, to be the first non-founder CEO of this company after 17 years and 18 years in business. We had shared an office with Trello and we moved out on our own, which felt like being 18 years old and moving out of mom and dad’s house. We renamed the company Glitch. Joel was incredibly supportive.
And then the team, the people here… It’s so interesting because we’re not trying to be retro. I don’t have any idealistic view of the good old days, but I think there were things on the web that we used to like that we miss. So we imagined a modern version of that and everybody aligned around that. It’s really interesting where there are people certainly of my cohort who are like “Oh I remember the old internet and I used to go to MetaFilter,” or whatever the old thing was, but most of them are like, “Oh I’ve never known that web. The web I’ve grown up on was — the wildest part of it was MySpace and everything else has been this blue box we shove our photos into.”
And the exceptions are around the edges. Definitely I had a WordPress theme that I used a hack on, or definitely I had a Tumblr thing that I would try to mess with the theme of. But those were the edges. It is satisfying to make something, and very little of their experience of the web had been that, and so they wanted to unleash that for as many people as they could.
We’ve been fortunate. We came out of beta a little over a year ago. People have built well over three million apps on Glitch, and it’s going up very quickly, which is fun. [laughs] They are all full stack web apps, they are 99.99% open-source, they are all remixable. You can view source on all the apps — and full stack, you can even view the server code. It feels like a bit of the promise of the web that got so many of us excited in the beginning.
MATT: So someone could think of it like a largely open-source code repository where all the code executes as well?
ANIL: Mhm, yes.
MATT: You can see how things work and if you build something, I can click a button, remix it, essentially fork it, software terms, and start my own version?
ANIL: Yes, yeah, exactly. So for everybody, if you come to Glitch, I comment it’s almost like an app store. There will be something fun today that’s like “Build a Slack bot” or “Make a fun game for your friend,” or whatever it is — very simple stuff. And if you just want to go, take that and play, you’re great, it’s fine, you don’t have to be a coder, you don’t have to dig in.
What we find is most people are like, “This is cool, but I want this button to be blue instead of green,” or “My boss wants me to add this one feature to this little tool,” or whatever it is. Then that idea of, “I’m going to remix this and customize it and make it my own.” The fact that you could do it in the browser, you click remix, you get your own copy, and behind the scenes it’s just a cloning a git repository.
But what’s happening is the editor — it’s like Google Docs. You can do live, real-time editing together on the code, and you can share the link with somebody. As soon as you get in that mode where rather than “I’m going to figure out what this is on my own,” but I can collaborate with somebody — and especially that you can just do it in your browser, you’re not installing a dev environment, you’re not configuring an editor, you’re not doing all the complicated things, you’re just doing the creative part — I think that has been very, very freeing for people.
There is this magic happening behind the scenes where that app runs and then if you type in code and you make a change, it immediately is running with that newer version. Those are things that have empowered people to sit there and say, “Now I’ve got permission to do this again,” maybe in a way that if I’m an older-timer and I’m used to doing it on GeoCities or on MySpace or something back in the day, but that has gotten hard. I think you and I both started FTP-ing pages up to a website. That’s hard as hell to do now.
MATT: Oh my goodness. [laughs]
ANIL: There’s deploy scripts and there’s cloud configuration and —
MATT: It’s gotten more complicated, actually, now.
ANIL: Yeah, yeah.
MATT: It actually always surprised me, Moveable Type had this feature in WordPress too, where you edit the template in the browser.
ANIL: Yeah.
MATT: How popular that would be and actually still is today. Like, we still invest in — I guess we build it on CodeMirror or something, which is an open source library.
ANIL: Yeah, so do we. And it’s essential.
MATT: Oh cool. People love those features.
ANIL: If you’re an experienced dev, you are going to have your whole toolkit, and you’re going to connect it all up. It’s the difference between a weekend woodworker or hobbyist, and the person who’s got the wood shop.
MATT: But collaboration is a super feature that none of the desktop tools that I’ve used have.
ANIL: Yeah, exactly. I think the biggest thing we saw is that you could — people already have the behavior. If you’re editing a Google Doc or whatever tool you use, you send them a link, or you Slack them a link, and you’re just in there. You don’t even think about it, you know, “What do you think of this,” “You might not —”
MATT: You’re not resolving versions, they’re just happening in real time, which I think is really powerful.
ANIL: Yeah. In the olden days when you would email Word doc final_final_REALLYFINAL_versionthree… [laughter] and you’re approving changes, it’s like, “Oh god, this is hell,” right?
MATT: Not old days, that’s current lawyer days, by the way.
ANIL: Yeah, yeah if it’s expensive, right. Legal contracts, sure. But the internal, for some announcement or something —
MATT: Totally.
ANIL: — you’re not doing that. And then code was still feeling like that. I love GitHub, we use it every day, it’s an essential tool, but I — probably every single day — type “man git.” I’ve been using it for as long as its existed. [laughter]
MATT: Yeah.
ANIL: I don’t think I’m dumb, I think it’s hard. [laughs] You know?
MATT: Yeah, yeah.
ANIL: Especially when you have other things to do. If that’s all I did, I think I could probably learn it, but I have to do other things. So that idea of, while you’re just remixing something, it’s already handled, and then while you type and both of you or all ten of are typing in your Glitch project, we’re auto-committing into git behind the scenes.
Then the biggest thing for me, after we launched in beta, that turned the corner for Glitch, was we introduced a feature called Rewind. It’s a timeline slider at the bottom, you can pop it up at the bottom in a window, and it gives you the same thing you see on a YouTube video, but if you want to rewind back to old versions of your app, you just slide the slider back. And again, could I undo a commit and revert and do the right thing? Yeah, I can do it, I’ve done it. I don’t feel confident at doing it, and I certainly don’t do it casually. I wouldn’t just be like, Let me try a different version of this and undo these things.”
MATT: Play around with it.
ANIL: Right. And again, I’m a spreadsheet nerd, in spreadsheets we do scenarios all the time. “What if it grows by 1.2% instead of 1.1%?” It’s trivial, right? So you are able to think more broadly. It un-bounds your experimentation, it changes the way that you’re willing to try something because there is a lower cost to it.
Rewind is about that. It’s “Let me try a different version of this app. I’m going to remix my own app with one click,” [and] three seconds later I’ve got another copy. Now I’m going to rewind back to last Thursday and “What if I’d used this other framework, tool kit, API, instead of this one? Now I can have them side by side and look at the difference.” That kind of creation, I have that in Garageband when I’m making music, I have that in turning off a stack of layers in Photoshop, when I’m working visually. I have that in all my other creative tools, and in code it’s way too hard.
MATT: The only thing I’ve seen close is maybe the computational worksheets from Wolfram.
ANIL: Yeah. I think they’re great. I look at the Jupiter notebooks, and in Python they get a little bit of that feel. Those are all adjacencies. I don’t think any of this is new. People have been exploring these boundaries for decades in coding culture and in computer science, but productizing it for something you could actually put a live web app on today instead of in the lab — I think that is the leap, that’s the thing we want to do, is take this out of…
We can imagine a million things, but can you do something that — you can use this and then ship a production app you’re using at work, like the actual… The thing we have a lot of — Slack bots for example — people are like, “I just want to get some data out of this whole legacy system and dump it into a Slack channel, and I know the connecting pieces are here.” So Slack, they created a bunch of examples that do the basic mechanics of it. Actually, Matt Haughey, an old mutual friend of ours —
MATT: Oh wow.
ANIL: — yeah, had built some of these examples.
MATT: And there is an amazing connection as well that the predecessor to Slack was Glitch.
ANIL: Mhm, yes.
MATT: In a different incarnation.
ANIL: Yes. Exactly. So the team had originally built Flickr, a lot of the same folks, and that started as Game Neverending, and they pivoted from the game into Flickr, which was a feature of what they were doing. The second incarnation of the game was called Glitch. And we had started…
Actually the first prototype that we had built was called Hyperdev. We went through a lot of iteration but I reached out to Stuart Butterfield and the team at Slack, and I was like, “Listen, you’re not using the Glitch name, we’ve got something good that we think is worthy, not just another generic photo sharing app, we’ve got some idea here,” and they believed us and they thought that was worthwhile, so they were very generous in cutting us a deal to get it. And we got the Glitch handle on Twitter and all that stuff, and that was it.
It’s funny because I’m always a little skeptical — names are names — the product, it’s always about the product in these things. But the truth of it is that changing the name was the biggest inflection point we had. As soon as that happened, people could understand what it was in a way. That was really surprising to me. In retrospect, I said, well if you get a Prince fan to run a company, they’re going to rename things, so… that’s just how it goes. [laughter]
MATT: I like it. Formerly known as.
ANIL: Exactly.
MATT: One of the things that was really an undercurrent there was a real optimism about what could be built and everything. You were also an early contrarian, perhaps a pessimist or realist, however you want to define it —
ANIL: Or at least critical, for sure.
MATT: — on the neutrality or goodness of technology and communities and things.
ANIL: Yeah.
MATT: Tell me about how — you have the receipts, so what were the receipts there, and what happened like you predicted?
ANIL: Like a lot of people who are changed by something, you have a crisis of faith. So I had been working on building blogging tools at the point I left that work, for seven-and-a-half years. I had joined a company that my friends had started that made a product that I loved. And by the time I left, I felt like none of that was true. They weren’t in charge, the company was unrecognizable, the products had fallen into disarray or decay, I wasn’t proud of a lot of the work.
More broadly, I had gotten very disillusioned with tech in general. I had been in San Francisco for, at that point, three years or something, and I would walk my dog around South Park where I lived, and hear three different people talking about their podcasting startups and I — [laughs] I was like I’ve got to get the hell out of here, I’ve got to go home, I’ve got to go back to New York, as I think happens.
There’s not some epiphanic moment where the clouds parted and all the sudden I saw this thing. I always follow my gut and my gut was like, “This is not good for me personally but something is wrong here, something is really wrong.” For context, that you will remember but that I think has been erased because our industry doesn’t have a great history, there had been a lot of effort around just before that — a thing called OpenSocial.
MATT: Sure, yeah.
ANIL: So Facebook had had its platform that had succeeded in people building apps for Facebook, which is funny because they killed that off too, but at the time it was the hot thing. Everybody else freaked out and said we’re going to respond to this. So the company I was at, we participated at Six Apart, and also MySpace was big in it and Google.
MATT: Evo, Google, everybody.
ANIL: Yeah, exactly.
MATT: Everyone except Facebook was a part of this.
ANIL: Right, exactly, right, this is a coalition of the willing. They had some big event at Google and all kinds of — I remember at the time thinking “Wow, these folks have a lot of money. And they did some big event and launched it.”
I had been very excited because I wrote about it. I was like, “Listen, the open web wins, and this is about the open web and Facebook is closed and it’s like the new AOL and it’s just siloed,” and all these things. The thing that got me excited was I wrote that blog post and it got linked to by a blog I had helped recently set up just before that, which was Marc Andreessen’s blog, and he said, “This is the smartest take of the day.” I was like, “Wow, the Netscape guy thinks I’m smart.”
MATT: That’s awesome.
ANIL: You fast forward not much later and Marc’s on the board of Facebook and OpenSocial is dead and in fact all of the work I had tried to do on OpenID and pretty much everything except OAuth of that era died. A lot of that was the user experience was bad, the technology was too hard, it wasn’t user-centric enough — there’s a lot of legitimate criticisms. But the motivations behind them were all legitimate, that no one company should own identity, that we should have ways to share identity pseudonymously between sites — there were a lot of really key pieces there that were dead on.
And that we should be able to control our information and where it goes and have a record. One of the important ideas that totally got dropped that was an underpinning of things like OAuth, was that you would have a record of where you signed into and where your data got sent to, and it would be this audit log. And you imagine how different that world would be and one of the —
MATT: TypeKey was the identity provider that had an open —
ANIL: Yeah, yeah that was… And we built a product around —
MATT: It was great because it would show you where you had —
ANIL: Yeah. And it would show you the history and also that we documented the protocol and said you can implement your own, and we never… It was a thoughtful design. I think, again, the user experience was too hard. There were a lot of legitimate reasons it didn’t work but there was a very informed, thoughtful perspective, and one of the last big projects I had pushed on was —
So the company I was at, at the time, we had Moveable Type and Typepad, which were two big, serious publishing platforms. And then we ran LiveJournal, which at the time was still one of the biggest social networks in the world, but it was probably the first to get to 10 million users.
MATT: I think also, in addition to pioneering so much, was largely open-code or open source?
ANIL: Entirely open source.
MATT: Open source. You created Memcached, a lot of things.
ANIL: Created Memcached, yeah, yeah, exactly.
MATT: That Mogile and everyone uses today.
ANIL: Yeah, exactly. There is this hugely generative platform. They invented a lot of — a functional social model and of the underlying technology and open source, it was really thoughtfully done. But we were adapting to the new world. And so Facebook reached out and said “Will you use this new feature we have, where people can share their activities on” — I think it was still “the Wall” at that point.
MATT: Was that Beacon?
ANIL: This was Beacon. So we pushed back and I leaned on our lawyer and we said “We’ll do it but it’s opt-in and our users have to be informed.” And it was actually, to my mind, the basics that you do. People don’t share their information without consent. We were the only launch partner of Beacon out of dozens, and the commerce sites and everything, who made it opt-in. And Facebook had pushed back really, really hard.
I was shocked because I had just assume everybody would do this. I thought, “Oh they messed up in their defaults but they… of course they want users to consent to sharing data with them.” I was astoundingly naive. In retrospect, I didn’t even feel stupid. I should have felt stupid, and instead I was just like, “I have misunderstood where I am.”
MATT: I wouldn’t put that on you. I would say that there was a general zeitgeist of openness and sharing with good intentions.
ANIL: Mhm, and that was the social expectation that we all had of each other.
MATT: Yeah, yeah.
ANIL: I mean, we were competitors, but we both believed, “Oh this is how you do these things.”
MATT: And we support the same standards and things like that.
ANIL: Yeah, yeah.
MATT: Facebook bootstrapped on exploiting that, whether that’s address book APIs or things like Beacon or whatever, it was that kind of — [they] took advantage of some of that good will in a way that wasn’t ultimately two-way. Although they tried to be two-way as well. Let’s be fair. Their platform, the API, a lot of the stuff they now get in trouble with, was to try to open up Facebook.
ANIL: Well, right. I think part of it was the reason they exposed data that people didn’t expect is they collected data people didn’t expect to share. Right? And talking to people who were there early at Facebook, one of the things that is interesting is they weren’t even intentionally exploiting — it had not occurred to them that we had these norms, they weren’t of the community.
We had all come up reading Joel and Software and Zeldman and Shelley Powers’ Burningbird. There were these people who were I think in retrospect we would call it “tech ethicists,” who were thinking about the impacts. And also, I think you and I both were like, “We want to be cool to these people.” You want the nod and you want them to link to your blog and all these things. And that healthy impact of them being skeptics and thoughtful, as well as those of us who were coming in, saying we want to get the nod from them, all led to, in good and bad ways, a set of norms, and they didn’t understand the import of — Zuck was not from that. So it wouldn’t even occur to him to try to conform to the norms of somebody he’d never heard of. Like, who would? You know? And so it was just like, “I’m a stranger in a strange land, I’m just going to do what it takes to grow or… I’m not saying, “Why didn’t you have the same values as us?” because, like I said, we got a lot of things wrong, but that was telling.
To your starting point here about how did I go from the cynicism to the optimism, and the truth is, I still have a lot of both. At that point, I reached a breaking point. I genuinely thought “I will never work in tech again, certainly never work at a startup again, I am done with social media as a business. I have to be here because I need it for my career,” but I got as far away as I could.
I came back here to New York, I started working at a non-profit, doing research, I spent a couple years trying to get a grasp on, honestly, what I felt I had been culpable in, like, “What have I helped cause to happen?” and “Is it good?” And then I also had thoughts about my — I had spent a lot of time when I was younger as an activist and involved in a lot of really morally and ethically-based movements. I didn’t feel like what I was doing contributed to the values that I had come up with, and the people that had opened doors for me and inspired me.
So I just looked around and, in particular, I looked at who was in the room when we built these things. And it didn’t look like who was in the room when I had worked in the music industry or when I had worked in media or I’d worked in activism. I thought, there is no way we’re thinking about these things.
I wrote this series of posts on my blog in maybe 2009. I think I had said I was leaving Six Apart, but I hadn’t left yet or something. You know there’s that senioritis moment.
MATT: In between, yeah.
ANIL: Yeah.
MATT: Oh, senioritis. [laughs]
ANIL: Right? I wrote about basically every major tech company and what I thought was wrong. I did one a week all summer long that summer. I genuinely thought I had blown up my career. I got PR people that were like basically, “Who the hell do you think you are?” [laughs] And the end of that was — The Social Network had just come out.
MATT: The movie about Facebook?
ANIL: Yeah, yeah, exactly, the movie about Facebook. And they had a story tied to that in the New Yorker, and I gave a quote basically saying what I thought. I just said, “If you’re Mark Zuckerberg you don’t know what you don’t know, and of course you think everybody can have one public identity that’s yourself because if you’re him, you’re not going to get vilified for it, you’re not going to get kicked out of your house for it, you’re not going to be violently abused for it.”
All the back channels lit up. People were like, Facebook is not happy that you are quoted in this and that you’re seen as somebody credible. I really thought, “I’m never going to work in tech again.” That was my belief.
You fast forward anyway to 2017. By the time I had, you know, dabbled, even what Gina and I were doing, we very assiduously avoided the conventional startup world. I didn’t go to Sand Hill Road and look for VC funding and all those kinds of things.
But I had a really great conversation with my wife and I was saying “I still want to change this industry for the better, I still want to have impact.” I haven’t given up on the potential but tech is itself one of the major social pillars that influences culture. The other is media and entertainment, broadly, and obviously I deeply care about pop culture and those things. And then the third was policy and governance.
I had spent a lot of years when I was doing that nonprofit work, working with the Obama administration, and [I’d] gotten access in policy and government, and I started to see “Okay, there’s some things that government can do here but it’s by design, slow. And also very corruptible or capture-able by interests.” Okay, we know those flaws but we didn’t maybe know the extent of them, but we knew that was there.
Then media and entertainment, I had a little bit of an in, and people knew me. They didn’t know why. They’re like, “I don’t know why this guy writes about Prince all the time but like… [laughs] and he seems to know what he’s talking about, this is weird.”
MATT: I think you’re a worldwide Prince expert.
ANIL: Yeah, you know, I’m not the most knowledgeable Prince fan in the world but there aren’t ten ahead of me. [laughter] So people were like “OK.” And not just that, but they’re like “OK, he understands how the entertainment industry works and that’s interesting.”
I thought about how you triangulate fitting those pieces together into shaping tech to be something better. And the truth is, I had as much access as you could have, and I hadn’t been able to have any affect. I had been there, banging the drum, and to talk to the Chief Technology Officer of the United States, and be like “Here’s an issue about data privacy,” and they’re like, “We’re trying our best.”
To see people in his office that spoke up on net neutrality and had their lives destroyed by companies trying to lobby to keep net neutrality from happening. This all happens behind the scenes, but I would see good people who were targeted by the AT&Ts of the world, by the Comcasts of the world, who were like, “Do not let this happen.”
And then even in media. At the time, not long after that, I got a column in Wired. So for me as a writer that felt like the pinnacle.
MATT: That’s making it.
ANIL: Yeah, exactly. In tech influence, it’s like, this is this opinion column in a magazine that at least has the impact. I would write there and it would just get dismissed and bounced off. They’re like, “Oh that’s nice, you brought your blog into a magazine.” It didn’t land.
What I realized is that even seeing the most credible academics, like I think about dana boyd, who is just brilliant at this, and her research institute, Data & Society, would document all this stuff, and it’s incredibly valuable as the underpinnings but it doesn’t cause the change to happen. So ultimately the theory of change I arrived at was you only change the tech industry by being a founder and by having a hit. There is nothing else you can do. Anybody else will get dismissed.
MATT: That’s true, yeah.
ANIL: “You’re not in the game, it doesn’t count, you’re just an outsider, you’re just jealous.” I see VCs say this all day long on Twitter to every valid criticism. It’s like, “You’re just jealous because we’re rich,” basically. They’ll frame it different ways but…
As we’re speaking right now, there is a lot of criticism of WeWork ahead of their IPO, and there’s a lot of fundamentals there that are a little iffy. Now people are turning the corner into “Well, okay, maybe there’s some stuff here that’s not as rigorous as it should be,” but the first wave of defense was all “You’re just jealous, they’re a unicorn, you don’t recognize their vision and da da da.”
I’m like, yeah, there are times I miss a vision of something, but the reality is, this is real estate, this isn’t magic. And software doesn’t make real estate magic, and you have to be able to say something is what it is. Interestingly, there is a willingness to hear it if you are at a certain title — CEO, founder, and if your product is a hit.
MATT: And here we are.
ANIL: Yeah.
MATT: That’s a good full circle. On Glitch I noticed the careers page had some interesting stuff. A series of pledges, including no endless meetings.
ANIL: Mhm.
MATT: Allyship, best practices, reasonable work hours.
ANIL: Oh yeah.
MATT: Do you ever worry about being held to these things in the future or is everything on there something that you feel like is…?
ANIL: I hope to be. Yeah, the good news is a lot of these date back to Fog Creek, and even to the earliest days, which at this point is 19-20 years ago.
MATT: Which are the ones you think are most important for people?
ANIL: Oh that’s a good question. I think the fundament is respect for the people on our team. Joel Spolsky, as our founder and our chair, said from day one, “We treat our people well and we give them a great working environment.” And it is a very deeply held view of his. I agree but that’s the ultimate authority, that’s my boss. And that has been true from day one.
MATT: Orient it a little bit. How many people do you have here in the office, how many remote?
ANIL: The company overall is 56 people. We just had two people accept, so soon we will be 58. Of those, 30 are remote. So 26 here.
MATT: The majority, yeah.
ANIL: Yeah. And what’s interesting is that is shifting. This has never happened in the 12 years the company has been doing remote. People are starting to move to New York to be in HQ, to balance it out. And it’s always been the other way, which is the remotes were the one-offs and so people were like — obviously you don’t have to twist people’s arm to be in New York, but it was an interesting sense of people — the balance of both.
The majority are remote. There’s an interesting mix of people that have been in the commute-to-work-everyday thing and don’t want to do that anymore. I really love that here in New York, we all take mass transit, but nobody at the company has to drive to work and be stuck in a commute. Nobody around the world does that, so that’s really powerful.
Then importantly, you know, we make sure we pay attention to — there are people in leadership that are remote. There are people in every role and every team, in marketing, in engineering, in infrastructure, [for] everything we do, there are remote team members, in media, all the things that we do, there’s no one side or the other.
MATT: I’m excited to hear your thoughts and learn a little bit more about how you operate in a distributed fashion at Glitch.
ANIL: Joel Spolsky, who is our founding CEO and co-founder of the company, he had a lot of things to say about how you should set up your tools, your software and [how] everybody should have a really nice, big monitor, and all this stuff.
Then he had this one principle which he still is very adamant about, and in fact he mentioned it in the board meeting we had last week, which is that every coder should have a private office with a door that closes. He really feels it makes a huge difference [in] productivity, and that there is a lot of research and evidence that shows having the space is very valuable, which I’m a full believer in.
I had never — before I worked at Fog Creek and now Glitch — had seen a workplace where that was true. I saw that they were able to have these results for a long time, and then when they built Trello they really started to grow the company and they ran out of offices. So they were sort of like, one, we can’t just expanding forever here but, two also, there’s lots of talent, or people that didn’t want to move to New York City. Those two things led to the obvious, in retrospect, conclusion of the company should be open to remote contributors.
It’s interesting because the impulse there was in order to keep doing the structural things they were doing. So remote workers at the company are required to have a private office at home, a room with a door that closes, and that is not your kid’s nursery or where your greenhouse is that you’re growing your plants. It’s its own space.
In exchange, the company, we provide a sit/stand desk, if you want a motorized one, a really nice chair, we’ll pay for the internet connection, we make sure you get broadband, all that stuff is taken care of. But it’s very much this sense of — to create the same atmosphere as what we have in the office. Then there’s a whole set of processes around how everything works to make sure it’s uniform, whether you’re in HQ or not, for coders. And that was something that was probably the biggest culture shock when I joined.
MATT: Having an office with a door is good for developers, why not for everyone?
ANIL: That was the first question I had, as somebody who is not a developer, right? [laughs] Can I get one of those? I can write a couple lines of code, like, what do we gotta do? And actually what we came to really talk about — and this was really catalyzed in particular — because we had shared an office with Trello as one of the other spin-out companies, and they were growing leaps and bounds around and after their acquisition by Atlassian. We were growing our team, and it was really crowded, we had this shared office in downtown Manhattan. People were getting doubled up in offices, and there was a question, “Why are these people over here and these people were there?”
What I came to understand as we built out a new office here is there’s different work modes. I’m someone that definitely falls into this where I have one way of working when I’m writing, which I try to do a lot, one way of working when I’m coding, for sure, and then of course you end up in a meeting, you’ve got to be in a conference room and sit down with people. There’s all these different ways of working.
I found one of the things that I find for a lot of people really consistently is they’ll say I’m most productive on email when I’m on a plane and there’s no WiFi, or I do a lot of writing at a coffee shop, even though I’m not talking to anybody else that’s there, I like that energy.
MATT: Totally, I can totally relate to that.
ANIL: Yeah I have that experience with libraries. Yeah, right? So there were different work modes and that was what really was the epiphany — even though we’re very effective with giving coders private offices, at the time the company was just that. There were really only coders. As recently as in the past decade, Fog Creek was a company where there was nobody who had a title of marketing, there was nobody with the title of sales, there was nobody… [laughs]
MATT: Wow.
ANIL: I mean there’s entire business functions that did not exist. It was a very, very extreme environment. And good in a lot of ways — obviously it had a lot of success — and then bad in a lot of ways. So you couldn’t do normal things like having a couple of people get together to talk about messaging or design because those functions didn’t exist and you didn’t have any place to do them if everybody is warrened off in their own little room.
Finding the balance of how do you have different ways of working was really powerful. In HQ, it translates into conference rooms. We have a space that I literally set up to be like a coffee shop, and we’re doing that with our new headquarters that we’re building — it’s going to feel like a coffee shop. You have the nice couch and you get some caffeine whenever you want.
MATT: Cool.
ANIL: So that’s there. But the biggest thing was the very first day I joined we had a meeting, an all-hands. We still have them every week, and everybody, even in headquarters, even at desks, if they didn’t have a private office, put on their headset and joined the video conference from their desk independently.
I had had this in many other companies that I had worked for or worked with. It wasn’t the scenario where if I was remote, everybody in HQ was all around one table, in one room together, and then I was on the other end on some weird conference phone, like one of those Polycom phones, and they forgot I was there and they couldn’t see me.
Or the weird creepy thing [where] your video shows up when you talk so every time you talk you know you’re on some giant 10-foot screen with everybody staring at all the pores on your face. These were the only two modes of interacting that I had ever had. [laughs]
MATT: Right.
ANIL: Instead, everybody had the exact same set up, the same camera, the same kind of headset and could see each other, and it didn’t matter if you were in HQ or if you were thousands of miles away, you had the same experience at that meeting. And everything changed.
MATT: It sounds like y’all — it must be a delight to work there. I’m sure some listeners are like “Oh, I need to check out their careers page.”
ANIL: As I said, we have a weird background. The company overall is — in two months, we’re going to be 20 years old. But we really started reinventing the company about three years ago. Some of the things that we changed: one, the top level, one of the very first things I did was around recruiting and hiring.
Very early on, Joel Spolsky, our co-founder and CEO, had said, “A good tool, if you want to assess people’s skills as coders is to use a white board and talk to them about their thinking about code during the interview process.” This is something, as I’m sure you’re aware, that became almost a cargo cult thing. Right? People would do this, what to me felt like a hazing ritual, of demonstrate your memorization of some algorithm by writing it on a white board from scratch, which is not how anybody in the world ever codes, especially not when we’re the company that had co-created Stack Overflow! [laughs]
MATT: It’s all about Googling things, yes.
ANIL: Of all the places. Right, yeah, of all the places you should be able to just copy and paste from Stack Overflow, it should be here. So his impulse had been right, which is like, let’s see how people think, and don’t put them through all the pressure of having to set up a dev environment just for an interview.
But I think in the absence of the steady hand saying, “Here’s the principle behind it,” it became, as I said, almost a hazing ritual. I felt very personal about that because one, I care a lot about inclusion in the industry and anything that’s a barrier is really dangerous. And then for me personally, I had worked as a coder for years and yet I knew I couldn’t pass that test. So what did it say about the utility of that test? Clearly it was testing something else, you know, to be standing at that white board and be put on the spot that way.
So we changed that. But it was the beginning of a change in the culture overall, which was interrogating which assumptions were about us being different for a real reason and which things were rituals that we had held onto from the olden days. Things changed pretty quickly after that.
For example, we had always had a pretty public set of rules around how the company ran, but we formally turned that into a public handbook that people could look at for our HR policies. And that both helped us refine and sharpen what we shared but also, again, helped in recruiting, because people outside could be like “Wow, I know how that company runs and how processes are going to work for me and whether I’ll be taken care of.”
We did that around compensation. Joel and Michael Pryor, his co-founder, had set up an engineering compensation ladder, gosh, probably a dozen years ago. A long time ago, but it hadn’t been kept up to date, and it hadn’t been modernized, and it was only for engineering. We turned that into a full salary transparency document within the company where we had documented what compensation and pay would be for every role, including non-engineering roles, which we introduced and actually defined. [laughs]
That was, again, it’s far from perfect, there is a lot of work to do to improve it, but it built so much more trust where people, especially underrepresented people in the industry, could be like “At least I’m being paid fairly compared to the person next to me. There’s always improvements to make in compensation but I’m not being targeted because of who I am, to be exploited, to be paid less.”
So there was a lot of this stuff where we took the building blocks that were there and then modernized them or updated them. That took a year, a year-and-a-half of work, but it really, really paid off in terms of one, attracting a new wave of incredible talent that were every bit the peer of anybody who’d ever worked here — which is extraordinary — and then we grew this company and this product while hiring at a fast clip, while expanding to a new headquarters, while doing all this other stuff simultaneously.
It’s very hard to walk and chew gum at a startup at the same time, and I think we were only able to do it because we had built that level of trust around the process, and especially around treating people in that basic way that they expected in the workplace. And some of that is about being remote friendly, some of that is about being friendly to people who are underrepresented in the industry, some of that is just about building fair processes for how everything works day to day.
MATT: Why not go fully distributed? Why do you still keep the New York office and why and how is it still important to you?
ANIL: We talked about it. That was a consideration actually before I had joined. There are a couple reasons that I had decided to keep it.
The first is I am, at the personal level, a very unapologetic New York City partisan. I’ve been somebody who cares deeply about the tech community in New York for almost two decades now, and I felt like the company is a symbol to the city of our tech culture and community. So there was a sense of which of the old guard, classic New York City internet startups were still relevant and pertinent and here, unapologetically here.
The other part was that, at a real pragmatic level, we were able to attract talent in certain ways because we’ve got options. There are people that one, like to work around other people. There are people that like to have camaraderie and they like to have a connection to the people around them. Certainly we see that especially in some of the other roles we had brought in, where we have a team doing media and we have a team doing community and all these other things, and they like to be able to commiserate and share ideas. So that was really powerful, and we unlocked that.
Also, there were people that want to live in New York City. [laughs] So we were just able to attract talent of people that were like, “I get to work at a cool tech company and be in New York? Sold.” The wild thing about that is that it’s cheaper than living in San Francisco!
MATT: In-person is so powerful so how do you keep those ties, being so much stronger and that communication being better?
ANIL: It’s something I’m very mindful of, and we are really disciplined in a couple ways. One of the things is no hallway conversations about work. And actually, one of the telling things is that we as a company have always done lunch together every day in HQ. So everyone in New York, really, meetings stop, calls stop, whatever is going on, everybody sits down, actually company-wide because it tends to happen in other locations as well, but really in HQ we provide lunch every day and everybody sits down and has lunch together.
Understandably remote folks worry about — that first day they’re like, “Wait, everybody there is going to be talking about stuff and I’m not going to know about it.” And the great thing is, saying “We’re not going to talk about work, we’re not going to make decisions about work in that lunch,” makes it a social place. It’s actually much more low key.
MATT: Do they really not talk about work? That’s so hard to believe.
ANIL: Yes, well because — it’s not that hard because there is so much stuff that’s interesting, well, one being in New York and two, at a social level. People like to put it away. We have really good boundaries. And also, they feel a real out-loud sense of “I’m not going to have this conversation without her here, without him here, without that person who is in charge of that.” Because we have leads, we have people who are leaders in the company that are remote, so it’s not — you couldn’t have a full conversation. Half the company is not there. So you couldn’t have the conversation without them.
So that’s really powerful, and then we already have a habit of taking notes at every meeting. If three people are having a meeting and they’re all here in New York, we’ll sit in a conference room. There’s not some weird ritual thing where we will refuse to sit together. But even there, there will still be the notes that are shared, just like they are for any other meeting.
So I think those habits, because the habits are deeply ingrained, and at this point for 10 years, there just isn’t that impulse. And it has been very clarifying to us about, one, just real life and what affects people, but also it helps with not being insular to just — to think about what’s happening out in the world to people. I think it can be really powerful.
That, for example, led directly to a policy we had created around paid climate leave. And originally the catalyst came from a worker of ours who is in Florida and was being displaced by a hurricane, and then we simultaneously had somebody that was being potentially displaced by a wildfire at the same time in California. So we made a policy to accommodate them. So it’s paid leave if you’re displaced by extreme weather.
But that core combination was one also informed by — we had had our headquarters displaced by Hurricane Sandy here in New York, when that hit. But that sense of just, we have people in different places, and we build policies that work for all of them. And that rigor, that perspective, I think it makes us run better, it makes us much more disciplined, it makes us have to be intentional about communication.
Those things are superpowers. They make our work better, faster, more efficient, more reliable, more trustworthy, because we have that discipline. And we honestly, I think we would be lazy if we were not distributed, if we were not rigorous around how we communicate, and in ways that would hurt our long-term opportunity.
MATT: Well and I think it’s one of the reasons that listeners will find the example of Glitch so fascinating, because you do put a lot of thought into all of your policies. One of the ones that I’m a little curious about, especially given you have a hybrid structure, is how you approach onboarding. Do people fly to New York and do some of that in person? How does it work?
ANIL: We do onboarding here in New York. The most extreme was actually back in the spring when we were really scaling up, we had nine engineers join in a week. Interestingly, we have a number of leads, whether they are director level or higher in the company, who are educators.
Onboarding, in its fullness of the plan, onboarding is something that we spend months on, so it’s three or four months. But the core of it is about those first two weeks, that’s the experience that we really design most deeply. And the first week is school. People come in, and the first day is like, “Get your laptop, get plugged in, get connected to Slack.”
We time it so that people join during the monthly all-hands. That’s when, in addition to an overview of how the business is doing, we share financials with the whole team, but also we do our bravos. That’s acknowledgement of people, thanking each other for the work they’ve done, when they’ve gone above and beyond on certain work.
They get to see — a new employee on their first day — how we share gratitude to one another within the company, and they get to see a meeting where everybody is dialed in, in the same way, whether they’re remote or not. And they get to see us model the behaviors of what we are in the first day, and then they spend some time getting two-factor all set up and all that other annoying stuff. [laughs]
Typically the rest of that core onboarding process — and this varies by team — we do a big overview of how the business runs, what the mission is, what the history of the company is, what our goals are, what the road map is. I spend a lot of time talking about the values and the vision of the company, and that’s typically in one-on-one sessions with people who have joined so they can have room to ask questions, or sometimes with their lead. That’s the better part of a day, usually right towards the beginning of the week when they have joined.
We have a much more social get-to-know in small groups, people across different teams. Typically we’ll have a dinner with some folks so they can say hi to other people in a little more social way. We will always bring in a person to HQ for onboarding and bring in their lead if their lead is remote. So people do get face time. We do think that has value. There is a way to deploy that as a tool, and especially for social interaction, when people are getting to know each other and have to build a relationship, so we’ll do that for a full week with the person and their lead in for a week.
The two biggest anxieties when people join a company are basically, “Am I going to know where I fit into any of this?” And then variations on what I think of as the problem we all had in junior high of “Which lunch table am I going to sit at?” [laughs]
MATT: Oh totally.
ANIL: We are very intentional about that, because we all eat lunch together every day, we’re like, “This is where you’re going to be, and everybody is going to sit with you, and you don’t get picked for a lunch table, everybody sits together.” And that stuff is — nobody wants to talk about it, but even if we’re adults, even if we’re decades removed from those points, that’s still that lizard brain in the back of your mind — that is always there. And so we do a lot to accommodate that.
Especially because the majority of our team, including management, are women or non-binary folks, and that is very rare in tech. And that’s true whether you look at race or LGBTQ representation, we over-index in a lot of ways there compared to the rest of the tech industry. So I try to be much more mindful of — there is a higher percentage of our team who will not have been in that scenario where somebody accommodated them and somebody asked “What do you want here?” or “What do you need?”
Just that little bit of accommodation or thought I think has been extraordinary for people where they feel overjoyed at “Oh, I wasn’t crazy in my last job when I thought it was wild that they didn’t even tell me who I report to or where I sit.” [laughs] “And that this place will tell me ‘You’re going to sit here and this is the work you’re going to do and this is why it matters.’” That’s all it takes for people to feel like they were welcomed.
MATT: We have talked a bit about benefits and I know equity is really important to you. So if I’m not in New York, how do you think about — I don’t get free lunch every day. Or if I am in New York, do I get a free internet connection?
ANIL: [laughs] No. So that’s where we go to. It’s not going to be exactly the same. We want things to be fair but they don’t have to be identical. There are things that are going to be better or worse, stronger or weaker in HQ versus remote. We try to, again, to document them and to be clear, and I think those are really good examples.
And it’s hard, right? We do cover internet access for people who work from home and we don’t cover it here. And we’re iterating on this stuff constantly. But one of the big things we do is we just talk about it, we are able to raise it, we have people — leads are encouraged to ask their team about it. People want expectations to be clear and they want to know that things are fair, but they don’t demand that they be exactly identical.
MATT: Anil, thank you so, so much. This has been Anil Dash from Glitch on the Distributed Podcast with Matt Mullenweg. We’ll see y’all next time.
MATT: That was Anil Dash. You can find him on Twitter at @anildash. That’s A-N-I-L Dash.
It’s good to know that people like Anil Dash are out there running companies and redefining what the tech industry can look like from the inside.
On the next episode of the Distributed podcast, I’ll be joined by my colleague Mark Armstrong once again. We’ll talk about the things we’ve learned over the last year, discuss some of our favorite takeaways from the podcast, and take a glimpse at what awaits us in 2020. I’ve learned a lot about how other companies are doing distributed work, and I’m excited to collect my thoughts and maybe make a few predictions about where we’re headed.
On this episode of the Distributed podcast, we get an insider’s look at the Grand Meetup, Automattic’s annual weeklong all-staff event, where employees have an opportunity to collaborate, learn from one another, and hang out face-to-face. Folks from across the company share what makes this gathering so special, talk about social cohesion in the context of a large distributed company, and reflect on what’s great (and what’s tough) about the distributed lifestyle.
The full episode transcript is below.
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Mark Armstrong: Okay go.
Josepha: The song that’s in my head right now is “Good morning. Good morning.” My name is Josepha Haden Chomphosy. I shouldn’t say it like a question. That is my name. My name is Josepha.
Mark: Great to see you. Thank you for stopping by the Automattic podcast booth. Josepha what do you do with Automattic?
Josepha: Great question. A little bit of everything. I am the lead of the .Organization Division, which is the division that supports and helps to guide a lot of our open-source work with the WordPress project itself.
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Mark: Who are you? Tell me your name.
Aaron Douglas: My name is Aaron Douglas. I am a Mobile Wrangler for Automattic. My official job title is actually Chief Tater Tot Officer — I neglected to change that and it just stuck. I work on the WooCommerce mobile app as my primary thing, but everywhere around Automattic I try to help out where I can.
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Mark: OK. Here we are in the hallway again. What’s your name and what do you do at Automattic?
Brandon Kraft: Hi, I’m Brandon Kraft. I’m a Code Wrangler working with our Jetpack plugin.
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Mark: What is your name?
Sheri: Sheri Bigelow.
Mark: And what do you do at Automattic?
Sheri: I am an Excellence Wrangler.
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Rocío Valdivia: My name is Rocío Valdivia. I am from Spain and I’m a Community Wrangler at Automattic.
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Achaessa James: I’m Achaessa and I’m with the Legal team.
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Will Brubaker: So my name is Will Brubaker. I am the Chief Mechanical Officer.
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Erin Casali: So hello, I’m Erin Casali, often referred as “Folletto,” and I currently work as the Design Lead of Jetpack. And how long? It’s been a while now, six years.
Mark: Where are we now, here?
Erin: So we are — I think — in Orlando, because we are inside a hotel, and have been a while, so I’m not entirely sure where we are? Your hotels look all the same. But we’re in Orlando. I lost count of time. I think we are on day three or four of the Grand Meetup.
Mark: It really is a blur, isn’t it?
Erin: It is.
Mark: Thank you for being here.
Matt Mullenweg: Howdy howdy, I’m Matt Mullenweg, the CEO of Automattic, and the host of the Distributed podcast. Those voices you just heard? Those were Automatticians — folks who work for Automattic — and today we’re going to be hearing from them about this year’s Grand Meetup, and more broadly, what distributed work means to them. Back in September, Automattic held its annual Grand Meetup, which is the one time during the entire year that pretty much everyone at Automattic gets together in one place. The other 51 weeks of the year, we all work from different places all over the world — over 70 countries now. So this is a chance for some of us to meet face-to-face for the first time, and for everyone to catch up with old friends, discuss our work and align around our goals, and hear great talks from folks like Stephen Wolfram (who was a guest on this podcast a few weeks back). We set up a recording booth at the meetup and talked to a bunch of folks from around the company to hear about their experiences with distributed work. My colleagues Mark Armstrong and Ben Huberman were on the ground, asking questions throughout the meetup. Mark and Ben are from Automattic’s Editorial team, and they’ve also been helping out a ton with this podcast. We’ll kick things off with some Automatticians talking about why meetups matter for distributed teams, then get into an interview with Megan Marcel, our Director of Global Events & Sponsorships, about what it takes to pull off this huge event with so many people — I think we had around 900 this time. Then we’ll hear some remote work tips, and finish with some stories about why these folks have chosen the distributed lifestyle. OK, let’s do it. Take it away, Mark.
Mark: OK, thank you, Matt. Now that we’ve met some of our colleagues from Automattic, let’s go deeper and learn a little bit more about their experiences at the Grand Meetup. If I can set the scene a little bit, Ben and I stationed ourselves at different tables outside in the hallways of this conference room in Orlando — just a few miles from Walt Disney World. We just flagged down people as we saw them, or people would see us with a microphone and say, “Hey, what’s that? Can I get interviewed?” I have to say it was super fun to have an excuse to pull people aside and interview them and ask them about their experience at the Grand Meetup. It can be such a nerve-wracking experience to be surrounded by all the people you work with, so it’s just fun to take a step back and look at the scene, and ask some questions of each other on what it’s all about and why we’re even there in the first place.
Mark: Now we’re here at the Grand Meetup in Orlando, Florida. What is the Grand Meetup?
Josepha: The Grand Meetup is basically like a company all-hands. I think that’s how corporate places call it, where we get everybody from the company who’s able and willing together in one place to do some additional training, additional team-building, and a lot of [the things that have] to happen when you work in a distributed company. So when you work in a distributed company, every time that you interact with your colleagues via text, or however you are away from them, you are taking out of your social bank account with them. And so when you get people together, that’s when you have the opportunity to see each other face to face, remind everybody that you’re all human beings, and fill that social capital back up, because it’s so hard to communicate via text. That’s one of the main benefits of bringing everybody together this way. Of course we have a lot of trainings and a lot of opportunities to have high-bandwidth conversations. But I think that’s one of the main benefits, and it’s almost a side-effect benefit. I don’t think anyone thinks actively about that when they bring everybody together for this.
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Mark: When did you join Automattic?
Achaessa: November 1 in 2018, so I give a flash talk this year. It’s my first GM.
Mark: Fantastic. So what how has it been so far?
Achaessa: The GM? I love it. I love it. I’m meeting all these people who I’ve been working with all this time and it’s so awesome. It’s like the best in the world.
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Will: It’s a very energizing experience to be here. My job is very demanding, and my life is very demanding, and everything around us is very demanding. I start to get de-energized in about July or August, and it’s also like things are physically — it’s hot outside, and things are more difficult in this time of year, at least for me. But then I get here, and I get around people and I ask questions there that are on my mind and what I’m passionate about, and I want a real answer here. And you know what? I get a real answer, and I get an answer that inspires me and makes me want to go home and work harder. You know what? I’m empowered now to fix the things that have exhausted me, and we’re going to start over, and we’re going to move towards the next year’s goals, and I’m very clear what those are. And that’s what this does for me, is that it’s a reset. It energizes.
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Ben: So right now we are in Orlando for the annual Grand Meetup. What does the Grand Meetup mean to you?
Rocío Valdivia: Wow. The Grand Meetup means a lot of things to me. I love the energy. I come back home with all my batteries charged for the rest of the year. I’m very aligned with the values of this company and I’m very aligned with the kind of people that I find here in general. Nobody’s normal, right, and everybody’s different in so many different ways. And in this company you can be however you want to be, and [be] nice to each other. And something that I will highlight as well is that everybody helps each other. I love that. And what I value the most about the GM is the connections that I create in person, that I can use them. It’s like I take advantage of all the connections I create in person during the GM the rest of the year. I learn more what people do. For example, I sit down and I meet someone during lunch and hey, this person just tells me that [they] work in marketing or [they’re] working on this and that. And then we have a conversation and we realized that we have so many things in common. And then for example, I am marketing seeking help maybe with WordCamps, and then we start planning. “Oh we should do this. We should do that.” And I love it. Because normally those kinds of things don’t happen during the year because you are so focused on your daily-basis job that you can not find the time to just hang out in different teams’ channels. I don’t normally do it because [I am] so busy. Right?
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Mark: What was your first Grand Meetup like?
Josepha: Oh, my first Grand Meetup was terrifying. I’m a wild extrovert, especially compared to a distributed technology company standard-issue employee. Wild extrovert.
Mark: What are you talking about?
Josepha: “I’ve never heard of such a thing!” I was told by my team lead at the time that I didn’t need to prepare for anything because I was so extroverted. And so I arrived and I had no idea what to expect or who was there. I joined a tiny team — like seven people, maybe six even — and so I joined and I knew them and that was it. I didn’t know that there was this whole other company going on. I didn’t know that we had classes we had to attend. I just showed up to stuff randomly on the day that they were happening and it was really stressful. Even for me, I remember thinking at the end of it like, “I’m not sure that I’m an excellent fit here.” I wasn’t prepared. Everybody knows everyone. I don’t know anyone. I have nothing in common because of course I hadn’t spent any time trying to figure out where I was headed. It was really stressful. But I made it through.
Mark: It’s a sensory overload, isn’t it?
Josepha: Yeah. It’s like the first time you go to CES, in case anyone does. You can make it about two-and-a-half days before you’re like, “This is terrible and I’m going to hide in my room until everyone is gone. And then I’m going to get on the first very slow transportation out of here, and that’s it.”
Mark: But it’s like CES, but they are everyone you work with, and a bunch of people who you have already chatted with, but you have never met them in person.
Josepha: Exactly. Exactly. And you’re not sure whether you inadvertently offended them. And sometimes you completely forgot to respond to them cause you hadn’t figured out how to use all the communication channels yet. And they’re like, “I asked you something two months ago, it probably shouldn’t have been time sensitive, but now I’m mad and it is.” So you run into all these surprises because you hadn’t figured out how to communicate. You hadn’t figured out how to work with all of the information that comes in because there’s so much information all the time and you have to be proactive about finding it, which is good, in a way, and also really difficult in ways as well.
Mark: We’re in a big hotel complex in Orlando, Florida right now. We’ve got a bunch of employees in front of us. How does this compare to your first Grand Meetup?
Josepha: It was so much more casual, because, if you think about the difference between 300 employees to almost a thousand employees, and the types of employees, and the roles that they have — that we’ve taken on since then — it was so much more casual. It was almost familial before. And I don’t know if it’s mostly a matter of the way that my work has changed, but I remember that I was in full discovery mode the whole event and just trying to figure out who did what and why, and where all the work came from, and what we were doing, and why we did it. And now it feels like — and I don’t know if it’s accurate or not — but it feels like for the most part, everybody already knows where they’re supposed to be, what they’re supposed to be doing, how the work is supposed to go. We show up and everybody already has this excellent plan and a goal for what to do for the week, even if that goal is “finish my support rotation.” And I think that’s a really nice thing, to have a really easy, collegial sense, which before was a “Hey, casually figuring out what to do now that we’ve arrived.”
Mark: Now there’s another element to Grand Meetups that continues to this day, although it’s evolved a bit. Your first Grand Meetup, correct me if I’m wrong, you did not know that you were going to have to present a flash talk?
Josepha: Yeah, I didn’t quite know. I had never seen a flash talk. I didn’t even do any research. So I arrived and someone had told me, “This is a thing that has to happen but it’s really easy, because you’re an extrovert, and so you show up and you talk for four minutes, it’ll be easy.” Now I love public speaking and I’ve done a lot of it, and four-minute presentations for me are way harder than 45 minutes, because you have to choose and plan what you’re going to say, every second of all of that. You don’t have any room for extemporaneous chatter. And so I showed up and they were like, “Oh we never received your slides.” And I was like, “What slides? Why do I need slides? What is it? What is the flash talk?” It’s short. I thought I just had to get up and say my name. And so I had to suddenly pull together slides and it was the most boring, bland title for a talk I could have ever imagined. It was like “Learning to be a better mentor,” which is super on-brand for me. And also, especially seeing what I do now, super on-brand for the future of my work here. But I didn’t know that at the time. No one else knew it at the time. I was just someone here to manage meetups. Man, I felt so stupid because everyone else is “Making paella the best: why Spaniards hate your stupid ham.” And mine was like, “Be a better mentor.” I was so serious. I showed up and I was serious and it was mildly embarrassing, but I survived.
Mark: I have to say, I think I remember watching your flash talk and saying, “Yes, Josepha is here.” I really enjoyed it. I remember enjoying it. Kudos to you.
Josepha: Thank you.
Mark: But it is a funny thing because you come in and you think the flash talks are going to be half about work or maybe some lighthearted stuff. But very rarely they’re about your day-to-day work. I have learned we have such a talented group of people at this company and that’s what I feel like I learned so much from these flash talks. People have such diverse interests and hobbies and passions.
Josepha: It brings back that human element, and humanizing people again and reminding people that we’re more than just a Happiness Engineer or someone on Editorial. There’s more to who we are than just that one thing. And I think that’s really special and really important and something you don’t get in corporate settings that are this size.
Mark: What are some other pro tips for attending a Grand Meetup?
Josepha: I think the thing that is most important is to consider what your boundaries are before you come. It’s so easy for introverts and extroverts to get swept up in the excitement of it, and like — are you willing to stay up until two in the morning in the party suite? Because that’s where the people that you had dinner with ended up. Because if you don’t, you don’t prepare for it. If you normally go to bed at at 10 o’clock at night and wake up at 6:00 AM and have a really clear routine, and then you get so far off your routine because you’re so excited and you want to connect with people and learn more about them, you can really forget to prepare yourself for that and just wear yourself out long before the event is over. Because especially now, we have these really — this year we have these big Team Days for the first day-and-a-half, and then a bunch of individual trainings all the way through, and ways that people can learn and do high-level planning and teamwork throughout the week. You want to be remotely fresh all the way through that. And if you just don’t remember that you plan to be an extrovert this week and so your introverted self forgot to have lunch by yourself in your room, you’ll feel really overwhelmed by the end of it. And so just planning for that, knowing what you’re wanting to do and how it’s going to change your routine, and being mindful of that for yourself is the biggest thing I think anyone can do before they come.
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Mark: What’s been your favorite part of the Grand Meetup so far?
Brandon: That’s a hard question. There’s so many great parts of the Grand Meetup. In some sense we have some amazing keynote speakers. And hearing these folks that we would never meet in person otherwise, and having some really great insight there. But frankly, really it’s just this time here, like right down the hallway between sessions, being grabbed by you, Mark, just to talk for a few minutes. I really like that ability to meet with different people like that, that we wouldn’t normally ping each other on Slack because we don’t really have an operational reason to. But we know each other and we see each other and we rekindle that relationship, even though we don’t work together day-to-day. And if we never had the Grand Meetup, we wouldn’t be able to keep that going. I think the best part is just seeing people that I know from other parts of the company. And even if it’s just a quick hello, or a handshake, or a cup of coffee, or five minutes on a podcast. I really think that’s the most valuable part of the Grand Meetup.
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Mark: Now what are you doing this year? Are you doing a project?
Erin Casali: The last few years I’ve helped with organizing the classes. This year I just taught a couple of classes — well, more workshops. I prefer the full workshop format myself. And this year I was helping out with one on floor storming, which is a workshop technique to synchronize and discuss processes. We worked on one on fast design — how to generate ideas quickly, how to push ourselves to create wild ones that then can become useful to projects.
Mark: What else happens at a Grand Meetup?
Erin: A lot of things. This year is probably one of the most varied ones. So you have a combination of assigned tables, which is something that at the beginning you’re like, “Why are you assigning the table to me?” But then if you feel relaxed because you’re like, “Yeah, I know I need to go to the table, and I know it’s going to be all new people.” And so you chat, you know new people. And then there are keynotes, external speakers, and then there are projects. And then there are a lot of occasions to catch up with people and coordinate things. One of the most beautiful things is how some of the — in the free time between activities — how naturally some discussions pop up. For example, today I’m just out of a discussion that was organized one hour earlier. And because some teams felt the need to discuss some critical topics, some problems they found. And they pulled in the right people, and in an hour we were able to identify some problems, identify some steps forward. It’s still a challenge, but now everyone is synchronized. And it happened just because someone was like, “Yeah, let’s pull the right people in the room together.”
Mark: When you have something like that happen, do you sometimes ask yourself, “Why do we not get together more often?”
Erin: Frankly, I think there is a balance there. There are times when you’re like, “Oh, I really need to pull people together.” But remotely, you still can. Sometimes it’s just a matter of spinning up a remote chat and sometimes it’s also faster remotely because everyone’s just typing away. You send that private message and that’s very simple in a way. For me that’s one of the powerful — that is a bit understated when we talk about remote work because in practice, very few discussions actually require people to be there in person. What you need is people to synchronize, and there are many ways to synchronize. In this case, I think this could have happened digitally. But it’s just effective because we are here.
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Mark: How does it feel to you seeing the evolution of the company and the evolution of the Grand Meetup, for you to be in this giant hallway and surrounded by a thousand of your closest colleagues?
Sheri: It’s so many people. That’s really funny because I came into this meetup like, “Oh, Grand Meetups are not the same. It won’t be the same feeling anymore. This one, it’s too big now. It’s like I don’t know anyone anymore.” I’ll just be walking around and I won’t know anyone. I won’t see anyone that I know and how will that feel? And I thought “Oh, maybe it won’t be as good.” But when I got here, I found that I just see someone, I can’t move through the hall without stopping like 20 times. So it takes me really long to move from one place to the other because I recognize someone, I see someone I worked with, I see someone I’ve only met online ever before and I want to say hi to everyone. And so yet again I’m here saying “I love everyone,” but I haven’t met — I don’t think I could possibly meet them all, actually. There is some really nice balance for me in the sense that I can have some great deep conversations and see my teammates. There was time set up for teams in the beginning, which I greatly valued and that whole “this is massive” feeling, like, “Oh my gosh, look at this room that we filled with people who are my people. They’re just like me.” And that’s one of the things that I thought when I — the very first WordCamp San Francisco that I went to, I was like, “These people are just like me. These are my people.” I feel a strong connection and [hold] a special place in my heart for everyone before I even meet them because I know that if you work here you’re probably pretty great.
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Mark: Had you met any Automattic employee in person before the Grand Meetup?
Achaessa: In person before the Meetup? Yeah, a few.
Mark: So just to clarify, before you joined the company — the interview process, none of that was in-person, right?
Achaessa: No, none of it was in-person. None of it all. But I’ll tell you the reason that I even applied. So I saw this job posted — the corporate paralegal position posted. And I was like, who is this? What’s this company? And so I went and I did my homework and when I got to the HR page, there was the link to the Diversity and Inclusion videos. I went there and I started watching those videos and tears just started shooting out of my face. And I was like, these are my people. I don’t know, it’s just — every single one of them spoke to my heart. In 2016 I got laid off from a consulting job and I had to take an in-house job that required me to be in an office in San Francisco. And I will just tell you that I feel closer to the Automatticians than I felt to those people sitting next to me in that office. Because in an office, sometimes you form cliques and so — I’m 60. You can see my hair, you know, and these were all very young people and they were — they partied a lot. They were still in that age. I’ve been through that age, but I’m not there anymore. And so it was very hard for me to integrate myself in that community. But at Automattic we have interest groups, I guess you would call [them]. We have Slack channels for every level of interest, and I have never felt more included in my life. I have people coming up to me at the gym: “I know you from this channel,” “Oh yeah, I love what you said here,” “Are you going to do this?” And “Let’s do this!” It’s like coming to family, you know, it’s like a family reunion.
Mark: Tell me about your flash talk.
Achaessa: Ooh. Okay.
Mark: What is a flash talk?
Achaessa: So a flash talk every first year. Now I hear I lucked out because it used to be every single person, every single year had to do a flash talk until what year?
Mark: I would say that would have been 2016 or 2017…
Achaessa: I just lucked out. So now it’s every person at their first GM has to give a “Four minutes about me.” So whatever — not necessarily about you, but whatever you want to talk about, you’ve got, maximum, four minutes to do it. And I really freaked out at the beginning, which is funny because in my industry, equity comp, I do speaking engagements all the time. I used to run an education program. I did talking all the time. But this “four minutes about me” was just like, “Ugh.” But I did it. Well, I haven’t done it yet, but I prepared. I prepared my flash talk. It’s about aging and adventure. It’s called “When Does the Adventure End? 30? 40? 50? 60?”
Mark: Spoilers? Can you tell me when the adventure ends?
Achaessa: Never. It never ends. It absolutely never ends. It just depends on how you approach it, right?
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Mark: Now how does this compare to your very first meetup? When did you join Automattic?
Aaron: It was barely two months before the Grand Meetup. That was in San Francisco, and also Santa Cruz, California.
Mark: How many employees at the company at that time?
Aaron: Oh gosh. I think I was number 220 at that point. So it felt like a large company to me at that point, and having not come from the WordPress community. I’ve used WordPress, but I have an iOS developer background, some Android as well. My sphere did not include the community around WordPress, so I felt a bit out of sorts when I first came to the Grand Meetup because I felt like I didn’t belong. But it was maybe an hour in after sitting on the couch at the old Automattic headquarters that I immediately knew that I was at the right place, connecting with the people that were there and just felt very welcomed and included. I was already in on the jokes on day one, so it was great.
Mark: That’s fantastic. So how does the vibe compare, 220 employees, to — here we are with going on over a thousand employees?
Aaron: Realistically the vibe hasn’t changed all that much in my mind, because there aren’t that many times that you’re all together in the same room. So I will say that if we’re doing a major Town Hall or we’re doing a keynote and you happen to turn around, then yes, it’s very obvious that we’re a lot larger. I’m one of those people that tends to sit in the front row. So my perspective hasn’t changed all that much. When it comes to the hallway conversations, we tend to do training or classes — people hold classes for other Automatticians to teach their own things that they’ve learned. Those are still relatively the same size and those conversations haven’t really changed their format at all. So yes, we’ve grown in scale, but really the heart of what the annual Grand Meetup is, is still the same, at least in my mind.
Mark: Why, if you’re a distributed company, why would you have a Grand Meetup? Why would you do this every year?
Aaron: Financially it’s a hard hit on Automattic’s books because you’re flying everybody into the same space, you’re giving them a place to sleep, and feeding them fairly well, actually. But the reality is, it’s hard to quantify what the Grand Meetup gives us — in material things, swag, I guess we get. So that’s cool as an Automattician, but the reality is I’m developing relationships with people across Automattic that I may not have a chance to work with on a daily basis. I have not crossed paths with you all that much except for a few Editorial PR-related things. But we’ve had a ton of conversations at the GMs over the years and what I like to call — well we use Slack, so I’ll just say Slack. The Slack Effect is that, when I’ve met someone in person and I’ve heard their voice, and I’ve seen their eyes and their face. If I have further conversations with them after Grand Meetup, my brain has a hard time discerning whether or not the conversation happened in person or in a Slack or offline asynchronous manner.
Mark: So you’re able to project that personality in conversation under all sort of communication thereafter?
Aaron: Yep. If I’m reading a message from you, your personality bleeds through into how I’m interpreting things to be written. If I haven’t met someone yet, I have a general Automattician voice, [I] assume positive intent and all that. But I think it really helps make me not feel like I’m alone at my house when I have all the Automatticians’ voices, when I’m interacting with people through electronic means. So to me the Grand Meetup is essential for me to feel successful.
Mark: What tips would you give in terms of how to navigate the Grand Meetup?
Aaron: Listen to yourself. If you’re in a state where you are overwhelmed, or if there’s so much input — too many voices, too many smells, too many places to go — you feel like you’re being left out of things. It’s OK to just find a quiet place, sit for a bit, process your thoughts, and then continue on with the day. If you need to go hide in your room for a little while, that’s perfectly acceptable. It’s a lot to take in. You are quite literally, from waking up to going to bed, always subject to things happening. It could be meals, it could be keynotes, conversations in the hallway, and — we all work from home. We have a lot of control over our day and here you have to give up a little bit of that control, and that can be overwhelming, so, self care is really a big thing. The other tip that I would give any new Automattician is just to say hello. It’s amazing what I’ve been able to do by meeting people here at the Grand Meetup that I don’t normally work with on a daily basis. How that’s helped me even years later when, I do need to get something done for my job [that requires input from someone who] happens to work with a team that I haven’t been able to work with before. I can look at someone on a team — like, I had that conversation with them at lunch that one year, and suddenly when there’s a conversation about work, there’s a level of respect or a level of known truth coming from you to that person, because they had a previous conversation. You’re not just some unknown. It’s a very subtle difference, but just knowing who you’re talking to and having that conversation in the past has really helped me in a lot of cases.
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Mark: So what is your name?
Sheri: Sheri Bigelow.
Mark: And what do you do at Automattic?
Sheri: I am an Excellence Wrangler, so we do automated testing, manual testing, and keeping track of all the bugs for — I specifically work with a mobile division right now.
Mark: And how long have you been with Automattic?
Sheri: Going on 11 years.
Mark: That’s pretty close to the founding of the company, Sheri.
Sheri: It’s quite close. Closer than it is far. A lot actually.
Mark: So explain to me what your first Grand Meetup was like. Did you have a Grand Meetup when you started?
Sheri: No. When I started, we used to all meet up at WordCamp San Francisco.
Mark: Got it.
Sheri: I’m very extroverted, but I was so nervous, so nervous to meet new colleagues. I looked up to everyone so much and — one thing that I still laugh about and tell quite often — I told Matt, “I love everyone.” And he just kind of looked at me and he said, “You haven’t met everyone yet.” I said, “I love them all anyway.” I was so excited. It was a really fun time.
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Ben: Thank you, Sheri. Hello everyone, Ben Huberman here. The Grand Meetup is a huge undertaking that takes years to plan. We’ve heard from people from all over the company talk about what it’s like to attend the GM. Now let’s talk to someone who knows what it takes to actually pull it all together and make it happen.
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Ben: Okay. Hello?
Megan: Hi.
Ben: Could you tell us your name and title please?
Megan: Megan Marcel and I am an Events Wrangler on the Events team at Automattic.
Ben: Could you tell us a little bit what an Events Wrangler does?
Megan: Sure, so Events at Automattic. An Events Wrangler ranges from sponsorships, to our internal meetups — and the biggest meetup being our Grand Meetup, which is when the entire company comes together for a week of team bonding and learning. Really the one time we’re all together in person.
Ben: When did you start getting involved with planning this event?
Megan: I got started working on the Grand Meetup when I first got here. I got off the plane at the Grand Meetup and I was helping people get on buses, but really sticking to it full time for the past two-and-a-half years, last year being the first that I completely owned the Grand Meetup. I’m leading.
Ben: I can imagine that people who’ve never been to a Grand Meetup might not have quite an idea of how complicated this process is. Maybe you can tell us a little bit about what this process entails.
Megan: Right now I’m starting to plan for 2021 locations.
Ben: So two years from now.
Megan: Two years out. But the real planning begins about a year out. We’ll go to contracts, potentially earlier than that. And the real planning starts about six months out. That’s when we start doing it full time — all of the logistics, from people getting visas to come to the Grand Meetup, booking flights — and then we start getting to the stuff about when they are actually on site.
Ben: How many people work with you on this? Cause this is a huge undertaking.
Megan: It’s a huge undertaking and definitely not one I could ever do alone. We have two full-time folks that work with me on the Grand Meetup, and then our extended teams. So on site we have about 10 people dedicated to working on the Grand Meetup, and those folks will help a couple of weeks out and get them all ramped up for what’s to come on site. This way they can easily transition into the Grand Meetup once we’re here.
Ben: Right. Maybe one thing that we are curious to hear about is how you choose the locations. Right now we are in Orlando.
Megan: So we want to choose a hotel that’s able to accommodate us ideally for two years in a row, because we try to go back to the same place two years. For people who attended before, it’s a little easier for them. And then us, coming to plan it — it’s a lot easier because we have those connections with the vendors that we’re working with. So everyone from the hotel to the AV team, to the transportation company and everything in between. Making sure that they can accommodate us two years in a row, that many people. And we’re also looking for a lot of meeting space. Also hotel rooms. We try to keep everyone at the same hotel — just really creating our own hotel. We actually have our logo on the building this year, on the hotel.
Ben: It looks great and I know many people who listen to this could not have seen it, but it looks pretty fantastic.
Megan: Yeah. So we just try to incorporate all of that and work with a hotel that understands we have a lot of different needs that we have to accommodate, with people coming from different cultures. We have different dietary [concerns], so we’re working with a chef that is willing to work with us to make sure everyone’s comfortable.
Ben: What are some of the most challenging aspects of planning the GM? I can imagine that, for example, working on the menus is one of them, because there are so many parameters to consider. Are there some other things that we might not expect but in real life are super challenging?
Megan: Yeah, for a couple of fun examples… My credit card has gotten declined many times — when you try to order 600 yoga mats to do a breathwork session. Right before we were coming here we were dealing with a hurricane and an airline strike. So, trying to figure out how many people we could rebook on a flight for the very next week we have to…
Ben: Sorry to cut into it, but just to make sure that we know how many people are actually here. Right now.
Megan: We have 808 people here right now, not including speakers. We also wrangle all of our speakers, so all of the programming, researching speakers, then connecting with them, contracting them, getting them here, doing rehearsals with them, and we doubled the amount of external speakers we have this year for keynotes. So we have eight this year and that’s not including any of our workshop speakers who are coming in.
Ben: Do you have any favorite memories either from, I know this GM has only kind of started, but I don’t know from either this one or previous ones. Moments where things kind of clicked for you and you thought, “Oh this was all worth it. All my hard work has paid off.”
Megan: Yeah, just seeing people, the smiles on their faces, the small details. If someone’s birthday is this week, getting them a birthday cake, it makes a world of difference when they’re away from their families during this time. I would say being in a general session and having a speaker on stage where the audience is just completely connecting and the thank you’s and people just being so gracious. Everyone is really happy to be here, and just making those connections and seeing people make those connections is just incredible. You see it in the hallways, you see it everywhere. Also, just making the culture of Automattic come to the hotel wherever we are. It’s Automattic.
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Ben: This is Ben again. Everyone at Automattic has their own experience of distributed life. Some of us are constantly on the move. Others log into Slack from places like Tasmania or Uruguay or Nova Scotia. Some work from home, where they might also take care of family members or pets. Others, like me, mix it up a little between our home office, a favorite cafe, or a coworking space. One reason the Grand Meetup is special is that it gives us all a chance to learn from one another about what’s possible once you join a distributed company. We were able to capture a few of these stories, so let’s hear some of them.
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Will: So for the previous three years I was in a camper. I was on the back of a pickup truck and on the Pan-American Highway for the most part. There were some diversions into Brazil, into a lot of Argentina, a lot of Bolivia.
Ben: How does that even work logistically? Can you just park somewhere, get internet, and then just do your work? How does it work in reality?
Will: You know, this is the age of the internet. Anything is possible. There are apps. And so we relied on an app called iOverlander. This is this crowdsourced app and it was people who lived the same lifestyle we lived. They would drop a pin on a map and they would leave a comment like, “This is a campground, it has WiFi, there’s hot water (or not), there’s electricity (or not),” or “What is the voltage?” So all of this data is all right there. And then you can spend a little bit of time extrapolating all of that data and putting it on a graph or a map or whatever. That’s how we lived, was mapping out the route based on connectivity.
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Sheri: I just joined a coworking space actually, and I don’t want to go there often, but I want to go there sometimes, so I can be in a different space and have a different experience and have some more working social time. I love-hate working from home because I’m extroverted. Love that I don’t have to do a commute. Hate that I don’t get to be around my colleagues more often. Not only that, remote. I hate that I can’t go and see friends that I’ve made at the company in the city where I live, or even several hours nearby, right? There’s friends from all over. So the Grand Meetup is really nice and really connecting, and it helps you work so much with people.
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Josepha: When I got here, everyone was like, “It’s great because you can work in your pajamas if you want to.” And for the first six months I did. I didn’t have a dedicated office area and I just sort of got up and started working whenever I felt like it, and finished working whenever I felt like it. And I found that that was not a good choice for me, especially in the work that I have to do. It ended up making me less resilient, more reactive, and also I had no concept of when work started and stopped. Our brains compartmentalize the information that we need in various places, and so when I lived and worked and did all of that stuff all in the same area, my brain was like, I guess we work all the time now, cause we work in our pajamas and we work on the sofa, which is also where we don’t work. And so this is just what we do. We work 24/7 I guess. It was a rough first year for me frankly. My first year here I really felt like Automattic and Matt had made the wrong decision in hiring me, because I was having so much trouble getting used to it. So now I have a dedicated office and I have my work computer, which does not come out of my office unless I have to write. If I write, I go to a different room that has a taller ceiling.
Mark: Explain that.
Josepha: I’m just going to tell you everything about how I have hacked my focus. So I have found that when I’m in a room with a shorter ceiling, I’m able to focus better. But if I have to do creative work, I have to go — or rather it is easier for me if I go to someplace with a higher ceiling, because it frees up, it just changes this idea of what I’m doing. It changes how I feel about it. And so interestingly enough, when I have to do really unpleasant writing work, which sometimes happens, I do that on airplanes, cause it’s a very constrained space, but I’m 30,000 feet in the air. I don’t have any place to go. I’m very focused, but I still I’m able to get that really creative, generative feeling so that I can get the writing done, because I’m flying through the sky on a tin bus.
Mark: So when you’ve got a tough email to write, you’ll just book a flight somewhere?
Josepha: Yes, I do all my emails on airplanes. No, no. If I have a tough email to write, generally for an email because it’s that short, I will just get up and walk into the high-ceilinged room and then walk back to my computer.
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Mark: That’s great. Now tell me, at home in your house, tell me about how you work at home, and where that is, and what your days look like.
Aaron: My day’s fairly structured in terms that — I get up in the morning, I put the coffee on and I change clothes. I don’t work in pajamas normally, so I have a ritual where I feel like I’m starting work. I’ll hop online and check out things that people have messaged me about overnight. My team is very geographically diverse, so when I come online in the morning, they’ve been working for several hours, if not longer. So I’m playing a little bit of catch up, but I also don’t let that be the focus of my morning. I figure out “Where am I most useful at this point in time?” Because within maybe an hour or two, some people may be going offline. So there’s very little chance for overlap with a lot of people on my team. About midday, it’s when I usually try to get outside. I have ADD, Attention Deficit Disorder, and did not realize that until I started at Automattic. So one of the founding things that I realized — in order for me to be successful, I need to do some sort of physical activity at some point during the day to help reset my brain. It feels like I’ve had a good night’s rest and it’s like another cup of coffee, if you will, but it sustains me for the rest of the day. Then I don’t feel like I’m trapped within the four walls of my office. So I’m also one of those weirdos that’s out at -10 degrees Fahrenheit in the winter, going for a run. Just because the feeling of being outdoors is really what recharges me, and then I come back and finish my workday. Sometimes I’ll split it up and get some tasks done during the light hours and then in the evening I might catch up a little bit on the things that were maybe less deep work. So, shallow work — things that maybe don’t need my full concentration.
Mark: One of the interesting things I’ve noticed is that Automattic has the ADDmatticians channel and neurodiversity channels for folks to swap tips. What are some things that have been shared among the group in terms of how distributed work works for neurodiversity and for how you work within that?
Aaron: I think the big takeaway is that like most people that belong to any type of unique group, if you have neurodiversity, it means a lot of things. It includes people on [the] autism scale or in my case, Attention Deficit Disorder. In my mind it’s a collection of things that you can’t see that affect a person to see or feel the world differently. So the biggest takeaway that I have, that I’ve shared with other people, is that you have to be responsive to your own signs of being overwhelmed. You have to — self-care is a really simple way of putting it, but you have to develop a mechanism to address when you are feeling overwhelmed. I’ve tried to lead my team with vulnerability, both from myself, and I try to encourage other people to be vulnerable. I think that’s what the ADDmatticians channel and being open about neurodiversity does, is that it establishes that we all have — I’m not going to call them faults — but we have unique things about ourselves that are different. You can only work better with people if you know what unique things make them different from yourself. In my case specifically with ADD, if I’m having a day where I can’t concentrate, it affects how I’m leading a meeting or how I’m having a broken conversation with someone because I’m doing several different things. Then I’ve asked people to call me out if they feel like I’m not giving them the focus that they need. So I’ve been very open with how my brain works and if I tell people, look, I need to go out and go for a run, my brain’s just not working. They know that I’m not just trying to get away from them. They just know that I’m trying to be in the right moment or in the right spot for them and it’s — I don’t know how I could do that without coming across as being non-committed to the team, without telling them with honesty about what is going on in my brain. So me leaving them to go for a run doesn’t mean that my running is more important than them. I’m actually doing this to help me be a better team lead and a better coworker.
Mark: It seems to me overall that distributed work is a huge positive for those that are differently-wired or operate different. Just in terms of — you’re in control of your surroundings in a much deeper way than having to go into an office. Is that your finding?
Aaron: It is, for those of us that are fortunate to have the ability to have a quiet space or to be able to model an office that supports their needs. I feel very fortunate that I’m in a place where I could buy a house that’s more suburb or more rural, and I don’t have a neighbor necessarily outside the window with a leaf blower during the middle of the day. I feel empowered to be able to change things, to make the environment as best as it can be. There’s no requirement for me to have a certain chair or certain desk, and granted, Automattic does give us the ability to buy a really great chair and a really great desk and have the computers that we need, so that eliminates that from being a concern, which is a huge deal for me. Having a great posture and having comfortable things to work on, that’s a majority of what I need. But not everybody else, from previous jobs I’ve worked in — places where the air conditioning didn’t work right. Or one person was fiddling with the thermostats. I have complete control over that. I can move the thermostat as much or as little as I want. Or if I’m having a day where I just want to go work outside, grab the laptop — as long as the WiFi reaches, I’m good to go.
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Josepha: I’ve worked in high-stress environments my entire career, so being resilient no matter where you’re working has always been very important to me. And this is a particularly difficult thing, because when you work in a distributed fashion — and I work with the open-source community, so volunteers also — all three of the major risk factors for anyone working with employees come into play there. So you have to delegate things. And for volunteers you’re not delegating, you’re asking them to take part in that. So you are delegating things, which is this huge level of risk. You have all these people that are far away from you so you don’t see them every day, not only [do you not] see them physically every day, but so often we lose track of them because your DMs close so that there’s less noise, but then you forget to go and reach out, and so there’s that one. And then of course the third one, which is the fact that we work in a cross-cultural space, not only geographically cross-cultural, but for the community itself, for open-source WordPress, the different cultures of distributed work versus co-located work. Those are massively different cultures. And if you’re not aware of how that works versus this works, those two different entities, you never have any concept of how to invite yourself into the space in a way that that works for both sides. I spent a lot of time thinking about how to make sure that all of my teams are resilient because we do really hard work on behalf of the community and on behalf of Automattic in the community. And it’s important to me that they’re happy and healthy and safe for as long as they want to work here.
Mark: That’s great. Can I ask you about Slack real quick?
Josepha: Mm-hmm.
Mark: So do you have Slack on your phone?
Josepha: I do.
Mark: You talk about keeping your computer room and having a set specific time in which work and personal do not overlap as much. How do you deal with that, with your phone and managing your own phone time and asynchronous versus synchronous?
Josepha: I feel like Slack has become the new email. So there’s that. And I do have Slack on my phone. I am in about 15 different Slack channels — Slack instances on my computer, but only two on my phone. One that is Automattic and one that is the WordPress community, not in anything else. And that is specifically for emergency situations, or when I know I have to be moving, but I want to be able to be available for people. I am incredibly aggressive with my do-not-disturb time. It starts at 8:00 PM every night and turns off at 7:00 AM the next morning. And mostly it’s there in case I need it. And I have just convinced myself of that to be true. That’s the only way. A lot of times you just have to remind yourself constantly “this is not for me to be a slave to that information.” It’s in the event I have to get it. And so there’s that. But also I have themed days for what I work on, and also specific times of day where people can expect me to actively reach out and answer their questions. So at 10:00 AM and at 4:00 PM I will go through and respond to any open questions that people have given me over the course of the day or the evening. And I have themed days. So Wednesday, I always do my community check-ins. I check in all the team reps — well not all of them, as many team reps as I can get hold of. I check in with all of them all day on Wednesday. Thursday is a strategy day, so everybody comes into basically a very long meeting with me where they can drop in and out and discuss strategy problems that they have. And Fridays are when I follow up on everything that people need to be responding to me about that they’ve forgotten about. And then Monday is internal Automattic days. Tuesday is external blogger for the community days. I don’t know why I started with Wednesday and worked my way back around.
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Mark: So you have not only worked in this structure for a long time, but you’ve studied it and written about it for a long time. How would you say Automattic’s distributed work model has evolved while you’ve been here?
Erin: It’s super fascinating for me because I come from a background in consulting where I was actually helping enterprise companies to work better together. And one of the first things I understood coming here is that the way Automattic was organized, even at the smaller size it was, is that a lot of the practices inside Automattic at that small size were the same practices that I was trying to put in place for companies 1000, 10,000-people large. So I was like, “Oh, that’s interesting. They’re already doing all the good practices because working remotely forces them to.” So that was one of the very first insights I had because that also means that scaling that stops being a logistical issue, a tool issue, and you can focus all your efforts, instead of on the people on the leadership, on the processes. So all the things that instead are actually the problems between people that need to scale. And I think that’s one of the biggest advantages we had. And that hasn’t changed because we were 200 people. We were using certain tools. Yeah. The chart we were using at the time is not the same chart we use today, but it’s still the same kind of scope and tool. And we are now a thousand people roughly. And this structure in that sense is still the same.
Mark: Now given that you have studied this, written about it, consulted — what is Automattic doing right and wrong with distributed work? We must have some bad habits that exist, that maybe frustrate you.
Erin: Yes. So let’s start from this. What we’re doing right is, in terms of what is usually referred for example, as a flat organization — but we’re not flat. So the way I would define is that, there is no boundary in contacting anyone in the company. I should probably find a better, catchier way to say this, but we have a hierarchy, but the point is not the hierarchy. The point is that I can reach anyone in the company in any given time and, may actually encourage it to do that, if there is effectiveness. Again, you touched on a topic that is not really about the tools, right? It’s more about the culture and interaction between people. And I think that there’s a little bit of an obsession in the sense that, “Oh, the company’s failing because this information that I used to post, before everyone read it and suddenly I have a problem because I don’t know anymore where to post or where to discuss things.” But we grew, right? We are a larger company and we all know from, for example, social psychology, that we can hold in our mind roughly 200 people, 250 people, as our close connections. And of course it doesn’t limit work, but let’s assume for a second that 200 people is limited to work. Now if you’re a 200-people company, you pretty much know exactly where to send the right message to the right people. It’s natural, it’s implicit. You don’t even think twice. Where you are a 500, a 1000-people company, 10,000-people company, suddenly you’re like, “Oh, wait a minute, my information. How to propagate? How to make sure the right people listen to it?” This is not a problem solved with any tool. It just a matter of skill. Shaping the information channels is part of, in a way, the management, the leadership that should act as a filter. And this is one of the reasons why I’m not a huge fan of flat organizations because I believe that a structure — organization hierarchy works, if it’s a communication hierarchy. It doesn’t work if it’s a power hierarchy, but if it’s a communication hierarchy, it’s effective in helping convey this message.
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Mark: Hi everybody, Mark here again. Distributed work is a mode of doing work. But it also changes the ways we live our lives, and it expands the possibilities for work/life balance. Ben and I talked with some folks about what distributed work means to them, and some of the conversations that came out of that were pretty moving. Here’s Ben speaking with Will Brubaker to start us off.
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Ben: What are some of the other challenges that being part of a distributed team like yours bring into the picture that you wouldn’t necessarily encounter if you’re all in the same office?
Will: Well, time zones is kind of obvious. When are people awake? This is also very important to “When can we have the best impact? Where are the people who use our product? What time of day are they asking for help? What time of day do they need our help? When do we need to be solving problems?” So we have to balance all of that out between our own needs because we do have our own lives, and we have people in our orbit — our spouses, our children, our parents, our friends, our — everybody. So we have to balance all of that.
Ben: Do you have any kind of system or tools that help you stop work when it’s done? Cause one of the challenges of being at a distributed team is that, if you work from home, for example, your home and your office are the same space.
Will: Boy, this is a… Yeah, your home and your office is the same space, and this is such an interesting thing. And also your question about how do you balance all of this. It becomes a question of “Do I work from home or do I live at work?” And that’s its own thing.
Ben: Is it still a work-in-progress for you or is it something you’ve figured out by now?
Will: You know, I’m very much in a transition mode right now myself in a lot of ways. And this is — part of the changes that have occurred as the company has grown over the last couple of years is that we have to be a little bit more rigid. We’re covering a lot more ground. Things are happening a lot more rapidly. We have to be able to react in a much more predictable way now. So I need to be able to say that, you know, next Tuesday I am working from this hour to this hour, and I need to commit to that. And so this has been a challenge to get there, but it’s also… I also get to decide that. So if I need to move all of my work hours until the afternoon so that I can do the things that I’m obligated to in the day, I can do that. When we were asked to start working weekends, I was a little bit resentful about that, and I had a very, very strong team lead who supported me, and we ended up working out a really brilliant solution where now I am working every Sunday and I am happy about it, where I was digging my heels in against working weekends. But we found a way to make this work to my benefit, to the company’s benefit and it’s a win-win situation, and this is the company that allows that to happen.
Ben: What are the benefits to being — you just mentioned a couple, but what are some other things that have made working for a distributed company better for you or for your life in general?
Will: To put it in the simplest of terms, I’m working for a company that allows me to be me, and I believe that to be true across the board. And I look at people who were in onesies as cartoon characters, and this is who they want to be. And everybody is really cool with that.
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Rocío: There is a map where you can see all the heads of Automatticians. I was the only one there in that super big island full of snow. Basically, my husband got an offer, a very interesting professional experience to work there. And it was scary at the beginning, but we said, “Hey, let’s take the chance, let’s have that adventure and let’s see how it is.” There is nothing to lose. So I was working remotely at that time already. And living there, it was when I joined Automattic, because for me it was clear. I want to work remotely to be able to live there. So for me, it was awesome. It felt like, “Wow, I can be here, in Greenland, in this extreme weather, right. And to be working for a company that I love and doing what I love without a problem. Wow, that’s a nice feeling.” If someone wants to try to work remotely, I will say “Try.” And don’t expect people to be behind your shoulder checking work you’re doing. Just be proactive on finding solutions, doing stuff, and asking for answers when you don’t know how to do something. When you’re working remotely it’s very, very important to communicate as much as possible with your colleagues because it’s the only way for you to say, “Hey, I’m here,” and to learn from them. If you are in the office and you are new and you don’t know things, you just turn your shoulder to the right and ask for questions to your colleague next to you. But we don’t have that when working remotely. So I will say if you don’t feel secure about things, just ask. Because in this company, everybody knows that communication is oxygen, and we really apply it. Ask for questions. People are going to be helpful and never, never feel ashamed of it.
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Mark: As you can hear, there’s so much more to distributed work than hanging out at home all day. Here at Automattic, we try to find solutions that make our work more effective and collaborative — but it also allows us to tailor our own work and environment based on how we’re wired. My colleague Aaron Douglas has some great insights on this…
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Mark: Now, you wrote a blog post that made the rounds inside of Automattic. Which is basically, How Remote Work Saved my Life.
Aaron: Right? Yep. That’s it.
Mark: So tell me a little bit about that.
Aaron: About two months after I started Automattic, I was overwhelmed, and I knew that my brain works differently than a lot of people, in terms of my focus and attention. It was never really an issue because I had ways of handling that, and actually working in a regular office where you’re constantly being interrupted, being asked to come into meetings, or the person next to you starts having a conversation you’re listening in. It actually worked really well with how my brain’s wired, but then when I started working at home alone, it was really only my own mind defeating myself. So it was all on me to keep that train going during the day. I didn’t know how to cope with it though and so I talked to my physician to say, “Hey, I think I have ADD, I think I’ve had this all my life, but I’ve just never needed to worry about it.” So that sent me on a path of talking with a counselor, [to] start developing a tool box of things to help combat the issues I was having with focus.
The frustration was pretty real and I needed to walk away from my computer one day and it was, I literally walked outside, took a short walk, which is something that normally I’ve been doing. In a regular office, you go for a walk during lunch and you come back all sweaty and you’re worrying about smelling and not every place has a great shower room. It just was an excuse for me not to do something more physical during the day. But at home, who am I trying to impress? As long as I look presentable for a webcam, I can wait till midday to take a shower if I want to go for a walk. But what I realized early on is that, when I came back from those walks, my brain felt almost reset for the rest of the day, and that turned into a daily habit over time. There’s a lot of bits of story in between, but essentially, I went from the occasional walk, to riding my bike, and then to doing running as well, and it’s now a daily habit. I feel strange when I don’t have the ability to get outside and do that exercise, and it’s part of my toolbox.
Before I started at Automattic, I was having issues with atrial fibrillation, and that is where the electrical system — your heart just goes wonky and it doesn’t beat right. The major issue with that is it can induce strokes, because when your heart’s in a stopped pattern, and the blood’s in an area where it shouldn’t be, it can pool and form a clot and that can go into your brain. So I was really scared when I heard that. So that combined with needing to be outside, to help reset the brain, which is like a one-two punch to motivate me. My focus this entire time has just been on my focus. The side effect is that I’m actually, I’m over a hundred pounds lighter than I was before starting at Automattic. I feel like even though I’ve aged, I feel like I’m healthier and I feel younger than I have, and I attribute a lot of that to Automattic and working remote, my coworkers for helping encourage me, and finding friends to just socially run with them, like Strava, Runkeeper, one of those services. That’s been a big part of what’s kept me going and now I’m returning the favor, and also helping other people motivate themselves. So yeah, that’s effectively how I think Automattic helped me save my life. Because I’ve gone from being dependent on medication for atrial fibrillation and feeling defeated, to feeling fairly successful with my attention problems and being off of the medication for my heart, and overall just being in a healthier place.
Matt: Hey everybody. Matt Mullenweg here again. As Automattic has grown, so has the number of perspectives on the freedom, flexibility, and occasional challenges that come with distributed work. It’s really amazing and humbling to listen to these stories, and to be able to relive the magic of the Grand Meetup too. Thanks to everyone who shared, and to Mark Armstrong and Ben Huberman for capturing these powerful stories.
As you’ve heard, hosting the Grand Meetup every year takes a lot of work. Booking hundreds of flights and hotel rooms, the food, the speakers…it’s a lot! But we think the value of the connections that people forge with their coworkers vastly outweighs the cost, which is now getting into the millions of dollars. This meetup, and the smaller ones that our individual teams have throughout the year, are vital for a distributed company.
On the next episode of the Distributed podcast, I’m going to catch up with an old acquaintance of mine, Anil Dash. Anil is a pioneer who really helped define what blogging looked like back in the early aughts. He cares a lot about the Web and about technology, the direction both are going, and how they affect everyone.
Anil runs a semi-distributed company called Glitch, which has developed a social platform for building and sharing apps. The team at Glitch puts lots of thought into creating a work environment that centers employees’ wellbeing. I’m interested to learn how the company’s decision to go distributed fits into their commitment to employee care. They have an office in New York, as well as being distributed, which is also very interesting to me, now having an office in New York at Tumblr.
Thanks so much for listening and see you next time.
Episode 14: InVision CEO Clark Valberg on Distributed Design
Nov 14, 2019
InVision CEO Clark Valberg needed a tool to help his distributed team collaborate on design projects. So he created it — and it became the company’s flagship product, one that every Fortune 100 company now uses. In this episode, Clark joins our host Matt Mullenweg to discuss how he built his distributed company, and how that structure informs InVision’s collaborative-design products.
The full episode transcript is below.
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MATT MULLENWEG: Howdy howdy. Welcome to the Distributed podcast. I’m your host, Matt Mullenweg.
My guest this week is Clark Valberg, the founder and CEO of InVision, a company that makes a collaborative design platform that’s very popular with distributed teams. It does ideation, design, prototyping, sharing… and it all lives in the cloud. No more emailing files back and forth — it’s pretty slick.
Clark founded the company seven years ago in Brooklyn, and now they have over 5 million users at places like Airbnb, Amazon, Netflix, Starbucks, and my company, Automattic.
Like Automattic, InVision is fully distributed. And they’re similar to us in size, so I’m interested to hear from Clark about his experience leading and growing a distributed workforce.
Alrighty. Let’s get started.
MATT MULLENWEG: Welcome, Clark.
CLARK VALBERG: Hey, great to be here.
MATT:Y’all are one of the other big fully distributed companies. Tell me a little bit first about what InVision does for people in a cave who might not know yet. And tell me a little bit about the scale of what y’all are doing in the —
CLARK: That was my opening to you, by the way. Oh y’all are one of the other largest remote companies. This is a constant debate, by the way, internally, which one is bigger.
CLARK: Okay so Clark is the CEO and Founder of a company called InVision. InVision is a design collaboration platform. Most of the products — I hope most of the products — that you use everyday, if they’re well designed, if you love them, if you feel excited about how they work and how they fit into your life, it’s because the design of the product is good. And so that’s where InVision comes in. We are the place where those products are designed, tested. We’re the stakeholders that make that product great, are engaged, we are both the design tool and the place.
MATT: So if you were to describe what it’s like to use an InVision product. Let’s say I’m a designer, I’m collaborating with another designer, what will we do?
CLARK: If you are a digital product designer, you need a place to design, you need the place to actually create the screens that make your product beautiful. That’s InVision.
MATT:So before, I would do this in Photoshop on my computer and now it’s happening in a web app?
CLARK: Photoshop or a cave wall, depending on how old school you are. So yes, you would’ve done that there and now you do that [in] InVision and then InVision is also the place where that design comes to life in a collaborative sense. It’s the place where you put your design so that others can look at it, engage with it, give you feedback on it.
The question you’re asking is fundamental to this transition of design altogether, which I can talk about for a long time, but design is no longer a job to be done, it’s now an organizational discipline in a world where the screen has become the most important place, or one of the most important places in the world.
MATT:When and how did design become important to you?
CLARK: I ran an agency and dealt with what was the general operating dynamic of agencies at that time, and probably still today in many respects. You have a client, they have an idea of what they want, they have some business problem they’re trying to solve and you’re trying to put together some kind of a requirements document, some kind of a contract that hopes to look into the future and imagine everything they’ll ever need to accomplish whatever business goal they’re trying to accomplish, and define that today, or at least in the next few hours until we can get this thing signed and move forward.
So this idea of up-front definition bothered me, that was a deep intellectual itch. How can I, instead of creating a contract that separates me from the client and hopefully mitigates the legal risk of giving them exactly what I told them that I would give them, and we’re charging by the hour, how could I align my values and go on this journey with them together side by side? How could I act as their guide toward the business reality that we would ultimately end up discovering together?
Any time there’s a client, there’s that dynamic of — you know what you want in your head; it’s impossible for me to get that out of your head and get it into my head. And by the way, even if I could, hopefully if we do something right that will change over time, the more articulate that vision of the future becomes.
MATT:How did this agency look? Clients, were you meeting them in person, were your colleagues in person?
CLARK: Both. It was my first dip of toes into the world of being able to work with people seamlessly online. So a lot of the fundamental inventions, collaborative inventions that we have here at InVision — 900 people, totally remote — came from that world of just trying to make clients happy at a much smaller scale, sometimes remote.
MATT:How big did the agency get before you switched to doing the product work as your primary thing?
CLARK: The biggest ever? I think it got to 25 tops. So it was a small agency. The word “boutique” sounds much better than small, doesn’t it?
MATT:There’s probably a lot of people [who are] part of or running agencies, listening to this [who have] that dream of switching to be a product company. What advice do you have for them? What made it work for you? Because there’s so many examples of that not working.
CLARK: I’ll tell you, I did not have a vision of becoming a product company. It happened as an extension to the reason why we started this agency in the first place. So the agency was founded on, “Hey, instead of ending up in these weird litigious, semi-adversarial relationships with clients, what if we could figure out a different operating model, a different communication model?”
So we started by building prototypes, and we would write those prototypes in code, we would show them to clients early, we’d be able to have a diverse conversation across the organization, instead of just dealing with one project manager, we’d be able to embrace all the different business leaders that represented the parts of the business that we were trying to serve with the software. We’d have holistic, multi-dimensional, diverse conversations. That was the whole idea.
I wanted to be an agency that loves its clients. I want to be on the same side of the table. These were all the different key words, [laughs] the key phrases that we used to make ourselves sound different and differentiate. But I think it sprung from a place of what we saw wrong with the industry. And then that tool called a prototype just evolved over time.
And at some point someone — not me — said “Hey, what if we just took designs out of Photoshop and connected them together and turned them into a little simulation that was almost as high-fidelity as the coded prototypes that you were building? It would be almost good enough and probably you could — we’ll just run it as an experiment but it’ll take an eighth of the time to build and maybe we can use that as a communication device.”
MATT:Who was the first client you tried that on?
CLARK: It was a company in upstate New York. So this is one of our few fully, fully remote engagements, like we went to see them maybe once a quarter but other than that everything was happening online. I’ll reserve the name but a large education-product company. They created educational products that they sold into school districts. And we were building essentially a totally custom ERP solution for them — every part of their entire business modeled into a piece of software, every experience that exists between two people in that entire company was modeled into a screen some place.
MATT:Wow.
CLARK: So a very sophisticated piece of software. And it would have been an absolute nightmare had we not employed this process because there were just too many stakeholders with too great a diversity of perspective on what needed to be built, and it just had to be a conversation that happened over time. This was a “Let’s try this new thing. What do we call this new thing?” I think literally the time that we’ve been on this call so far was the time it took us to come up with the name InVision. [laughter] I think it was the second idea, like, “Oh, we’ll just change it later, that’s fine.”
And we had absolutely no interest, almost an explicit disinterest, in having anyone outside of the company know what this thing was. This was just for internal use only. Somebody even said “Hey, what if we wrote a blog post about this? What if we..?” And once it worked, once we saw that it would totally change the game for us, and it really did in very profound ways, this is like a whole new movement for agencies, this would be a cool thing to talk about. I said, “Absolutely not. This is our differentiator, this is our competitive advantage in this agency, maybe let’s just keep this under hat.”
MATT:Ha!
CLARK: Luckily someone — it’s good to have a lot of people who disagree with you all the time around you, otherwise you end up being a victim of your own vision.
MATT:So at this time, it sounds like you have an office and colleagues in that office. At what point did you switch to being fully remote and using these tools to enable that?
CLARK: Even the agency was hybrid. And in New York City, my entire movement into a fully remote world — again, never had a vision for it, didn’t think this was the future. I’m still not sure if it’s the future for everyone, okay, this is a matter of significant debate and worthy of debate. It was a necessity thing. So the agency was a hybrid but let’s call it a reluctant hybrid, like “Hey, we can’t find enough people in New York so we’ll hire people who aren’t here and we’ll just deal with the overhead and managing that overhead, that collaborative overhead as a cost of doing business.”
When we transitioned into InVision, so yada, yada, yada — we’re yada yada yada-ing through the birth of an entire company — but this product is cool, what if other people liked it? Let’s put it in front of the world and see if they bite. They did. We raised some capital and then we had to transition out of the agency and into the product company. I sold the agency to a — basically a hostile takeover. I sold it to my wife for a dollar. Literally, it’s a whole big story where the company, InVision, sort of launched its for-pay model on my wedding day.
So here we are with $1.1 million and an office that my co-founder and I are sitting back-to-back in a tiny Regus space in midtown Manhattan. I think it was the year that Google opened up the Google megaplex — I don’t know if it has an official name, but the building in Chelsea?
MATT:Yes.
CLARK: We just found that every conversation we were having with an engineer, designer, anybody, everyone — they were also talking to Google, they were also talking to Yahoo and Facebook. Anybody with a New York office with a more fashionable name and better ping-pong tables to our no-ping-pong tables was just destroying us for talent, and I found that we were spending all of our time wining and dining engineers we weren’t hiring.
MATT: Wow.
CLARK: And so we got together after about three weeks of slogging through this talent thicket, and asked ourselves an existential question. We did what we called a pre-postmortem — I’m sure you’ve heard this idea. Let’s look into the future, let’s imagine the things that don’t work out and let’s guess, based on what we know today, what are the likely sources of that failure?
And the biggest one for me was not spending enough time on the things that really make a business successful. At the end of the day, product-market fit is where it’s at, at this critical birthing stage. We have to get a group of people vehemently, maybe violently excited about this new product and talking about it to people. It has to have independent lift, it has to have word of mouth, groundswell. And what will we probably be doing instead of focusing on the design of the product, the marketing of the product? We’ll probably be trying to hire engineers and moving way too slow.
And we just opened up the envelope. And again, it may not have been me, somebody thought, “What if we just hired the people that we had worked with as contractors in the agency?” We had a pretty significant bench of folks that we pulled in who were full-time other places and just did little side jobs for us in exotic, far-flung destinations like Phoenix, Arizona… Houston, Texas. Places that were secondary, tertiary tech markets, folks that we just knew, knew from conferences, because they were developers in the same language that we were developers in — what if we just hired them full time?
So we said, what if we just did this at scale? What if we somehow figured out how to make collaboration work where everyone was remote? And I had a piece of advice. I don’t know if he even knows that he gave me this advice and how pivotal it was for me. Do you know David Cancel from Drift? I called him up. He had just sold a company to HubSpot. I ran the idea by him, like, “Hey, what do you think about this remote idea? What do you think about this talent hack — instead of hiring people in New York, we’ll hire them anywhere. We’ll actually pay them above market.” That was our thesis originally, to pay them above their local market but arguably below the New York market. And there is a very, very wide spread there, at least there was then even more so than it is today.
And then sell them on this lifestyle change. Sell them on getting rid of their commute, sell them on work/life integration. This is the time where everybody talked about — the common theme was work/life separation — how do I turn off my phone, how do I turn off my email at a certain time a day?
We said, well, the people that we work with, they were moonlighting for us while working full time, they clearly have more passion, more interest in being involved in the work they do than 9-5, so maybe it’s not about a certain time of the day where you just die from work. Maybe it’s about having more control over when and how. Maybe there’s a work/life integration idea that we can start selling people that may actually be more meaningful than that separation.
And he liked the idea but he gave me a piece of very firm advice that we still follow today, which, you’re not following, by the way. I just want to throw this out there. It’s don’t go half in/half out on this. There has to be a sense that everyone has equal access to the executive team, to each other. And the way he put it, which I thought was a beautiful way to encapsulate it — there can’t be a place where someone is not. Your office, whether if they work in marketing, it’s the head of marketing. Everyone has to feel equal proximity.
MATT:And that avoids a classic problem, right, why I actually don’t like the term remote, that some people are more like second class citizens in the —
CLARK: 100%. You have a room and then there’s that guy on the wall who’s trying to get a word in edgewise. I said, “Well how far do we go with that? Can we have some kind of a New York office?” He said, “I would say not.” And I think the next week my partner and I decided to disband the office, to shut down the office and to actually go home and work.
Even though we had been commuting into the city — I live in Brooklyn and he lived in Manhattan, he was a few blocks away from the office — even though we had been commuting and spending time together in person, and you’d think, “Oh the founding team, they have to get together and they have to collaborate, move at warp speed and problem solving and collaboration.” I said, “I think we should discipline ourselves to be able to make this remote thing work even between us, and if we can figure that out, then that will scale to everyone else.” Big decision. Bold. I would say it was an absurd decision in some respects. [laughs]
MATT:I would call it radical actually, yeah, especially for the time. Because what year was this?
CLARK: Eight, nine years ago now.
MATT:Yeah.
CLARK: The only company that promoted itself as remote or promoted the idea of being remote or distributed was 37 Signals. And so they were the original inspiration for this or at least inspired us to believe it was possible.
MATT:Totally.
CLARK: So we did it, said “Hey, this is a design problem essentially, like many things in life. We’ll just design the people, practices, and platforms of the business.” We think about these three Ps all the time to establish a healthy rhythm of connection. And by the way, Joel Spolsky, another — I’m just calling out all the inspirations for this because it definitely didn’t come for me — wrote a book called “Joel On Software,” which I’m sure you’ve read, everyone has read.
MATT:Classic. I highly recommend it actually.
CLARK: Classic. He was a proponent of this idea of having an office with a door that closes. Now we think about it as deep work. This is a common theme that’s used in tech today. And I had this thought — I’m still not sure how valid it is — but that the percentage of intellectual focus — deep work — that happens in your business is a significant driver or limiter of the success of that business, to some degree.
If you have a large group of people who are really talented and have a lot of time to focus on the work they do well, and there’s an environment that brings them together when they need to be, but that ebb and flow of focus time, that intimate craft time and that kinetic energy of collaboration, but not at the same time. There is a dual-modality model that one can leverage to get the best out of both.
MATT: What percentage do you target for yourself there, and what percentage would you target for an individual contributor with a vision?
CLARK: The more creative your work, the more focus you need to move through the work that you do. I think real creative work is done alone. You know when you need to collaborate, you know when you need that validation from a third party, or your rate of innovation starts to slow to a certain point where you need to start sparking and stoking those flames of creativity through communication with other people. You have to build a system that makes that reliably happen at least at some point for each person on the team.
So early days, we had a stand-up, every team in the company. At that time we had three teams and 15 people. Every team had a stand-up. That stand-up had a ritual. It happened at the exact same time every single day. So 1:00, whole company, three or four questions. I think it evolved from three to four questions for each person, round robin. Obviously that’s much more difficult to pull off at 900, but that is scaled in different ways. Let’s make sure that everyone knows or is aware of the work that everyone else is doing.
That’s the fundamental platform that creates that connection. And then people go off and they do their own work as individuals or as groups, and they reconvene regularly to check back in.
MATT:So if I were an ideal designer or developer at InVision in this model, would I be spending 80-90% of my time in this deep work?
CLARK: I would imagine probably 70. I think probably people at InVision would tell you that they get less than that because there are many meetings, and at scale, obviously there’s an overhead, a connective tissue overhead to managing very large projects at scale that are cut across multiple departments and disciplines. Again, there’s no perfect formula, it’s just making sure that people can preserve that time, or as much of that time as they can.
MATT:I have a selfish question, which is, as a CEO of a distributed company, what do you think your percentage is of that work?
CLARK: Mine is probably closer to 30%. I’m not a production person. I don’t have a work product necessarily that I put into the world. I don’t have a screen that needs to be designed to an excruciating level of detail and iterated on over time.
MATT: I would say at this moment I’m probably under 10%. So that’s something I’m working on increasing because I feel like the time I’m able to invest in writing helps a lot, and the company is, of course, a product I think about a ton, and need to spend more time than I currently am investing in how that product is designed — the product of Automattic itself.
CLARK: Here’s a little weird hack. I don’t know if this makes any sense for folks. I like to sometimes just go to conferences, even though I’m 50% interested in the content, just because being at a conference blocks off your schedule, it puts you in a room with a lot of that kinetic energy, of buzz, of people who aren’t distracting you because they don’t have any interest in you, they’re there for other things, they have no connection to you, but it’s a room that’s vibrant with the energy of people. And there is someone talking and there’s time in between. And I find that just disconnecting and absorbing ideas on drip ambiently gives me a ton of headspace to have divergent thinking time.
MATT: That’s a cool hack. Now we opened a lot of threads there. I’m going to loop back to some of them. One, if you were doing a pre-postmortem today for InVision, what would be on your list?
CLARK: Oh without a question it’s the cohesion of the company. I mean it’s a risk being a remote company. There are things that happen in a co-located environment — that’s what we call the world of on-site work, co-located — there are things that happen there between the seams that people don’t even understand are happening. They don’t consider it an explicit part of the work.
A loose example — the watercooler. There is this — I’m bumping into people in the kitchen, in the hall. There’s this ambient transfer of energy through “Hey, you’re working on this? Hey what are you up to?” We have to figure out how to allow that to happen deliberately. If what we’re doing now is 80% as good as being in-person in some ways and 130% better than being in-person in other ways, how do we make sure that we take that 80 and get it to 100 so that we’re not leaving a liability on the table?
MATT: I’m particularly curious about that watercooler. What did you figure out and what has worked well so far?
CLARK: What I have learned in these settings is driving to solutions in real time. Again, going back to that ebb and flow of together time and alone time, it doesn’t work in larger groups of people. You can seed things, you can create good traction around the idea, but I think a longer, more thoughtful, more deep-work-enabled process of driving to a solution is important.
Where we are beginning to think about this is making sure that the time that we have together as an executive team, even the online time — two hours every two weeks we have something called the Strategic Alignment Team Meeting — so that group of people meets online, just putting more ceremony on that. So rather than getting together and just having a random group listing of things that we want to get through, maybe doing a little bit more pre-work.
So one idea that surfaced was taking a facilitator that wasn’t a part of the group — the Head of Biz Ops or Chief of Staff — and making that person responsible for interviewing all the members of that team individually, one on one, with a set of pre-defined prompts to pull out the value and get that value on the agenda ahead of time.
Because if I pulled you into a meeting, Matt, right after this call — I don’t know if you have a meeting right after our little podcast here, but if you did. you probably would not be in a state to pull out the most important thing that’s going on in the business or the biggest threat or the biggest opportunity or some weird HR thing, or opportunity or great idea that you thought about two weeks ago. You wouldn’t be in a state to evoke that unless you’re just a — you meditate a lot more than I do. I don’t know.
There has to be a mechanism, I think, for tilling that soil with those executives ahead of time, or with anybody in that case, ahead of time. So how do we create a list of questions? For example, what’s the biggest threat to the timelines that you’re facing, what’s the biggest HR or people or resource or talent issue that you’re facing? I’m just making up examples of kinds of questions we would ask. What’s the thing that you need the most from who on this team? I’m imagining a world where there are about five or six questions that we ask each executive one-on-one before getting into that meeting and that those questions ultimately end up tilling the soil and driving the agenda of the meeting.
MATT:One thing that I’ve heard that’s unique about InVision that I’d love to confirm is that y’all have everyone on East Coast office hours?
CLARK: I do believe that you need a certain number of hours of overlap. So we have a kind of a loosely held standard set of operating hours. I think it’s like 10AM to 6PM. The recommendation that is fairly closely held is that there should be a three hour overlap between most of the team because within those three hours you can negotiate when your stand-up meeting is. If you’re a team that works together, you can get to the wide-wide meetings, generally speaking, unless some people in Australia watch those the next day or a week later. I don’t know what the time is in Australia right now but you get the idea. Generally try to aim for three hours of overlap.
MATT: So does that mean you don’t have many people in the Asia Pacific region?
CLARK: I would say not by design. We probably lean out of hiring one-off individuals. We’ve done acquisitions, for example in Australia. We do have people in Asia Pacific for sure, but there is probably a light bias towards folks that fit into teams that have a schedule with more overlap.
MATT:The number I heard for you all, and this is the other day, is around 20 or 25 countries that you’re in?
CLARK: It’s got to be. Yes. I mean 900 people? Yes, probably 25 countries I would imagine.
MATT: We’re at a very similar size, I think we’re at 68 countries. I would say there’s definitely a cost and a tradeoff to having that kind of time zone overlap as an explicit part of the hiring, and it definitely means that there are certain teams that are more Asia-Pacific-centric, because that overlap is important. And if you have a single team with people in what I think are the three zones, South America, Europe, Africa, and then Asia Pacific, there is no good time for anybody.
CLARK: 100%. You have to be getting something out of the remote thing. It’s an interesting question. When people ask about remote, they assume that I’m a remote zealot. I’m not. I’m not someone who believes in remote as “this is the future.” I’m just not religious about the topic at all.
What we needed out of remote very early on is we needed it as a talent hack, as a talent arbitrage. Hire the best people wherever they happen to be, figure everything out later, hire them quickly, get them in the ship as early as possible and start seeing results. How can I just hire the best people no matter where they are? If you’re not hiring, if you don’t find that your talent density is significantly greater than your contemporaries that are co-located in whatever city you happen to be in, then you’re not leveraging that arbitrage the right way.
MATT:That’s a really good way to put it. How long do you think that talent arbitrage exists? Stripe famously now has remote as their new office engineering center?
CLARK: Sure.
MATT: How long before Google, Facebook, etcetera, the same people you’re competing with in New York, open into the distributed world?
CLARK: That time is probably now. It just means you have to be more creative. Also, even if ten of the biggest tech companies in the world were out hiring, the talent supply is big enough for us all.
MATT: Playing off on site versus off site, we have talked a lot about how you work in a distributed fashion. How and when do you bring people together?
CLARK: We have a company all-hands on site, a global all-hands, called IRL, InVision in Real Life.
MATT:Ha! I like that.
CLARK: This year it was in Phoenix, Arizona. We took over an entire resort and that was an intense, amazing, high-energy experience that brought a lot into the work that we do, that we have done since. And the year before that — also really incredible — in Los Angeles. I definitely like the format of all of us together in one resort better than all of us split up between a few hotels. So all company, all hands, IRL.
And then we have miniature IRL. So the product department has a product managers’ IRL, which I think was two weeks ago in New Jersey. And I think this week, if I’m not mistaken, is the all-designers’ IRL in Chicago. They pick a city that just makes sense. And I think there was CFT, the Customer Facing Team, was in Denver a couple of weeks ago. So departments have an IRL, the whole company has an IRL, and then individual teams can tap into budget to get together in person.
MATT:If I joined InVision, how many weeks or days out of the year am I going to be at these IRLs?
CLARK: My guess is probably three throughout the year. We also encourage folks to go to the InVision events that we have, the customer-facing events. Design + Drinks, we do panels, not a week goes by that there isn’t some sort of InVision customer event happening at some bar someplace in the world.
MATT:That’s really cool.
CLARK: And so we try to encourage some folks to get together that way. Again, this is personal, my personal principle behind this online universe is it’s called Cloud Culture — that’s what we call it — Cloud Culture versus the IRL stuff, when you’re in real life I prefer us not to be doing work.
MATT:Interesting.
CLARK: I prefer us to be connecting as people. If you gave me a week with the team together in person I would really like 80% of that to be stuff — it could be conversations that sound like work but conversations that really bring us closer together as people. My mental model here is that we have little scale models of ourselves. Even if we’re in person, we’re not really relating to the person we’re looking at, we’re relating to our little mental model of that person that rests in our mind. Does that make sense?
MATT:Sure.
CLARK: The more time that we spend together, the more articulate, the more detailed that mental model of you becomes. So when we’re online you get to a certain level of precision, [I can] take a long time to get to know you as a person and get to know how you behave and act in different contexts, how you react to certain things as individuals or as groups. When we get together, the fidelity of that model increases exponentially. And we take that mental model into the online environment. That’s the reason for the on-site, in-person experiences.
MATT: I’ve heard — you talk about the screen a lot but I have also heard that InVision — rumor — that you’ve banned slide decks.
CLARK: It makes a great headline, doesn’t it? [laughs] It’s not exactly true. What I’ll tell you is that we encourage visual collaborative communication in meetings more than prepared slides, only because that visual communication tends, number one, to be much more democratize-able. You can get more folks who are of a greater diversity of connection to the problem space.
If you’re going to present something to a product team, that’s one kind of collaboration but arguably a lot of those product conversations should reach far beyond the engineering, product, or designers who work on it. You’d like to be able to engage business stakeholders, domain experts that exist within the business, or folks that are impactful. You’d like to have your Head of Finance on a product call and to have them totally track an influence.
So staying visual, being sure that you just have a strong bias to visual communication, visual storytelling, getting visually-driven artifacts that are real to the customer, real and true to the customer experience, I think are really important. You generate better conversations than you would with a deck. It happens to be that we’re all trained when we see a deck. It’s like a movie, like “Now is our time to take out the popcorn, kick back and let someone else do the talking.”
When you do a Freehand sketch — we have a product called Freehand, which is basically a gigantic, online white board — or you’re actually showing screens of an experience, and tying the conversation around pricing into the user experience, that drives that conversation around pricing to the customer — two things. Number one, you’re being super customer-centric, you’re orienting all of the people on the call around the front line of that problem space.
Pricing is not a number conversation. Pricing has financial impact, pricing needs to be within financial guardrails, but ultimately pricing is not about a number, it’s about a customer experience. All of the leverage you have around pricing, all of the acceptance from the market that is required to make that price the right price — and now I’m spinning off into a pricing conversation, but you’ll understand how this is a microcosm for all these things —
MATT:Totally.
CLARK: — comes down to somebody looking at a screen at some point and feeling good or bad about it. So if you can have that pricing conversation through a lens of design — and by the way, this is what InVision principle number seven is meant to imply — being design-driven. How do we get into the mind and the heart of the customer and have the business conversation while we’re having the customer conversation?
Design conversation and business strategy conversation, all in one. If you can do that, you can have a much greater diversity of people in the conversation, your Head of Finance doesn’t feel like they’re on a product call, the product people don’t feel like they’re in a finance call, everyone feels like they’re in a creative problem-solving call.
MATT:I love it. Thanks again.
CLARK: Pleasure.
MATT: That was Clark Valberg. You can find him on Twitter at @clarkvalberg. That’s “Clark,” then “Valberg” — V-A-L-B-E-R-G.
We’ve got a special treat in store for the next episode. Back in September, Automattic held its annual Grand Meetup in Orlando. The Grand Meetup is a time for all Automatticians to get together in one place. We get to meet some of our colleagues face-to-face for the first time, hear some great talks from folks like Stephen Wolfram (who was a guest on this podcast a few weeks back), and of course hang out and have fun together too.
We set up a recording booth at the meetup and talked to a bunch of folks from across the company to hear about their experiences with distributed work and the importance of in-person meetups for keeping people connected throughout the year.
Thanks for joining us and see you next time.
Episode 13: Attorney Lydia X. Z. Brown on Making Work More Accessible
Oct 31, 2019
Because of their background in working with disabled and marginalized people, attorney and activist Lydia X. Z. Brown has a deep understanding of how different workplace environments can best serve diverse workforces. Today they join our host Matt Mullenweg to discuss what distributed companies can do to make workflows and working conditions more inclusive.
The full episode transcript is below.
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MATT MULLENWEG:Howdy howdy. Welcome to the Distributed podcast. I’m your host, Matt Mullenweg.
Today’s guest is Lydia X. Z. Brown, who is a… well, Lydia wears many, many hats — we’ll get to that in a minute. Lydia once gave a talk for Automattic about disability inclusion, and today we’re going to continue that conversation.
Lydia spent much of their life feeling left out, and they’ve dedicated their career to advocating for marginalized folks of all kinds. As the CEO of a distributed company, I’m curious to know more about how we can make the hundreds of Automatticians across the world more comfortable at work, and I know Lydia will have some insightful thoughts to share about that.
Okay. Let’s get started.
MATT MULLENWEG: Hey Lydia.
LYDIA X. Z. BROWN: Hi Matt. Thank you so much for having me on your podcast.
MATT: You are a multi-hyphenate. It says here you’re a writer-advocate-organizer-strategist-educator-speaker and attorney. How did all those things come to be for you?
LYDIA: I have believed from a very young age that every single one of us has a moral obligation to use whatever resources we have — time, money, knowledge, skills, emotional energy, access to physical resources — however that might be defined — that we each have a moral obligation to use those resources in service of justice, and fighting against injustice and oppression and violence in all of its forms, structural and individual, subtle and overt.
And since the time I was young, in grade school up through high school and now as an adult, I have done that. And I have been enormously privileged in many ways, although I frequently talk about experiencing marginalization in others, I have an enormous amount of privilege and I have experienced some of that in terms of access to some resources. And for me that makes the journey quite natural and quite intuitive. It wasn’t so much that I chose “I’m going to be this thing, I’m going to be an advocate, I’m going to be an educator,” so much as I have to. I have an obligation to, and I have the skills necessary to develop, so that I can be successful in doing it.
MATT:There is so much injustice in the world. How did you pick the areas that you focus on?
LYDIA: The work that I do is deeply personal to me. I am a multiply-disabled person. Most people who know about my work primarily know me from the autistic community. And not only am I autistic but I also live with psychosocial disabilities and other cognitive disabilities. And not only do I move through the world as a disabled, neurodivergent person, but I also move through the world as a queer person and as an openly non-binary trans person, and as an East Asian person of color living in the U.S.
And all of those experiences of marginalization, and what some of us might say is hyper-marginalization, people who live at the margins of the margins where there is so much that is stacked against us, and how society is designed, and who society assumes is normal and healthy and the ideal, and who society decides shouldn’t really be at the center, shouldn’t be in the lead, should be denied opportunities, should not have access and all of those things, it gives you a very different perspective than when you grow up in the world with access to more privilege and resources in ways that I didn’t, even in the many ways that I have had some privileges.
And for me, going through school, targeted all the time as a freak — that was one of the most common refrains of my grade school and middle school bullies — and making it to high school, where I was falsely accused of planning a school shooting because of stereotypes and stigma about people like me.
MATT:Oh wow.
LYDIA: And then making it through college and law school, where you would think that people might have a more egalitarian approach. Well, that’s laughable because sometimes the people that are in what are supposed to be the most progressive kind of spaces — forward-thinking, innovative — sometimes were the most damaging and the most harmful precisely because they already believed that they were incapable of inflicting such harm.
And moving through those spaces, constantly receiving the message that I didn’t belong, and at the same time that I couldn’t speak for or alongside or even in support of other hyper-marginalized communities, because, well you do have this privilege — it gives you a fire.
MATT:How do you develop empathy for someone whose lived experience is different from your own?
LYDIA: For me it starts with recognizing firstly our shared humanity and secondly believing deeply in and being passionate about a commitment to valuing all people and all configurations of people’s lives and experiences, and how their bodies and minds work, whether they are like mine or unlike mine.
And if we all start at that premise, that every single human is valuable for who they are in all of their complexities, in their many identities and experiences, not in spite of them, because we are not the same and that’s a good and okay thing, but as all of the things that they are, then we can recognize that even if we don’t understand intellectually or emotionally what another person’s experience is, it doesn’t mean that it’s not valuable or that they’re not valuable as a person, or that that experience or part of their identity somehow detracts from their personhood.
MATT:Can you tell us a little bit about what you’re working on today?
LYDIA: Right now I’ve been working on developing a project called The Fund for Community Reparations for Autistic People of Color’s Interdependence, Survival and Empowerment. We call it the Autistic People of Color Fund for short.
I launched the fund last summer, 2018, using some award money that I had received from a disability rights organization, as well as the proceeds of “All the Weight of Our Dreams,” the anthology that I edited, along with two other folks — Morénike Giwa Onaiwu and E. Ashkenazy — featuring 61 writers and artists of color who are all autistic. And we used those proceeds and that award money to seed a fund that provides micro-grants to individual autistic people of color as a form of direct support and mutual aid.
The fund so far has given out over $12,000 in funds in grants of between $50 to $500 each to people from a variety of countries, as young as toddlers and as old as our elders, to help them with everything from accessing mental healthcare to covering a shortage in rent money, to escaping an abusive situation, to buying textbooks for school or art supplies or posters for a protest, and everything in between.
And that project, every several months is reinvigorated with donations from our community because we’re always running low on funds. So something that I’m working on today and this week is hoping to gain more sustainable and long-term sources of funding for the fund because right now we are in a place where the vast majority of our donations are small gifts from individual community members, many of whom are low-income or no-income, who are disproportionately unemployed or underemployed or have only precarious access to financial stability rather than having general access.
Every time I open my inbox, there’s anywhere from five to 25 emails from people who are seeking to apply for money through the fund. And we never have enough money to meet the need because our community is facing so much. And when you are negatively racialized and autistic — and most of the applicants to the fund have many other experiences of marginalization on top of that — the likelihood that you’re facing circumstances that are far beyond your control in terms of access to healthcare, access to safe, affordable and accessible housing, or simply being able to live and enjoy your life, go on vacation, see a movie is just so difficult and so hard to grasp.
And that’s something that I’m hoping we can begin to change. I know we already have with what we’ve done but it’s also not enough.
MATT:If people listening wanted to support this organization, where could they go to donate?
LYDIA: You can donate funds to the Autistic People of Color Fund by sending a check, money order, or PayPal payment to the Autistic Women and Non-Binary Network, AWN. If you donate to AWN, you’ll need to include a note that it goes to the Autistic People of Color Fund and they’ll include it in our budget.
MATT:Great, thank you. What’s your current work environment like?
LYDIA: My current work environment is in a traditional office location in downtown Washington, D.C. As an attorney, I work as a fellow for the Bazelon Center for Mental Health Law. In our offices there are 12 floors, there’s different law firms and organizations, legal and non-legal, who all share the same building. And in our office space, Bazelon is the primary leaseholder for this very large office suite.
We have seven staff currently here and we also have three other organizations, one law firm, and two nonprofit organizations that sublet space from us. So we all share this large office suite together in D.C. I’m sitting in an office right now where I have a very nice lamp that I got to replace the horrible fluorescent lights, I have a door that shuts and it’s wonderful because when I need alone time I can shut the door and when I need social time I can walk outside the door and say “Hello, my fellow workers, we all exist here, who would like coffee?”
MATT: Tell me about how traditional co-located office experiences are like for different kinds of disabled people.
LYDIA: For some disabled people, having a traditional co-located office space is a boon. It’s a boon to mental health because it enables and provides and a built-in way to connect with and share space with other humans. People were built to be in community, that is how we evolved, evolutionarily speaking, if we want to go to basic biology. And that’s true even for those of us like me who are more introverted.
People were built to be in community. And if we don’t have access to other people in our daily experiences and throughout our lifetimes we can end up living lives of enforced isolation, and that can be especially true for many disabled people, whether it’s someone who is physically disabled or whether it’s somebody who has mental disabilities or both.
Having access to a workplace where we can actually see other people, potentially have the opportunity to build social and professional networks, can be great for that reason. It can also be helpful in that if the workplace itself offers features of the building design and of the space design itself, the office layout, that maximizes access for a particular employee, it can make workflows occur better. It can make it more efficient, it can make it more easy to complete. It can enable the employee ultimately to feel better about the work that they are doing and to produce higher-quality work.
So there are a lot of potential benefits to having this type of office location. There are also, of course, downsides. And of course there are many potential configurations to these kinds of offices in the first place.
So here where I am, for the most part, we each have separate offices with separate doors. And for some folks like me that works great. Like I said, it enables me both to have privacy and to be able to work alone when I need to be alone and focus, but it also enables me to connect with others by choosing when to keep my door open and shut and choosing when to move in and out of this office space that was designated for me.
Other people who are in a co-located office location may prefer to have more of an open-office layout where there are multiple desks or workspaces that are not really separated or only have partial walls or partial dividers. It enables that same kind of ratio of having a bit of a dedicated workspace for you but also supports and enables more open conversation and collaboration with people who are physically present with you. Or to give what my partner Shain will often talk about as having a kind of ambient people existing where we’re all existing in the same space and that’s comforting in a way but it’s also not creating an obligation or a necessity to have to engage in conversation if that would be distracting or unhelpful to your workflow.
MATT:How should people think about physical disabilities versus neuro–atypical folks in regards to office environments?
LYDIA: Everyone is different, whether you are neurodivergent or physically disabled or both. And many people are both, all the time. Your needs are never going to be the same as anyone else’s, just like people who are not disabled. There are no two people who function best in the exact same type of environment.
Where disability comes into the picture is thinking about how someone’s body or mind might function best in an environment, a built environment or an emotional or communicative environment or infrastructure that perhaps wasn’t designed to begin with with that particular person’s bodily capacity or neurodivergence in mind when that design was first conceptualized and then implemented.
So when people ask me how do we then design a workplace that best fits people with physical disabilities versus best fits neurodivergent people, my response is [that] there is no one size fits all. So for example, in the autistic community, there are some autistic people who I know who need to have daily access to natural sunlight, and quite a lot of it, in order to function well. And if the room is closed off and there’s no windows or there’s very few of them, and it’s only artificial lighting, that can make it incredibly difficult to function, let alone to get work done.
And at the same time, I know many other autistic people for whom the sunlight is actually physically extremely painful and being around sunlight is emotionally draining, it is sensory overstimulating, and it physically just hurts.
Obviously those two needs are by definition incompatible. Those two people, one from each of those groups, cannot share a workspace in the same room because either one of them is very well supported and is functioning very well with that type of lighting, whichever one is there, and the other one is miserable and/or in pain. For me the question isn’t so much, “How do we design a workplace or one methodology of supporting employees in terms of infrastructure,” as it is “How do we make sure that each person that is involved with our company or our organization or our community is able to access the type of environment and space that works best for them.”
MATT:A lot of people listening here will be at or running fully–distributed companies where there is not a physical co-location place. What should people in those environments keep in mind when designing how they interact with their colleagues?
LYDIA: For the people who need to function best having more constant communication, having access to other people around them who are working or certain forms of scaffolded support from their manager, it can be hard to do that in a distributed way.
So, for example, with some people who have ADD or depression, it can be very difficult to manage one’s own workflow, which some people might say, “Well that’s a prerequisite. If you want to work for a company that has a distributed workforce, you need to be able to self-manage your time, you need to be able to self-manage your workflow prioritization, you need to be able to self-manage how you initiate tasks and follow through on tasks and insure completion. And if you can’t do that, maybe this isn’t the right workplace for you.”
And my response to that would be perhaps for some people that may be true, there may be some people who already know about themselves from their own experience that that’s not going to work for them, so those people are probably not in your workforce if that’s where you are. They might be and if they are I sincerely and genuinely hope for their sake that they are able to find an opportunity that they are excited about that will support them in excelling in an environment that they would need for them.
But for people who aren’t at that point where it’s actually an impossibility and completely inaccessible but who would struggle with the lack of formal and physical access to structure that would traditionally come with a co-located office, my suggestions would be to always go to the employee first.
If you believe that someone might be struggling with their workflow management, or they’re struggling just in general with their job, or they have already told you, “I’m really excited about this, this has been going great, however I’m beginning to have some issues and I want to make sure we intervene before those issues worsen and affect my work and affect my performance on this team,” it’s for you to ask them, “What things work well for you, what things don’t, and how can I support you in getting the things that work well?”
So, for example, if someone in a distributed company says that they need to be able to be around other people at least during part of the day to get work done, but all your employees are in different locations, then it might be worthwhile for that company to invest in paying the membership of a co-working space for that employee so that they have access to a location that has some of the features of an office — it’s a workspace, people are primarily there to do work, there might be some desks and a printer, so it can feel more like a workspace than your home or a cafe might — but it also enables that person to stay where they are and doesn’t require the company to make that investment in horrifically expensive real estate, and for a workforce that is primarily not in one location and in fact may have, at most, perhaps five employees in one location, and they don’t want to share a space together.
For somebody else it may be not so much, “I need a physical space,” but “I need to be able to have regular access to my manager, to be able to have conversations throughout the day.” In a distributed work environment, it’s not that that’s not possible, you of course already know that’s very possible, but it may be working with that employee to figure out [if] Slack work[s] for [them]. And if it’s not working for you, if it’s not meeting your need to be able to pop in and ask your manager questions throughout the day, then what are the other possible interfaces for communication modality that might meet that need instead?
MATT:It seems like this could require a big degree of self-awareness. How do people find out if they need certain environments like you describe?
LYDIA: Some people are able to figure it out better than others. And you’re definitely right that to be able to express and articulate what you need and what works well for you often requires a level of self-awareness that unfortunately not everybody has. But this is where good management and good team-building comes in.
An effective manager in a distributed work environment needs to develop the skill of asking precise and information-gathering questions to elicit this kind of information. Because even if the employee might not be able to produce this information on their own, or might know it, but not necessarily know how to communicate it in a way that would be applicable and useful in a work environment, an effective manager or an effective supervisor should be able to develop the skill of asking, “Okay, so in your last work environment, let’s talk about the setup of your office.”
Like you asked me, “Was this a good setup for you or not? What were things that you liked about it, what were things that you didn’t like about it? What was frustrating for you? What excited you when you came to work? Can you describe a time when you were really productive? What changes, if any, were made at any point during your time during this other work environment?” Or if they haven’t had a work experience, perhaps when they were in school or perhaps in some group that they volunteered with or they were part of in their community, whether it was their softball team or whether it was crochet, whatever it might be.
It’s taking some of the kinds of questions that we might ask someone either in an assessment or an evaluation and/or in a job interview, but asking them with an eye to detail, being open-ended but also narrowly defined enough to capture the kind of information that will help the supervisor, the manager, and any HR support staff in figuring out how to then apply that information into the person’s current workplace.
MATT: How common is it for people to be neurodivergent but not realize it themselves?
LYDIA: I don’t have statistics on that and part of the reason I don’t is because by definition it would be incredibly difficult to capture a number or a percentage of how many people are objectively determined to likely be some type of neurodivergent versus how many people know that about themselves.
But what I can tell you, based on anecdote and experience in working with thousands of different neurodivergent people over the last decade, is that it’s very common for people to know that they learn in a different way than others, whether that’s in a way that got them labeled stupid or in a way that got them labeled gifted.
And it’s also very common for people to have received some type of label of disability or giftedness, or both, even if that specific label might turn out to be inaccurate, but it captured some aspect of their neurodivergence that somebody observed that this person didn’t fit into the mold of what society assumes is typical of how to learn and communicate and process and deal with emotion and all of those things that make our messy stuff in our brains.
There are folks that discovered they were neurodivergent when they were in their teens, whether or not they had language for it. And there are also people who didn’t realize it until their forties, fifties, sixties, and even seventies. I’ve met some people in their seventies and eighties who figured it out at that late stage in their life.
And it tells you a lot about us as a society of how we simultaneously assume that you don’t really count as disabled or neurodivergent if it’s not affecting you in a way that we treat you horribly over. “Well you must have functioned fine.” They probably didn’t, they were just very good at trying to hide it when they weren’t. Or that we say we knew about it so we labeled you all kinds of derogatory and terrible things, we recommended you for institutionalization, we assumed that you would never be able to make your own decisions, never be able to choose and form your own relationships, anything like that.
And either way, neurodivergent and other disabled people will find ourselves in the double bind of being expected to overcome and mask being disabled for the comfort and convenience of non-disabled people or of being assumed that we will never amount to anything by any definition, that we are completely incompetent, that we are incapable, that we don’t belong and that we shouldn’t belong. And it’s always one or the other.
But really they boil down to the same kind of ableism and that ableism is the devaluing of disabled people’s experience, that to live life as a disabled person of any kind means that we’re living a lesser life. But the reality is, is that disabled people have so much to offer ourselves, our own communities and the entire rest of the world because we have lived our entire lives learning how to function and survive and sometimes, when we’re lucky, to thrive in a world that was literally designed not for us.
MATT:I have heard of workplaces that actually target and try to hire disabled people. What are some of the superpowers that those companies might be trying to benefit from that people might not appreciate?
LYDIA: You know, it’s really interesting every time we talk about disability-targeted hiring initiatives for me because there’s a lot of cognitive dissonance. On the one hand, many of us appreciate that there are companies out there that are trying to seek out more of us to hire us, recognizing that we actually do have talents and capacities individually and perhaps to some extent there may be some patterns of some talents among some people, at least sometimes. And that’s great, especially given the astronomical rates of un- and underemployment for disabled people, especially those of psychosocial, intellectual, and developmental disabilities.
But at the same time something that really worries me in many conversations around employment and corporate hiring initiatives are that many hiring managers creating these programs will say things like “We love having disabled employees because they’re so motivated, they show up to work every single day, they never call out sick, we can depend on them, they’ll be loyal to our company forever.”
And you know, at the surface level, when you don’t really think about that too deeply that sounds great. Like, yeah, that means that disabled employees tend to be really dedicated, we should hire more disabled people. But what that says to me is actually that because of our astronomical rates of un- and underemployment, we have become sometimes an exploited labor force.
Where there are some companies that mean well, they’re not necessarily doing this out of malice, but they are aware at least on some subconscious level that it’s more risky for many disabled employees to call out more. That it’s more risky for us to do anything but excel far above and beyond what our non-disabled peers need to do in order to make sure that [we] keep [our] jobs.
And that makes me really sad and it makes me really angry. Because I don’t think we should be hiring disabled either because of stereotypes that might or might not be true, e.g., that all autistic people are savants at math or that all blind people are prodigies at music, when sure, some are. There are some autistic people I know who are math geniuses and there are some blind people I know who are incredible musicians and there’s also plenty of us that aren’t. Like, I’m autistic and I suck at math. Also I’m Asian so I just broke two stereotypes at once, which is fun. [laughter]
We all have different skill sets and they may or may not be tied at all to our disability but we should be hiring people based on whether that person is going to be able to do the job and do it well, disabled or not. And we should be hiring people because we want them and we believe that they belong in our workplace, we want to support them in being part of that workplace, and as being more than a person who simply does a job but as someone who belongs to the community of people in this workplace. That’s what we want to do.
And so if the question is, “What are superpowers that we bring?” My answer is, how about we not talk about superpowers but we talk about why each and every single one of us deserves to be able to do work in a way that’s meaningful, that makes sense, that makes us feel good, that is not doing something horribly unethical, hopefully, and that at the end of the day enables us to be able to live in a system that unfortunately isn’t really set up for most of us to thrive?
MATT:Let’s talk about why — why people deserve to have that.
LYDIA: I believe very firmly that every single person deserves to be able to live in a safe community and to be able to live a self-determined life and to be able to live authentically and true to themselves and to be able to live as part of a community where they can receive care, they can receive support, they can receive love, and they can feel a sense of belonging.
And I believe that that is inherent to human dignity. It should never have to be earned. Somebody should not have to earn the right to live without fear of violence. Someone shouldn’t have to earn the right to be able to afford safe and accessible housing. Nobody should have to earn the right to be able to receive healthcare.
And unfortunately in the society that we live in our society presumes that those are things that need to be earned and that if we don’t think someone is contributing enough or we don’t think that they are productive enough, that maybe they don’t really deserve those things. And if we’re nice, maybe we’ll give it to them, at least a little bit or at least for part of the time, but until and if and when society says, “Oh, you’re pulling your own weight, we think it’s contingent and we think it’s conditional.” And that to me is incredibly inhumane and unjust.
MATT:As a wrap–up, was there anything we missed that you wanted to talk about?
LYDIA: I just think it’s important to note that when we’re talking about employment and disability, I believe that the corporate sector has an opportunity to take leadership in fighting for fair and living pay for people with disabilities. Many people don’t know that it is still 100% legal in the United States and in many other countries around the world to pay people with disabilities pennies on the hour or the equivalent.
MATT:Really?
LYDIA: In the U.S. it’s emblazoned into federal law, in section 14(c) of the 1938 Fair Labor & Standards Act. Section 14(c) is still on the books today and there are many for-profit and not-for-profit organizations that take advantage of section 14(c) to pay disabled people as low as cents per hour for menial labor and it’s 100 percent legal. And this is horrific.
There is a bill before the Congress right now called the Raise the Wage Act, which, if passed, would eliminate the use of what’s called sub-minimum wage in the U.S. And that’s pretty awful that such a concept exists. If it’s minimum, there is supposed to be nothing below it. But in the U.S. we call it sub-minimum wage.
There are other nations in which there are no labor protections at all for people with disabilities, either in terms of non-discrimination or wage protections. And while I’m not an expert on international labor law, what I do know is that companies around the world, all of the folks that are listening here, have an opportunity not only to prioritize and speak publicly on ensuring that you’re paying folks a living wage and a fair wage that is not based upon backward notions of productivity, but also to fight for the end of sub-minimum wage and other unfair labor practices that devalue disabled people’s work even more.
MATT:If people want to follow youmore, where can they find you online?
LYDIA: You can find me on Facebook under the name Lydia X. Z. Brown — Autistic Hoya. And you can also find me on Twitter @autistichoya. All one word. My home page is autistichoya.net. And my blog is autistichoya.com. That should really be reversed but that would require a type of web engineering that I am not capable of doing alone. [laughter]
MATT: Well I’m also very honored that you use WordPress for many if not all of your websites.
LYDIA: I use WordPress for almost all of my websites and I love it.
MATT: Awesome, I very much appreciate that. Finally I will mention as well what you said earlier. Autismandrace.com, which is where they can donate to the project and fund that you mentioned earlier. And there are some instructions on that website for how to do so.
MATT: That was Lydia X. Z. Brown. You can find them on Twitter at @autistichoya. That’s @ “Autistic” and then “Hoya,” H-O-Y-A. You can also find Lydia blogging at AutisticHoya.com.
It’s really important for folks who run distributed teams to remember that employees don’t fall into binaries of “normal” or “abnormal.” We all find ourselves in different spots on different spectrums of ability throughout our careers, and hopefully, with more flexibility around workspaces, work hours, or work styles, we can all feel included and productive no matter what professional setting we’re in.
On the next episode of the Distributed podcast, I’ll be speaking with Clark Valberg, the CEO of InVision, which is a very popular cloud-based design platform that many distributed teams, including Automattic, have adopted. InVision started out as an agency, but after they built this internal tool for their designers, they realized that it was big enough to be a flagship product. InVision is similar in size to Automattic, so I’m interested to hear about Clark’s distributed journey.
Thanks for joining, and see you next time.
Episode 12: Toptal’s Taso Du Val on Finding the Top Distributed Talent
Oct 17, 2019
When hiring managers interview a candidate for a high-level role, they want to be sure that the person they choose will be productive and able to work well with their prospective team. But what if the hiring process takes place over video chat? A growing number of companies outsource the vetting process to a company like Toptal, a freelance marketplace. Toptal’s CEO Taso Du Val joins us on this episode of the Distributed podcast, with Matt Mullenweg.
The full episode transcript is below.
***
MATT MULLENWEG: Howdy. My name is Matt Mullenweg, and I run a company called Automattic, with over 950 employees distributed across over 70 countries. We’re growing quickly, so I spend a lot of time thinking about how the company is going to find the very best people. Since our team leads might never meet a far-flung applicant face to face until well after they’ve been hired, our hiring process has to be comprehensive, so sometimes it can be a little bit of a slow and long process.
But what if you need to hire top talent quickly? What if you need a world-class project manager on a short-term basis, and you don’t have time to rigorously vet a bunch of applicants or set them up on a payroll platform?
Well, you might turn to Toptal, a freelance marketplace that aims to provide companies with a fully-vetted pool of talent that represents the top 3 percent of their network’s applicants. Toptal’s CEO, Taso Du Val, joins me today to talk about how he built his company, which happens to be distributed all over the world, and about how current approaches to recruitment are undergoing a major sea change.
Let’s get started.
MATT: All right, we are here today on the latest episode of Distributed with Matt Mullenweg, and we have CEO and Founder of Toptal, Taso Du Val. Welcome very much.
TASO DU VAL: Thank you, Matt, for having me.
MATT: Just for listeners who might not know what Toptal — do you mind explaining your journey to Toptal and then you can introduce what Toptal is?
TASO: I was doing some consulting work and working with some companies doing contract software development, and at the time I was mentioning to them that they should use some other resources to be able to get software developers. I mentioned the freelance marketplaces on the internet. And so many times they said to me, “Those are terrible places. You can never find good resources there.”
Meanwhile, I was having a great experience finding great resources there. So I said “Hmm, this is fascinating, I keep hearing time and time again that people are having terrible experiences finding top talent, yet I’m having a very consistent experience finding top talent. What is the difference?” And the difference really came down to my domain expertise, being able to identify and screen that top talent. And that was really the genesis for what Toptal is today.
MATT: And your background, like myself, is engineering.
TASO: Precisely.
MATT: And in fact, we met at — was it a MySQL open source conference 14 years ago, or something?
TASO: Yes, in 2007, 2008, after the first MySQL camp at Google. So that was a really long time ago.
MATT: So Toptal is, if you were to summarize it, a site I can go and say, “Hey, I want X, Y, Z?”
TASO: Mhm.
MATT: You cover a few areas now — developers, designers…?
TASO: Project managers, product managers, and finance experts. We just launched recently project managers and product managers, and that has been phenomenally successful. So I would say the demand and the experience that people are having with product and project managers far surpassed what we thought it would by a long shot. So it’s been really cool to see a management type of role take place remotely and be so successful.
With developers, they have a long history of working remotely, even designers, and that is in part because individual contributors can contribute more rigorously to a project. You have, in the case of software development where you can commit code, in the design world now lots of tools are evolving to be something similar.
MATT: InVision, Figma, and things like that.
TASO: Precisely. So if you look at it from that perspective, it’s very conducive to the remote working process. When it comes to management, it’s still a little bit new, of course not for us internally, and for many distributed companies, but for outside consumers it’s a little bit more new. They’ve been very receptive to it, and it has worked really, really well, more so than we anticipated.
MATT: So if I’ve got a job to be done, I can go to Toptal. I hire someone, and I can now hire someone to come into an office, or is it all through the platform?
TASO: We do some on-site work. Generally what we do is 95% remote. And so when a client or someone wants someone on site for a certain period of time, we allow for that, however we are not generally the conduit for facilitating on-site work.
MATT: The advantage of going through you all versus just finding freelancers, is you ensure the quality of the talent?
TASO: Mhm.
MATT: And you have tools to mediate the experience, right? I don’t need to worry about how they’re getting paid, I could just pay you and you take care of it all?
TASO: Precisely. And I would say the biggest value-add is the time it takes to acquire the talent and the energy it takes to screen the talent. We have done all of that for you. And so — no kidding, this is a real stat — our send-to-hire ratio is about 1:1.5. For every 1.5 “candidates” that we send you, you will hire one of them.
MATT: Oh wow.
TASO: We aren’t a recruiting shop, we aren’t a typical staffing company whereby we send you ten resumes and you say “Okay, I want to screen and talk to all these folks.” We generally send you one. And the reason that we are able to do that is because we actually have a lot of process and domain expertise internally to be able to vet those talents, whether it’s in finance or software development, to ensure that that person, before we send them to you, is the perfect match.
So it’s about getting information from you up front in a more modern way than a staffing or recruitment company generally does it, and then facilitating the matching process through software and processes that are reinforced through software.
MATT: Let’s do some level setting around the company. I know you’re private.
TASO: Yes.
MATT: But to whatever extent you can talk publicly about how many people is it, how many people are on the platform? If you can talk about revenue at all…? Just to give the listeners an idea.
TASO: In terms of a core team we are approximately 500 full time internal folks. Those folks work on software development for our platform, for the website, for different technologies that help facilitate the screening and matching processes, and so on and so forth. And then we have other folks who work in operations, marketing, and so forth. So that team is about 500, let’s say.
MATT:Were you distributed from the start?
TASO: Yes, we were distributed from the start. I started the company on a handshake and then contracting out a software developer to a company almost without a website. So that is really how the company started. And I was in Palo Alto at the time. The individual who was contracted out — actually, we pretty much had two — were in Argentina and South Africa. And I was actually going to an office that my roommate’s family’s friend allowed me to have as a way to go to work everyday.
However, the point was rather moot. I was going into an office but not seeing anyone or interacting with anyone except myself. So it almost was this zombie-like walk to the office every morning where I’m going to the office because I go to work, but I don’t see anyone who I work with. [laughs] And so I actually started waking up and just working on my computer at home.
And then I said to myself, “Well why am I even working from home? I should just go somewhere else because I’ve never really traveled!” So I ended up going to Europe and all sorts of different places. And that’s what took me on my remote journey, so to speak.
MATT: So, FotoLog and Slide, places you were before, did those have distributed teams or were they mostly co-located?
TASO: Those were in-office companies. I went into the office pretty much everyday. The remote working nature was there, but it was very light.
MATT: So 500 people. I know a couple years ago you said it was over $100 million revenue, so I imagine it’s beyond that.
TASO: Yes, and this year we are likely to be in the nine figures in net revenue, which is a really big accomplishment for the company.
MATT: Congratulations, that’s huge.
TASO: Thank you, yes.
MATT: Again I think it’s good to set this up because not that many people know about Toptal yet.
TASO: [laughs] Well said.
MATT: And after this podcast, at least dozens more will.
TASO: A few dozen, a few dozen.
MATT: One of the worries people have about building distributed companies and distributed work is this hiring aspect. How does that work for you all? How do people find you? How do you screen them? What can you tell us about that process?
TASO: A lot of people find us through our brand. Freelancers find us in different countries as we are generally the best source for them to get good jobs remotely, especially within the United States and with Fortune 500-type companies, companies that are doing more serious engineering work and are longer-term engagements.
So our reputation has permeated in those types of environments on the talent side. On the client side, I would say it’s similar. Now, of course we do marketing, however, we do often have referrals, and word of mouth is a strong way that we get a fair amount of business. So those are, on both sides, really how people know about us, generally speaking.
MATT: How many applications do you all get?
TASO: Oh my gosh. Here’s an interesting stat actually. At this point in time, I believe, and I’d have to double-check this, it’s over a million a year.
MATT: Wow.
TASO: And to put that in perspective, Google as a company gets approximately 1.2 million applications a year as a company.
MATT: Wow.
TASO: So if you look at it from that perspective it’s actually a pretty sizeable volume. It is a little bit apples and oranges because all we do is screen talent, that’s it.
MATT: But it probably speaks to how much global talent there is looking for remote opportunities, which is one of the big advantages of being in a distributed company.
TASO: It does. And that is kind of the miracle of it, I suppose. While we are doing a million applications a year, I think that absolutely pales in comparison to what’s out there and what we could do if we put even more effort behind it. My assertion, if we went pedal to the metal and we started doing a lot more advertising, we actually worked to amplify it, I think we could get easily four to five million applications a year globally. If you think about —
MATT: Wow. I can’t imagine that applicant tracking system.
TASO: [laughs] Well we built our own because all the other ones were certainly not sufficient. If you think about it from that perspective, that not only highlights the amount of people that are talented all over the world but it also highlights the amount of people that want to work remotely that are not today. And so the far majority of our applications want to work remotely, meaning they are not working remotely today but they are applying because they see it as a huge, life changing opportunity for them. And so it’s really interesting to see the dichotomy between what is today versus what we’re seeing people want tomorrow to look like.
MATT: So I’m an engineer somewhere, I want more flexibility, I go on Toptal. Let’s say my resume makes it through. How do you determine whether I’m top two, three percent or not?
TASO: Well it’s a subjective process, and so I can’t state it’s perfect, but we err on the side of conservatism so that we have a near-guaranteed great experience for our clients, in a similar sense that McKinsey does or that some other top-tier firms that offer top talent, so to speak. The real high-level deals are that you go through what is in effect an interview process.
MATT: Like you’re going to be hired?
TASO: Like you’re going to be hired at a Google or a McKinsey or a company like this, depending on the vertical.
MATT: How important are their technical skills versus their people or soft skills?
TASO: They are both incredibly important to us. So we have looked at, for example, how McKinsey screens people. And we have actually taken some of those processe and refined them and introduced them into our screening processes. Same with Google, same with some other companies that are keen on hiring good cultural fits. I wouldn’t say in terms of our own network there is a unified culture, but there are certainly elements that unify people in terms of soft skills.
They have high integrity, they have punctuality. No kidding — something we screen rigorously for. They have good judgment, which we are able to screen for in different areas. So if you think about elements like that, you can actually screen well beyond hard skills. Do you know how to write an algorithm in constant time versus quadratic time, or something of the nature like this, which is still a very important skill to have. But I would actually say the soft skills are, especially when working remotely, more important.
MATT: So even if I’m a brilliant engineer, if I show up late to your interview, it’s going to be a mark against me and you might not hire me if I don’t have those good soft skills?
TASO: Oh 100%. The punctuality component is very, very real. So if you show up just a little late you will literally be rejected automatically.
MATT: Wow.
TASO: And people get pissed on this point. They’re like “Hey, I was on another call, I went through the—” Hey, look, that’s our integrity on the line. If McKinsey and the best companies have survived by upping the bar in terms of integrity, we’re going to do the same.
MATT: I was going to ask how you test for integrity, and punctuality is an interesting window into that.
TASO: Yes.
MATT: What are some other things that you feel like are really important to the Toptal culture?
TASO: One element that I can speak to is the character of the person. As many people know, great engineers can be very abrasive. And I would say there was a point in my life, if not still in many cases, I can be abrasive. But if you go into an interview process and you understand it’s professional, you have to show your best self. And if you are abrasive when you’re showing your best self, it doesn’t go uphill from there. Right? [laughs] It kind of goes downhill.
So you have to be very judgmental on those factors because if they are introduced to a client that then experiences Toptal as a group of abrasive but brilliant people, that’s not going to resonate with them very well. So you have to take elements like that, that are a little bit more subjective, a little bit more nuanced, and factor them into the equation, because it’s not just about whether you can write algorithms or not.
MATT: Like all distributed workforces, like your own, for a lot of people English is not their first language.
TASO: Correct.
MATT: So are there resources you point to or anything or is that something people need to learn on their own?
TASO: Internally at Toptal, we have provided English lessons before. We don’t anymore. But it’s generally something, both in our core and externally in our network, that we expect people to know coming into Toptal, whether that’s through our network or through the core team.
MATT: I actually was pitching this to Austin from Lambda School. Part of what they’re doing is taking people who don’t know how to code and teaching them to code.
TASO: Sure.
MATT: I think there’s a huge opportunity in that there are probably millions of great engineers who are great coders and don’t know English well.
TASO: I would say that’s the case.
MATT: So versus teaching someone how to code, teach them English. I don’t know which is harder, to be honest. They’re both learning a language, just an artificial versus natural language.
TASO: We have thought of putting people through different re-skilling programs. However, I’ve never thought about it as well — if you already know blockchain but you speak Chinese, can we just teach you English and will you be able to work with people internationally?
MATT: How do you decide if who you’re hiring goes to the Toptal internal team versus clients?
TASO: It’s very separated. It’s very separated so that we have clear client expectations and KPIs and we have clear internal KPIs in processes. You would think we would mix them, that we would leverage the incredible technology that we’ve built for our network, but it wasn’t so easy to compartmentalize.
MATT: So Toptal itself is not a client on Toptal?
TASO: We are in some instances but we are not using it to the extent that people would think we would use it.
MATT: When you say KPIs, what are the differences?
TASO: We are looking at time to hire, time to fill, so on and so forth. So we would have to disable all these components. In regards to how we do our screening we have capacity, metrics and triggers that exist in there to help manage the pipelines. It’s a really big system, rightfully so, for Toptal the network. Internally it’s a little bit difficult to decouple from the purpose that it has already been constructed to serve.
MATT: Let’s zoom into the virtual wall.
TASO: Sure, sure.
MATT: Tell me a bit about how the company is set up. Who are your direct reports, how is your hierarchy and what’s your structure? How should people think about Toptal?
TASO: Let’s kick it off with how the company operates. I think that’s a good window into how we work and gives you some good insights into how structured we are, how we set goals, how we actually work day-to-day. We have an OKR method that we use, like many companies, to set objectives quarterly, annually, so on and so forth, and we are very rigorous about it. We are very methodical about it.
MATT: As CEO you have some OKRs and those..?
TASO: I do, yeah.
MATT: What are some off-the-shelf tools you use?
TASO: Slack, Zoom. In terms of product management we use Jira. What I find really interesting is Confluence. I find Confluence very interesting.
MATT: That’s their internal blogging thing, right?
TASO: It’s actually more like a Wikipedia slash —
MATT: Yes, like document management plus some internal — what I would call blogging, but you can use it instead of email, right?
TASO: Right. It’s still a little bit cumbersome, still a little bit big in some instances, but it is a really good tool.
MATT: I know Atlassian runs on it religiously.
TASO: Yes.
MATT: They say it’s their secret weapon, it’s the thing that makes everything work.
TASO: We’ve started to go down that path actually for knowledge management, and for documenting processes, and for other elements that are important for the company to be unified on.
MATT: So those are some off the shelf ones. Any others that come to mind? Google Apps, Office 365?
TASO: Yes, Google Apps. Yes, I would highly recommend it. [laughs]
MATT: Yes, it’s pretty good. They did a good job there. Who’s on your exec team? How did you meet?
TASO: Sure. So our executive team is pretty traditional. It depends if you’re looking at a more traditional company or an internet company. We have a fair amount more executives that report directly to me. That’s a personal choice.
MATT: So is it flat at the top?
TASO: I have about 12 direct reports. And from what I’ve seen via conversations and from what other companies are doing, that tends to be on the larger side of things. I have seen companies with 20 and I think we even had 20 at one point, not realizing how bloated that was. And so we —
MATT: So what reports directly into you? Is there a CTO, HR?
TASO: CTO, CAO, we have a chief administrative officer, that person is really working to refine all the processes, the data analytics, business insights. A VP of people, a VP of brand marketing, a VP of growth marketing, a VP of design, a VP of comms, a VP of finance and probably two others that I’m missing.
MATT: How do you all get together? Where are those people located?
TASO: Well our VP of finance is in Pennsylvania. Our general counsel is in Massachusetts. Our VP of product is in Greece.
MATT: So these people are all over the world.
TASO: They are all over the world.
MATT: And do you meet weekly, every other week?
TASO: We meet biweekly, so every two weeks we have meetings. And that is the cadence at which we meet. We also have an all-hands that’s monthly. And so that gives you insight into how often our all-hands occur with our company.
MATT: We do a similar thing where once a month we do — we call it a Town Hall. Typically the questions come in via text but everyone is on video now. We can all be on Zoom. You can get hundreds of people on Zoom pretty easy now and it’s — so sometimes they come in real time. I really like it. I also enjoy not knowing what’s coming next. We don’t pre-moderate or pre-screen the questions or anything. It’s just whatever pops up at the time. Everyone sees the question being asked. It’s not like I can skip them if I don’t like it. And sometimes the conversations are difficult, sometimes the answer is “I don’t know” or “Maybe we made a mistake,” or things like that.
TASO: Right. We used to do it via text. Now we’ve just chosen to do it in a free-form style, so that it’s a little bit more engaging. We also had a method by which you could do it anonymously, which we have totally abolished across all of Toptal. We don’t have anyone have anonymity. And while I understand that there may be ramifications of people not being as forthcoming as they may, it’s really our duty to ensure that we create an environment where they can be.
MATT: When did you do that and why?
TASO: We did that because you’re actually taking an action that encourages hiding and we don’t believe in hiding anything. We believe in radical transparency, radical truth, bringing difficult conversations and difficult topics to the forefront. And by taking that action, you’re saying “We actually believe in hiding something.” Well I don’t believe in that and I would say our executive team doesn’t believe in that, so we have abolished it.
MATT: When did you abolish it?
TASO: About seven or eight months ago.
MATT: Pretty recent.
TASO: Yes.
MATT: I’ve got some quick ones as we wrap up. Tell me quickly what is your ideal workspace? Where are you productive?
TASO: I am productive sitting at a desk I am familiar with.
MATT: Do you have a big monitor? What’s your —
TASO: I don’t have a very big monitor, I have a regular sized monitor, but I’m just familiar with the setting, it’s something about the familiar setting that allows me to be focused. So if I’m in a hotel room, my first impulse I suppose, is to get out of the hotel room, go to a meeting, go connect with someone because you’re traveling. It’s not to sit down and focus and go through Excel and dive deep into the nitty-gritty details of whatever it might be, whether they’re financial reports or they are reports about whatever it might be, and scrutinize them.
Likewise, when I’m on a plane, I’m always reading. It’s just my natural state, so to speak, on a plane. And so whenever I’m at a desk that I’m familiar with, with my computer that I’m familiar with, I can do work much more productively.
MATT: How often would you say you’re home versus on the road or traveling?
TASO: I’d say it’s 80/20 now. So I am more so settled, working, than I am traveling.
MATT: That’s a good thing to note, that a lot of people think remote or distributed means you’re on the road all the time.
TASO: Oh no.
MATT: And actually I think the vast majority of people at Automattic at least, they’re in the same place 95% of the time.
TASO: 100%.
MATT: How about meetups? When does your team meet up in person, if ever?
TASO: Yes, our executive team probably meets up on average every 18 months. So not so much, but I don’t see it as a requirement. When we meet up, it’s generally when there are some executive changes and we are unfamiliar with one another. And so —
MATT: And are there other meetups within the company?
TASO: Yes. Actually, as we’re speaking right now there’s a function that’s having a meetup in Miami.
MATT: So like all the designers, all the engineers might get together, something like that?
TASO: Precisely. It’s a little bit too large for the engineering team, being about 200 people, to be able to do that, but yeah. On a functional basis, especially with some of the smaller functions, they’ll be doing that.
MATT: Do you have any must-have equipment that makes for ideal work?
TASO: A laptop and a phone. [laughs]
MATT: That’s it? Nice. You mentioned Zoom, Slack, phone? Do you make phone calls? Do you talk to people? How much are you on text versus video, versus audio?
TASO: I would say I have moved to mostly video. When I’m mobile I don’t do video generally because my battery is dying. [laughs] But generally I’m on audio when I am traveling and I’m on video when I’m situated.
MATT: Last question. Let’s fast-forward 20 years from now, what percentage of jobs do you think will be distributed or remote?
TASO: I believe that at least 50% of all technology jobs will be distributed.
MATT: That’s wild. Because it’s probably, I don’t know, what is it today? Probably under 10%?
TASO: It’s under 10%, but it is growing so fast and there is such a strong movement across the world for this. You have all of these strange companies, Toptal, Automattic, InVision, GitLab, so on and so forth.
MATT: We’re not that strange. [laughter] But I get what you say. Right now it’s the exception. In the future I think it’s the rule.
TASO: Exactly. And they’re looking at us saying “Okay, yeah, they created a billion dollar company. It’s a billion dollar company, we’re a $200 billion company. This is hogwash,” right?
MATT: It’s a toy. Yeah.
TASO: Well more and more people are doing it. More and more people are picking up on the fact that this is the future and that is becoming more and more compelling to the talent. So more talent are keen on working for those companies — the Toptals and the Automattics of the world. And that’s just going to grow.
So what’s going to happen is, all these small companies where they’re working remotely, well actually that’s going to be the majority of the talent in the world. And when these companies can’t recruit them anymore and there are millions of people working remotely that are skilled, and they’re saying, “Well we want you to work in our office,” they’re going to say, “You know what? I don’t work for companies like yours because you’re the old, stodgy company. You’re the company that doesn’t understand the future and opportunity and innovation.” And that’s when it’s going to come and force them to be remote.
So you’re going to see that happen because the workforce of talented people is going to be more keen on remote work than not. And people don’t see that now but once they’re unable to recruit at all from anywhere, in effect, that’s when the change is actually going to happen.
MATT: Amen. [laughter] I think that’s a great place to end it. Thank you again, Taso, and I hope to continue this conversation in the future.
TASO: Thank you.
MATT: That was Taso Du Val, and I’m very glad he was able to join and share his experiences.
On the next episode of the Distributed podcast, I’ll be speaking to Lydia X.Z. Brown. Lydia is a lot of things: a writer, advocate, organizer, strategist, educator, speaker, and attorney. I’m interested in talking with Lydia about how distributed work can make work more accessible to people with all kinds of disabilities, and learning more about what inclusion means in a distributed context.
Thank you so much for joining us, and see you next time.
Stephen Wolfram on 28 Years of Remote Work
Oct 03, 2019
Stephen Wolfram started out on an academic career path, but eventually realized that founding a company would allow him to pursue his scientific work more efficiently. He’s served as a remote CEO of Wolfram Research for the last 28 years. In this episode, Stephen shares with host Matt Mullenweg — another remote CEO — his perspective on the value of geo-distribution, and the processes his partially-distributed company uses to make world-changing software.
The full episode transcript is below.
***
MATT MULLENWEG: Howdy, howdy. Welcome to the Distributed podcast. I’m your host, Matt Mullenweg.
I got the chance to catch up with today’s guest, Stephen Wolfram, because my company Automattic invited him to give a talk at our annual company meetup in Orlando, Florida. This is a magical occasion where all 950+ Automatticians (which is what we call ourselves) get together to meet up face-to-face. This gives us an opportunity to hang out, break bread, and collaborate over the course of a few days. We also invite a number of speakers, smart people like Stephen.
Stephen’s been leading Wolfram Research for 32 years, which is a really long time for a tech CEO. The company has pioneered a lot of different technologies in computation and education. Wolfram Research has about 850 employees, many of whom are scattered across 29 countries, so it’s pretty close in size to Automattic.
But Stephen’s been doing the remote CEO thing for way longer than I have — about 28 years! So naturally I wanted to pick his brain, which is an amazing brain, on why he chose to go the partially-distributed route, and learn about how he’s led his company remotely for longer than just about anybody.
Alright. Let’s get started.
MATT: Welcome. This is Distributed with Matt Mullenweg, and today we have Stephen Wolfram, who is the Founder and CEO of Wolfram Research, known for things such as Mathematica, an amazing tome called A New Kind of Science — which I guess you worked on for about ten and a half years — created Wolfram Alpha, which is one of the intelligence engines behind Alexa and Siri…
STEPHEN WOLFRAM: Siri and other things, yeah.
MATT: Yes, and of many other things. And just an incredible amount. I encourage you to google him. Go down the rabbit hole of all the amazing stuff and people he’s worked with and everything. Thank you so much for joining today.
STEPHEN: Nice to be here.
MATT: Part of the reason, in addition to all those fun things, that I wanted you to be here is your company is a similar size to Automattic, around 800-900, and is geo-distributed as well.
STEPHEN: Yes.
MATT: You have been a remote CEO since 1991.
STEPHEN: That is correct.
MATT: And your company goes back to..?
STEPHEN: Late ’86.
MATT: Possibly one of the older geo-distributed companies I’m familiar with.
STEPHEN: I think so. I mean, I know —
MATT: It’s got to be one of the longest, if it’s not—
STEPHEN: Yes, you’re right.
MATT: Maybe there’s something out there but that’s got to be one of the longest.
STEPHEN: Right.
MATT: That’s pretty cool. What caused you to be geo-distributed at the beginning?
STEPHEN: So OK, the first thing was, I started the company. This was the second company I started. The first company I started, I started when I was 21 years old and that was in Los Angeles, and that company was a pretty traditional company. It was venture-capital funded, I brought in a CEO, I didn’t CEO it myself, I was the technical person —
MATT: Did they call it adult supervision back then?
STEPHEN: No, no they didn’t. I mean that company went through various mergers and things and eventually went public some time in the 1990s in a very undistinguished IPO. So anyway, so my first company was not distributed at all, it sat in this building near the Los Angeles International Airport. [laughter]
I was involved in basic science and I had developed this area of science that I guess now gets called complexity theory, and so I tried to figure out what university would give me the best deal to start a research center in this kind of science. So I went around to lots of universities, and the one that won that was the University of Illinois in Champaign, Illinois. But I said, “OK, I’m going to start a company that builds the tools that I want to have for myself and that I perfectly well know are going to be useful to lots of other people in the world.”
So we started the company in Champaign, Illinois, which is not probably most people’s first choice for where to start a tech company, even back in 1986, but it was great. We got terrific people from the area — it’s a good university, producing a lot of interesting graduates. We were the only game in town, so to speak, and I think we’re still the largest tech operation there. So we started in a slightly outlying place. Then [we] got off to a very quick start, up to a couple hundred employees, maybe 150 or something. I was injecting ideas into this thing at a very high rate.
MATT: So when you inject ideas, you’re coming and saying, “Hey we should do this thing.”
STEPHEN: Yes. And getting more and more frustrated that they weren’t getting done. I have to say that just a few years ago we finally finished my 1991 to-do list.
MATT: Ha! [laughter]
STEPHEN: So it’s done, that one is — it finally, finally happened.
MATT: That one’s… Yeah, the thing that got you to leave is now all the way complete.
STEPHEN: Yes, right. My original plan had been to build these tools that will, among other things, allow me to do the basic science that I wanted to do. I said, “Let me step back a bit and let me go off and spend some chunk of my time doing basic science, and let the company grow up and we’ll see what happens next. Maybe there will be a coup and somebody else will say ‘I can run this better than you can’.”
MATT: So everyone was in the office except for you?
STEPHEN: Not quite. What happened was — I’m trying to remember how many people weren’t in the office at that point, but I was definitely the main go-offsite person.
MATT: What were the tools at that time? Was that because you had been in a university setting and were familiar with email or internet?
STEPHEN: Yes, well I started using email in 1976. So that was —
MATT: That was pretty familiar to you.
STEPHEN: Yes, right. It was modems dialing up. My email would arrive in bunches every 15 minutes. And I was on the phone a bunch. I had hired a chief operating officer.
MATT: I was going to ask what the exec team looked like. You had a COO who could be the on-the-ground lead?
STEPHEN: Right, who was with us for six or seven years. And he did a good job of maturing the company from being high-growth to something which had good systems in place and could roll forward.
MATT: And this second iteration of the company, did you also raise venture capital, or did you decide to take a different approach to have the longevity?
STEPHEN: No, no, not at all. Version two — I was the CEO from the beginning and forever type [of] thing, no outside money ever. It’s been a shame for me that I’ve never really had a quote “business partner.” I think of myself as pretty average at business kinds of things but I’m not totally incompetent.
Personally I view it as an optimization. You can do things that are very commercial, but a little bit intellectually boring. And it tends to be the case that you’re doing a lot of rinse-and-repeat stuff if you want to grow purely commercially, so to speak, or you can do things that are wonderful intellectually, but the world doesn’t happen to value them and you can’t make commercial sense that way. And I’ve tried to navigate something in between those two where I’m really intellectually interested and where it’s commercially successful enough to sustain the process for a long time.
MATT: I love finding that intersection.
STEPHEN: Oh yeah.
MATT: And it feels like now that the world has caught up a little bit to voice assistance and the natural language processing stuff you’ve been working on forever, that you found — is that the main business model for Wolfram Research now?
STEPHEN: No, no.
MATT: Oh, I would’ve thought that licensing drove it because there must be billions of users of these voice assistants.
STEPHEN: There are. Yes. And it’s a good source of revenue. At this point it’s fairly diverse. There’s a big chunk of licensing software but a lot of that — there’s, for example, the academic sector, there’s site licenses to universities where basically the goal is to make the software free for people to use at universities, and we’re complete now in the U.S. in the sense that all the major universities have site licenses. So if you’re any kind of major university in the U.S., you will be able to use our software for free. And there’s a lot of commercial use of software where we’re basically selling pre-packaged software. It’s been nice that it has been gradually quite diversified between different kinds of channels.
Back to the whole no venture capital do. It’s been great. I don’t have a boss. I recommend it. [laughter] And also I can do things —
MATT: I feel like you always have a boss. It might be a customer or all of the customers in the world.
STEPHEN: Yeah, at some level —
MATT: It could be the employees for whom you’ll respond to if they reach out.
STEPHEN: That is correct. Yes, that is really what happens. But in the first approximation you think, “Oh, I can do anything,” and then the second approximation is, “Oh, we have all these customers. Oh, we have all these employees.” I take those responsibilities really seriously. But I’ve been doing them so long that they seem natural, so to speak. It’s a thing where there is a certain kind of intellectual freedom, that I at least believe that I have by virtue of the fact that I’m just responsible to myself.
MATT: I will say that I think, as a result of so much capital flooding into the market, that there now are very long-term investors who, if you choose them correctly, can be aligned on longer time spans than the standard five to seven [year] fund life of some of the historical venture capital.
STEPHEN: Right.
MATT: And founders now are able to retain a lot of control through voting mechanisms. They might sell economic interest but [you’re] no longer selling control interest.
STEPHEN: I always wonder how that’s going to come out in the end. I thought about taking my company public back in the early 1990s. We were on a great trajectory and etcetera, etcetera, etcetera. But then I was like, “Hmm, I don’t know.” Actually the final thing was my employees saying, “Why are we doing this? This doesn’t seem like a way to have a good time,” type thing.
MATT: That’s great that you had the kind of culture where people felt comfortable challenging that as well.
STEPHEN: Yes, yes. I think it’s fair to say that we have a culture — We have a lot of very bright people who have a lot of opinions. And I like to believe that we have a company where what we are mostly interested in is finding people who can be productive in our environment, and they have very different personalities. Some of them, I think I at least, have the view that they pretty much couldn’t work anywhere else because they’re —
MATT: [laughs] Unemployable.
STEPHEN: They have very unusual personality traits and poor internal politics skills and so on.
MATT: What makes them successful at Wolfram?
STEPHEN: That they do good work. That’s the thing that I —
MATT: Part of good work is working with colleagues and the teamwork aspect.
STEPHEN: Yes, yes. But I think that the role of management is given who these people are, how do you fit them together with what we are trying to do in such a way that you take advantage of their good traits.
MATT: So to end the business thread, do you grow the employee base of the company along with the revenue or with your scope of what you’re trying to accomplish?
STEPHEN: Good question. We have been lucky enough, touch wood, that we have been profitable every year for 31 years now. That is achieved by a very simple process, which is, spend less than you make. Thankfully we have never had to have a big “Oh my gosh, the revenue is less than we expected, let’s let people—” No. We’ve fortunately never had that. Our general principle is we’ll pay Champaign, Illinois rates for a certain set of people. Other people, it will be based on where they are, but we’re never going to go above that.
So that means when people wind up in San Francisco or New York, we’ll often lose them because we’re not going to pay the rates that people expect and need in those places. On the other hand, if they find some obscure place somewhere, they’re going to be doing really well because —
MATT: I recommend Houston, where I’m based. Not too obscure and a very reasonable place to leave.
STEPHEN: Yes, we have quite a number of people in Texas. I think we may even have a couple people in Houston. I’d have to look at the map.
MATT: I read some really interesting research hypothesis around why geographic mobility has gone down in the United States. You would think people would move more for economic opportunity but it has actually gone down. And the conclusion of this was the blocker was two-income households.
STEPHEN: Yes.
MATT: Where if one person were moving, and the sole breadwinner, you only have to find one job. And now you have to find two jobs in the new city, which is at least twice as hard.
STEPHEN: That’s interesting, yes.
MATT: But when one of the partners has no geographic attachments, you end up following. I just talked to a colleague who ended up in Copenhagen and he’s from — I forget where — some place very far from Copenhagen. He said, “Yeah, my wife got a research job and now we’re in Copenhagen for a few years.”
STEPHEN: Yes, we find that all the time. There were some obscure ones. Like there’s one guy in our user interface team who’s been at the company a long time, but he said, “Well I’m going to go remote and I’m going to this island off the coast of Nicaragua because my wife is a primatologist and she is studying… What were they? Some kind of monkey-like creatures on this island. And he got a microwave link set up, and there he was, being perfectly productive.
MATT: Impressive.
STEPHEN: To me the focus is on — Can you be productive? Are you doing good stuff? And then where you live is your independent business, so to speak. There is a certain amount of complexity in scheduling things and meetings and so on when people are in all different time zones, but somehow that doesn’t end up being that horrifying.
MATT: Is there some sort of predetermined taxonomy or is it more of a free-form?
STEPHEN: It’s free-form. One of the things that is fun about my company is I think of us as a microcosm of what goes on, because we have people from the history PhDs who are actually doing history stuff for us, to the people who are doing — whether it’s graphic design or whether it’s some software engineering, server infrastructure thing.
One of the things we’ve done — I don’t know how you’ve done this — but the company is pretty vertically integrated in the sense that we don’t outsource anything really. It’s all in-house graphic design, legal, this, that, and the other. Partly because we’ve got enough stuff going on that there’s not really a group that’s going to have nothing to do. And it also really, really helps to have, let’s say, designers who really know and understand our technology, and they’ve met customers of ours and they know the story. And plus some of the people in our design group become really good Wolfram Language programmers.
MATT: Cool. Actually some of our best developers and architects started off as designers.
STEPHEN: Yes, I think it’s a really good field to start in. It’s funny, because I track where people come from and so on, and physics, for example, is good. For the techies, it’s a really good export field, so to speak, and I think graphic design is another one of these good export fields, where you learn a certain discipline of thinking to do good graphic design.
For a while it seemed like UX was — we were pretty early in the hiring of official UX people and it seemed like that might be taking off more in that direction, but I think it’s a little bit merged with the graphic design. And I feel like sometimes the designers — they always have something to show for what they’ve done, in a sense, whereas UX is a little bit less clear. Somebody made this flow diagram or something but that turned into something different from what finally came out.
MATT: The visual communication helps a ton, right, for getting people on the same page?
STEPHEN: Yes.
MATT: It’s one thing we’re trying to do more, is just draw something, even if you’re not an artist or a designer or anything, so you really are on the same page, literally, with what you’re trying to communicate.
STEPHEN: Yes. I don’t know in your geo-distributed setup, but we never use video conferencing, I mean really never, to the point where —
MATT: It’s always screen sharing and voice?
STEPHEN: It’s just screen sharing and voice.
MATT: It’s mostly video actually, with us. And what was interesting to me observing it from the outside, is before Zoom, we had very few meetings because I felt like the process was so frustrating to everyone, we just didn’t do it. And Zoom spread like wildfire in our organization because there was just something to it that made it — It worked just a bit better, it got over that threshold, whatever that uncanny valley was that kept us from using it before. And now I think we have too many meetings, perhaps. But video is a thing, and people think about their background and try to have good lighting. Good audio is really important to me personally.
STEPHEN: Yes. Good audio is very important to me. I am always complaining about that.
MATT: I will send you a link to the Sennheiser headset we like. It’s USB and it’s only about $34. It’s become very standard.
STEPHEN: OK, I’d like that. Yes, we’ve spent lots of effort on headsets for people and complaining about people not having the right audio setup and so on. And I am glad to know that I’m not the only person who really cares about that.
MATT: It makes a huge difference. I’ll use this opportunity to tell people to check out your blog post. Was it “Seeking the Productive Life?”
STEPHEN: Yes.
MATT: On your WordPress-powered blog.
STEPHEN: Indeed.
MATT: Which is a very comprehensive view of your entire personal operating system and productivity, which I found — well, it’s impossible to summarize. And then two, we used this to point to [the fact] that you have started livestreaming many of your design meetings.
STEPHEN: Yes.
MATT: And so I could probably google “Wolfram livestream” or something?
STEPHEN: Probably, yes, right.
MATT: And so these actual internal meetings are now broadcasting publicly, which is pretty unique and fascinating.
STEPHEN: That is correct. This livestream meetings thing, I started doing it about a year and a half ago or something because I thought, these meetings are fascinating. It’s a shame for these things to just go off into the ether and nobody — so I thought, let’s do this.
MATT: It’s mostly screens and then audio?
STEPHEN: Screens and audio, no people. We’ll get people who are both expert users of our product and often world experts in the particular thing that we are talking about. And they show up and they contribute useful things.
MATT: It’s interesting. You have a lot about your company which is very much like how open source works, but a lot of what you do is not open source, correct?
STEPHEN: That is correct.
MATT: There is a post I read about this while doing some research, 12 reasons — I think one of your colleagues wrote it — that Wolfram Language wasn’t open source. And one of them was, things like language design aren’t benefited from being more open, is how I interpreted one of them.
STEPHEN: Yes, probably, yes. I think — look, it’s a complicated thing because my goal is to be able to produce this intellectually valuable, long-term thing. And the question is, given the world as it is, what is the best way to do that. And we have built, back 33 years ago, when I started the company — it was like, OK, we’re going to sell pre-packaged software. And I didn’t know whether that industry would survive. I mean back at that time —
MATT: It wasn’t clear, right? Piracy was huge.
STEPHEN: Yes, piracy was a big problem. Another big problem was, what was the price point going to be for software? Because at that time there was Borland versus Microsoft. Borland was at $100, Microsoft was at $500 for typical software. And it’s like, who’s going to win in that space?
MATT: How much is Mathematica?
STEPHEN: Well it’s very complicated. [laughter] It ranges from —
MATT: How much was it at the beginning?
STEPHEN: It was $495. But no, I think what we’ve done — it’s a thing I’ve thought about quite a bit — what is the right way to slice — We are trying to do a long-term, intellectually valuable thing, having something — maintaining that kind of coherence over a long period of time, I don’t know what the best way to do it is. I think we have found a pretty good scheme. Wolfram Alpha has been free from the beginning to use.
We recently introduced this thing, a free Wolfram engine for developers, which people seem to like. And the deal is, using it for development, it’s free, you can do whatever you want with it. But if your work product is what it is producing, if it is actually in production, that’s when you have to start paying something for it.
MATT: I think it’s interesting, you’re adopting some of the elements of what helps open source become ubiquitous, and some of the open things that, by the way, open source didn’t invent — they came from academia and many things before, in terms of the collaboration — and I think it’s very cool.
STEPHEN: An important thing for us is the alignment of where we make money versus who is actually getting value, who our real customers are. And I think some of the cracks that are happening in some of the areas of the technology industry — I think come from a lack of alignment between — who are the actual customers? Well the actual customers are advertisers, they are not the people who are — whatever else. And I think we have been both lucky in that our customer base is wonderful people we really like.
The thing that tended to happen though is these projects that — it starts open source and then there is some kind of bait-and-switch somewhere. And it just drives me crazy. We keep on —
MATT: I totally agree. And that was the open-source model for a long time. We’re going to be open source but then hey, that open-source license is really scary, don’t use it, buy our proprietary license, or things like that.
STEPHEN: Right.
MATT: Or we’re going to put all the good, new stuff in this proprietary version of the license.
STEPHEN: Right, right.
MATT: That’s why I want to talk more about open source at some point because, if you look at — They’re not always the best products, Wikipedia was not the best, WordPress in some ways you could say is not the best. Chromium engine — I don’t know if you saw the engine behind Chrome was just actually adopted by Internet Explorer.
STEPHEN: Yeah.
MATT: So we’re getting a ubiquity and a de-facto standardization of a code base that becomes so useful.
STEPHEN: Right.
MATT: You could never force Microsoft and Google to say, “We’re going to do the same thing.” But they have, through their own personal utility maximization, have chosen to collaborate in this one area, which is really beautiful.
STEPHEN: That’s interesting. There are these different things, like, let people see the source, right? I don’t care if people see the source, that’s not the issue. I mean that’s not the point. Although we did have an interesting experience.
So one thing happened because our products get used for lots of fancy, tech-y things. At the very beginning we would have the following sort of thing that would happen. Some mathematician would come up at a trade show and say, “How can I trust your stuff, I can’t see inside how everything works?” And I’d say, “Well how can we trust these papers you’re writing?” It’s kind of like, their mechanism for validity is peer review. Our mechanism for validity is software quality assurance, which is a lot better.
MATT: I take it you have some opinions on peer review?
STEPHEN: Oh, it’s terrible. I think peer review is — I always thought it was broken, even when I was in the business, so to speak. My point of view was, if I have an original paper or idea, it’s going to be really tough to get it through a peer review process. 1986 was the last time I published a paper in an academic journal. I decided they were a bad idea and I wasn’t going to do it.
MATT: And now you have a blog, which is even better.
STEPHEN: Yes, the blog is — some of the things I write on the blog are quite academic. And it’s really interesting, I remember I was writing a piece about Ada Lovelace, actually, at the time of her 200th birthday celebration. And I happened to, at the last minute, I decided to go to England and go to some fancy celebration that was happening about it.
And I was visiting some museum that has a bunch of her papers and so on, which I’d already got copies of most of. But the curator there was saying, who was used to academic stuff, was saying, “When do you think you’ll be publishing this?”, thinking the answer would be a year from now or something. And it’s like, well no, I’m going to publish it tomorrow morning before I get on a plane. Because you can write anything there.
MATT: And you do.
STEPHEN: And I write some stuff that’s quite technical and some stuff that is quite product-oriented.
MATT: Back to that live-streaming of meetings. I think it’s great that you say the meetings are kind of like they were before you live-streamed. They’re not too performative or anything.
STEPHEN: Yes.
MATT: I’ll add something else to that, which is you said you’re a CEO for life, more or less, there is a lot of authority vested in you and this company, but it also seems simultaneously that people are comfortable with challenging you and presumably the other executives. What do you feel like you’ve done to foster that culture where there is a comfort, it sounds like, at many levels to challenge you very directly?
STEPHEN: Yes, it’s an interesting question. I suppose that I’m actually prepared to listen at some point. Some of these things get quite heated. It’s hardly as if — I don’t necessarily — I kind of know myself well enough to know by the time I’m getting heated, I don’t know what I’m talking about. That is the typical — and I will even say that because if I can explain myself, I’m just going to explain myself. And it’s always frustrating when people don’t speak up and don’t say —
MATT: Do you do anything to encourage people who you might feel are hanging back a little in the meeting?
STEPHEN: Yes. I am enough of a people person. The fact is that having been running a company for 33 years, if I wasn’t a people person it would have driven me nuts, OK?
MATT: Or them away and there wouldn’t be a company. [laughs]
STEPHEN: Yes, yeah, right. I like people, I find people interesting. Sometimes I would say, more cynically I would say, after I’ve been managing people for 40-something years, and you might have thought you’ve seen every pathology that could possibly happen. But no, there is always a new one. At this point I just find it faintly amusing that — “Oh my gosh, another bizarre thing I’ve never seen before.”
And I see a large part of my role being that I’ve got all these talented people, I’ve got all of these projects we’d like to do, how do we match talented people with projects we want to do?
MATT: Do people feel like they’re moving around or is there some stability once they get onto a project?
STEPHEN: There is as much stability as they want, basically. There are people who have worked at the company for 20 years, and have never done management even though I can tell they have a good personality to do management. And finally we persuade them, you should do this, and they say, “Oh this is actually quite interesting.”
MATT: Is that more in your head or do you do any sort of testing or other objective ways to determine people’s strength or potential abilities?
STEPHEN: No, nothing, other than the Who Knows What database of just factual information.
MATT: And does this all come from you or is this also the rest of your executive team?
STEPHEN: No, there is a bunch of people who have gotten experienced at doing this, I would say. When I look at org charts of companies I always —
MATT: I love org charts.
STEPHEN: Yes, right. That was probably a decade ago, I was like “Oh, our org chart is such a mess.” For a long time, our org chart was classified because there were people, it was like, particularly one person who was with the company for a long time, and has now spun off doing related things, but who was an executive at the company and was always like, “We shouldn’t really tell people what all the weird reporting arrangements are.” I wasn’t a big believer in this but it wasn’t…
But then, look at our org chart, and it seems messy in many ways. And then I was working — actually that was with Microsoft — and somebody who is actually now an even much more promoted executive at Microsoft, said to me, “We were trying to understand how it worked.” He said, “There’s this company on the outside that has reverse-engineered the Microsoft org chart, we just buy their stuff to understand what’s going on.”
MATT: That’s funny.
STEPHEN: Yes, right. So I get this thing and it’s a big foldout thing and it’s fascinating because it’s a huge mess. I mean, I don’t remember whether it’s still a mess but at that time it was a huge mess and you could see lots of historical stuff. And so after that I felt so much better about our org chart. Although, our org chart is now much cleaner, I would say.
MATT: It’s the map and the territory, right? Our org chart is currently clean but it’s not comprehensive, so there are some things that aren’t represented on the org chart, which sometimes a person is in two different places, that might be represented, but then they have informal authority in an area that we don’t try to demarcate necessarily.
STEPHEN: Right.
MATT: We have had a lot of success, actually, removing everything compensation-related from the management structure. So there’s only a few, only the centralized HR deals with all that and everyone else just focuses on getting the job done and peer feedback and everything.
STEPHEN: One thing at our company, which was a long-time joke, was the claim there are more projects than people at the company.
MATT: Yes, we have the same thing, wow.
STEPHEN: It has been a running joke — can we actually inventory all the projects? Well now we’ve, thankfully — I’ve got this team together to just go and do that and it has been a good process actually.
MATT: Are you familiar with Marie Kondo?
STEPHEN: Sure.
MATT: You know her thing is you put all the stuff that is the same, like all the clothing, in one pile. It sounds like you’re doing that from an organizational point of view.
STEPHEN: Yes, yeah…
MATT: You’re trying to get all that stuff together so you can sort it out.
STEPHEN: Right. I’d certainly like to apply software design methodologies to the way that we’re doing things. Look, the thing that we have done that I think has worked pretty well is we have pretty good project management, tradition, and infrastructure. And part of that is, I’ll come up with some crazy idea, actualizing that has to be flowed through the organization.
Now to be fair, I think I am probably — one of my less-bad traits is that I’ll come up with these ideas and then people will say, “How on earth are we going to actually do that?” And I will actually know, that is, if they don’t. It will be like, because I know enough about engineering and the whole technology stack, that I’ll be like, “Look, we can — some thing or other thing has to be authenticated here, and do this and that and the other, and I can actually dive down to a pretty high level of detail about how it should be done.
And I think part of my role is to explain why things aren’t impossible. And I see increasingly with a lot of projects we have done, the first response is, “That’s just impossible.” I’ll have some idea and it’s — and actually I am happy when people say that. When I’m not happy is when people say, “Oh sure, we’ll do it,” when I plainly know there is no way they can do it, it’s too hard. And so then I’m trying to figure out, “OK, so let’s see whether we can figure out how to do it.”
I think the other thing that I find I do a lot of now is, we have all these projects connecting — I’ll be in some meeting and somebody will be talking about, “Oh, I’m doing this, this, and this,” and I’ll say, “Oh, you should talk to so-and-so because they’re doing something similar.” And we were doing stuff to do with external storage systems. We have this group that’s been doing database integration and a blockchain group, and they all have things to do with this external storage story, and that becomes part of the role — explaining, just knowing enough about what’s going on around the company.
MATT: And how in this — I’m curious from a software point of view — how does maintenance work in this structure?
STEPHEN: Well that’s a good question. First of all, a lot of things we do in the language are quite modular. There’s a function, it fits into the language, but it doesn’t have a lot of nasty, dangling interdependency.
MATT: Gotcha.
STEPHEN: We’ve gotten a lot of experience and good systems for doing software quality assurance, and I think we are pretty good at doing that. Some of the QA we have to do is kind of hair-raising, like a lot of real-time things, which are always difficult, but even for Wolfram Alpha, there is — the natural language is a fundamentally non-modular thing.
MATT: Yes.
STEPHEN: So the classic example is if you type in “50 cents,” you have money, if you type in “50 Cent,” you get the rapper as the default thing. What happens when there is another rapper who is called “30 Cent” or something? That’s a very non-modular thing, and you have to be able to deal with all those kinds of situations. But I think we have done pretty well at that.
What we tend to do are these big subsystems. They get swept through every some number of years, and then a lot of stuff gets — a lot of things that we’ll fix —
MATT: Who decides to sweep through the system? Is it because a number of bugs accumulate?
STEPHEN: No, it’s not as organized as that. That’s a good question. It ends up being the people who run those engineering teams. I have to say that I am pleased with their level of responsibility in the sense that we are going to rewrite a bunch of the UI stuff because it’s out of date.
MATT: On the converse side, sometimes I believe it’s easier to write code than read code.
STEPHEN: Yes.
MATT: And so you get sometimes new engineers on an area who want to rewrite it partially to understand it.
STEPHEN: That’s true.
MATT: So how do you keep the over-read factor?
STEPHEN: Yes, right. Well I push back on that and say, “Why are we doing this?” In fact, I was just doing that yesterday, a particular thing. It’s like, we can do this wonderful thing — why are we doing this? This is not an important feature, this is just not the time to do it.
MATT: Are there programs around learning and developments or ongoing training?
STEPHEN: The one constant is a lot of our development, most of our development is in our own language. But at this point, most of the people we hire know it.
MATT: Before they get there?
STEPHEN: Yes, it’s kind of scary that the system is older than many of the employees. And they’re like, “Oh yeah, I started learning this when I was ten years old” type of thing. So that’s —
MATT: I’ve started to have conversations like that in WordPress and it is very humbling.
STEPHEN: Yes, yes, right. For some areas I let different managers have different rules about how they set that up, but some people insist the person should come to an actual office for some number of months when they start to get —
MATT: This is onboarding.
STEPHEN: Yes, right. And that seems to work well in some cases. And I don’t know whether it’s really necessary, I haven’t really — we haven’t done a —
MATT: Would a prospective employee know what kind of team they’re joining?
STEPHEN: Yes.
MATT: Are you hiring for specific teams or are they generally open roles and you try to place people based on their —
STEPHEN: We are placing people. But by the time they are actually joining, it’s pretty clear what they’re going to be doing, for sure.
MATT: You’ll say, “Hey, you’ll need to come to Champaign for two months,” or something?
STEPHEN: Yes, right. sometimes we’re hiring people where it’s like, “When I finish my PhD I’ll come,” and they’ll start in some number of months and we’ll say, “Well we’ll have something interesting for you to do.”
MATT: By then.
STEPHEN: Yes right, yes.
MATT: Let’s say I’m a coder in Houston and I apply to Wolfram. What is my process like on the way to being hired, assuming I will get hired?
STEPHEN: That’s a good question, actually, I don’t — I have to say, I regret the fact that I don’t get to see most of the frontline applications, only some of the more senior ones. I used to look at a bunch of these things. Cover letters are, to me, a critical part of the story. I haven’t been reading them recently because I have —
MATT: That’s why I don’t like applicant tracking systems, or form applications. I want to see how they email, what client they used, what fonts there are, how they formatted it. I want to see everything about the application as free-form as possible.
STEPHEN: Yes, right. What I find is that when I used to read these things a lot, the ones that were just, “Oh my god, I can’t believe this.” “I just graduated in computer science from this place and therefore I am qualified for whatever.” It’s like, no. And then there are other ones which say —
MATT: There are some cover letters though that are such a good story, and you can get a sense for someone’s clarity of writing.
STEPHEN: Yes, yeah, right. Well, also some of the ones that are more fun are things like, “I’ve been reporting bugs in your software for six or seven years now, I want to come and help fix them,” type of thing. That’s kind of cool.
MATT: What are the characteristics that you feel particularly makes someone successful at Wolfram Research?
STEPHEN: A certain independence of mind, that they can think about — that they keep the thinking apparatus engaged at all times. Oh, yes, a very important one — no bullshit. That’s a —
MATT: How do you detect that though?
STEPHEN: It’s really easy, I think. You just listen in the interview how people will say, “Oh, yes I know all about that process.” Well, I know a tiny bit. And sometimes —
MATT: Some people can be more humble in their —
STEPHEN: Right.
MATT: So interviews are very high-pressure. We do a lot of our interviewing on text, on a chat.
STEPHEN: Oh that’s interesting.
MATT: And that’s partially because we found that there is a class of people for whom a real-time conversation like this can be incredibly intimidating. There’s an asymmetry as well. They’re hoping for a new job and they just don’t perform well in that situation. That looks like almost nothing else we do in most people’s daily work. The interview, it’s very artificial. But the text chat looks a lot like what an average developer might do most of the day.
STEPHEN: That’s interesting.
MATT: So it can allow people that kind of space to — it’s like a take-home test a little bit. They can take five minutes to respond to something, they can Google something, if they get really freaked out by the question, they can take a walk around the table.
STEPHEN: I have to say, in all the interviewing that I do, people sometimes come into it tense but I don’t think — I think if you’re doing interviewing right, the people aren’t that tense.
MATT: It’s probably an inherent power dynamic that is impossible for you, in particular, to remove.
STEPHEN: Maybe, maybe.
MATT: Well text removes that even more.
STEPHEN: Yes. I would say that at some level, if the people are sufficiently intimidated, that’s probably not a great indicator, because the fact is, in our company, there are a bunch of strong opinions and people will express themselves. And if somebody is like, “Oh no, I can’t deal with that,” that probably isn’t a great indicator.
I have to say, it’s a different thing with more senior folk, like business people and things like that. That’s a horrifying world of interviewing, for me at least. Because people who have, who are used to a very polished presentation, it’s just so difficult to find out who is the actual person here.
MATT: How do you balance that pattern matching? Not leading the confirmation bias or where the company might need to evolve, which might be different from where it has been in the past?
STEPHEN: I’m a guy who likes new stuff, so that helps me be more change-oriented. I have to say that by the time it’s working smoothly, I’m not the person to be dealing with that. I have for myself and my personal life, I have endless systems that I have developed and they work, but also sometimes they stop working and then I’m like, “Oh, this doesn’t work anymore, I’m going to change it.”
For example, it could be the case that the things that I like and that resonate with me and that are the directions that I think of going are just not the ones the world happens to be keen on. A couple years ago I was like, “Let’s look at VR and AR.” And it’s like, well, I have a bunch of long-term people at the company, and they said, “You told us that in the early 1990s.”
MATT: That’s funny.
STEPHEN: What a bust that was at that time. You’re going to have to do better this time to convince us. And I have to say, I couldn’t. I couldn’t really convince them. Or IoT is another area where we’ve done a bunch of stuff, a bunch of interesting things, but it hasn’t quite taken off the way that I think some people thought it would.
This question of, when you’re the CEO, when do you fire yourself, type thing, and do you change, or is the thing going in a direction that you just don’t want to change it?
MATT: And your name is in the company, so how does that happen?
STEPHEN: Yes, right.
MATT: Is it just “research” at that point?
STEPHEN: Right. That’s an interesting issue. I was thinking —
MATT: We joke Automattic would be just “Auto-ic.”
STEPHEN: Right, right. I’ve been thinking of this. I was thinking at one time if I had a club of people who had named their companies after themselves. And you’ll be a partial member, right?
MATT: Thank you. Well we luckily have, I think, 17 other Matts at the company, so it could keep going without me.
STEPHEN: OK, OK. But I think —
MATT: Yes, I do joke — the egotistical founder, we always slip our name in. I want to ask two things as we wrap up. You have a lot of trust, it sounds like, which just allows this very candid communication, candor between folks. Do you have something like the meetups that we’re doing here?
STEPHEN: Yes, it’s not quite as formal. Once a year we have a technology conference. Users come, they have a good time, they get to meet a bunch of our employees. The employees come, they have a good time, they get to meet a bunch of our users.
MATT: Cool. Well after all this time, would you consider management or running a company computationally reducible?
STEPHEN: [laughs] That is a good question. This is one of the embarrassing things about people who like to think they’ve invented paradigms for thinking about stuff. The question is, “Can you live your own paradigm?” And it’s often the case in these things where I can see something developing at the company — I’ve been doing this a long time so I know how this story ends.
From the point of view of science and technology, there are things we’ve invented, I’ve invented. I could be very worried. Is the world ever going to pay attention to this, is the world ever going to care? Maybe I’m just too arrogant, but the fact is, I just know it’s going to go that way. This thing about computational language and the importance of having a rich language which can express computational thoughts, this is inexorable. This is going to be really important. I don’t know how long it will take the world to realize how important that is.
MATT: It’s not if, it’s when?
STEPHEN: Yes, yes.
MATT: Well that’s a good place to wrap up. Stephen, thank you so much. This has been an endlessly fascinating discussion and I’m looking forward to continuing it over dinner.
STEPHEN: Sounds good.
MATT: This has been Distributed with Matt Mullenweg and we’ll see you next time.
MATT: That was Stephen Wolfram. You can find him on Twitter at @stephen_wolfram. That’s Stephen with a PH, underscore, Wolfram — W-O-L-F-R-A-M. He also has an awesome blog, if you just google his name and “blog.” It’s powered by WordPress of course, and it’s really good.
Stephen says that he set out to build a company that would, quote, “allow him to build the tools to do what he wanted to do.” And by that he means working on projects that he calls “intellectually valuable.” It’s easy for CEOs to come up with lofty mission statements, but very few actually follow through. I’m inspired by Stephen’s steadfast commitment to intellectually valuable work and the organizational freedom that has allowed him to pursue it across three decades — and hopefully for many more to come.
Next time on the Distributed podcast, we’ll be talking to Taso Du Val, the CEO of Toptal, a freelancer network where employers can access a highly curated pool of remote contractors. Toptal itself is fully distributed, and they’re trying to convince blue-chip companies to integrate remote talent onto their teams, so I’m excited to talk about how this could help usher in a distributed future.
Thanks for joining us, and see you next time.
Automattic’s Sonal Gupta on Communication and Chaos
Sep 19, 2019
Sonal Gupta leads Automattic’s Other Bets division, a team that builds products that aren’t yet core to Automattic’s business, but keep the company innovating and pushing it to explore new territory. In this episode, Sonal and our host Matt Mullenweg talk about how important communication is in the organized chaos of a fully distributed company.
The full episode transcript is below.
***
MATT MULLENWEG: Howdy howdy. I’m Matt Mullenweg, the CEO of Automattic, and the co-founder of WordPress. Automattic is the company that makes WordPress.com and a bunch of other things. At Automattic we have a division called Other Bets, which encompasses a host of experimental projects that aren’t directly related to our core business. When we started thinking about this department, I knew we needed a renaissance person to lead it — with a background in legal, finance, and entrepreneurship, Sonal Gupta is just such a person.
Sonal’s been with the company for coming up on three years, and I wanted to get some time on the calendar to talk to her about what made her want to work for a distributed company, what she likes about it, and what she finds challenging.
Alright, let’s get started with Sonal.
MATT: Today we’re going to go inside a company I know a little bit more about — Automattic, which is a company I founded in 2005. Today, Automattic has over 850 employees working from 68 countries.
So to understand better how Automattic works, I’m joined by one of my colleagues, Sonal Gupta. Thank you so much for joining today, Sonal.
SONAL GUPTA: Thanks for having me.
MATT: She is the lead for what we call the Other Bets Division, a name we borrowed a little shamelessly from Alphabet, which oversees a number of different emerging businesses, including our latest bet, which is focused on tools that power our distributed work model, Happy.tools.
Sonal is both a tech founder and a lawyer. She joined Automattic two years ago as a legal counsel after a successful run as cofounder of Rank & Style. And Sonal, you’ve also been named as one of Fast Company’s 100 Most Creative People. So when you joined Automattic, it was your first distributed work company. What made you want to apply for it?
SONAL: Yes, actually the distributed nature and culture of Automattic was one of the things that really drew me to it in the first place. I was really intrigued and loved how open and transparent everything was and the amount of autonomy Automattic places on its employees.
I had had all sorts of experiences with different offices as a corporate lawyer for a big part of my career. I worked in a big corporate office here in New York City where I had my own —
MATT: How big?
SONAL: 500 employees.
MATT: Wow.
SONAL: Not huge but for one office it was pretty big. The office itself was nice, but the expectations around face time and just being in the office just in case a client might need you, those types of expectations made it a little bit difficult to keep up that kind of lifestyle.
I have also had other different types of office experiences. I have worked in open plan offices, I have worked in a cubicle at a bank, I have also done the co-working space at WeWork. So my experience in offices really runs the gamut. My two years at Automattic [has been] definitely the best fit in terms of the way that I work, the way that makes me most productive, and overall life/work balance.
MATT: So one question that comes up sometimes is, “What’s the first day?” There’s no desk you go to or computer. What was your onboarding like?
SONAL: Well it’s funny because you start your first day and you’re sitting in your living room and your friends or family say to you, “Do you really have a job?” [laughter] The first day at Automattic was great. Automattic requires every employee to do a two-week support rotation so that everybody can understand the product and how customers see our products.
MATT: You log on that first day, you’re in your living room, you’ve got a laptop. What was your first impression?
SONAL: I think my first day I thought that there would be more video chats but all your onboarding is done —
MATT: All text.
SONAL: All in text. So that’s —
MATT: Were you paired with someone? How does it work? I haven’t been onboarded in a really long time.
SONAL: Yes you’re paired with a buddy — mentor — for your support rotation. You’re trained completely on Slack with a group of others who are also starting that day.
MATT: And going from law to doing customer support, what was that like?
SONAL: It was interesting. I did interact with our customers. I hadn’t really experienced anything like that.
MATT: One thing people get on the first day is — internally to Automattic we have something called the Field Guide, basically our internal handbook, but it’s a WordPress blog so anyone can edit a set of pages. There is a headline on the Field Guide that says “Welcome To the Chaos.” What did you think when you saw that?
SONAL: Seeing that just gives you comfort, immediately. Because it is overwhelming. You’re getting pinged from every direction. But as soon as you learn to embrace the chaos rather than resisting it, it makes it so much easier to understand Automattic’s culture.
MATT: What does it mean to embrace the chaos?
SONAL: To embrace the chaos to me means just surrendering to it and understanding that there is just going to be a barrage of information coming at you from all angles and it will take a little time to have a process in place, but you’re not expected to just get it immediately.
MATT: One of the things that I’ve always thought is — recovering lawyers or attorneys — you write a lot in school, you read a lot, you are consuming and writing massive amounts compared to almost any other modern-day trade or industry. Automattic has a basis of a lot of written communication. Were there any things that you learned as you were training to be a lawyer that helped you in that, or that you found made you better able to consume and produce written stuff?
SONAL: Yes, absolutely. Being successful at a company like Automattic — you have to be able to communicate effectively via text. As you said, we’re using all different kinds of messaging and internal blogs in order to communicate with the entire company. So I think my legal background was really helpful in being able to convey messages and information to people in a very clear and succinct way.
MATT: How many hours did you work in a given week before versus now? Did you burn the midnight oil in the corporate job?
SONAL: Oh yeah, definitely. I had times where I was working overnight or till four in the morning, but there are times at a law firm where you have downtime too. I think at Automattic, I wouldn’t say that overall I work that much less but I just work in a way that really works with my schedule and my life. So that is just something that is really important to me.
MATT: What’s an example of you using that?
SONAL: We use Slack and internal blogs for communication and it’s all async. While I try to get back to my colleagues or external partners as soon as I can, there is an understanding that we’re working with people in all different time zones around the world and you might not be working the exact hours, or maybe I take off three hours in the day and make it up later in the night. However I want to make my schedule is allowed.
MATT: You joined as a legal counsel and you made the switch to running a division. Automattic has four divisions; you run one of them. Tell us about Other Bets. How many people, what does it do, etcetera?
SONAL: We develop or acquire products that fall into three categories — things that we need to exist for Automattic’s operations, things that we build as experiments or that are useful tools for our community, and things that have the potential for substantial revenue growth. A lot of our products cross multiple categories. We are currently 40 people in the division, spread across six different teams.
MATT: And I think part of the design goal of Other Bets is that we want about five percent of the company always working on the future.
SONAL: Yes, exactly.
MATT: Taking the thing that could be the next WordPress, could be the next Jetpack, could be the next WooCommerce, going from zero to one is really, really hard, and it’s different than going from 100 million to 120 million. We don’t disclose revenue, but we can say that Other Bets is about 10% of the revenue at Automattic, which is now starting to be quite substantial.
SONAL: Absolutely.
MATT: Tell us about some of the products.
SONAL: Well we’ve got about 20 products in the portfolio, not all actively developed at the moment. Some of our products are Crowdsignal, which is a poll and surveys platform.
MATT: Competes with Survey Monkey maybe?
SONAL: Exactly. And we’ve got our new suite of products, Happy Tools. Our ads business is also part of the portfolio.
MATT: One of my favorites is actually Simplenote. It is a simple notes app, and it runs on Android, iOS, Mac desktop, Windows, everything. It’s just ultra- fast synchronization of super clean notes. A lot of other notes apps become not that simple over time but we have managed to keep this one pretty lean and mean.
SONAL: That’s correct. So Simplenote is one that we’re constantly building and improving.
MATT: Let’s talk about communication. You have 40 people, how many time zones does that generally span?
SONAL: We work with people on both coasts in the U.S., a ton of people in Europe, and a couple people in Asia.
MATT: One of the things that’s interesting is, people think of distributed as being location-based. What do you think is the key to synchronous versus asynchronous communication? What can make that asynchronous collaboration productive?
SONAL: The fact that we’re in so many different time zones and people are working at different hours, you can pass the baton to the next person, especially on the development side. So if you have somebody working in the U.S. and then they go to bed at night when somebody in Asia wakes up, it makes it very easy and seamless to just keep continuous work on different projects.
MATT: Do the teams have regular meetings? How do they work?
SONAL: The teams do have regular meetings. Usually they use video chat, using Zoom. For teams with people in different time zones, they just try to find a time that really works for everyone. Sometimes they also communicate via Slack. We also communicate via our internal blogs, which we call P2s. Between the three, there is generally very seamless communication.
MATT: When do you use a Zoom, a Slack, a P2, what do you use these for?
SONAL: For Slack I think it’s great for conversations with one or a smaller group of people where you’re just trying to stay on the same page in real-time communication. Our internal blogs are really useful for keeping the entire company up to date on our progress or different updates. They’re really helpful for being able to search our entire database of P2 posts so anyone coming to the company in the future can always get all the backstory on a specific conversation or product.
MATT: If you met with a partner, you would post notes from that to P2 or to Slack?
SONAL: If I met with a partner, I would post notes to a P2 and just make sure that everybody at Automattic who needs that information can easily access it. If I’m making a quick decision about something and I just needed somebody’s input, I would probably use Slack. I have one-on-ones with each of my direct reports on a weekly basis and for those I generally use Zoom video chat. I really do value in-person or face-to-face communication so I think Zoom helps fill that gap.
MATT: It’s funny because you’ve used face-to-face and Zoom a little interchangeably and really that’s screen-to-screen, right?
SONAL: That’s true.
MATT: And video communication is obviously higher bandwidth. So you get a lot of value from that. When do you get together in person with people?
SONAL: Most of the teams meet up at least once or twice a year on their own and then there is also an all-company Grand Meetup every year where the entire company gets together. I, as a division lead, try to meet with each of the teams as much as I can. So I’m generally on the road.
MATT: So you have six teams meeting twice a year. That’s 12 meetups. Do you go to a lot of those?
SONAL: I wouldn’t say that I go to every single meetup but I try to make sure that I get some time with everyone on my teams at least once a year, and then at the Grand Meetup as well. So between team meetups and conferences, I’m probably on the road once a month.
MATT: What makes a great meetup?
SONAL: If a team comes up with a meetup project that is something they can complete in a week, I think that always feels really satisfying. Or if they’re just in the middle of developing a product and they can come together and make some progress on that, I think that always feels really fulfilling. And then the team bonding is a really big part of it too. They’re all working together, every day, all year long, and they get about two to three weeks of in-person time together. So most people find it really valuable. That catching up over dinner and really getting to know each other is an important part.
MATT: A common question that managers at distributed companies could ask is how do you know your teams are working?
SONAL: I’d say that posting on our internal P2s is one way that you can have a sense of how much people are working, how many ideas they’re sharing, what kind of meetings they’re having. So I think we do put some value on how much people are posting but other than that…
Personally, I’m not a micromanager. I like to trust people and give them autonomy. But I keep in touch with them very regularly and I think it becomes clear pretty quickly if somebody is not doing work. We look at performance, and we look at communication at a distributed company. Communication is oxygen. So it’s just really important that people are constantly communicating. I think we probably veer closer to over-communication. In some ways you have to make sure you know how to sift through all the different communications coming your way but I think it’s an effective way of understanding what people are working on.
MATT: Think of your best team — you don’t have to tell me which one it is — but what are some things that they do that you think makes them very effective?
SONAL: I think my best teams are great at communicating via P2 and having roadmaps and plans in place, and making sure that they’re meeting their plans or, if not, updating me.
MATT: So Sonal, you do a lot of recruiting and hiring for your division. How does that change when you’re hiring from everywhere in the world, versus when you’ve hired for startups or companies in the past, and how does that interview process work?
SONAL: It’s very unique. The benefit of hiring at a distributed company is you have access to a global pool of talent, which allows you to bring in the most diverse qualified candidates. As far as the interview process — it is quite unique. Some teams hire completely through text communication without ever hearing a candidate’s voice. I personally haven’t done that yet but I generally interview on the phone or via Zoom or sometimes if a candidate is local I’ll meet them in person.
Everybody we hire, we have them go through a trial project process first, which usually lasts about a month. That really helps us figure out if the candidate is a good fit and it also helps the candidate figure out if a distributed culture works for them.
MATT: So like a two-way evaluation?
SONAL: Exactly.
MATT: Thank you very much, Sonal, for joining us today on the Distributed podcast. If you want to learn more about Happy Tools you can sign up for a demo of Happy Schedule at Happy.tools.
SONAL: Thank you so much for having me, it’s been great to be here.
MATT: That was Sonal Gupta.
Automattic has grown so much these past few years, and at over 950 employees, it’s not always easy for me to get a ground-level perspective of what’s going on in the various parts of the company. It’s great to be able to catch up with people like Sonal, who keep me up-to-date about all the exciting projects going on, and about how our distributed work model complements those projects. Thank you for joining us, and see you next time.
Author Scott Berkun on Managing Distributed Teams with Respect
Sep 05, 2019
Scott Berkun wrote the book on distributed teams. Literally. He spent a couple of years at Automattic and wrote about his experience as a manager in a distributed company. In this episode, Scott talks about that experience, discusses how things have changed since, and explains how today’s managers can cultivate a shared vision in a distributed team.
The full episode transcript is below.
***
Matt Mullenweg: I want for you to imagine that you’ve been hired as a manager at a scrappy startup where there are no meetings, no hierarchy — not even an office. How do you make people feel like they’re part of a team? How do you brainstorm, and how do you make sure the work’s getting done? Is it possible to cultivate a shared vision, structure, and goals by only meeting in person twice a year?
That’s what Scott Berkun faced nine years ago, when I hired him to join a little company called Automattic, which is the parent company of WordPress.com, which I founded in 2005.
As you know from listening to this podcast, Automattic is fully distributed, with no central office and more than 900 employees working from 68 countries. When Scott joined us, we were quite a bit smaller, we were using IRC instead of Slack, and there was a lot that we were still figuring out.
Scott wrote a book about his experience at Automattic called The Year Without Pants, and since then he’s written a whole bunch of books about management, culture, and how we work. Today he’s a sought-after speaker on creativity and innovation.
I caught up with Scott in Seattle to talk about his experience at Automattic, and everything he’s learned since then. Has the future of work panned out like we first imagined it?
Matt: We used to work together, actually.
SCOTT BERKUN: We did used to work together. I used to work for you. [laughs]
Matt: Well let’s talk a little bit about how that happened, because that was an interesting arc in the story.
Scott: Yes. That was probably 2009 that you asked me to come to an Automattic Grand Meetup and you wanted me to advise on the team or lack of team structure at the company at the time. That was the first time that we officially were working together.
Matt: That’s an intriguing hook.
Scott: Yes.
Matt: And I guess that was a point when Automattic was totally flat, right?
Scott: Yes.
Matt: It was like 50 or 60 people all reporting to me. I don’t know how that worked, actually.
Scott: That’s right, yes. [laughs]
Matt: I don’t remember.
Scott: We talked a few months later about me joining Automattic as a lead of one of the newly formed teams at the company.
Matt: Before that you had been at Microsoft for a while?
Scott: I was a team lead, a project manager guy for about nine years there and I wrote a book about it, which is — probably how we first knew of each other is that you were on my mailing list that was about project management.
Matt: Oh was that the Art and Science — the Project…
Scott: Yes. That’s how we first titled the book. And then when WordPress launched I used it for my blog and that’s how we got to know each other.
Matt: Can we plug that book really quick? What’s the new title?
Scott: The title is Making Things happen. That’s the title of the book now.
Matt: I highly recommend it. That’s the one with the matches on the cover, right?
Scott: That’s right.
Matt: I really enjoyed that book.
Scott: But that was the beginning of my full-time remote work experience was working for you at Automattic. And I remember one of my biggest reasons for wanting to do it was that it very clear in your mind and in my mind that this was an experiment. Can we bring this experienced manager from a traditional company into a company like Automattic that has all these special things — being remote is one of them — but the high autonomy that every individual employee had — continuous deployment, was another. And then the notion of teams itself was an experiment. And then there was also this other notion that you knew that I was going to write a book about this, which was this other curveball to the whole thing.
Matt: Yeah.
Scott: And that combination of experiments — I love the word experiment, and when you used that word, I felt like no matter how this went, it was going to go well. For one of us, at least. [laughter]
Matt: Yeah, sometimes those book documentary projects don’t go as well.
Scott: No. The distributed work element wasn’t my greatest concern. I was worried about that but I was more worried about — do my skills as a manager in a traditional company where it’s an open office — you see people everyday. Could those skills transfer well to distributed work and to a far more autonomous culture in terms of the individual’s relationship to their work — how much control they had. I was more concerned about those things than distributed work.
Matt: I think this is a big concern of a lot of managers who have worked one way their whole career and then might be thinking about joining or starting or working in a distributed fashion. What did you see your superpowers as when you were in these in-person cultures?
Scott: I don’t know that I ever thought I had a superpower. I thought —
Matt: Well you’re a modest guy so let’s call it “medium-powers,” that made you effective at what you were doing.
Scott: I thought that, and I still think this, that most managers are really not very good at managing. Most people you talk to, when they come home from work, they’re not that happy about how well they’ve been managed — they have complaints. And that may extend out to the way the team is organized or the way the goals for their product has been set.
I thought that I was a good team manager in that I remembered all of my bad experiences as an employee and I tried to work really hard not to repeat those mistakes. And I gave a lot of autonomy to employees because I was one of those employees who liked a lot of control. Once I’ve earned some trust I wanted to be able to run and go at full speed. And the best managers I had are ones who are comfortable giving me that much control. And I tried to rely on that as a strength coming to Automattic. Because everyone was already independent. I have to start out by saying I may not actually add any value at all. I need to observe first to see how things are going before I have any reason to change anything.
And that’s a common mistake that new managers make everywhere, that they come in and they’ve got this new salary, this new job title, and it kicks their ego in and now it’s about them — How am I going to change the team, how am I going to change the organization? But you don’t know anything, you don’t know these people, you don’t know what their strengths or weaknesses are, you have no data.
So the best thing you can do — and this comes up in the book that that was what my strategy was for two months — I’m just a note taker. When we have meetings, I’m just going to take notes. I’m going to observe, I’m going to reflect back. And then little by little, once I have something useful to say, I’ll put it into — well it was IRC then but it’d be Slack now — little by little I’ll just try to show, A, I’m not stupid, B, I’m not trying to get in your way, and C, I may actually have some insight that will help you be more productive or successful or happier. And you have to earn that even if you’re the most senior person on the team or the company or whatever.
Matt: How do those meetings happen?
Scott: Well obviously there weren’t teams yet so there were no meetings. [laughter] So what we agreed to do was —
Matt: Were those Skype calls?
Scott: It was all text.
Matt: Everyone would be there at the same time, once a week?
Scott: Yeah. And we would chat about whatever everyone was working on. And it started off really short and little by little we added more structure, then we moved to Skype and then eventually the big breakthrough was we switched to audio! Woohoo! It was a big deal because everyone was fully paying attention.
Matt: We’ve had different experiences on audio meetings.
Scott: Yes…
Matt: Just to define some of those terms…
Scott: Yeah.
Matt: IRC is a text-only chat.
Scott: Correct.
Matt: Think of it like Slack but with a really old school version, like almost terminal-like interface.
Scott: Old school, yes, old school Slack.
Matt: Skype is a messaging platform plus voice.
Scott: Yup.
Matt: And is that what you did the voice meetings on?
Scott: Yeah. We agreed we’d keep the meetings really short but every communication tool is good for some things and bad for others. And text has the advantage that you have time to think but the downside is that written language takes away a lot of data. You can’t hear someone’s inflection in their voice, or pick up on how loud or quiet they are. There’s a lot of data that you lose.
And having a moment every week where we were on audio, even if it was just for five minutes or ten minutes, emotionally, in terms of your relationship, in terms of understanding people’s nuances and sense of humor, their sarcasm — you could only get that through audio. And you don’t need that much, you don’t need to have two-hour meetings, but ten minutes a week to hear everyone, what they’re talking about, what they’re excited about — you get more data. And I think that helped us throughout the rest of the week.
Matt: That was enough for you to get what you needed to be an effective manager to this team?
Scott: That was enough to help prove that I had some value. Because people would leave those meetings when they were run well saying “Yeah that took 25 minutes but now I understand what Andy is working on, and I see now that’s going to help me later.” That was 25 good minutes as opposed to the typical way people feel about most meetings, which is [that] it’s about other people, it’s all just FYI, stuff that doesn’t go anywhere and it seems that the person running the meeting cares a lot about having them, even though no one else really is engaged.
And then little by little it became natural for the team to look to me to set the goals and to help decide what features should be next or what things should be built. But you can’t do that as a leader without having some forum for those things to happen. And that’s what the weekly meeting was for us.
Matt: Is that how you saw managers come up in Microsoft as well or was this a unique approach you created for this opportunity?
Scott: I saw a wide range of styles at Microsoft. And this was more like the style that I preferred. I wanted to start off by trusting everyone and extending trust before I ask them to trust me. That’s just good —
Matt: That’s a really powerful concept, yeah.
Scott: That’s good relationship management. But I knew there has to be cadence. That’s the fancy word. There has to be a rhythm. If you’re on a team there’s a rhythm. You think of people who are competitive rowers, and there’s that person at the front of the boat who’s just — their job is just to yell out the rhythm, that’s all that they’re doing, the coxswain, right?
Matt: Yeah.
Scott: They’re taking up weight on the boat simply to be the person who’s controlling the rhythm. And any team, even if people are working individually for the most part but there’s some things that overlap, someone has to be setting the rhythm for the week, the rhythm for the month, and to help people set their own rhythm for the day. And that’s what I thought my job was.
Matt: One thing I hear a lot about people who have had a lot of experience in a physical office is they get so much value from the kind of drop-in or walking around because you get — what you said you get with just a little bit of audio is an even higher bandwidth, right? If we go text, a little bit, audio better, video more — you can see faces — and then in person. Let’s call that the best. How do you deal with not having that?
Scott: All the claims people make about serendipity, you’ll lose all the serendipity of meeting people in the hallway or — you can replicate all that. That’s what the group chat rooms are for where you jump in and you’re bored and you see all the other people who are procrastinating on something. You don’t see them but you can chat with them. There’s randomness and surprise that can happen in any group situation.
And all the one-on-one direct, more intimate communication, you have now fifty different tools to do that. You can send someone a private text message. “Hey, it seemed like you were upset in that meeting, should we talk?” Or you can make a Skype call. You have all of these tools to make the equivalent of what I would do at Microsoft, which is to go down to someone’s office and say “Hey, can I talk to you?” and close the door.
Matt: What about when that trust gets broken [and] someone doesn’t follow up on what they say they’re going to do? How does your approach there vary when you were an in-person manager versus being a distributed one?
Scott: I really have become a universalist about this, that as the manager — not even the manager — as a person, if someone has made a commitment to me and they’re not honoring it, part of my first thing to do is check in. “Hey, how’s it going, are you still on track for this thing on Friday?” I’m just checking, is my sense of the world in line with your sense of the world? If you do that periodically, especially when you don’t see them posting on Slack or giving any visible — you have no passive indicators that they’re following up on this…
Matt: So is quietness a warning flag?
Scott: It is a warning. And this is one of the things that I learned from you about Automattic was that if you don’t make your work visible it’s invisible. No one can see it. And if you’re not over — what feels at first like over-sharing — or making sure that your code commits show up in the team channel, [or] whatever you’ve agreed on, then that puts someone who is the manager and the responsibility now going, “Well that person’s been quiet for four days, I have to reach out.”
So my first thing is just to check in. Do we still have the same expectations and view of the world? Yes. That sets me up then to come back two days later and go “Hey, we talked a couple days ago, we have a problem here because if you don’t get this done then Sally can’t get her thing done and now it’s going to cascade. So what’s going on?”
90 percent of the time, there is a reason. “Oh, this other issue came up that was more important, I forgot to mention it to you.” I’m like, “OK, great, now I understand, I can recalibrate.” But someone has to be that check-in maintainer that is driven by whoever is in the leadership role. The hard part is when you check in on someone and they keep — there’s something broken still. They’re not getting their work done, they’re frustrated —
Matt: Or there are broken things in the past. It was due on Friday and now it’s Tuesday.
Scott: Right. You really want to avoid having deep, personal conflict conversations over text.
Matt: Why? It seems so efficient.
Scott: It’s efficient until it’s only making things worse.
Matt: Ping, Berkun.
Scott: [laughs] It’s what I mentioned before about what you lose, that you don’t get the nuance that is so important to empathizing and understanding what someone is trying to say. And if I have an employee who [has] some issue that’s going on that’s personal that’s got nothing to do with work, they’re less likely to type that in.
But if I can get them on the phone and they hear my voice, and I can offer them my true empathy for — “I want you to do well, my job is to see you do well.” They get that empathy. Our brains respond to that more directly through voice and eye contact and facial expression. They’re more likely to respond back and share a little bit more about what’s really going on, which could turn out to be something simple, that the way that I assign work or the way that I make decisions bothers them in some way, but I didn’t know that. And they were afraid to offer that to me before.
Matt: So you created that safe space for that to be communicated.
Scott: Yes. I also think that even if you don’t agree with my point about intimacy, I think that every medium has strengths and weaknesses. And just by switching the medium it changes now what the strengths and weaknesses are going to be. To switch from Slack to SMS, although they both seem like text, there are subtle differences in the way people think and translate what’s in their head into communication. And so whenever I am stuck, I will always try to — and I feel like I don’t really know what’s going on here — try to switch the medium. The one that I always feel is the go-to one if I’m confused is voice. And often it’s faster.
Matt: I think that’s great advice and it’s a cool feature of the new tools, like Slack. They have audio built in so you can initiate a call right there.
Scott: I have this experience with my friends. We’ll be going back and forth on SMS on something we’re not agreeing about and I know from all my experience at Automattic, I know that sometimes a 30-second phone call —
Matt: Would fix everything.
Scott: Instead of a 20-minute — yes, we are asynchronous, I’m half watching TV while I’m doing it. But it is 20 minutes of time spent arguing about something that’s a nuance that would be completely obvious if we spoke on the phone for 30 seconds.
Matt: It was interesting, we just had a leadership summit at Automattic. It was a training one, and we decided that the focus for the week would actually be feedback. And in my mind going in, it was more about how to give good feedback, some of what we just talked about. But the facilitators, who were quite good, ended up focusing probably the bulk of it on receiving feedback. Let’s say you’re on the other side of things and you’re getting some feedback over text or something like that, what have you found works well or poorly for that?
Scott: I think that you have to start from separating out your personal identity with the work that you’ve done.
Matt: Hmm. What does that mean?
Scott: Well I’m a writer, so that’s the easiest place to start. I’m a writer, I write books. And people write reviews of books and a lot of them are really mean. Making Things Happen has a two star review on Amazon where someone says it was about as useful as a piece of toilet paper or something like that.
Matt: By the way, toilet paper is super useful.
Scott: It is super useful. [laughter] It’s all context-dependent though, right?
Matt: It’s interesting though, every author I know has this where at some point, even if they know they shouldn’t, they’ve read the bad reviews and they can usually quote it word for word.
Scott: Yeah. Oh yeah.
Matt: But maybe you can also quote a really good review but they typically don’t have that same vividness to the probably 10 times more good reviews that it’s gotten.
Scott: Yeah. I read every review.
Matt: Yeah?
Scott: I think every review… not all the GoodReads ones but every Amazon review, every magazine review, and I feel like that’s part of my job. So I write a book and I do work knowing that there are going to be people who have valid criticisms of what I have made. And it doesn’t necessarily mean that what I did was bad, it just means that there’s many ways to decide what good is. That’s part of the job.
And I feel like that’s part of the job as a manager, that’s part of the job as a developer, that’s part of the job as a designer. You are making stuff and putting it out into the world. That’s what I mean by splitting out my personal identity as Scott from “I made some thing that someone might not like”, or in the management case, “I made a decision that someone really is upset about.”
Matt: So if I were to rephrase that — you created something that someone thought was worthy of two stars but that does not mean you, Scott Berkun, are a two-star person.
Scott: Correct. I might be a two-star person but not just because of —
Matt: Of this one review.
Scott: Right. Not just because of that book that I wrote or a thing that I did.
Matt: Or a thousand two-star reviews, ya know?
Scott: Sure, yeah.
Matt: That sounds hard though. You even started with saying, “I am a writer.”
Scott: That’s why feedback is hard because we, especially people who are passionate about their work, they don’t have much psychological separation between their identity as a worker and their identity as a human being, and that is a kind of maturity that you need to have.
The helpful thing [is], I have a curious mind to ask clarifying questions. I’m not going to defend anything. I’m going to run with the assumption that they are correct. There’s something flawed in the decision that I made. But I have to be an investigator now. I have to — “OK, when you say this, do you mean that or that? When you say that you thought the decision was unfair, did you mean it was unfair just to you or to the team or to — ” I have to go into that —
Matt: That’s a tough one because it can feel aggressive.
Scott: Yes.
Matt: Because on the receiving end it’s like, “Oh I’m doing all this extra work to justify my feedback I’m giving you.”
Scott: Yes. I think you’re pointing out how much trust is required to be a good leader, that I have to somehow convince someone who thinks I have done a lousy job that I genuinely want to learn more about why they feel that way and how they think about it. They have to trust me and I have to have earned that trust, that they’re willing to make themselves vulnerable and telling me more about this very uncomfortable thing.
Matt: So how do you build trust besides giving it? Or is that the only way?
Scott: The last therapist that I saw, she said that that’s the only way. [laughter]
Matt: Oh!
Scott: She told me and my wife, we were in marriage counseling, that that is the way. If you want to trust someone, the only way to do that is to give them something that you’re entirely sure you should trust them with. There’s no other way.
Matt: Hmm. That’s powerful and terrifying and everything all at the same time.
Scott: It is, it is. But if I have a dog and I need someone to watch it and you’re the only friend I have around — I’m not sure how good you are with dogs, I can’t half-have you watch the dog. Like, either you’re going to watch the dog or you’re not. Or either I’m going to let you cook a meal for me or not. Or I’m going to let you drive my car or not. There’s no — you can do things to insure and mitigate the dangers but either I am trusting you to do something or I am not.
Matt: I will say also that’s something I learned a lot when you joined because as one of the first middle managers, it was a lot of letting go for me.
Scott: Mhm.
Matt: The book is so interesting, especially looking back at it now, because it was a vignette in time and so much has changed since then. In fact, some things in the book quite embarrass me now. I was like, wow, I can’t believe we did that or like, we were so early in our journey in a lot of ways that the company in a ton of ways is unrecognizable in a way I think is really positive.
You mentioned earlier that people still ask you about the book, you still get questions about it, so I guess people are still reading it, which is cool. How have those questions changed or what have you seen as the things that you look back and are like, “Oh, I’m glad that that’s better now,” or that we know more now?
Scott: I get asked a fair amount about the genderedness of my point of view. And it’s a regret.
Matt: I think it’s also a mistake I made when creating that team.
Scott: Well, maybe. That’s for you to — [laughter] I know that — I thought about it in writing the book and I knew the culture of our team was a particular way because of its makeup. I should have put that in some kind of context and I didn’t. And part of that was — the book was supposed to be this insider view and I don’t do that much context-setting about these wider issues in not just tech culture but culture at large. I totally understand that perception and I’ve tried to explain it. I don’t think that was an accurate reflection of the whole company. I was trying to reflect what was going on in my team and I didn’t do enough to set that in some kind of context. I regret that.
But people ask me about the book because they’re switching to a remote company or they’re thinking about going to work for a remote company and they want to understand [what it’s] like. A lot of my answer is I don’t think remote work is that big a deal. I don’t understand why people obsess about it. I was at the gym today walking around the gym, I see people who are on their phones, people who are talking to their friends, they’re not necessarily doing remote work, they’re doing remote interaction with other people.
Remote is such a part of our culture now. Anytime you’re on your phone, interacting with another person through a screen, and it could be an iPad or a laptop, you’re doing remote work. People do remote work at their non-remote jobs all the time and in some cases it’s 50 or 60 percent of their time at work.
Matt: They’re not always talking to people presently, they’re often chatting or emailing with them.
Scott: Exactly, yeah.
Matt: They just happen to be in the same building.
Scott: Just email alone, ask people how much time of [their] day is spent on email. Guess what, that’s remote work. Remote work! But somehow there is this phobia and stigma around it that is really still strange to me. There’s this fear of it being this completely different way to work. Now it could be if you took a centralized team and one day just said everyone you’re going to go to different countries on the planet, that would be a radical difference because people’s lives would change. But in terms of how work gets done, we’re already remote workers. Everybody.
If you do email, if you’re on the — you send text messages, Skype meetings, Zoom calls — to me it’s all remote work. And I try to tell people that and they still think there’s some other magical secret. And I’m like, no, I don’t think your problem with remote work is about the remoteness of it. Your problem with remote work is probably you don’t trust your team, your boss is a micromanager, you don’t have clear roles, you don’t have a good way to define who does what projects or to track them. And that’s got nothing to do with remoteness, that’s just basic competence as a team.
Matt: I think part of it is it’s tied in with a bunch of other things. I like to say any organization over 25 or 50 is distributed already, they’re just maybe not conscious of it. But people, when they hear remote, they also think “Oh I’m working from home.” And their context of what they do at home is very different from what they do at work and sometimes it’s hard to bridge that. Like, how could I work at home with my cat bugging me all the time, or my kids knocking on the door and wanting to play? So that all gets bundled in with some of that. And some of those are real challenges.
Scott: Sure. Part of the stigma around this topic, it’s there is a totality to it that people feel that somehow they’re going to be forced to do things they don’t want to do. I have friends who commute to work and it takes them an hour and a half to go each way to work. I would never do that. There are so many different styles and formats and the demands on you as a person, what you have to wear as a dress code — No job is perfect for everybody. And so I’m an advocate for remote work, I think there are so many advantages to it, but I would never say that everyone is going to love working remotely all the time. I know this is true at Automattic, that some people join and after they’re there for six months — or any distributed company — they discover some things about their own needs they didn’t know before. They need more social interaction, they need more this or that.
Matt: Yeah. In-office work bundles a lot of things and for many people it also becomes, like you said, part of social — people you get lunch with everyday. It’s your connections outside of your normal circles. It’s maybe, depending on where you work, who you play volleyball with or who you exercise with or all these number of things. I think that’s actually one way that companies draw people in quite a bit. I frequently give the advice when someone joins to get some hobbies, go to some meetup groups, find some things where you can interact with other homo sapiens outside of this remote, computer-mediated interactions.
Scott: Yeah.
Matt: The people who often have the most trouble with it are [the ones] where it’s their first job out of college.
Scott: Interesting.
Matt: You probably remember some of this. You wind up with this thing where someone is not being as productive after a little while and you’re like — I mean it’s a little silly but like, “Are you leaving the house?” [laughter] “Are you showering in the morning, are you eating things other than pizza?” You do need a level of discipline and an approach to healthy habits.
Scott: That is true.
Matt: Another key point and a prominent feature in the book and your experience at Automattic that you helped create was meetups. So we’re distributed, why do we need to get together?
Scott: That’s a bigger version of the voice comment that I said before about how our brains have old programming, we respond in certain ways regarding intimacy by being around people. Facial expression, body language, sharing a meal together.
Matt: Breaking bread, yeah.
Scott: Breaking bread, yeah, there’s a real power to that that you can’t quite replicate it, not in the same way. And so the meetup thing was something that you offered as a policy. It just so happened that me and my team decided to be the — [laughs]
Matt: To really take off on it.
Scott: To run with it. But I thought it made total sense to me, that at least a couple times a year, get everyone in a room together, and then we could flip the way we work and we could work more like a traditional team and take on a bigger project where we all have to be working on the same thing together for two days.
There’s a different way you learn to work with each other when you have that kind of commitment. I think that helped us a lot as a team because then we’d go back to our regular style of working but now we just spent two days really working hard on something that stretched our relationship and our working styles in a very important way for us.
Matt: How was your trust before and after those meetups?
Scott: Probably better. This gets back to human psychology again. When you share a house with someone, you share a meal with someone, you trust someone to go get the groceries or pick up the car or do a dozen logistical things that happen to be required. It’s a little bit different than this person that you work with but it’s all through digital and virtual stuff. And I don’t know that a team needed to meet up as often as we did. We probably met three times a year and then there’d always be the grand meetups. That’d be the fourth, but we all really enjoyed it and we were all mostly — we didn’t have kids or families so it just fit our team style for the most part. That would change more as the team got bigger.
Matt: I think this is probably an independent variable from being distributed or not but I’m a big believer in it, that if you give teams autonomy to try things out, hopefully the best practices then spread organically. And then occasionally you might come down from on high and say okay, everyone must do this.
Actually the last time I remember that was with Slack because we had portions of the company on IRC and Slack and the network effects of having everyone on the same communication tool was too big, too important to let that be too balkanized. But the initial adoption of Slack was just on a team here or there.
Scott: Yeah, that’s smart how you’ve managed that. I think the autonomy is really important to creative people and not in a superficial way. I think that their tools are so important. A big corporation that hires programmers and tells them you have to use this old computer or something, that’s a lack of respect for what you hired them to do. They’re going to be really tuned in to what tools are going to make them most efficient. Continuing to have that flexibility as Automattic has grown — that’s a cool thing. A lot of companies struggle with that as they grow.
Matt: One thing that comes up a lot is people not sure how to do — is like, “OK. my team is in five different countries, how do we brainstorm? How do we do that sort of creative frisson that seems much easier to spark when you’re in person and have that white board on the wall?”
Scott: For me, I didn’t struggle with that that much. I felt that if I have good people, and there’s a clear goal, then there will be an abundance of fodder. As long as stuff is being offered, as long as there’s that loop of feedback: idea, opinion, critique, new idea. You’re doing above the bar for most teams at most organizations.
Matt: Similar to one of your earlier answers that maybe it’s not as big a deal as people worry about.
Scott: I don’t think so.
Matt: So they should just try it.
Scott: I think they should try it. But again the things I mentioned are not common. Talented people? Not common. People who are comfortable offering an idea and getting feedback on it? Not that common. People who are good at giving critique? Those kind of conversations? Most organizations don’t do that well. That’s really the problem to me. And no tool is going to solve that. It’s these other factors that are harder to deal with and probably have a lot to do with you as the boss.
Matt: I’m a new manager at a distributed company. What should I do every day?
Scott: Lurk where your team communicates. Just lurk, just hang out. Spend an hour not jumping in. It’s very easy to jump in. Just observe. Because you may observe the team is just fine without you jumping in.
Matt: And then do you stack something on top of that later?
Scott: The thing that’s coming to mind is whatever feedback loop you have with each individual person on your team — and there is a set of questions that I developed. It’s in the book. I think the four questions were: what’s going well, what could be going better, what do you want me to do more of, and what do you want me to do less of as a manager? That’s how very one-on-one conversation I’d have — which would be like a half an hour, whatever, once a month or so — would be framed in those four questions.
Matt: Twenty years from now what percentage of jobs do you think will be distributed?
Scott: Well, so I spent a fair amount of time, not recently, with some of these statistics because I get asked a lot and it’s weird how they measure these things. This will be my way that I dodge the question is to talk about survey design instead.
Matt: Telecommute.
Scott: A lot of the surveys are designed, they ask the question in the sense of you being a hundred percent remote or days where you’re a hundred percent remote. So it’s really weird because there are some companies that have liberal policies for you taking one day a week to telecommute. Is that remote work? Well it is but how does that fit into a percentage, like what you’re asking? It’s a weird thing.
Matt: We can make our own definition here. If you were to pick an integer that was a percentage and let’s say people who work not in an office the vast majority of the time, the plurality of the time…
Scott: Yeah I think all the numbers will go up, to cut to the chase. I think it has to. The tools — I’ve already made the joke that most people are already doing remote work even though they don’t call it that. That’s just continued to grow. The tools will get better and better and all the things that can be done digitally, which is the cliff to get over, the curve to get over before you can do it on your phone or your tablet, will continue to grow as technology gets better.
Matt: So a hundred percent? Wow.
Scott: Well it can’t be a hundred percent because you don’t want your brain surgeon working remotely or your —
Matt: There was famously the doctor that wheeled in on one of these iPads-on-a-wheel thing and delivered a terminal diagnosis and the person was upset.
Scott: Yeah. I see. Yeah that’s a tricky one. That’s a whole other case though where —
Matt: It’s a good chance to switch mediums.
Scott: Yes, that is a good chance to switch mediums. Someone else should’ve given the diagnosis I think. Yeah. But I’m very positive just because I think that more worker autonomy just makes for better work. I really believe that.
Matt: Just pick a number off the top of your head.
Scott: What do you think, this is five percent now? Of jobs that are distributed?
Matt: Sure.
Scott: I don’t know, ten percent? I don’t know, twice that, maybe three times that.
Matt: So somewhere like 25 to 35 percent?
Scott: Yeah. I think it’d be. And that’s enough for it to be normal.
Matt: All right, we’ll get you on Episode 15,000 of the podcast and we can check it out.
Scott: [laughs] Reserve my slot for that.
Matt: Where can people find you if they want to hear more?
Scott: I am ScottBerkun.com and I’m @Berkun on Twitter.
Matt: Scott, it’s always inspiring. Thank you so much for talking with me.
Scott: Thanks for having me.
Matt: That was Scott Berkun. His latest book is The Dance of the Possible: The Mostly Honest Completely Irreverent Guide to Creativity. You can find him at scottberkun.com.
Thank you so much for joining us and see you next time.
Automattic’s Cate Huston on Building Distributed Engineering Teams
Aug 22, 2019
Cate Huston is the Head of Developer Experience at Automattic, where her team is responsible for hiring, onboarding, and retaining some of the best software engineers in the world. In this episode, Cate talks with Matt about what kinds of people thrive on distributed engineering teams, and how team leads can keep their engineers happy, productive, and connected to their colleagues.
The full episode transcript is below.
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MATT MULLENWEG: There are all sorts of approaches to distributed work. Some people work from home or at a café in their neighborhood. Others are digital nomads. I’m Matt Mullenweg, the CEO of Automattic and co-founder of WordPress, and I travel around 300 days out of the year. I appreciate that I get to spend time with my family in Texas, but I love life on the road too, and being able to hang out with friends and colleagues all over the world, and meet WordPress users wherever they might be. One of the nice things about running a fully-distributed company is that even the CEO gets to be just as remote as everyone else.
Today’s guest is Cate Huston, who is a true digital nomad. All she needs is a cup of tea and a place to set up her laptop and she’s ready to go. Her home base is the city of Cork, in Ireland, but you’re just as likely to find her in any other corner of the globe.
Just because Cate is always moving doesn’t mean she has trouble staying connected. Her role at Automattic requires her to be in close contact with her team, and it’s her job to help make sure that all of her fellow engineers stay connected, too.
After leading several engineering teams at places like Google and others, Cate became the Head of Developer Experience at Automattic, a team responsible for helping all our engineers at Automattic stay engaged, productive, and professionally fulfilled.
I knew we had to talk to Cate on this podcast because she lives out the distributed model so fully. She also has a comprehensive point of view on what kinds of engineers excel in distributed environments, and how companies can create the conditions that help engineers thrive.
Alrighty, let’s get started with Cate.
MATT: Hello Cate, thanks for joining today.
CATE HUSTON: Hi Matt. I’m ready for a one-on-one.
MATT: [laughs] Ahh I forgot to tell you we’re recording it.
CATE: [laughs] You should warn people about these things.
MATT: For the audience, can you catch us up a little bit on some of your experience that led you to Automattic?
CATE: I worked at Google as a software developer and then spent a year roaming the world and doing my own thing, and then joined a startup and was a questionably-legal migrant in Colombia for a while, and then that startup kind of imploded. And around that time, you sent me a GIF of a raccoon being adorable and I was like, “Okay, he can be my new boss.”
MATT: [laughs] You joined to lead the Mobile Team at Automattic.
CATE: Yeah.
MATT: But that has grown. So talk a little bit about that.
CATE: I joined towards the end of 2017 to lead the Mobile team, which was amazing. And then after about 18 months I went on rotation to the Jetpack Engineering team, which was also super interesting because, as you know, I’ve been using Jetpack for a long time too. But when that came to an end it was clear that I was more needed elsewhere. So I didn’t back to the Mobile team, and I got to work with you, and rolling out Gutenberg. And now I lead our Developer Experience team. So we work to support our entire developer organization, and that includes owning the engineering-hiring process.
MATT: What is developer experience at Automattic? I’ve heard of user experience but what does developer experience mean?
CATE: I mean: “What does it mean to be a developer at Automattic, what are the challenges of development at Automattic, what are the challenges of development in a distributed, remote context, how can developers learn from other developers, how can they have the support that they need to chart out their own career path?”
We have a lot of autonomy at Automattic, which I think is amazing, but that autonomy can be a bit overwhelming. So can we turn it for people [from] “Write your own MadLib,” into “Choose your own adventure,” [giving] people that kind of support. Also a critical part of the developer experience is the hiring experience going through into the onboarding experience. So how do we give people in our hiring process a good experience so that they can see if this is the right fit for them and we can see if they are the right fit for us, and how do we carry that through into them joining their team and becoming successful?
So one of the ways that we think about developer experience is — our engineering organization is quite big and we’re only so many people. So what we talk about is, “How do we find the pivot points for individuals in teams so that we can be present at those pivot points and try and make them accelerants where possible?” An example of that is when the team gets a new lead, that’s a pivot point. So we want to be there supporting that new lead, bringing them into the kind of support that we have for dev leads, helping them develop and iterate on their process so that that new lead can take that team to new levels.
MATT: There are probably some engineers listening right now who would love to be hired at Automattic or another distributed company. What advice would you give to them?
CATE: The first thing I would say is, “Be patient, because I think all distributed hiring processes take a little longer.” I think people feel — I don’t know if it’s true — that they get a stronger signal in a day of face-to-face interviews but I think people feel like they have a stronger signal in a day of face-to-face interviews.
And distributed companies, you can’t tell really if someone doesn’t show up to work. I mean, you can eventually tell, but it’s much easier to disappear. The level of trust required is much higher. And so there is a portion of the process that is earning that trust. We really believe that people can be successful and we’re looking to make people successful. There is no “prove it again” after you get hired. I think that’s really important.
So the first thing is patience and just understanding that the processes take longer. The other thing is that these jobs tend to be more competitive, especially for more specialist roles. There’s not always as many of them as you might want. So you want to craft what you’re doing a little better. Tell a good story in your cover letter, get excited about that company specifically, not just remote work in general. I’m sure all remote companies get a lot of the kind of applications that we get, which is like “Yeah, I just want a remote job so that I can travel around the world.” And it’s like, “Okay, it’s cool to travel around the world, I do it, you do it, but it’s not easy to do that on top of a full time job.”
MATT: So what’s the key for maintaining high performance, as you do, in all these far-flung locations?
CATE: I get pretty rigid about certain things. Like breakfast, I’m very rigid about. So every morning there’s breakfast and then I –
MATT: That’s very British.
CATE: [laughs] Very British. British being rigid or breakfast being important?
MATT: I think breakfast.
CATE: [laughs] So I try and carve my day into two four-hour blocks. And I just don’t expect to do anything fun during the week, so I do my tourist-ing on the weekends. I really just go and spend a month in a place and try to live there. And honestly I live like that most of the time. When I’m in Cork, because I live in Cork, I try to do things on the weekend, get away from the computer, go out and see things. So if I’m doing that in a different place, it’s fine.
I have my certain needs, which are pretty minimal, like breakfast and some form of exercise and that’s it. And so I just orient myself on “This is breakfast and here is a place to work, there is tea, and this is how I’m going to get regular exercise,” and then, honestly, that’s fine, that’s all I need.
I’ve probably paired down these needs over time. I don’t know if I started that way, and it is quite hard if you need more stuff. I think sometimes people want peace and quiet, for example, or they need more social contact or whatever, and things that take more time to build, but for me, a laptop, a pair of headphones, a good amount of tea, everything’s fine.
MATT: When you’re hiring engineers, what are you looking for as part of this process besides obviously some base technical-level skill?
CATE: Probably two really big things. One is the ability to work with the kind of code base that we have. WordPress has been around for a long time, there’s probably still code you wrote floating around in it, and that’s quite hard. Not everybody has the experience, the desire to work with truly legacy code.
And it is a very complex system. It’s not just about technical capability but it’s also being able to grok the complexity of what we had. And this is something that we saw in the mobile apps as well. We would have people on trial for that. There would be three networking stacks because the mobile apps have to speak to WordPress.com, they have to speak to Jetpack, and they have to speak to every other WordPress site too via XML-RPC.
There’s just a huge amount of complexity that comes with that. And if somebody has not worked on something that is really complex before then they’re going to have quite a bad time with that. And we want to see how they can adapt to that complexity, how they can work with it, and how they can deliver things.
The second thing that we pay a lot of attention to is how well do people respond to feedback. We are not really hiring people just for what they’re capable of today, but we see it as a long-term commitment. These people, we want them to stay with us for a long time, right? So we’re also hiring them for their growth and the growth that we believe that they can do. And the best predictor of that is that they respond well to feedback. So if we give people feedback and they take it and multiply it and do a lot better, then we feel way more excited about hiring those people than the people who take the feedback and they’re okay with it. And then of course the people who don’t take the feedback well at all, we reject them.
MATT: How have you grown in learning how to take feedback well?
CATE: The first thing is working on self-awareness. When people are not self-aware, you can’t really connect with them because you are always being indirected by their ego. And so developing your self-awareness is super important, something that I work a lot on.
MATT: What does it mean to be self-aware and how do you develop that?
CATE: Do you tell stories about yourself? Do you have things about yourself that you really need to believe are true but might not be?
MATT: What’s an example?
CATE: Some people want to be seen as really nice or really caring, for example, but they might not be very caring. And so they’ll talk a lot about how caring they are but they’re actually not. And so this gap between the way that somebody talks about themselves and their actions will show you this gap in self-awareness.
MATT: How do you cultivate self-awareness?
CATE: Just disabuse yourself of all your illusions.
MATT: You make it sound easy.
CATE: No, it’s horrible, it’s a lot of therapy and coaching and just being willing to confront the pieces of yourself where you know you’re not as good as you would like to be. Second thing, broadening your perspective, being more open to possibilities outside your worldview. So reading fiction is demonstrated to make people more empathetic, but then reading a broader variety of fiction written by people who are not like you can also broaden your self-awareness. Cultivating a broader network of people, making sure that you’re connected to diverse voices and people who are not like you. And then traveling outside your comfort zone. We talk about the digital bubbles we live in, but a lot of us also live in physical bubbles. And for me, I spent a lot of time living in Medellin, and existing in my third language was a profound exercise in human limitation and empathy.
MATT: Totally. I’d also say you can travel outside your comfort zone without leaving your city.
CATE: One hundred percent.
MATT: There’s probably parts of your city or places that you haven’t been to, buildings you haven’t gone into, places of worship, neighborhoods, stores, barbershops, that can be a journey as well.
CATE: Totally. I am right now in a part of Cork that I had never been to before today. I did not know it was here. So shedding defensiveness, you know? I think people’s first reaction to feedback is to be defensive. It creates conflict, it means you don’t really learn what’s happening, and it shuts the conversation down or it makes the conversation about your feelings rather than what this person is trying to tell you.
Something my coach always tells me is “get curious.” So learning to be — if something makes you uncomfortable not to shut down but to lean into it and to ask questions and really try and understand it is super helpful. Something that people do here is offer context. So people give you feedback and what you give them back is context. And to a certain extent that’s fair enough but too much context is just a polite way to defend yourself.
MATT: Someone says, “You need to improve X, Y, and Z.” And you say, “Well this and that and this was going on.” Is that what you mean by context?
CATE: Yes, or maybe like, “Oh, you know, I didn’t like how you responded to X.” And then it’s like, “Okay, but for context this set of things was happening.” It’s not really helpful. It’s also getting ahead of that, right? If you say, “Cate, you’re missing your goals.” And I say, “Now let me give all the reasons why this is hard,” that’s not a healthy conversation between us. Right?
So I’m always trying to get ahead of that with you and be like, “Okay this is where we’re at, this is what’s going on, this is what I’m worried about, this is what I need your help with,” so that you know that you’re not finding problems and giving to me because I know my own problems, and I am on top of them, and I’m telling you what’s going on and what I need from you, so that you should know that you can trust me.
MATT: Got it.
CATE: Asking for advice is also very helpful in self-awareness. Often people are afraid to give feedback because they don’t want to upset you and they are particularly unwilling to give you feedback if they think you’re doing a good job. It’s like, “No, no, no you’re good, you’re good.” But they might have some advice for you.
MATT: So just changing the word you’re using can change how people respond?
CATE: Totally. We have all these negative connotations about feedback, but feedback is really just your own being-in-the-world and being-at-work, for example, being reflected back to you. And it’s neutral really, or it should be. When I’m writing feedback for somebody, the question that I will ask them when I give it to them is, “Did you feel seen when you read this, did you feel like I see everything that you’re doing that’s great and everything that you’re capable of, and how you can do better?”
MATT: Something I try to remind myself, especially when I’m receiving feedback that might be tough, is that good feedback, and by good I mean it’s thoughtful, is a gift — feedback is a gift. And when you receive that you can use it well or you can use it poorly. And I love what you said around getting curious. That is a nice way to reframe something that might be challenging.
CATE: Yes. If somebody cares about you enough to tell you that they think you should do better then it means that they believe that you could do better.
MATT: What else is on the list?
CATE: There’s two more. The other one is stop giving advice. [laughter]
MATT: That seems incompatible with receiving advice.
CATE: Most people are way too willing to just give advice without context and often without even understanding what someone is trying to achieve. Declaring a moratorium on advice can at least make us pause and ask questions and get context and reflect back to someone what they’re saying to you.
And the last one is to own up. If you can admit what’s not going well then it’s much less scary for people to talk about the details of how that didn’t go well or what’s not going well. So again you can just make it easier for people to give you information that you wouldn’t otherwise get.
So my team doubled in size recently. I put up a post on our P2 and I was like, “Okay, so our team has doubled in size and clearly my job is going to change too, and these are the ways where I currently see myself not doing as well, and what do you think? What do you need from me?” And I asked these structured questions to get feedback around what’s the most useful thing that I do for you or what do you think I should stop doing.
And I got all this amazing input from my team. And if I hadn’t just straight-up admitted it in public, maybe they would be in private being like, “Ohh, Cate seems really frazzled, I don’t know what I can expect from her, I guess I understand that the team is bigger now…” But they might be afraid to tell me what they were experiencing. Whereas instead, putting it out there and having that conversation together made it a team change and a — My job is just the piece of how our team works and we are all deciding and designing that together.
MATT: I know you’re passionate about engineering management. One area where engineers do this a lot is in code review.
CATE: Right.
MATT: Pull requests, etcetera. So what do you see there and what are you working on or want Automattic to work on there?
CATE: I think code review is a core function of a healthy engineering team. Code review done well is such a powerful collaboration tool because both people, or anybody involved in the code review, is learning what the person who wrote the code did, the questions the other person asked, and the reviewer asked. It’s a structured way to have a conversation about the task itself and also the long-term [project] of the code base.
MATT: What else makes a great engineering culture?
CATE: Something that we used to talk about on the mobile team was that a senior engineer makes the whole team better, but we don’t want to be prescriptive about how people made the team better. That was up to them. There were options, but that was the expectation for everyone on the team. It’s like, you come in, you’re an experienced engineer, we expect you to be making the whole team better in some way, and what that looks like is up to you.
That captures my aspiration for a great engineering culture because one, it suggests that everybody is additive and two, it suggests that everybody is allowed to be unique. And three, it suggests that everybody has the autonomy and the support to operate from a place of strength.
MATT: How much of this is specific to being distributed? How much of this was true when you were at Google versus what might be different now in a distributed company like Automattic?
CATE: The thing I think about distributed is that it makes the things that are hard explicitly hard. I don’t think it really changes anything.
MATT: Tell me more about that.
CATE: You might say that getting a team to be coherent and inclusive and what have you, is just intrinsically hard. And if you are collocated, then you might say, “Oh no, my team is very coherent, we have lunch together everyday, and we do stand-up together every morning, and every so often we do some group activity together. Our team is very good.”
Whereas if you’re distributed you’ll be much more intentional about it. You’ll say, “Okay, well now I have a new team, and I want that team to be coherent, so how do I make it coherent? How do I make sure that the team understands what their mandate is? How do I make sure they understand what their priorities are? So how do we really maximize the value of a meetup so that people come away the most aligned that they can be?”
MATT: I think it’s helpful for us to be very real on this and talk about the downsides of distributed as well as some of the upsides, which we cover pretty extensively. So to be real and candid about Automattic, what do you think are our biggest challenges and weak points right now?
CATE: I think that we have not always done a great job of hiring and onboarding senior leadership especially into the distributed context. Sometimes we hire people who see distributed as a thing that needs to be mitigated or worked around, rather than a thing that you work with. I don’t think we’re delivering particularly well right now. I don’t think we’re shipping enough and I don’t think we’re shipping enough user value.
MATT: Totally.
CATE: And I think we’ve evolved our org chart in ways that have been more disruptive than we realize, and have created a lot of gaps that it’s not clear how we should fill or if we’re going to fill. The way that I think about org charts is that they’re really just our chosen optimization, and we can choose what it is, but we have to manage it.
And I think the thing about a distributed context is that sometimes you can choose your new optimization but if you don’t do the change management it’s not always as obvious what’s going on. Like if you’re in an office and morale is low, you feel it. But in a distributed context it feels different.
MATT: Cate, those are definitely some good challenges. One that has been on my mind recently is I’ve noticed a lot of negativity in some of the teams and some of the feedback. What are your thoughts on that and where does it come from? What can you do to address it?
CATE: I think people get increasingly negative when they don’t feel heard and when they don’t feel hopeful. And so I have spent a lot of time listening to people be negative, and have them not see the value of things that I’m doing. Hearing them out has always been really important and some people will never come around, and some people just need to feel like they’re heard, and to get some of the context that they may be missing, and to have a reason to hope.
In one of my Quartz articles I wrote about how, in any kind of period of change, the people who struggle most are the low performers and the high performers. And the low performers struggle for very obvious reasons, like, change is difficult for them because it’s potentially threatening. They know they’re not amazing. And so for those people, often you can make change good for them, because hopefully you can help them level up. I don’t believe anybody thinks, “Oh I want to be mediocre at work today.”
But then for the high performers, the things that they struggle with, is that they have found a way to succeed in the system as it is, and so any change seems unnecessary to them because really, the problem is that other people haven’t figured it out the way they have. And so those are people where — they’re to some extent right and to some extent wrong. And so helping them have the context, see the empathy, experience the empathy and see some reason for the change and helping them see a sense of improvement is really, really important, because you need to bring those people with you.
If your high performers are not bought into what you’re doing, then other people won’t be bought into what you’re doing either. So you spend a lot of time, or I personally have spent a lot of time on the high performers who are like, ‘Yeah but really other people just need to be better.” It’s like, “Well, yeah, they do, and so we’re going to help them be better now by doing these things,” and eventually they’ve seen the value of it. And that has generally brought me a disproportionate amount of credibility with other people on the team.
MATT: Who might distributed work be excluding that might be more included in an office environment?
CATE: Extroverts. Offices give people a certain amount of structure and community, and in the absence of that you have to create your own, and not everybody can or wants to. Work is really just one part of life. When you talk about distributed work, that’s great, there’s all these things that we can do. But when I onboard people into a distributed context, especially for developers, they don’t tend to struggle with the work aspect of it.
But what they do struggle with is the life aspect, especially people who have not worked in a distributed context before, or a remote context. They struggle to give themselves the structure in their day. They can start work whenever and so they do, and then they finish work at 2:00 in the morning. And at some point, some people are genuinely nocturnal and — fair play, but most people are not actually nocturnal. And starting your day at 4:00 in the afternoon and working until 2:00 in the morning is maybe not that good for you. It’s normally quite bad for your social life unless you are friends mainly with bats.
So there’s a bunch of knock-on effects to that, which affects your social life, it affects their life-life, it affects their health, because they’re not getting enough sunlight, exercise, what have you. So as someone’s manager, I care about them as a human being, but I’m not their mom. And so that can be quite hard because often it affects their personal well-being more than it affects their work, but it will ultimately affect their work too.
MATT: How can managers encourage inclusion, especially when they might have people across normal categories that we talk about, but also across countries and everything?
CATE: You have to be explicit and talk about it and measure it. In all our reporting on hiring, you will find the same words, which is “Diversity is more than gender, and gender is not binary.” But this is what we can measure and so we measure it, but then we do almost nothing that is just targeted at women. We just use it as a metric and as an indicator of diversity. And we talk about it very explicitly, constantly.
And I think being explicit like that is really, really helpful. I think being very vocal that it matters — in tech now, I feel like we have talked about diversity maybe too much, inclusion — not enough. And now if you’re not saying, “Oh inclusion is very important,” then you’re clearly a terrible person. So we’re all saying inclusion is really important, but what are we doing?
And then the final thing is building that human connection and checking in with people. I think there are a lot of things that we miss when we don’t see people in person, and you have to notice when people are quiet. And that actually is something that requires a lot more attention.
MATT: Cate Huston, thank you so much for sharing both the good and the bad about distributed work. I think there’s a lot of wisdom in the things we’ve covered.
CATE: Thank you, Matt. I appreciate you.
MATT:That was Cate Huston. You can follow her on Twitter at @ C-A-T-E-H-S-T-N.
I mentioned earlier that there are different approaches to distributed work. And that’s not just true for travel habits. People with different personality types prefer different levels of socialization, communication styles, and leadership styles. Some managers love to have lots of meetings and others would rather keep things moving in the Slack channel. This diversity of styles can make Cate’s job challenging, and as a leader of distributed teams, it can make mine pretty challenging too.
But I also think this is one of the things that makes the distributed model so exciting. It’s easier for us to meet people where they’re at and give them a custom work experience that suits their personal style. This ideally makes for happier employees and better work.
Next time on the Distributed podcast, we’ll be talking to author Scott Berkun, who once worked at Automattic and wrote a book about the experience called The Year Without Pants. I’m going to talk to him about his time as our first Team Lead, and about how the distributed-work landscape has changed in the last seven years.
Thanks so much for joining us and see you next time.
Leadership Coach Leo Widrich on Emotional Wellness for Distributed Workers
Aug 08, 2019
Leo Widrich co-founded Buffer, the social media management software company, in 2010. But like many founders, the frantic pace and daily stresses of startup life caught up to him. After spending a couple of years in a Buddhist monastery studying mindfulness and learning to build emotional resilience, Leo now coaches other business leaders. In this episode, Leo shares tips for distributed workers on how to build healthy habits and avoid the “loneliness spiral.”
The full episode transcript is below.
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Matt Mullenweg: Imagine starting a company with your buddy, turning it into a multibillion dollar business, and offering a service used by brands all over the world, and then walking away from it all to live in a monastery. That’s exactly what this week’s guest did. We’re going to hear all about why he did it. With the startup Buffer, Leo Widrich has achieved success by any measure. But something was missing. His dissatisfaction with the lifestyle led him to pursue deeper truths that he came to realize cannot be found in the pursuit of material success.
Leo studied Buddhism. He spent some time living with monks, and learned to appreciate an intentionally slow lifestyle. Now, he coaches entrepreneurs and even other coaches with the goal of helping them manage the stresses of their careers with a combination of ancient wisdom and a sprinkling of modern neuroscience. He wants people to learn how to build emotional resilience, and the ability to self-regulate their emotions so they can deal with their issues and avoid the full-scale burnout that he suffered.
Buffer is a remote company, so it’s clear that Leo has a passion for unconventional work arrangements. However, he’s extremely sensitive to potential emotional and psychological pitfalls associated with working from home. In this episode, I learn about the loneliness spiral, what can happen if you don’t exercise your social engagement circuits through regular social contact, and Leo shares a few tools that we can use to care better for ourselves and the people we work with.
Leo Widrich: I started a company called Buffer close to a decade ago with a friend and we worked completely remotely.
Matt: Where were you both when it started?
Leo: We both first lived in Birmingham, U.K., so in England, we both studied there. And then we flew out to San Francisco and said hey, Silicon Valley is the spot. That’s how we got started. And we went through all the startup struggles and ups and downs and a couple of the things that were really wonderful as we built the social media management software. And we did it eventually fully remote also, to a level of transparency where I really wanted to put everything on the table about what was going well and what wasn’t going so well in the business.
Matt: An unheard of level of transparency. So Buffer publishes its revenues, its salaries, its options. Everything, right?
Leo: Right. That was a real desire for us to bring that level of transparency to the business world to reduce some of the sense of secrecy and some of the sense that this is a fight and make it a little more collaborative.
Matt: Tell me about the why there. Why were you distributed if you started in the same place? And then why the transparency? And are they related at all?
Leo: I think that the distributed part — we were in San Francisco and the team was growing and I’m sure you know that as the team grows in San Francisco, your office space needs to grow. And we were in the middle of — should we expand and get a new office? And I remember even meeting with some brokers, and the prices, they seemed incredible. And we were like, huh… And some of us were barely even coming to the office.
And I think that was a moment where we all thought, “Well why don’t we try not being in the same office.” And we had tried that before because of visa problems. So at first that was totally not a choice, we just had to be all over the world because we couldn’t stay in the U.S. My partner, Joel, he was from England, and we had a third cofounder, he was also from England. I was from Austria. So it was really hard for us to actually be in the country, so we had to be distributed.
But eventually it was a question of cost and a question of joy and ease too, right? Like, “Oh, why don’t we get to work from wherever we want to?”
Matt: Great. And when was this?
Leo: It must have been 2013, over six years ago, that we decided — before it was unclear, more like an unwritten rule, because we were so small. But then we decided, no, I think we will allow people to be wherever they want to be and then make that a more official commitment, so to speak. And that was also the time when we did start to be more transparent because we wrote down our values, we were very inspired by a company called Zappos at the time.
Matt: Yeah, of course.
Leo: Right? Tony Hsieh is a real mentor in that space of really defining your values and having your purpose. And that was also one of the things that came out of that. So committing to working remotely and committing to being transparent as a way to share with the world what we are learning and to foster a sense of collaboration and openness.
Matt: What was your biggest lesson from being distributed like that?
Leo: At first it was so wonderful. We were traveling around the world, we got to really live a life as well as we were working. So we weren’t deferring enjoying life, so to speak. But over time for me personally what started to creep in a little more was this sense of loneliness, this sense that I feel not as connected. I don’t need to have a base so I’m not committing to a base, that untethered-ness, the longer it went on, the less enjoyable it became, the more almost-painful it became, I would say.
Matt: When you left Buffer, what was next for you?
Leo: I started to feel like I was hitting a wall. This thing that I always dreamt of, to have a profitable company, to be financially secure, to have a team, like a lot of things that I started to aspire to when I got in touch with this idea of startups early on — I felt that having that success, having some of that financial security — it left me unfulfilled in a lot of other areas. In the sense of deep lasting connection and also just a lack of emotional resilience to deal with the ups and downs that startup life comes with.
So I felt exhausted and we weren’t quite fully in agreement anymore with my cofounder. And I took that as a sign and said “Maybe this is just no longer the right thing for me.” And I took my hat and I left and it started this really interesting journey from outwardly doing stuff and accomplishing stuff — which was the only thing I knew at the time — to go inward. And I started to go and live in Buddhist monasteries and do some therapy training and really start to understand — “Okay, there is so much I was externally striving for but what’s actually here? What’s this foundation, this house that is my body and my psyche?”
Matt: Wow, that’s a big step. Tell us about this Buddhist monastery.
Leo: It’s a big step and a lot of people at the time, they looked at me and they said, “Oh, you’re crazy.”
Matt: I’m so curious, is there an Uber for monasteries? How do you find where you go? Where did you end up? Just walk me through the whole thing if you don’t mind.
Leo: [laughs] Right, for sure. I started to become very interested and soothed by the writing of a Buddhist monk called Thích Nhất Hạnh, and that is really the person that I think brought me into this world. And he wrote this book called Peace Is Every Step. That was the first book I read. It really touched me. It set something off in me.
He talked about a sense of living in the world and being in the world without that constant striving. And here I was finding myself striving so much, trying so hard to make something successful, to be successful, and he was challenging that idea. And so I saw him speak in 2013. That was when that was more on the sidelines. I was just learning about this stuff.
And I was living in New York and there is a monastery called Blue Cliff Monastery in upstate New York that I wanted to check out. And I went there for a few retreats, to see what is this life like that seems the exact opposite from the rapid fire startup life, where these Buddhist monks and nuns were living, going so slowly, barely any agenda on the day, every day. And so it was this very different life, very slow. There was very little content, other than what was bubbling up from within me, right? So it was really making a lot of space.
Matt: So you went from startup founder to — I don’t know if you’d call it a monk but you were at a monastery for several years.
Leo: Right.
Matt: And now you’re like a coach. So you work with clients.
Leo: Yup. I call it emotional resilience training, that’s the tagline I have.
Matt: So assuming that you can’t tell your clients to also go away for two years…
Leo: [laughs] Right.
Matt: What’s a middle ground?
Leo: Yeah, you don’t need to go off for two years. But there needs to be some sense of regularity to coming inward, to coming internal. And that is what allows us to build that muscle of emotional resilience where we can not be so cut off from ourselves in the face of difficulty that happens to us and instead to flow with it, to surf the wave of pain, of anger, of sadness, whatever it is.
And I started to incorporate that with executive coaching, with a framework that — yeah, and you want to also keep contributing to the world. A lot of people don’t want to just step away. Often times, they can’t, right? They have a family to support, they need to keep working or to have a startup to run. And so it became and it is still becoming this combination of offering this deeper emotional work alongside more dialed-in direction-setting for where you want to take your company or your career or your life.
Matt: Give me an example. You say you need this daily habit. What would be something I could do to start to connect and avoid that burnout?
Leo: If it’s possible to you, I would recommend to find something that is not solitary.
Matt: So not self-meditation?
Leo: Yeah, not self-meditation. I would recommend against that unless that’s the only thing available to you. I would recommend that, if you can, to find a therapist or find a coach or find a mentor in your company that you can have regular conversations. Or even a trusted friend — there is a beautiful practice that people can google, it’s called Empathy Buddy Calls. And if there’s a framework for this — how to have these deeper conversations with a friend because often they — even though we might trust someone or have a great friendship they don’t always go to these deeper levels and it’s a great framework.
That would be my suggestion, to have some support. And the reason I think this is important is because the very idea to do things alone, especially for the likes of me, are only further perpetuating the way I see the world, that I need to be hyper-independent, that I need to pull myself [up] by my own bootstraps, that it’s about strength and doing things alone. And I find that again, back to an evolutionary science, is not really how we evolved, it’s not how our brains are wired, and it’s not as effective as doing it with another person.
Even when I lived at the monastery, it was so interesting that none of these monks meditate alone. Every meditation is together. And this monk, Thich Nhat Hanh, he emphasizes sangha so much. He says if you don’t have a sangha, which is a Buddhist word for “community,” it’s almost impossible to really go to the depth that you need to go to, to deeply transform within yourself.
Matt: That’s so interesting because I’ve definitely read also — I want to say it was Naval Ravikant who sort of made fun of how Westerners turn solitary things like yoga, meditation, into group activities and team sports.
Leo: Interesting, interesting. Yeah.
Matt: And I forget the exact tweet but I took it to heart a little bit because I do often like to exercise or meditate with at least one friend, if not more, and I was like, “Oh am I doing it wrong?” Maybe I need to be more comfortable being alone.
Leo: Right. And I can see the point of that too. I can see the point of that.
Matt: But your advice is different for your clients.
Leo: Absolutely. It has become different. If you had asked me four years ago, I’d been meditating on my own for years and years before going to the monastery. And I agree on the point that if it becomes a sport or if it becomes a co-exercise — that is not what I’m talking about. What I’m talking about is to enter spaces together that have a certain depth where you and I say, “If we were to do this together, I might still have a solitary experience, by you holding space for my experience.”
But from a nervous system perspective, the charge that is needed to allow some of these deeper things to come up through the vagus nerve and through my amygdala — in order for that to be held — the amygdala is the fear center in our brains. For that to be not going all over the place, having a second nervous system there to create a sense of safety, I believe is so extremely vital.
Matt: So that would be your advice to someone starting out, say, find a buddy and do some of this more mindful activity together?
Leo: Absolutely. If that’s possible then I think it’s — and talk about it.
Matt: We’ve used the word burnout already. What does that mean to you?
Leo: In the same way that the word stress — I like to use it less so. Because it doesn’t really give us a sense of what underlying thing that is happening. I think I even like to use the word PTSD better.
Matt: That’s a heavy one.
Leo: Right, for most people that would sound heavy but most of —
Matt: And it has stress in it.
Leo: And it has stress in it, right. But the interesting thing, when we talk about PTSD, and I don’t talk about the way it’s defined for psychologists, I talk about posttraumatic stress. And maybe we can leave off the “D” of disorder because I don’t really think it’s a disorder. But I think it’s anything that when we feel tense in our bodies, it’s because it’s posttraumatic stress. There has been a certain event in our lives and there may have been in our childhood or there may have been, you know, in a meeting or a presentation, and our brains weren’t able to integrate fully what was going on.
So I’ll give you a common example. Maybe you’re a founder. You have a meeting with your board, and there is a very heated debate. You’re not getting the buy-in, you’re not getting the agreement for something that you really wished you could do. And you leave this meeting feeling quite distraught, feeling quite activated. Your nervous system is charged, you feel angry or you feel sad or there is something — you’re no longer regulated.
Now most people don’t have a way to resolve that. They have a way to auto-regulate and it’s different from self-regulation. And I’m bringing in a few terms here. But most people then auto-regulate. They have a glass of wine or they have a drink or maybe they watch something on TV to soothe themselves.
Matt: What does auto-regulate mean?
Leo: The way it’s defined in neuroscience terms is our natural, unconscious coping mechanisms to deal with deregulated states. And deregulated states means when we are not relaxed, in a relaxed alertness. So that means eating sweets, right? That’s a common auto-regulation pattern that I have. When things get tough, my mind sometimes goes to the ice cream tub in the freezer.
Matt: For me it’s a matcha latte.
Leo: Right, right. [laughs]
Matt: If I’m tired from the day before I just like — you know, the afternoon comes along and I’m like mmm, matcha latte.
Leo: Right.
Matt: I deserve this.
Leo: Right.
Matt: And I get addicted a little bit to that. I don’t have very much caffeine usually. So it does have a big effect on me.
Leo: Right. And that’s a wonderful example. Auto-regulation doesn’t mean it’s bad. We all have that. It can have extremes, like heroin is auto-regulation in the same way that going for a walk in the forest is auto-regulation, right? It’s things that we don’t think about too much that just come to us that have been ingrained patterns and habits and we do them.
Matt: Is burnout avoidable?
Leo: I think so, when we have self-regulation. So self-regulation is a way to deal with the actual effects of what happened in the meeting and to fully process it, for example, if you go back to the example of the board meeting. The body always keeps the score of whatever we haven’t fully processed.
And so the more of these episodes you have, and in a startup very quickly you might have a lot of meetings where things don’t go well and if you don’t have the time to self-regulate, to talk through this with a friend or with a therapist or with a coach or somebody or with a partner — some people have very healthy self-regulation coping strategies there, you’re actually getting to the root.
After the meeting, say I had a hard meeting and you’re my good friend Matt, and we sit down and you ask me, “Hey Leo, how are you doing? You look a little upset, you look a little tired.” And I get to say, “Yeah, I’m so upset, this just sucked, this meeting.” And you reflect that back to me, you help me, and say, “Yeah it just sounds like you weren’t heard and you didn’t feel seen and that sounds like it was very painful,” and you just keep holding space for me. And I might cry because it just makes me so sad and I might shake my fist because I’m so angry, letting the bodily states come in. I can’t shake my fist at the investor in the meeting.
If I have a chance to self-regulate with someone I trust later on, then something magical happens, then this stuff doesn’t build up and five, ten years in you don’t feel like all of a sudden your body is tense from so many different things, you don’t even know why, and you just need to lie down. And we call it — when really if you looked closely, we could trace it back — that it’s all these individual episodes of moments that haven’t been processed.
Matt: Let’s say that I had a friend who had been through something tough. How can I best hold space for them?
Leo: The most important thing that you can do to a friend that’s going through a hard time is to offer what neuroscience calls warm accompaniment. It used to be called empathy but empathy has — it’s got a little — empathy is feeling what someone else feels, it doesn’t really encompass anymore what is meant or what makes it understandable.
So warm accompaniment means that you refrain from giving any advice, you’re not trying to fix anything. You’re not trying to tell them about your experience, you’re not saying, “Oh this reminds me of my time when I was sick,” you’re not trying to do anything but ideally — and this is from a practice that I also really enjoy called non-violent communication — you just offer back what you are hearing and that can be as simple as reflecting back the exact words.
And that’s not always the right thing for people but if you’re just getting started, just saying — if you were doing this with me, Matt, if you said, “I had such a hard day at work,” for me to just say, “Wow, it sounds like it’s been a really hard day for you,” that is the warm accompaniment to be I am right there with you without being carried away by your experience. And so, reflecting back what you heard somebody say, noticing whether you can be present.
You know, if you get carried away and you might say, “I also had such a hard day at work” and your day was so hard, now we’re not co-regulating.
Matt: So I shouldn’t try to match it.
Leo: Right.
Matt: Should I say “I know how you feel?”
Leo: “I know how you feel” is sympathizing with another person, it is not warmly accompanying their experience. When someone is having a hard time, what is important to them is to understand, for their nervous system to understand that what they are feeling is okay. And I think that’s what you’re trying to say when you say “I know how you feel.” But more important is to offer up the reflection with warmth so that they can see “Yes, that’s what I’m feeling and this person is not triggered by this so I guess it must be okay and my body can relax a little bit.”
Matt: What are some other examples of warm reflection?
Leo: The main way we use to communicate as mammals is through the tone of voice. And there is a term in neuroscience called prosody that means the emotional content that your voice carries. And there’s thousands of nuances that we have in our voices to communicate how we are feeling without the information or the data of the words we are saying. So the most important thing that you can do is just to — the way you say, “Mmm,” or the way you say “Uh huh,” or the way you say “I get it,” — the emotional content of your voice is the most important signal of safety, and we want to do that with the resonance of our voice.
And the best way I know how to do this is purely by understanding that you can stay present to cultivate that yourself, right? It’s hard, it’s gonna be hard for you. If you don’t know how to —
Matt: It’s hard to listen.
Leo: Right? It’s hard to listen if you haven’t had enough listening from yourself for yourself or from somebody else for yourself so you can hold space. So that is the long-term practice. But looking into needs and feelings, guesses from the non-violent communication framework is a really wonderful, specific thing you can do.
To say, “Are you feeling really upset because there wasn’t enough understanding in this meeting?” So that now the person has a chance to either say, “Yeah, you’re getting me,” and can expand, or can clarify what their experience is and accompany that warmly, and can say, “No, I’m not upset because I wanted understanding, I’m really upset because there is no harmony in this company.” A-ha, it’s not about understanding, it’s about harmony, right? And so now the closer — the more precise we can get to experiences, the more likely our nervous system can discharge this and let go of it.
Matt: The classic book on non-violent communication is by… is it Marshall Rosenberg?
Leo: Marshall Rosenberg, yeah, exactly.
Matt: I would particularly recommend it to anyone who is a manager because I think one of the most important things you can do as a manager is listen to people and really hear them.
Leo: Right, mhm.
Matt: And that’s very difficult. I think especially if you’re a new manager there is a temptation to make it about you.
Leo: Right. When you’re a manager and you haven’t done — All the sudden you work with people and you haven’t done your own inner work and your own inner training, it’s gonna be hard to hold space for people, which to a lot of people is a first when they first become managers.
Matt: And that’s a lot of what I’ve been thinking about as well, is people who are becoming managers for the first time in distributed organizations. There’s lots of people who are freelancers but when you start to get to managing fifty, a hundred people, in a distributed fashion, there’s just not that much out there about it.
Leo: Totally.
Matt: You’ve written about something called the loneliness spiral. Can you introduce that for the audience?
Leo: The loneliness spiral is associated with the fact that we have — as mammals evolved to be in groups, we are very unfit to survive alone. When we are alone for too long of a stretch of time many people report to feel a feeling that they name “I feel lonely.” And that feeling is simply our nervous system’s alarm system to say “Hey, if you spend too much time alone you’re not gonna survive in this world. Go make some friends, go be with family, go be with other humans.” And we need that physical touch, really in the same-room interaction for that, often for that feeling to dissipate.
The problem with the loneliness spiral is not that we feel lonely, the problem is that often times when we feel lonely we feel scared at the same time. And actually even if I feel lonely, what I want to do is go out and meet friends, but if I feel scared now I start doing things, because I’m not able to hold that emotion very well in my body, I end up maybe sitting on the couch, eating more potato chips because that fills me up, and then watching some YouTube videos.
Matt: It can distract you.
Leo: Exactly. So that can distract you but it’s not taking care of the underlying root cause. The thing that happens over time, if it’s not being acted on, parts of our brain — an author called Stephen Porges, who wrote a book called The Polyvagal Theory — he calls this heart of our nervous system the social engagement circuits. If they are not exercised through a muscle, through regular social engagements, through regular social contact — and this is one of my concerns with remote work — if that’s not exercised it atrophies.
Matt: So we’re talking right now.
Leo: Yeah.
Matt: It sounds pretty good, like you could be right next to me.
Leo: Right.
Matt: Does this also get activated by video calls, by phone calls, those sorts of things, Facetime?
Leo: It does, it does. That is good news for remote work.
Matt: That’s good. Because then I can connect with someone anywhere in the world.
Leo: It’s good news and, and I wonder if you’ve noticed this with remote work, is that most calls are scheduled, right? We are not here to just catch up, you know? We are not here to just tap me on the shoulder and say, “Hey Leo, how are you doing?” by the water cooler, “How was that concert you went to last night?” So the sort of social engagement that I’m talking about, that almost intimacy that can develop that happens most likely when things are unscheduled and spontaneous are much [less likely] to happen.
We have experimented with this at Buffer. We tried to have book clubs and social hangouts on Zoom and what not to create that. And I think that’s often what’s needed beyond the scheduled meetings where there is an agenda and you work through, and the informational content really is a thing, what it’s all about and not the emotional content that really is a thing that trains our nervous systems to know, “Okay, I’m not alone, there’s other humans that care about me, I care about them.” That thing.
Matt: How about if I’m in a crowd? I know personally sometimes I can feel very lonely even though I’m around a lot of people.
Leo: Right, yeah.
Matt: Just going to a coffee shop. But is that gonna help anyway?
Leo: It’s something. [laughs] It’s something but you can still feel very lonely. And my view on that from what I’ve learned about our inner states is that often that social engagement is activated only when we reveal something about ourselves, when we show something about our truth and about who we are. And that’s sometimes not very likely to happen in a coffee shop. You may walk around a lot of other humans but there is no heart to heart or there is no emotional connection.
I think of the CTO at Product Hunt. His name is Andreas Klinger. He had a great suggestion. He said, “I think it’s a good idea for remote workers, wherever they live, to find other remote workers and to start small offices together so they could develop a group cohesion, even though they don’t really work together.” I love that.
Matt: A lot of folks listening to this are probably on one side or another of a one-on-one with a direct report or a manager. So what would be some good questions or things for people to do when they are in those meetings?
Leo: The most important question I think for a manager is to ask the person how they are doing. It’s colloquially so common to answer that with “fine.”
Matt: It’s almost reflexive. If you said, “How are you doing?” I’d be like, “Yeah, good” or “Fine.” I wouldn’t even think about it really.
Leo: Right. Exactly.
Matt: Because it’s very vulnerable to answer something not —
Leo: Right. So it becomes a question [of] how can you give people a chance to open up. The number one way I know how to do that is to give space to the other person to resolve things themselves. As a manager, the best thing you can do is train yourself to hold space for yourself so you are not having a million things that you need to unload onto your employee, to keep making more room, to keep letting more things bubble up that can be resolved. How do you feel about this? What do you — To keep it with open-ended questions and to let advice maybe only come in at the very end.
Matt: You cofounded one of the more prominent distributed companies. If you did another company, would you make it distributed again or do you think the in-person is more important?
Leo: I would probably not start distributed. For a sapling to grow I have this feeling that being in the same room together could be really, really vital, at least the first two people.
Matt: I would actually — I think I would probably agree with that. WordPress, we were always distributed because it was open source. But for Automatic, the early folks, myself and Toni [Schneider], who joined as the CEO a few months after it started, we would see each other quite frequently in San Francisco. I was more based there at the time.
Leo: Right. So I think that early time, being together could be just extremely vital. And over time I think I feel I would be still excited to open that up and to make it fully remote as you go beyond ten people. And I would — remote work is a little bit like the Wild West. It has so many benefits, but there’s so much that’s not understood about the dynamics.
I would probably be even more conscious about, first and foremost, my own coping strategies to working alone a lot and setting myself up much better. Often times the people that joined later, they were way better set up than people that were wanting to have a job at the company, they already had their families set up, they were happy to spend more time with their kids and at home. Often times they were better set up than me as one of the founders to like — that’s all over the place all the time.
Matt: Let’s say we are doing a distributed company, we talked about some of the advice you’d have. Any other tips or things that you think from your experience folks in a distributed company, managers or founders, should think about?
Leo: Cultivating human-to-human connections as much as you can within the company. I had this one idea, I think what would be great is to have for these distributed companies in particular, to have a resident stress therapist that people could just go to and sit with for an hour and pour their heart out in relation to what is going on in the company so that they have some context.
And then to meddle with the less productivity-related things when I believe — productivity is always about emotional states anyways. When we are not productive it’s because the task at hand has some emotional charge that stops us from doing it. You know, we are scared because of how people might receive this. A lot of people are scared of being successful and being seen because there is a lot of underlying trauma around actually being seen for what people do.
So I think the reason when someone doesn’t want to do a task, there is some underlying emotional charge that’s not being taken care of and finding a way to get to that within a company through maybe a group activity, a regular structured or unstructured time where people can interact with each other, and to work with a manager, or to have a stress therapist or something like that, so that those aspects of your life that are often where you get stuck, they can get unstuck.
Matt: I’ve been asking everyone if you could imagine twenty years in the future, what percentage of jobs do you think are distributed or not in the office?
Leo: I would maybe say thirty percent.
Matt: Thirty percent. All right, I appreciate it. Well, Leo, thank you again so much for joining me today. A lot of good tips. And you’ve given me a lot to think about.
Leo: Thank you so much for having me on, Matt, it’s been a real pleasure.
Matt: That was Leo Widrich, and you can find him on Twitter @LeoWid, or his personal site, powered by WordPress, leowid.com. If remote work is going to become the rule rather than the exception, we’re going to need to come up with ways to cope emotionally with our new social environments. Maybe it looks like regular team meetups, maybe it’s a hangout in virtual reality, maybe it’s co-working spaces with happy hours. Maybe if people feel less pressure to leave their hometowns to go work at employment hubs, they’d be able to maintain stronger ties with friends and family.
The solution is going to look like all these things and more. Whatever the future of work looks like, I’m glad that people like Leo are thinking about the psychological traps that might be easier to fall into when working from home. I know that the next time I start to feel a little lonely, I might plan to go grab a matcha latte with a friend, so my vagus nerve gets some exercise.
Design leader John Maeda on how to foster creative collaboration on distributed teams
Jul 25, 2019
John Maeda has spent the last three years leading Automattic’s design team, and on this episode of the Distributed podcast, he reflects on what he’s learned with our host, Matt Mullenweg. John shares how to facilitate collaborative creativity across a distributed team, explains why smart managers blog (and vlog) prolifically, and discusses how giving and receiving feedback with a spirit of gratitude, humility, and empathy is essential for managers, especially in a distributed context.
The full episode transcript is below.
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MATT MULLENWEG: What did real-time remote collaboration look like 30 years ago, in the primitive era before Slack and Zoom? My guest on this episode of the Distributed podcast knows, because he was there.
Designer, author, and Automattician John Maeda spent the latter half of the 90s pioneering a new field called computational design at the MIT Media Lab, a legendary sandbox for researchers who wanted to explore and create the future of tech. Computational design was a bold new approach that applied design principles to the creation of hardware, software, and computer networks, and John helped define it from the beginning.
By 1999, John had developed enough of a reputation for Esquire magazine to name him one of the 21 most important people of the 21st century. Wired magazine once said that “Maeda is to design what Warren Buffett is to finance.”
My company, Automattic, has been lucky to have John working with us for the last few years, and he will be moving to Publicis soon. He’s been leading a team of 70 designers scattered all over the world, and before he left, I wanted to talk to him about what that’s like, so I’m thrilled that he’s able to join me for a discussion about creative collaboration at a distance.
We are here today with John Maeda, who leads what might be the largest all-distributed design teams, or at least that we know of. He is the author of three books, The Laws of Simplicity, which is actually what introduced me to John’s work, Creative Code, and Redesigning Leadership. And I believe there is a fourth book on the way, is that correct?
JOHN MAEDA: There is. It’s How To Speak Machine. And thanks for having me on.
MATT: Oh, no problem. So your title is Global Head of Computational Design & Inclusion.
JOHN: Mhm, mhm.
MATT: Computational design might be a concept that not that many people are familiar with as well. Tell us about that.
JOHN: Well actually, people ask me about that. That’s why I thought that How To Speak Machine is the first primer on that because when we think about the value of design right now, because of the technologies we use today, it isn’t a picture, it isn’t a clever drawing. If it’s computational, if it’s driven by code, or it’s tied to code, it can achieve scale, it can achieve behavior, it can be interactive.
If you think of an early computational design system, that would be WordPress. It’s interactive, I can use it as a tool, it’s not like a poster in the MoMA collection, but it’s a usable system that is running with computation. It never gets tired. Want to add a post again? Okay. Want to add another post? Okay.
So the computational system never gets tired. Whereas we’re in a room with a beautiful wooden table. This table, if we — we wouldn’t want to hurt this table, we don’t own this table, I know — but if we kept hitting at it, it would eventually fracture. It has physical laws. But computational systems behave differently because they are built out of programs.
MATT: Where do humans fit into this?
JOHN: Originally humans and computers interacted, like Hiroshi Ishii’s human-computer interface world.
MATT: Yeah.
JOHN: But now computers and computers interact, as you well know. They’re hanging out together without us, especially with AI. They’re hanging out. Like, “What do you got?” “I got this” or “I got that” “Well give me some of that.” So —
MATT: I love the concept of the AIs that train against themselves.
JOHN: Oh those are really cool.
MATT: Like the Alpha Go, [or] the other things where they have this adversarial learning against itself. So it can play hundreds of millions of games in a day.
JOHN: That concept you described used to be science fiction but now, because of the resources we have available to us by the cloud or everything we can buy now, that’s a normal thing. If our raw material has changed then design should have changed too vis-a-vis computer-based systems.
MATT: And has it?
JOHN: It’s trying to. That’s the one thing I’ve realized is so hard — this is across the tech ecosystem — is that there are a lot of designers who came from the past. And so when we look in this room, the person who designed the texture on that wall over there, that’s a kind of design, but it’s less relevant to the design of a new release of a new feature that needs something that actually has to ship right now.
And the distance between that design and a design that once it’s shipped now has to iterate and improve at a rapid velocity — that’s a different kind of design. I think most of the design, maybe over 90%, is stuck in the old design, not in computational design. So that’s why I wanted to highlight that when I joined your merry band.
MATT: Let’s say someone is listening to this, a younger person who is not currently in design and wants to go into it, and wants to be in this kind of present or future you’re describing. What should they work on?
JOHN: They should use WordPress. [laughter]
MATT: Okay, so that’s a good start.
JOHN: No, no actually not in that way. I have been using WordPress intensely, over two years now, getting on three, and it has really reminded me how the internet works. It has exposed the messiness of how information is transmitted, how it’s displayed on multiple platforms.
It’s like people who really love WordPress will hate hearing this but it’s kind of like infants, for them to walk, there is this baby walker thing, I’m not sure if it’s legal anymore, but there’s this thing where the baby can stand up in this walker thing and they can move, they can move around the room and it’s like, “Wow the baby is moving around.”
MATT: It’s like a little circular thing with wheels?
JOHN: A circular thing with wheels on the bottom, exactly.
MATT: I haven’t seen one of those recently but I know what you’re talking about.
JOHN: They must be illegal now for some dangerous reason. But to me it’s been like a baby walker because — I know a lot of the high tech stuff but I lost sense of the basics in many ways.
MATT: What are some of those basics that people should be familiar with?
JOHN: The basics are, first of all, collaboration.
MATT: That’s not a basic. That’s hard!
JOHN: Well I mean that’s a basic that comes — if you build software yourself you don’t have to collaborate, right? But by having a distributed system you have to collaborate. So just to get in touch with that, that’s been great.
MATT: What makes you good at collaboration?
JOHN: Listening. I think it’s the number one important thing is listening. What is the saying, two ears, one mouth? So two-to-one? [laughs]
MATT: But everyone can’t do that at the same time.
JOHN: Oh yeah.
MATT: Sometimes it’s going to be impossible?
JOHN: Yeah. The collaboration thing is key, the listening part. The second thing is being technically facile. Being able to write poetry in code. I think for a long time, because I was in the classical design world where coding is bad, like coming back into, via Kleiner Perkins and eBay and Automattic, I’m like, “Oh, coding is good.” And why is it good? It’s because you have agency. What does “creative” mean? It means I’m creating. And if you can code you can do so many things.
So collaboration is important and to be able to make code is great. The thing I love is how I think of what I’ve learned with WordPress — it’s like Lego. And people will say, “Oh it’s just Lego, it’s not like real wood, real marble, real concrete, it’s just Lego.” But in this world of having an idea, an MVP or an MLVP, you want Lego to be able to make ideas spun up quickly.
MATT: You brought it full circle. You said community-made platforms win or lose. Some people say that WordPress is not the best CMS, but it does have one of the largest communities and has been the most successful.
JOHN: Yeah.
MATT: You also said that the first thing that designers need to know is collaboration.
JOHN: Yes.
MATT: So it came to people.
JOHN: Yeah.
MATT: As we said in the intro, you lead definitely one of the larger all-distributed design teams. So if collaboration is important for design and you can’t have everyone in the same room around a whiteboard, what do you do? What are the challenges? And what are some of the benefits?
JOHN: You just reminded me how in the early 2000s or late ’90s I had made this system called Design By Numbers, and it was a system to teach anyone how to code. It was very limited. You could only draw in a 100 by 100 square in black and white. Super constrained system, super easy to teach anyone computation. And then two people on the research team, Casey Reas and Ben Fry, who were involved with this system, said, “I think this system should be less constrained. It should be color. And why is it limited to 100 by 100?”
And so they built this system called Processing and they did two things. The first is they built a community center portal around it and the second thing they did was they open-sourced it. And at the time I’m like, “That’s never going to take off. That’s just sort of a — what is this? It’s never going to happen. You should be working on something else.” And that’s why I never really believe anything I say because I could be wrong. I was so glad they didn’t listen to me and they went off and made this Processing thing. And I think there’s a gazillion books about it, there’s communities around it.
MATT: It’s extremely popular, yes.
JOHN: I had to learn from them the power of community because I spent most of my career making software by myself. Everything I made by myself, I designed every book by myself because that’s what I thought people did. The great creators made things by themselves.
MATT: Which is also amazing because, as you know, so many great artists had workshops, architects…
JOHN: I know, I didn’t know that. I didn’t know that Michelangelo didn’t paint all those.
MATT: Leonardo da Vinci…
JOHN: I didn’t know that.
MATT: Raphael. Yeah.
JOHN: Well, you know, I grew up with —
MATT: Today, Jeff Koons.
JOHN: — my family had no education, we had no books, there wasn’t internet, I had no idea.
MATT: The myth of a solo creator might be one of the most corrosive to creativity in general actually.
JOHN: Ohh totally. Oh my gosh. I almost died doing that. I got sick, overworked, I was in the hospital for three weeks. I went over the line, you know?
MATT: You told me about that before to caution me against it.
JOHN: Oh yeah, it happens, it happens. It goes past…
MATT: I appreciate those cautionary tales. It’s worth noting on this podcast itself is not a solo endeavor.
JOHN: I agree 100% and I think that the solo creator myth is something that I strive to break through sharing my own embarrassing failures around this. And then when working with teams the number one important thing that I found is respect.
MATT: In working together over these past few years you seem to exhibit an incredible amount of empathy, which is also important for design. Maybe we’ll add that to the list. Or I’ll put it on my list, you don’t have to put it on yours. How do you balance that empathy with that, [so you’re] able to get through these tough things?
JOHN: One of my favorite artworks I’ve made in my life — I don’t have many things I like that I did, but I was in a meeting at MIT where I was having this feeling of, “Whoa, this is feeling really ugh, you know?” I calligraphed on a piece of paper “thicker skin” 75 times. And it’s entitled “Thicker Skin 75 Times.” And it was sold at an auction for charity for UNICEF in Paris. But it’s my proudest piece of artwork because all of my feeling went into that simple drawing to remind myself that it really isn’t about them, it’s about me: Can I have thicker skin?
MATT: It’s a powerful concept.
JOHN: Yes. But it hurts still. It hurts. If there is someone that you really respect and doesn’t respect you, sometimes it works, sometimes it doesn’t. Does it hurt? Of course. Every time it hurts. Like, “Oh wow.” You let someone down and you don’t forget it.
MATT: But does that close you off to the full range of human emotions?
JOHN: That’s more a combination of thicker skin and gratitude.
MATT: Gratitude, okay, that’s one we haven’t talked about yet.
JOHN: Yes, thicker skin is there if you’re feeling bad and then the gratitude is there because it’s like, “This is an awesome world, like, this is so amazing.” Or you’ll feel gratitude for someone in your past and that activates something good in you. I always think about how I would not be where I am today if it wasn’t for my 11th grade high school chemistry teacher, Mr. Wakefield, who took an interest in me as being the number two smart kid in his class.
The number one kid was so much smarter but came from a really good background whereas I came from a background where I knew nothing. My parents had no education, we didn’t know what the future should be like. I was working after school at my parents’ shop, on the weekends. I hated summers because I had to work there all the time. And so Mr. Wakefield said to me, “You want to go to a good school, you’ve got to have stuff on your application that makes you credible.”
MATT: The extracurriculars?
JOHN: And I was like, “What’s that?” So he said, “We’ll make a science club,” and whatever, so we did that. And then he said, “You need to take a class at the local university over the summer.” And I said, “Oh my parents won’t let me do that because I have to work at the store.” And then Mr. Wakefield came to the store on Saturday, on the weekend, to talk to my parents.
MATT: Wow.
JOHN: He didn’t have to do that. He was a retired Boeing engineer, he never would venture into the Chinatown area. I mean he didn’t quite fit the whole thing. [laughs] He came and talked to my parents and said, “You want your son to go to a great university, let him take the summer off and do this, give it to him.” And they did.
MATT: And they did. What did you study that summer?
JOHN: Organic chemistry. I loved chemistry. I was going to become a chemist. I was almost going to be — at MIT the only class I didn’t fail out of in the first year — it was a really bad year — was solid state chemistry. I got one of these rainbow stickers on my tests. Oh it’s the one moment of “Ohh, I’m not an imposter. Should I be here?” I got the golden sticker that one time.
I think of Mr. Wakefield, I think of other people like that who gave me a chance and I feel gratitude towards them. And then it gets easy, like how can I serve you, how can I help you? It’s easier.
MATT: One area we didn’t fully cover was that chemistry for teams or the collaboration for design teams. In a remote setting does anything stand out?
JOHN: Oh my gosh, so this is all about distributed collaboration so I know — exchanges around commentary on code and ASCII text, etcetera, some images, some pull request is initiated, it goes through the shipping — I think of GitHub or GitLab or any of these systems, like a big ship construction site where the ship is going through this gigantic tunnel about to launch out there.
For developers it is highly developed but for designers it’s not developed. That’s why I think things like Figma are so popular because they closely emulate high-network collaborative spaces that remove the abstraction between storage and actual application. [It’s] super reliable, it runs fast and is social to the extent that it’s not actually annoying like Slack can be sometimes. [laughs]
MATT: Why can Slack be annoying?
JOHN: Slack? Oh my gosh. Slack can be annoying for so many reasons. And some people say to me, oh well you’re not Gen Z or Millennial so you don’t get it. I’m sorry, but I think I have been able to Slack with the best of them.
MATT: I’d say you’re a pretty big Slacker.
JOHN: I know, I try. I try to be a good Slacker. But the feeling I have around a system like Slack is that it moves things so quickly that you can’t think fast enough. And a quanta is so small, the message size is so small. And if the organization is a six-person start up — I think Slack is fantastic, but anything larger — it isn’t about the message, it’s about the feeling. Like, how are you feeling for yourself as a leader of all these people? You need to get a sense of how they feel. And from a Slack instance you can’t get that sense of feeling unless someone is really good at choosing the right emoji, you have no idea, is this the real reaction? You can’t tell.
MATT: I know creative work — I think creative work requires uninterrupted periods of time, of focus.
JOHN: That’s a good hypothesis. I think you’re right. Yes, you’re right because one of my favorite metaphors is by the late Gordon MacKenzie, and it’s about how he draws a graph — a graph across the — a horizontal line, and then the majority of the line is called “making milk time,” and the end point of the line is “expressing the milk.”
So a cow is sitting there eating, and you’re like, “Come on, cow, give me milk. Give me milk, cow, give me milk.” And then, “Where’s the milk, cow?” And the cow is just sitting there, chewing the grass. And it’s like, “This cow is not working.” But actually the cow is making the milk but the cow is only rewarded when they express the milk. The example is about how creative work takes eating-grass time and sitting in the sun, otherwise all you get is barely made milk.
MATT: And you’re leading 75-80 people around the world, 24/7.
JOHN: Mhm.
MATT: How do you find that making-milk time?
JOHN: Because we’re distributed and because we have all kinds of teams that work with designers, I think it’s up to the local zone of leadership to be able to create that time. The best that I can do is a round robin, asking, “What’s up, what are you doing, what are you doing outside of work?” And then someone will say to me, “But that’s not work.” And I’ll say, “It’s your work as a creative person to express yourself.”
So one thing I’m really happy about is our blog, Automatic.design. You may remember in the beginning it was hard to get off the ground because some designers felt like, “Well why am I going to blog? What is the point of blogging? What’s that for?” And my point is blogging is good for you. It’s mental health, it’s expression, it’s sharing your process with the world. And when you relate to the world, your standard of quality floats to that value of the world. It’s a market economy of ideas and by putting ourselves out there, you become relevant.
MATT: I’ve noticed, talking about that low-bandwidth communication of text, downsize to Slack.
JOHN: Yeah.
MATT: You internally and now externally are on your YouTube channel.
JOHN: I’m doing YouTube, I’m a YouTuber now. Oh my gosh, I love it.
MATT: Yeah, you create a lot of these videos.
JOHN: I do.
MATT: And I also perceive that you’ve literally created a lot of videos. You edit a lot, you insert emojis.
JOHN: I make the whole — It is the classical “I make it by myself thank you very much.” [laughs]
MATT: Yes, so why are you using video to communicate?
JOHN: Oh my gosh.
MATT: Internally as well. We have so many different tools.
JOHN: Look at you. You’re a WordPress-world person, you’re speaking into a metal thing, holding it with your hand, you’re not typing, you’re audio casting. So you see the diversity of the ecosystem. So YouTube to me represents really what the younger generation has figured out, is [it’s] so much more convenient.
MATT: Should managers at distributed companies or leaders learn video editing?
JOHN: A thousand, thousand percent yes. Because editing skills are ways to communicate in the same way that blogging is, but be careful to add a closed-caption, subtitled track because that makes it even more inclusive for those who have problems understanding spoken English, or for a language barrier.
MATT: One thing that’s cool, and actually one of the features I’m most excited about, is just launching. Our internal video player just launched —
JOHN: Oh yeah, congrats, yeah that was good.
MATT: — the speed thing.
JOHN: That’s important.
MATT: Which YouTube has had forever. So you can speed things up or slow them down.
JOHN: Yes.
MATT: I’ve found it’s interesting for meetings. What might be a synchronous status meeting that might take 15 minutes —
JOHN: Yeah, you could —
MATT: You can get through in ten minutes or eight minutes depending on your speed of processing.
JOHN: Whoa. You can express it.
MATT: Especially people who listen to the podcast, I imagine more than half, if not more, are listening to this sped up right now.
JOHN: That is wild.
MATT: So you actually train yourselves to be able to listen faster.
JOHN: Oh that’s so interesting.
MATT: And I wonder if I can improve efficiency.
JOHN: Well one thing I’m doing with the team around me is my direct reports, on Monday, and you don’t know this, but Monday what we do is I have a one-minute video requirement. On Monday you post your one-minute video and that’s your stand-up, but it’s async. And that way you can comment on the video. Any extra comment can happen by text. But you can also hear it in full fidelity how someone is experiencing their life and their work.
MATT: That’s really interesting.
JOHN: It’s an async stand-up.
MATT: What are some other things you do in leading the team? I know you have a Monday, Tuesday, Wednesday publishing schedule.
JOHN: Yes I do, yes.
MATT: Tell us about that and more.
JOHN: Okay. One thing I’m really excited about is learning the distributed universe and how hard it is to have a point of reference. If you work at a physical place, you walk in, you can tell the seasons, there is a Monday, there is a Friday. Monday feels so different than a Friday on-prem. So you lose your sense of gravity. There is that Sandra Bullock film — was it Gravity? Where she’s floating in outer space and it’s “Which way is up, which way is down?”
So one thing that I developed after a lot of feedback — I love feedback — every negative or positive feedback I’ll share internally, just with everyone, because it’s easier that way. If people want to talk about me, they have already talked about me because I’ve shared it and it’s easy. But one of the feedback points I got was that I was posting or sharing too much information. And then I realized, well maybe it’s because I haven’t given it structure. So I gave it structure.
But then I realized that structure isn’t as good as time structure. Because time creates gravity in a distributed organization. So Monday’s post is about the external world, the external realities, Tuesday’s post is about business, and Wednesday’s post is about organization. And I limit myself to posting in that cadence. People expect Monday to be a certain thing, Tuesday, Wednesday.
The other practice I developed in the team around me is I borrowed a technique developed by Joel Califa, he’s a designer I used to mentor, but now these people who I mentored are like my teacher[s]. It’s a spreadsheet where everyone posts what they’re going to do that week and then they rate how that goal has been achieved during the week. It’s like an old-style Japanese office-memo thing. And the reason I use a Google Sheet and not a special tool is because everyone authenticates. There’s no “Hey can I get a login, can I get a login?”
MATT: Yeah. At our company everyone has a Google account.
JOHN: Yeah, and that Sheet is open to everyone in the company too. I love the idea of transparency that you brought into the Automattic culture or created with your team members over these years. And I think transparency is so important but clarity also is key.
MATT: You said that you love feedback. Positive, negative, you love sharing it.
JOHN: Yes, I do. It’s good.
MATT: What do you think engenders a healthy culture? Does everyone on your team take that same approach? And how do you judge a healthy culture of feedback?
JOHN: I’m laughing because the best feedback is delivered non-anonymously.
MATT: I know you feel very strongly about that.
JOHN: For me I feel strongly about this because when you deliver it non-anonymously you can understand it better. I have two favorite sayings and they’re too long so I can’t memorize them. But one of them is by Coach Pat Summitt, and paraphrasing, “When you’re able to give someone straight feedback you’re showing them the compliment that they will be able to take it.”
And so when people give me feedback, does it sting that I am no good at something? Yes. I’m like whoa, I thought I was good at that. And I might think they’re wrong. But then when they say how I didn’t achieve something I’m like, “No, you’re right, I could improve there.” If you get it anonymously you don’t know the smell or taste of it. It’s like if I gave you —
MATT: It’s missing context, for sure, yeah.
JOHN: It’s missing — You have to fill in the rest of the story 80 percent.
MATT: It also seems you can’t get any anonymous follow-up on it?
JOHN: Well you can tell everyone “I got anonymous feedback, this is what I’m doing.” And then you give more power to anonymous people and those who actually give you the —
MATT: But you share all the feedback, anonymous or not, right?
JOHN: I do, yes. And one of my proudest achievements is the anonymous feedback and the in-name feedback is just as bad. [laughter]
MATT: So people are comfortable saying it either way.
JOHN: Right, right.
MATT: You also work a lot on inclusion.
JOHN: Mhm.
MATT: That’s from a position of privilege as well.
JOHN: Absolutely and I —
MATT: You’re very powerful and you’re John Maeda.
JOHN: People think that I’m something. An octopus, like, whatever. But that’s why a lot of what I do is reiterate that I’m only as good as what I do now.
MATT: How do you make people who might feel that they don’t have that privilege to give things to you directly, how do you make them comfortable with that?
JOHN: I haven’t cracked that one yet but it’s on my list of… how do I invite them into the fact that my only goal is to serve others and I cannot do that unless — think of all the user research. Unless I have high-fidelity user research, how am I going to improve? Maybe my goal is to center on that concept with more people that I do believe in agile development, I’m a computational system, organic, [laughter] and how am I going to iterate and improve if I don’t get really high-fidelity feedback?
Maybe I might become much more open to delegation of that. Because there are some people who feel that I’m in a privileged position and some people feel privileged enough to go straight with me. Like if you don’t feel comfortable with me, talk to them and I could just anoint that role —
MATT: But then you lose the fidelity.
JOHN: I do. And then I also do recognize that there are those who will always feel something. And it’s often not about me, it’s someone like me that in their past [with whom] they had a bad experience. So I totally understand why there would be no reason that they feel that they could be candid with me, because something bad happened in the past.
MATT: Are you also that candid with everyone you work with?
JOHN: Am I that candid? It depends.
MATT: Can everyone handle that kind of raw —
JOHN: That’s the challenge of getting older for me. When I was younger, I would tell everyone everything I thought. Oh my gosh, people couldn’t stand me, for good reason. I mean it was okay, I forgive them. Actually I hope that they forgive me. I would just tell them what I think and I was direct all the time.
And then I realized wow, this is not working. This is not working. I believe in the “I’ll show you respect by telling you what I think.” But it’s like, “No, actually he doesn’t want to hear what I had to say. Whoops.” So I changed.
MATT: Why is it bad if people are doing the same to you, not giving you the direct feedback?
JOHN: With people who I develop a strong working relationship with, then they are the ones who ask me, “Can I get your feedback.”
MATT: So conversely they feel more comfortable with the raw feedback from you?
JOHN: Yeah. And some instances, some people want that, some people can, quote, “handle it,” which means that they were privileged in some way where that became — where that’s doable. But there are some who just had a really difficult life that they just don’t want to handle that and it just hurts them in a way, it doesn’t help them. And so I’ve become much more conscious of “Huh, how do I adapt to what you need?”
MATT: In design you are also overseeing everything that goes out to all of our users.
JOHN: Mhm.
MATT: Everything we’ve been saying about feedback is pretty universal. Is there anything specific to distributed [work] that you want to throw in there?
JOHN: In a distributed organization I think that the value of it is that you can now control your life differently. I know so many people [for whom] distributed work has been able to make them better parents, better children to their parents as caregivers. Them coming from that point of view is the beginning of recognizing that this is an amazing job to have. And do you enjoy that aspect of those jobs? Yes. Great. Now what kind of work are we doing and how can we safeguard that wonderful thing that you are able to do because of this paradigm.
That’s what interests me the most, is that it’s a really special thing to be able to work distributed, and if you can start from the respect of that versus the wonder of it, then you have hard conversations about, “Now what should we do with the work to safeguard that?”
MATT: Tell me about your ideal work space.
JOHN: My ideal work space — I’m still QWERTY, we’re talking typewriter-speak. How do you say the other one?
MATT: Dvorak?
JOHN: Thank you. I don’t know how to pronounce it. Dvorak. I love a Kinesis keyboard because it has helped me I think —
MATT: Those are the curved ones, right?
JOHN: It’s the curved one. In my late twenties I had really bad RSI. It’s the way I hold my body, but that really helps. I like to have that nearby. I like it super quiet. I don’t like to put headphones on, it’s a bit constraining.
MATT: Do you put music on?
JOHN: No music, no music, but hopefully art around to distract me.
MATT: Besides the Kinesis, any must-have equipment? I think you use a custom camera, right?
JOHN: Oh my gosh, I have fallen in love with this new thing. You know how headset experimentation is so important for distributed? It’s almost like a hairstyle problem. I found that in-ear musician-quality microphone monitor headphones, they’re great because they —
MATT: Did you do the custom?
JOHN: There is this memory tip cushion thing that you can get that is super comfortable, sound-isolating. For audio quality it’s fantastic.
MATT: That’s amazing.
JOHN: I love good microphones. Podcast-quality microphones, the sound quality is so much better. I do love the Sennheiser headset for sound-isolation quality. Like, we can be talking and I’d be in the airport, and you’re like, I don’t hear anything.
MATT: Oh yeah.
JOHN: That’s bizarre how well that works.
MATT: Noise-cancelling not for you ears, for the mic. A noise-cancelling mic.
JOHN: That’s bizarre how good that is. But I do always feel a little embarrassed wearing it. You have no problem being in a restaurant wearing it. [laughter]
MATT: No, you look like you’re in a call center or something.
JOHN: I can’t go there. You wear it all the — I can’t do that. Yeah.
MATT: Zoom, Hangouts, Skype? What’s your go-to?
JOHN: Oh my gosh I can’t stand all of them. I like audio-only if I can. I like phone, yeah.
MATT: Hmm. So you make phone calls?
JOHN: I make phone calls, yeah. It feels good.
MATT: What’s your number-one tip for getting things done?
JOHN: Is if you’re lucky to have a good assistant, and if you are less lucky, having any good to-do note system, they always work. So the competency of making a list, oh, so good.
MATT: One thing I love about working with you is you’re go, go, go.
JOHN: Aww.
MATT: What is your drive there?
JOHN: My parents worked so hard all their lives. I think about my father. He’s 84 years old, he’s hunched over, he can’t stand up straight, because he was carrying so many heavy things all his life. My mother, because of the cold water involved in tofu — her hands — she can’t feel anything. They worked extraordinarily hard. They are an example that was set that tells me I should do more.
MATT: What are some of your habits that contribute to that, good and bad habits?
JOHN: I’m not good at vacationing. As you know, it’s not my forte.
MATT: That was a goal for the year.
JOHN: You gave me feedback and I took it, and I was like, “Okay, I’ll do this vacation thing.”
MATT: Although I think you worked the whole time.
JOHN: I had to get stuff done. [laughter] But vacation, not good at. I don’t read enough. You read a lot. You’re always reading. I don’t read enough.
MATT: You probably read all day. Do you mean books?
JOHN: Books, books. I’m consuming information. But I want to get good at reading books.
MATT: And finally, 20 years from now, what percentage of jobs do you think will be distributed?
JOHN: I think for developers, I think it will become a norm. I think for whatever we think of for designers it will be 50/50. Fifty for designers who are doing much more of the traditional creative, emotional type of work that requires more high-bandwidth collaboration, but it’s going to be expensive, that work. But the other half is all going to be computational.
MATT: Well, thank you so much, John.
JOHN: Thank you. This was fun.
MATT: That was John Maeda. You can follow him on Twitter at @johnmaeda. That’s J-O-H-N M-A-E-D-A.
Slack is a tool that’s so widely used it feels ubiquitous in the tech world. And when everyone uses a tool, sometimes it can be difficult to imagine how it might be improved, or how a different tool might be better. It’s a privilege to hear someone like John Maeda — someone who has spent much of his long career thinking about digital interfaces — dissect the technology and talk about the way that it works, and where it falls short.
Hearing about the live-video-chat-meets-virtual-whiteboard tool John helped create in the 90s makes me think about how distributed design teams might use that today. It’s a great reminder that devices and interfaces can always be iterated on, which is both a great lesson from computational design and one of the great pleasures of building digital tools.
John has a humble, thoughtful approach to distributed collaboration, and thinks about how humans operate as much as how computers do. When you’re working with people across the globe, sometimes the best collaborative tools are the oldest, like listening, gratitude, and empathy.
John’s time with Automattic will be coming to a close soon — he’s accepted an exciting new role with consulting firm Publicis Sapient — but I hope that his thoughtful and humble approach to distributed collaboration will live on in our design team, and I look forward to him contributing to Automattic as an adviser.
Next time on the Distributed podcast, we’ll be talking with Leo Widrich. Leo helped build a successful distributed startup called Buffer, and was living the Bay Area dream. But he felt something was missing from his life, so he quit his job and turned to ancient wisdom and mindfulness to achieve emotional resilience. We’ll hear Leo’s story, and learn how distributed workers can avoid the psychological pitfalls that are unique to working remotely.
Thanks for joining us.
Upwork’s Zoe Harte and Han Yuan on Managing People and Products in a Distributed Company
Jul 11, 2019
On today’s episode, two leaders at Upwork share how they do distributed. First up is Zoe Harte, Upwork’s Head of Human Resources and Talent Innovation, who speaks about her experience of overseeing a blended team of full-time and freelance employees. Then, I talk to Han Yuan, Upwork’s Senior VP of Engineering, who shares insights on the “soft” skills engineers need to work effectively in a distributed world.
The full episode transcript is below.
***
MATT MULLENWEG: Back in June we had the pleasure of speaking with Stephane Kasriel, the CEO of Upwork, the world’s largest freelance marketplace. Stephane laid out a compelling case for the distributed model as a way for talent-starved companies in expensive, crowded cities to do business with workers who live in places with comparatively sluggish economies.
But Upwork’s not just thinking about this in theoretical terms: they practice what they preach, with a distributed workforce of their own. In this episode, we’ll talk to two Upwork employees from two very different practice areas who give us glimpses of how their company does distributed.
First up is Zoe Harte, Upwork’s Head of Human Resources and Talent Innovation. Upwork’s legal, finance, and even HR departments are a blended mix of full-time and freelance employees scattered across dozens of countries and cultures. Zoe helped to grow the company’s workforce by 75 percent over the last six years, giving her a world-class perspective on how to expand and maintain fluid, flexible teams.
After a great conversation with Zoe, I speak with Han Yuan, Upwork’s Senior VP of Engineering. Han gives us an inside look at how his team’s diversity of culture and thought becomes a powerful asset. He says this diversity fosters curiosity and allows the company to tap into a wide array of perspectives and experiences.
OK, let’s get started with Zoe Harte.
ZOE HARTE: My name is Zoe Harte. I look after human resources and talent innovation here at Upwork. I’ve been here six years now. I started when we were oDesk, prior to the merger of Elance and oDesk, and have seen everything transform. I’ve been doing HR for almost 20 years at this point.
MATT: Wow.
ZOE: Yes. And I spent almost a decade at Yahoo.
MATT: Tell me a little bit about your HR team.
ZOE: There’s the traditional side of the house, which is — we have recruiting, we have the HR business partners.
MATT: How many people?
ZOE: We’re about 20 in that world. And then we have — there is another group of people who help do the onboarding for the talent innovation team — is what we call the freelancers, who work directly for us, and they help them with the onboarding, getting access to the Upwork systems in a compliant fashion and provisioning them, making sure their business documents and all of that are done in an appropriate way.
There are also people in our organization who partner with freelancers, who are working for our enterprise clients to help make sure that they are onboarded successfully onto the platform, getting access to those companies’ data or whatever it is that they need. That’s where making sure all the documentation, the independent business license and all those things are done. So it’s pretty varied in terms of what HR encompasses for us.
MATT: So about 20 for the full-time?
ZOE: Mhm.
MATT: So 450 full-time Upworkers.
ZOE: Yup.
MATT: About how many for that broader talent group?
ZOE: That’s about four.
MATT: Oh, so that’s pretty leveraged.
ZOE: It’s really leveraged. Yes. They would like to have a little more help there. But we also then use freelancers ourselves back to supplement the team too. Our team —
MATT: What sort of things do you use freelancers for in HR?
ZOE: For everything. We use freelancers to help us design learning programs. We’re moving some of our compensation to a different philosophy. We worked with a freelancer to do a video explaining the why and the how that impacts everybody. We work with freelancers when we’re looking to bring in different skills or scale in our organization.
So for example, when we were building out our Chicago presence and we were hiring a lot of sales people, we needed to do a big hiring push all at once. I knew we didn’t need a ton of recruiters full-time focused on that, but we needed a lot of sources to really dig deep into the talent network within Chicago. And so we did that with bringing people on in the platform. So that’s just a scale issue. And then for skills, like video design. I can’t do that. But this person made this video that’s amazing, and it makes it a complex thing that’s coming out of our department easily digestible and clear.
MATT: I definitely live in the distributed work world and until you started talking about that I had never thought about parts of HR being something that could be freelance.
ZOE: It all can. And that’s one of the things that is so great about how Stephane has set us up here, is that the expectation is every single organization within Upwork is a blended organization that relies on freelancers as well as full-time employees. So legal, finance, all of us, even the organizations that you’d be like, “That’s hard,” there’s always additional stuff that can be done.
MATT: Yeah. And the third bucket you talked about was enterprise. You might need to define enterprise just quickly.
ZOE: Mm, sorry.
MATT: And what that means in your business and then how many people work on that.
ZOE: So for our enterprise business, that is out of our sales function and so that’s working with our largest accounts. So the biggest companies with whom we work, Fortune 500 and Fortune 50.
MATT: So I might come to you say “Hey I need 1000 folks to do X, Y, Z.”
ZOE: Precisely. I need to translate these medical documents.
MATT: “And I want you to manage it for me.”
ZOE: So we do both. We have some where it is “I want you to give me just the output, you figure out how to do it,” and then we have others where they are more involved in the guidance themselves and so they’ll say for the marketing organization “We want a design initiative that’s X, Y, and Z and we’ll do it this way.” So Microsoft is a shining example of a company that’s partnered really extensively with us and knows how to utilize freelancers in a wide variety of projects.
MATT: Are there other big clients you can talk about like that?
ZOE: Companies like Dropbox and Pinterest are using us for a variety of different things as well. And then most of the bigger companies — we’ve got GE and other people like that — who are really digging in within different functions organizationally, be it marketing or some of the writing organization, or particularly web design. And the technology pieces — obviously a lot of engineers can really be scaled. We do that here, I’m sure.
MATT: HR is so critical to being a distributed company. How should companies be thinking about this if they’re starting to hire? Let’s say right now I have all my people in one office in Houston, Texas, and now I want to start to engage and hire people in other places, what do I need to think about?
ZOE: You need to think about a lot of things, like, “Is this going to be — I’m going to do this for one set of expansion, so I’m going to go to these three additional states and then I know that’s going to be pretty steady for X period of time.” If that’s the case then I would argue, depending on how many people it is, it may be worth setting up [a] nexus in those places and so then you’re beholden to pay the taxes there and set up all those legal and financial things that you need to do.
If not and you’re interested in saying “I’m going to need three people in this place for the next three months and then I want to explore the opportunity to have local translators in Brazil for X, Y and Z reasons,” then I think you may benefit by exploring a freelance relationship with those people where you can dial it up or dial it down.
And it allows both parties to really engage in a way that’s very clear and communicative about [how] these are the objectives of why we’re doing it this way, communication and transparency in terms of what the goals are, the deadlines, etcetera. But you’re not then in a place where you need to manage all the tax implications and all the financial and all the legal ramifications of setting up businesses in a myriad of different countries, which can be hugely taxing, pardon the pun. But in terms of what you need to do organizationally, it can be such a distraction and so much overhead that arguably freelancers in that way can be much more efficient for a business.
MATT: [Are] there ways to manage some of this complexity? Because even in the U.S. you have different worker’s comp laws, you have different tax rates, you have so much stuff.
ZOE: You do. Firstly I would say, have a really good tax person that you can use as a resource, whether that’s somebody you contract with or otherwise. You can, obviously if you’re doing it the freelance way — I would be wrong to not say Upwork will do a lot of this for you, right? We can help with a lot of that.
But I think in general it’s about being mindful and intentional about it. I think sometimes what happens is we fall in love with a person and a candidate and we think this person is perfect and you’ve already made some kind of oral commitment to them, like “I really want you to work with us on X, Y project,” and then you’re like, “Oh, but man, they’re in Massachusetts and the taxes in Massachusetts are a nightmare.” Or it’s whichever state it is where you realize, “Oh, one of our biggest customers is there and if we set up a nexus there, then we may have to look at our taxes differently because they’re also there. So what do we trigger for both our customers and for ourselves?”
So I think the biggest advantage you have — we have some great tax people here and it really helps us. And we have been very intentional about the places that we have full-time employees versus the places where we’re open to partnering with freelancers — which is worldwide, versus the places where we’ll engage with leased employees — because that makes it a lot easier for us.
MATT: And had you been at a distributed organization before?
ZOE: Personally I’ve always had a distributed team so I never have worked with a team that was solely in one place. And it’s funny, I hadn’t actually reflected and made that connection that I had never done it until I was thinking about talking with you about it. But I have always had that.
MATT: People probably think of a Yahoo as being almost famously all in one place.
ZOE: Well now, yes.
MATT: Help people understand how maybe that org was really large and…
ZOE: It was. It was sort of ginormous. I was there from ’99 to 2008. And so the company was about 14,000 at its biggest during that time, but certainly grew and contracted at various times.
MATT: That’s a wild time to be at Yahoo, by the way.
ZOE: You know what, I can’t say enough good things about it. We had various offices. So there was a large campus in Sunnyvale but there [were] also offices — we moved our customer service organization up to Hillsboro, Oregon. We had Broadcast.com, Mark Cuban’s thing, in Dallas. We were in LA and New York as well, and then of course all over the world there were Yahoo offices.
So even when I was just managing one person as an HR manager, she was based in Oregon, I was based in California. The other thing, towards the end of my time there, when I had left HR for a while, I was looking after the international customer care organization, and that was in 20 plus countries.
MATT: Wow, how many people was that?
ZOE: That was about 300 people at that time.
MATT: Wow.
ZOE: That was a really great learning opportunity and it also makes you mindful of time zones and different customs and different expectations about availability and responses over the weekend, or what it all looks like and how different it is in different places.
MATT: In the taxonomy of distributed versus all being in the same room, I guess I would call Yahoo or companies like that as multi-office.
ZOE: Precisely.
MATT: There’s offices all over the world, across all time zones. People would go into that office the majority of the time and —
ZOE: Yes, there was a lot less actual remote work. Like I’m in my home, you’re in your home, somebody’s in a co-working space.
MATT: So we just built a time machine. You can go back 20 years and talk to Zoe in 1999 at Yahoo.
ZOE: I know, she could be on it.
MATT: What would you tell her about what you’ve learned at Upwork, a massively distributed organization, that you think would help maybe someone listening to this who is in a multi-office type place?
ZOE: I think being precise and intentional about your communication cadence is probably the number one thing that you can do.
MATT: What does the cadence mean there?
ZOE: So to me that means saying, okay, our entire organization will connect this many times a year in this many ways. And so there will be an all-department meeting once a month, once a quarter, whatever is appropriate, and that we will cover these three priorities and in broad progress and how it’s impacting the business overall. And then the expectation would be that the smaller subsets of teams are meeting in this way. The leadership team is meeting in this way, and you as the overall leader are connecting with your direct reports on this regular basis, and then making sure that you connect with every single person in your organization at least once every *blank* months.
MATT: Are there some things you think are unique to how Upwork is structured or some processes you have like that, cadences that you have, that you’d want to share, like best practices?
ZOE: One of the things that is actually one of our greatest tools, which is a tool that I — everybody has got their own variation of it. Internally we use Upwork Messenger, the Dash Team. And there is just constantly the ongoing conversation that people have. So there is obviously a lot of work that gets done in that way. But there is also the check-in about like, “Hey I know your daughter should be hearing back from colleges she applied to, is everything going okay? Did she get into the one she wanted to get into?” And just building that camaraderie and that understanding. That’s not something that’s unique to us, it’s something that is drilled into us that we will continually make sure that we are connecting on a personal level as well as a professional level with individuals.
MATT: Just from the culture? Or the tool does that?
ZOE: From the culture as much as anything, and the tool really facilitates that for us. So for most of us that’s the first thing we do that’s work-related every day. So for my organization, we have a room for the leadership team and the first thing we do every morning is check in, say good morning — any personal updates, anything like “The kids are fighting so I’m going to be late to school and then late to work,” or whatever it is, right?
And then it’s, “Here are the three things I’m going to do this day, and I need your help in this thing. And, oh my gosh, the meeting we thought was a fortnight away is now next week! Can you help me get those metrics that I need earlier?” And it just allows us to constantly be recalibrating the work that our teams are doing and connecting them back to the bigger, broader picture of what we’re doing.
It’s really simple. I feel like I should have [these] massive words of wisdom for you and I don’t. I think it’s just, talk more, communicate more, be clear about what you’re asking and clear about when you need help.
MATT: Just because it’s simple doesn’t mean it’s easy though.
ZOE: No, that’s true. I mean it’s really hard, right? And if everybody could communicate well I think a lot of things could be different.
MATT: Is there something different you would look for when hiring someone to work in this kind of environment than you would if they were going to come into an office everyday?
ZOE: Obviously it won’t surprise you: Are they a good communicator, do they ask quickly for help and self-identify and see that as a strength that they’re asking for help versus a threat or a weakness.
MATT: But how do you screen for that?
ZOE: I’m a big believer in behavioral interviewing and asking for really specific examples and then walking people through scenarios and saying, “Hey, this happens” — and often it’s something that’s literally happened the day before — “What do you do in this situation?”
MATT: I know that one thing that Upwork does is these meetups.
ZOE: Yes.
MATT: From an HR point of view, what are the pluses and minuses of these meetups?
ZOE: [laughs] That is a great question. The pluses are getting together. Nine out of ten times that is really fantastic. It’s an opportunity to put a face to a name, it’s an opportunity to share more personal stories, connect, to see how the work that you’ve done has made life easier for me and vice versa and all those things. And to brainstorm and just have more synergy. Sitting around, talking over a cup of coffee, you do tend to come up with different ideas than if you’re in an official meeting.
Challenges can — it can sometimes be easier to relate to somebody via a screen. When you’re in person maybe there is just something you guys don’t like about each other, right? That can be hard. It also sometimes can feel forced, or like it has to be absolutely brilliant or it’s been a failure because they happen infrequently. They cost a lot of money, there is a big opportunity cost.
MATT: And yours are longer, right?
ZOE: Yes, right.
MATT: I’ve heard 10 to 14 days?
ZOE: They do tend to be long. So you’re also going deep for a long time with a group of people that you’re used to one very specific type of interaction with. And as much as we have hangouts that celebrate people’s birthdays, or whatever it is —
MATT: Wait, say that again. You’ll have a virtual hangout on someone’s birthday?
ZOE: Yes, absolutely. We love a virtual hang out. Probably not the greatest HR example but there are definitely virtual happy hours that happen with distributed teams around here.
MATT: Sure. [Being] in the same time zone helps that.
ZOE: Yes it really does. That’s when you’re like, “Ugh it’s 6:00 in the morning, no can do.” The challenge is that it’s a group of people. And you get any group of people together for X period of time — think about Thanksgiving. Lots of pros for Thanksgiving, also some cons when a family that’s not always together is together for an extended period of time.
MATT: I think much like Automattic, some Upwork meetups often happen and people stay at Airbnbs and stuff.
ZOE: Yes.
MATT: So that co-living is an additional variable. And by the way, you have to check the Airbnbs sometimes. We’ve definitely had it where something they listed as a bedroom was actually — you had to walk through another bedroom to get through and things like that.
ZOE: Oh yeah, no, no one wants that. One of the big things that I personally advocate for a lot is making sure that all employees, but in particular women, when they’re traveling, never have to be at a place that has — their bedroom door is a door to the outside. Just from a safety perspective, like an emotional safety perspective. I want you to have a hallway, I want you to have somewhere that feels safer than that.
And just making sure that physical safety is something that you’ve been really clear about with everybody, like here are the expectations around that. And being flexible. If somebody gets somewhere and is like, “I just can’t,” then you’ve gotta have some wiggle room around that. And so that may mean a buffer in your budget, which hopefully you don’t need it.
MATT: To get a hotel room or something.
ZOE: Yeah, like you need a separate hotel room? Totally fine, I get it.
MATT: You probably want to avoid cross-gender sharing of those…?
ZOE: Yes, yes.
MATT: Dishes and clean up.
ZOE: Ohhh dishes, yes.
MATT: I feel like you have something to say there.
ZOE: Sorry, I can — apparently that just hits a sore spot personally. It brings back bad roommate situations.
MATT: Tell me about dishes.
ZOE: Yeah, right? Who’s going to clean up the mess? Is there a rotation, is that clear, is that part of it? And this certainly, I heard a story about this, like an expectation about who was doing the keynote was based on gender, or there were two people with the same name, one was a woman who was a very senior leader, one was a relatively junior team man, who was a man. And it was first name only on the thing, and one of them was doing the keynote. And one of the remote attendees was like, “Oh I just assumed it was him.”
MATT: Hmm.
ZOE: Okay. Well A, whoops, you should know more about the organization to understand who is the leader in this situation. So I just think understanding that but also understanding specific — especially gender roles in different cultures. You don’t want to get into a situation where the expectation is that the woman is doing the dishes or whatever it is, or the men are taking out the rubbish all the time. You’ve got to just be intentional.
MATT: You just said something really key as well, which is “across different cultures.”
ZOE: Yeah.
MATT: If you’re distributed and coming together, there might be people from — ten people from ten different countries —
ZOE: Absolutely, right.
MATT: — and it’s easy to forget that. People live different in different countries. So you almost need that defined for your company. What are those expectations and the habits and culture of how you want to operate?
ZOE: Yes. Again the more proactive communication you have about this, the better off you are. Because it’s not just things about gender. Does everybody eat meat? Are there religious ramifications for how meat is prepared? All of those different things. Are there people who pray before dinner? What are the expectations of this? Do you have somebody who is a nursing mother who is going to need time to pump in between the schedules?
MATT: How about mentorship and learning and training? How do you do that particularly across your full-time versus freelancers?
ZOE: We have tended to focus on our full-time employees in terms of learning and development initiatives. One of the things about freelancers is, by the nature of their work they are re-skilling at a higher level than the rest of us who are in these corporate jobs.
MATT: It’s almost more Darwinian, being in the open market.
ZOE: Yes, they’re doing it constantly. They are much more aware of what is going on in terms of the influx of need for skills and things such as that. The research that we have done shows that the half life of a skill is about five years right now. So if you are an independent business who is working to garner your next project and the next client, you are much more mindful, and as such I should learn X new thing. So often we learn from that part of our community, “Oh goodness, we should be training on blank.”
MATT: Diversity and inclusion is something that usually is covered by HR. How do you think about that in a distributed organization and a global organization like you all?
ZOE: We’ve done frankly a lot of self-reflection. We worked with Paradigm, who is a consultancy who have a lot of attention right now, to re-evaluate every single full-time-people process in the company last year, which is not a small thing in terms of scope but also not a small thing when you really think you’re doing very well, and you care a lot, and you’re trying your best to realize all the places you’re flawed and can do better. By the nature of how our organization is structured, and the fact that it is a small portion of the people who are working to make Upwork “Upwork” that are full-time, we have a huge amount of diversity already due to the nature of the freelancers who are working with us at any given time.
MATT: As we close out, your biggest tips. Let’s say someone new is joining and they haven’t worked in a distributed manner before. What do you point them to?
ZOE: I point them to learning as much as they can about how our business works and the different roles that people have organizationally. I point them to not being shy and just proactively communicating. Like, “These are the four things I’ve been asked to work on, I understand these two really well, this one I think is like this — can you help me figure that out? And this fourth one, I’ve got no idea, I’ve never even heard of this before, who can help me?”
And then really making sure that they understand how their piece of the puzzle is impacting this incredible mission. I think every person who is associated with Upwork believes in our mission and our vision. And you feel it when you work here. And hopefully you feel it coming in and visiting us.
MATT: What is that mission?
ZOE: Our mission is to create economic opportunity so people have better lives. I’ve worked at many different places and you see values on the walls and you see a mission, and people talk about it. But I’ve never been in a place where the values are used to make business decisions at the executive staff level. It’s really inspiring and I think that makes everybody eager to do the very best that they can do while they’re here, because it’s not just for us.
MATT: As we look forward, from your HR point of view you’ve seen how work has changed. Twenty years from now, what percentage of jobs do you think are distributed?
ZOE: Gosh.. 70? I think a vast majority are going to be.
MATT: Wow.
ZOE: Because real estate is so phenomenally expensive, the things that are just happening to make it easier even than it is already, and I would say it’s really easy right now to do it. It’s going to be a non-issue. It’s going to feel like I’m here with you if you’re in Singapore and I’m in Sydney. It’s not going to matter.
I think the beauty of that is the world gets smaller and we learn more and we understand more, we have more diversity of experience in our day-to-day lives. I look at my grandparents who traveled a fair amount, but the people that my children know versus the people that they know — their circle will be so much broader and they will have so many more inputs. So that can only be positive for business, right?
MATT: That sounds like an amazing world for our current or future children to grow up in.
ZOE: It does. I hope so.
MATT: Thank you for [being] part of helping to create that at Upwork and also with sharing your stories for the listeners here.
ZOE: Thank you very much for having me, I appreciate it.
***
HAN YUAN: My name is Han Yuan. I’m the head of engineering for Upwork. I have been at the company for three-and-a-half years.
MATT: Had you worked distributed before joining Upwork? And how is engineering from a distributed or non-distributed view?
HAN: I have under multiple contexts. I think both from a, “I’m at a company and we have multiple offices around the world,” and also in situations where we had one or more agencies that we worked with directly and we collaborated in more of a — I would not say black box but more like a white box way. So really engaging with agencies in a staff augmentation way.
What’s fascinating about Upwork is that we’re pretty distributed. When we look at the engineering team they hail from over 40 countries around the world.
MATT: Wow, like currently living in 40 countries?
HAN: Right.
MATT: And that’s of the 350.
HAN: Right.
MATT: But we’re in an office right now in Mountain View.
HAN: Mhm.
MATT: Tell me about that.
HAN: Typically we try to make sure that all of the key meetings happen between nine to five West Coast time.
MATT: Do you have many people in the Asia Pacific time zones?
HAN: We do not.
MATT: That makes sense because those core hours would be tough to keep there.
HAN: Most of our personnel is somewhere between South America, Europe and Eastern Europe. We also find that because we have an agile organization, the leads of those agile teams are oftentimes not here in Mountain View. And in a sense they do have the authority or they’re expected to recruit and hire for their own teams. There is a tendency to hire within one or two time zones of wherever they happen to be. Geographic dispersion of our team is probably partially organic in that sense.
MATT: You come into this Mountain View office about how often?
HAN: I come in about four to five days a week.
MATT: Oh yeah, that’s pretty good.
HAN: I still come in pretty regularly.
MATT: What do you like about it?
HAN: I think I like the routine a little bit. And some of it is just my own personal situation where it’s harder for me to work at home. We also happen to have most of our product managers on premise. And so collaborating face-to-face with the product managers [and] designers is a key part of my job, and so I do tend to come to the office pretty regularly.
MATT: How do you keep the folks who aren’t here as in sync?
HAN: I think that’s a really good question and that’s probably one of the greatest challenges of leading a distributed team. And it breaks down to a couple of things. One is, “How do you maintain a consistent culture?” That’s a very difficult problem.
MATT: What does culture mean to you right then?
HAN: In a lot of cases it has a lot to do with how both the big and small things regarding how people interact and communicate with each other on a day-to-day basis and what their expectations are. So for me, it’s being very, very explicit in certain cases what people expect from each other.
So for example, how long can you sit on a pull request? Can you sit on it forever, can you sit on it for one day, three days? Without that code in place, different engineers from different parts of the world have potentially different points of view on what is being responsive to a colleague.
And so we spend quite a bit of time documenting and being very explicit about what we expect in terms of behavior from our engineers. And hopefully to the extent that we’re consistent, we reward and we also give feedback for behavior when it’s inconsistent. But I think that’s a key part of it.
MATT: Yeah.
HAN: The second thing I think is more of a practical thing, which is we generally bias towards hiring people who have strong written communication because we want to do things as asynchronously as possible. In order to do that, being able to write well is very important. I think chat is less interesting to us in general because it’s a little bit synchronous in nature. And so we want to encourage our engineers and our team to really put things down thoughtfully and clearly.
And then along those lines, as an organization, we spend a lot of time trying to create transparency within this working operating system of how we build the site. And so a big part of that is making sure that when there are issues everybody understands it, even from the executive standpoint — the engineering executives — and then also having the ability for teams to propose and communicate innovation at all levels of the organization or recognize people at all levels of the organization. And so we have various mechanisms to achieve that.
MATT: You mentioned if I were going to make a proposal you’d want me to write it out and really present it. How about when there are those technical agreements? Two great engineers, maybe on different teams, or maybe the same team, have a difference of opinion for which way they should go. How do you work that out, especially when you can’t get people around the white board or in the same room?
HAN: In a distributed organization there is a tendency, and rightfully so — you have tohave some structure where you say, “Hey you are the CEO of this problem.” And so there are times when I may come to an engineer or engineers come to each other and say, “Hey can you make this change” or “I’m really worried about this thing that you built, you should make this change,” and as the owner, of course, you could say no. But in that sense the decision making is very clear and absolute. But we have seen situations where the decision was the wrong decision or multiple people came to that decision maker and said, “I really think you guys are doing a bad idea,” and they said no multiple times.
And so over time, in order to flag these issues, what we encourage teams to do is, as soon as you have come to a place where you disagree, you follow our proposal process, which is the same format: State your problem, state each other’s point of view, and then bring it to the adjudicating body, which in this case would either be an architecture review, or we have a different body called eng staff, which is the top 30 senior people in the engineering organization, to adjudicate over this.
MATT: You had something really key in there I wanted to ask about. You said “make the other side’s arguments.” Tell me about that. Because that’s not a normal thing to do. Normally if I’m proposing something I would just make my argument.
HAN: We really want to encourage empathy in general. And so a key part of empathy is being able to try to see the other person’s point of view. And in an organization as distributed as ours where people come from all around the world, we view it as an essential ingredient to developing deep and meaningful collaboration.
MATT: What do you think is the main benefit of what you do that couldn’t be accomplished if you had a traditional office approach like you did in prior jobs?
HAN: I think there’s a bunch of practical things that people would often say, like, “Oh, we can do 24-7 development” or “you can have access to talent.” And I think those are valid. But if you were to ask me, the most important thing is diversity of thought. And I think that has a lot to do with different people from different backgrounds and different parts of the world who have experienced different things and have worked on different things, and that is quite powerful. I think when nurtured well it creates the conditions for things like creativity, empathy, collaboration, and things like that, and I think that’s very valuable.
MATT: Can you share an example where that came into play or you felt like that improved the outcome?
HAN: It happens oftentimes in big and small ways. For example, because people are very aware that they come from different places, they tend to ask more questions, which I think does elicit a little bit more thought from other people and it also forces people to normalize their communication, their language, and their reaction to things, that’s a little bit more neutral. But these are very subtle things. Diversity of thought comes from the place of actually interacting with somebody who isn’t very familiar with how you do things.
MATT: Are there any commonalities or practices of the highest performing engineering teams? Do they do daily stand ups? What sort of things do they adopt?
HAN: The highest performing teams actually have much smoother communication between the product team and them. There is context setting that — the transmission of context is just cleaner because when that happens, the engineers are brought into the solution space, not just in the implementation space.
MATT: Yeah. So let’s say I was leading an engineering team that you perceived [to be] bottom quartile at the company, wasn’t doing as well. How would you coach me to have a better context setting or connect better with my colleagues to be more effective?
HAN: For all of our groups we have them document what their vision and values are for that team and align around what’s important to them. So for some organizations, for example, if you’re on a platform team, you may value very, very clean code, maintainable code, and you may value doing things very well over speed. For teams that are working on things that don’t have product-market fit yet, we encourage them to break things, write things a little bit on the side, and that’s fine. And they can go ahead and say, “Hey this is what we’re going to do,” and explain why we’re going to do it.
MATT: How about in-person versus remote? Let’s say I was this engineering manager in Houston and I was like, “Hey there’s this product person in Mountain View I’m just not connecting with.” Would you encourage us to get together physically or are there meetups? How does that work across the full-time and non-full-time people?
HAN: In almost every case team performance has improved after they’ve met face to face. Once. [laughter] Now the gains that you get from meeting up twice, three times, four times, a hundred times, tends to fall off quite a bit.
MATT: Diminishing marginal utility.
HAN: Exactly. But the first time the gains are huge. So we typically fly groups of 30 or 40 folks on meetups. And since we’re so distributed it tends to be some kind of random city on the planet that is more or less geographically accessible to those teams.
MATT: Those would be freelancers and full-timers?
HAN: Yes.
MATT: Cool.
HAN: And then these meetups can last for a week to two weeks. So that’s usually enough facetime for people to get a feel for how they work.
MATT: Yeah. You mentioned you find it hard to work from home when we started. Tell me a bit more about what you find challenging working from home or not?
HAN: I think this is a personal quirk apropos of nobody else. But I really like to partition when I’m working and when I’m not. And to your point about isolated time, even during the work day, I have not had this in six weeks but historically I try to block off at least three hours. When I write code, and I still do from time to time at home, not at work, I’ve done a bunch of performance studies on myself and I know that I can only generate about four and a half hours of solid code. I’m very —
MATT: I’m curious how you knew when it started to drop off.
HAN: So if you really want to know…
MATT: Yeah.
HAN: This is what I did to myself. I would measure blocks of time of 30 minutes and then set a timer and every 30 minutes I would tick on a scale of one to three whether or not I did what I thought I was going to do in those blocks. When I start the next block I tell myself what I want to accomplish and then —
MATT: Very Pomodoro-like.
HAN: It’s very Pomodoro-like. This was back when I was, I would argue, gainfully unemployed, where I was working on my own thing. I ran this over ten hours a day, seven days a week for about 12 to 18 months. And so I had significant data on how I work and I found out that, generally speaking, my prime hours are somewhere between 11:00 and 3:00. And so once I figured that out I —
MATT: Morning or night?
HAN: During the day. And once I figured that out I was like okay, in the afternoon I’m going to go hang out, work out, do other things. As a result I feel like, at least for myself, I have a few hours that are good and most of it’s not so great.
MATT: That is utterly fascinating, first. What other variables did you find?
HAN: Sleep was really important too. So when I started to correlate the number of hours that I slept, that was really important.
MATT: How much do you need there?
HAN: I typically need six and a half to seven hours.
MATT: I do want to talk about tools a little bit. What are the tools that you use when you share this writing or these proposals? What do you rely on there, particularly on the engineering?
HAN: Day-to-day collaboration — I would say our most important tool is actually the G Suite. Being able to co-author documents in real time, comment, assign action items, it is a game-changer for us, especially when it comes to assembling information very quickly. When we have site incidents, for example, we really need to make sure that a document is written quickly so that it’s fresh on the top of people’s minds, and then we run the post mortem. That level of tooling is critical.
We have a messaging client on our platform which we use for day-to-day business but the challenge is that when the site is down, oftentimes our messaging system is also down, because it’s part of the same platform.
MATT: Oh yeah. What’s your fallback?
HAN: Yeah, so our fallback is typically Slack. And so Slack is still very important. In order to reduce mean time to response our tech ops team and site reliability teams always collaborate on Slack, and so they’re basically online on Slack. We also use Hangouts quite extensively just for video collaboration. But also during site incidents, Hangouts are important because usually —
MATT: You’ll spin one up?
HAN: We will spin them up just because we have found that chatting back and forth is usually not fast enough. Hangouts also give us the ability to see what’s on each other’s screens. And so during those kinds of events it’s actually more important to watch an engineer type instead of look at their face, their panicked face. [laughs] So I think that level of collaboration is very, very critical and that’s when we need to go full real-time but remain distributed. Everything else is probably standard tech text stuff, like Git’s important, things like that.
MATT: Jira, Github, what’s the —
HAN: We use Jira, and then, essentially all the Atlassian stuff like Bitbucket and so on and so forth. We don’t dictate what the engineers do on their own machines. We have a “bring your own device” policy and so people use different kinds of tools.
MATT: Favorite thing about distributed work?
HAN: The people you meet.
MATT: Least favorite thing?
HAN: Miscommunication.
MATT: Especially across cultures and languages, right?
HAN: Yeah.
MATT: Final one. Twenty years from now what percentage of jobs do you think will be distributed?
HAN: I think almost all cognitive labor can be distributed. I don’t know how many companies or what percentage of companies will be fully distributed and I think there will probably be a spectrum of fully distributed companies, like Automattic, and partially distributed companies.
MATT: Pick a number over all and we can check it in 20 years.
HAN: I would say most companies will be partially distributed. And that maybe 20 percent of companies will be fully distributed.
MATT: So that would be 35% of jobs?
HAN: Yeah.
MATT: Cool. I really appreciate it.
MATT: That was Han Yuan from Upwork, and before that you heard Zoe Harte, also from Upwork. You can follow Zoe on Twitter at @ZoeSHarte, that’s Z-O-E-S-H-A-R-T-E. Han’s not on Twitter, but he’s pretty active on LinkedIn — just search for Han-Shen Yuan, that’s H-A-N-S-H-E-N-Y-U-A-N, and you’ll find him.
As the world’s largest network of freelancers, Upwork has a big opportunity to define what distributed work looks like in a big, blended company. I’m glad that they have such thoughtful people throughout the organization who are thinking hard about how to create economic opportunity and great work experiences.
Next time on the Distributed podcast, we’ll be speaking with someone I’ve been working with for a few years now. John Maeda is an author and a certified design guru, if there is such a thing. He also happens to be the Global Head of Computational Design and Inclusion at Automattic. We’re going to talk about how the distributed model impacts design teams, and about the tools and processes he’s using to foster creativity among them.
Thanks for joining us.
Automattic CEO Matt Mullenweg on building a fully distributed company
Jun 27, 2019
On today’s episode, Automattic editor Mark Armstrong interviews our usual host Matt Mullenweg to discuss the history of the company and how its distributed culture emerged from conditions that many startups face. They go deep on the tools and processes Automattic has developed to keep everyone connected, even if they’re scattered across the globe.
The full episode transcript is below.
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Mark Armstrong: Hi everybody. Thanks for joining the Distributed podcast. I’m not Matt Mullenweg, I’m Mark Armstrong. I’m the founder of Longreads, which is part of Automattic, and I’m on the editorial team working with Matt on the Distributed Podcast.
So today I wanted to take a step back from the interviews Matt’s been doing and find some context for how Matt got here in the first place, how he became interested in distributed work, and it all starts with the history of Automattic. So that’s what we’re going to talk about today. We’re going to talk to Matt about how he got here, how he actually decided to build a company that had no offices, and what worked and what didn’t. Thanks for listening.
Now where are you right now?
Matt Mullenweg: I’m actually in San Francisco, California.
Mark: And I am in Seattle. This is basically how we record this podcast for people who are remote. We have a Zoom connection, we use GarageBand, a tool called Zencastr, and we put it all together and it sounds like we are having this intimate conversation right next to each other. But this is a very good symbol of how distributed work has changed and the technology has changed.
Matt: Yes.
Mark: So take me through the very beginnings of Automattic and how you ended up with a distributed work model in the first place.
Matt: Well at the very beginning I had moved from Houston to San Francisco, actually, to take a job with CNET Networks. And they were actually an early adopter of WordPress. So they offered me a job as a product manager to drop out of college in Houston. I drove across the country with my mom and got a little apartment in San Francisco.
Mark: Did you apply for the job?
Matt: So what had happened was, I had said if I hit number one on Google for the search term “Matt” I would shut down my site and go out on top, like MJ. So that happened. Partially because most WordPresses included a link to the main developers, of which I was one. And they all said “Matt” and so those links started helping me rank first for Matt. So I just replaced my site with a little black screen that said this happened and I came out to San Francisco. Because this got some news when this happened. A bunch of people reached out.
Mark: So at this point, you had already started WordPress. Did you already have in the back of your head the idea of building a company around WordPress or were you thinking, well this CNET thing will work out for a couple of years and see how it goes?
Matt: I’m guessing this was probably 2004. At the time, there was no indication that anything related to WordPress could ever make money. [laughs] It was very much a voluntary project. And there weren’t really examples, certainly not as there are now, of consumer open source becoming a commercial thing. But what I did know was I was already collaborating with folks all around the world having a blast and using basically all my free time to get online, hang out in IRC, which was kind of like an early pre-Slack chat system, and basically code with these people who were also passionate about making publishing easier.
Mark: So you’re doing all this work on something that you love and then you’re commuting into an office in San Francisco. What was the office experience like? Was this the moment where you were like, “I never want to work in an office again so I will never do that?”
Matt: No, the opposite. It was amazing. [laughs] CNET was one of the first companies to actually set up a headquarters in San Francisco. Most of the major companies were and are down in Mountain View or Cupertino or some place else in the Bay Area… San Jose… But I looked very, very close to the CNET office and then when I moved in, my patron there, a guy named Mike Tatum, got me this really cool office right above the door, like a corner office.
And I remember this VP came by and in the course of the conversation, “Hey, where are you from, how are you doing, what you going to do here,” etcetera, he started to look around and be like, “Man, this is a nice office.” You can guess what happened next. Two weeks later I come to the office and there’s a note on my door. “Oh we’re doing an office move.” And I got moved to an interior office in the same section, still on the third floor, but more of an interior, non-window office.
But then there was a general re-org in the group I was in, and that whole floor got taken over by GameSpot. That was doing really well. And they literally moved my group into the basement, [laughter] the very, very first area. So now I was not just no-window, I was in this very small area and that was around the time I think I started to think this might not be for me.
Mark: So you’re putting together the idea for Automattic as a for-profit company that then would contribute to the WordPress open source project. So you’re viewing this as an opportunity to merge the two ideas of the non-profit, open-source side and a for-profit company that feeds into it. Is that the original idea?
Matt: So the original idea I actually pitched at CNET. They had a lot of cool domains, famously com.com, download.com. And one day I got a list of all their domains. They had probably a thousand from different acquisitions and stuff. And I went through them and I was like “All right, well, could be cool.” And I came across one called Online.com.
So the idea in the pitch I made to them was let’s make a version of WordPress that anyone can start with. So instead of having to know PHP and configure a database in FTP and all these things, let’s make it self-serve, where you can just click a few buttons and get one. That could be Mark.online.com. It could be your online home and you could have a blog and a profile and all this cool stuff. So I really pitched that quite vigorously.
But at the time what was going on was this colossal battle between blogs and traditional publications and two, every single internet giant had a blogging system but they were scared to call it blogging. So Yahoo had one called 360, AOL had Journals, Microsoft had something called Live Spaces, and then of course Google had Blogger. And so it appeared that all the internet giants — and those were the internet giants at the time — all had something in this space and CNET, one, thought they couldn’t compete, and two, thought that blogs were just gonna be like noise and politics and mess and junk and they were really going to bet on professional publications.
They were at the time locked in — News.com, which was a tech publication, was battling — or ZDnet was battling with Gizmodo, which was one of the early blogs started by Nick Denton and the Gawker Network, and Engadget from Jason Calcanis and Pete Rojas and those folks were also just getting started. So they saw themselves locked in this epic battle of professional versus amateur and didn’t want to do with anything related to blogging.
So I said “Well, I have to do this. I’m going to leave and start this.” And CNET very graciously invested in what became Automattic but asked if I could stay a few months to finish up some of the projects I was working on. So I did. But in those few months, I went ahead and started Automattic. I already knew the people I was working with as the other lead developers of WordPress and started trying to convince them to leave their jobs. [laughs]
And the first one actually was a fellow named Donncha Ó Caoimh, who was over in Blarney, Ireland. And he had started a different fork of the software that became WordPress. His was called B2++, I believe. And we decided to merge that with WordPress and make that WordPress Multiuser, which later became WordPress Multisite — basically a version of WordPress that was multitenant, that could have lots of people clicking a few buttons and starting a blog. And I want to say the second was either Ryan Boren or Andy Skelton. And I was technically the third because I stayed a few extra months to finish up things at CNET, and then we started Automattic.
Mark: Already you’ve built the beginnings of this company and you’ve already got employees that are spread out all over the world. So was that simply, “Okay well, these are the people I trust and want to work with and so we’re going to build a company that way,” or was there more deliberation around that?
Matt: One aspect was definitely having no money. [laughs] I was just paying Donncha and these other folks out of my CNET salary basically, and for servers and things, starting to rack up some credit card bills. So it was very much like — well, moving is really expensive [laughs] and we’re already working together, and, in fact, those were the days when we’d all work very, very long hours. So if you’re working 10 to 16 hours a day, you’re overlapping quite a bit with someone who is, say, in Ireland. And we had this awesome, almost relay thing where I’d work until night and then he would wake up and start working. And then I’d sleep, wake up, and there’d have been a whole cycle of things done to the software. It actually allowed us to iterate very quickly and brought in some asynchronicity very early on to our interactions.
Mark: At this point, how are you communicating with each other?
Matt: Probably we used AIM. AOL Instant Messenger, which is now shut down, IRC, and we were either still on SourceForge, which was kind of like an early GitLab or maybe at this point had switched to hosting the code on WordPress.org.
Mark: So this is a lot of baseline foundational communication that sounds very familiar to me even in current day Automattic.
Matt: We actually still run IRC servers to this very day. [laughs] And some people like to use them.
Mark: Yes.
Matt: But the evolution at the time, AIM was definitely the most popular chatting platform. At some point we switched to Skype again for chat, not really for voice. But I do remember some of those early voice calls where we, for the first time, would talk to each other and have what maybe [were] our first meetings. And the average meeting cadence at that time was probably three per year. We didn’t do a lot of them. It was really very much a written communication style.
Mark: And you hadn’t met in person yet.
Matt: None of us had met in person. Around that time was when I hosted the very first WordPress meetup in the world, which ended up being eight people at an Indian place, which is still there on Third Street, called Chaat Cafe. Those eight people ended up being pretty interesting. There was Chris Messina, who at the time was involved with Drupal Project, and would later go on to invent the hashtag. Scott Beale of Laughing Squid, which is now a large WordPress webhost. Om Malik, who was a journalist at Business 2.0 and later started GigaOm, became one of the earliest WordPress users. And someone who I met for the first time, which was Ryan Boren, who was one of the first major contributors to the core of WordPress. And he was, I want to say, an embedded systems engineer at Cisco.
Mark: There is a point though where you are going to then bring Automattic to investors and raise some money. How did they react to this idea that you didn’t have an office, [where] everyone was all over the place?
Matt: We didn’t really plan to raise investment in the beginning, we were just focused on making money to be honest. So we thought that we could have add-ons for WordPress.com. I think some of our early ones were custom CSS for customization and domain names, so this would allow people to be a business model. This idea of ringtones for blogs so you could buy customizations or add ons, actually not dissimilar to what we do today. And then we started to also do partnerships with different hosting companies who provided hosting and then could pay us for essentially new customers.
So that was the early business model and that started to make a bit of money, enough where we could each take a modest salary of a few thousand a month. And that was the plan. We didn’t have a ton in the bank, there was enough for a few of us to work on WordPress full time. And that was really just a dream. I mean, the company was created to have a place where we could be paid to contribute to open source and so we were all happy as clams.
Mark: It seems like you had gotten far enough along with the growing group of contributors and employees that you were already proving that distributed work was working. So by the time you ended up bringing in outside investors or other partners, that wasn’t really a question anymore. Is that right?
Matt: I met some different investors, folks like Tony Conrad and others, but I was at this point 21, [laughs] so, pretty young. And that was the era, pre-Zuckerberg, pre-all these other things, where you brought in adult supervision. So the model was really Eric Schmidt. Adult comes in and professionalizes the business.
And I didn’t really want that until Om Malik introduced me to a fellow named Tony Schneider, who had sold a company called Oddpost to Yahoo It was the original Ajax Gmail predecessor that allowed you to have a very web-application feel in the browser. They were the first to do that, that I had seen. But he wasn’t going to stay at Yahoo. So Om had done a cover story on the company for Business 2.0, and he said, “Hey you’ve got to meet this kid from Texas.” And he told me, “Hey you’ve got to meet this guy Tony, he’s not going to stay at Yahoo too long.”
So we met and really, really hit it off. Tony is an amazing individual. He came from Switzerland, moved to California, ended up going to Stanford, had a few start ups under his belt, including this very successful exit at the time to Yahoo, and was a CEO. And I was like, “Ah, this guy is my business soulmate.” If this is the adult, [laughs] I can totally bring in an adult — this guy is amazing. And I learned so much from him.
That was with the expectation, that Tony would join the following year when he was able to leave Yahoo. [He] ended up raising the first round for Automattic, which was about $1.1 million from folks who we actually still work with today, like Phil Black at True Ventures, Doug Mackenzie, Kevin Compton at Radar — so that first early round. And I was the CEO for I forget how long, the first however many months before Tony joined, and then we started working together.
Mark: Was there ever any pressure to eventually — “Okay, this is great, I love distributed work but we also need some physical offices?” How much pressure had come in, in those early days?
Matt: Well first we’d just use our investor’s offices. So at the time Blacksmith, which was the predecessor to True Ventures, had a space in the Presidio. So Tony and I would just get together at restaurants and coffee shops and then, if we ever needed to have a meeting or something like that, we’d go to this awesome office in the Presidio.
Later True, when they formed, moved to this awesome pier called Pier 38. They very presciently were like, “Okay, we’re a VC, we’re only this many people, but we can get this office space that’s a few thousand square feet. Let’s just put a few tables at it.” So one table was GigaOm, one table was Automattic. Upstairs was Bourbon, which later became Instagram. So there was a cool center of early startups that would have a little desk here.
Tony and I would go in there and meet or work from there but there was no reason to try to move the rest of the company there, because they were perfectly happy being where they were. I think Donncha was just about or had just gotten married. Immigration seemed really tough; there were a lot of barriers. So I was like, “Well, this is working, so let’s just continue to hire people wherever they are.”
However at the time it wasn’t clear that that was the thing we were always going to do. A lot of investors said, “This will work when you’re 10 people or 15 people, but at some point you need to get an office or you need to bring everyone to one place.” So we always kept that in the back of our mind as something that we might need to do. And [we] always had this small headquarters, first a desk, in the True Ventures space. And then we moved across the hall to a bigger space where we hosted lots of events and meetups.
This idea that we needed something to be the official address of the company persisted really until… gosh, when did we shut down our office? Was that 2016?
Mark: It was a couple years ago, mhm.
Matt: We actually continued having a headquarters really until then. Partly this idea that on average, as we started to scale, about ten percent of the people we hired were in the Bay Area, and the ones who did like to go into the office in San Francisco. We assumed as we got bigger and bigger that the ratio would continue at 10 to 15 percent. And it turns out it mostly did.
But what changed was that traffic and everything got so bad, parking got so bad in San Francisco, that even the people we’d hire in the Bay Area didn’t really want to commute. And then the tools for collaboration got better and better and so they didn’t really need to.
Mark: It’s interesting because there is a lot of this early Automattic history that you’re in San Francisco and you need to be in San Francisco physically in terms of the existing power and money, I guess, to be able to get a foothold for the company.
Matt: I think I felt like that as the leaders of the company we needed to be in San Francisco but the rest of the company didn’t. So it was great for Tony and I. We actually didn’t really have any new funders until 2013, 2014. And we were relatively unique at the time in that we had one West Coast VC, Blacksmith, later True, but our other investor was on the East Coast, called Polaris. So we were already distributed from our initial funding and that was unusual for an East Coast VC at the time, to invest outside of their geography.
Mark: Will we ever get an office back in San Francisco?
Matt: Yes, we probably will. [laughs] If something really interesting comes back up we’ll get a small space but it will probably be a secret. It will probably be just for board meetings and investor stuff, not something that is really an office like we have had in the past.
Mark: I want to switch over to some of the culture inside of Automattic since the early days. Automattic has its own creed. For those of you who have not read it before, you can go to Automattic.com/creed. But one key line from that is “I will communicate as much as possible because it’s the oxygen of a distributed company.”
I know how it is today, and we can talk about that in a second, but in the early days did that mean that every single conversation was public, and there were no private conversations? What was transparency and communication like in those early days?
Matt: Yeah it really was, because there wasn’t really any reason to not have everything be open. The whole company was in one chat room. We had no teams, we had no managers, it was totally flat. We just organized around projects and code really. And there was such an advantage to knowing everything else that was going on. And we were doing enough things that you could know everything else that was going on and there was a lot of information sharing, or seeing the flow of code commits and code changes and conversations.
You got a shared collective intelligence of everyone at the company pitching in on every idea. So although we didn’t have formal product managers or a ton of designers or things like that, because everyone was using everything. We use WordPress ourselves, and seeing things that went through, you got a lot of real time feedback, almost like real time user testing with your colleagues, that ended up speeding up the iteration cycle and leading to some very usable products, even in the early iterations.
Mark: That probably brings us to P2, [which] I believe was introduced in 2008. So for those who don’t know, P2 is essentially a WordPress theme for groups to share status updates with each other. I personally still see it as the foundational tool of all communication inside of Automattic to this day. But I went back and looked up your first post on Update-A-Matic, which is the all-company blog inside of Automattic, and I can see that you wrote the quote “Finishing up meetings.” That was the entirety of your P2 post.
Matt: [laughs] Well it was pre-P2. We just had an internal blog and we used it much like Twitter, which at the time was called TWTTR. The idea was just that — originally the prompt on Twitter, which is “What are you doing?” or “What’s going on?” or something like that. And so you would post literally whatever you were doing at that second. [laughs] So, finishing up meetings…
Mark: This is like people tweeting what they had for breakfast or whatever?
Matt: That was the goal, actually. So a way for us to put things on there. And then we started to see that it was useful to have a place that you could have comments on or could do threads. We used it for keeping data.
Mark: So P2 was not introduced yet as an actual thing, this was still just the internal blog?
Matt: It didn’t come until many years later. So it was really just this internal blog in IRC. What was, from the very beginning of Automattic, was this concept of meetups. Actually early on we did two ,I think, in one of those early years with five to 15 people.
One that stands out in my memory, because it was an utter disaster, [laughs] was Stinson Beach, which is a place where I think we all fit in one, maybe two homes. We went on Stinson Beach, which is north of San Francisco, and we didn’t really know what to do at a meetup. So I think we assumed that we should just have all day long meetings and debates. [laughs] This drove, I won’t name who, but it drove someone crazy and it ended up being — I think there was a walk out of one or two people. [laughs] Voices may have been raised. It did not go well.
At the time the valid feedback was, “Why are we sitting around, just arguing about things for hours and hours, not getting anywhere, not driving to decisions? And, by the way, we could do some of this written. Why does it need to be in real time, people reacting to information versus considering it, thinking about it and writing a response in a deliberate way?” Which — if you think about it — is a much, much better way to have a debate or an exchange of ideas than people just reacting in real time to whatever information is popping up in their head.
So that first meetup was a little bit of a disaster [laughs] and we decided to move them to once a year [laughs] and make them more organized. So we introduced the concept of meetup projects, or hack weeks. So the idea is we would get together and start and launch a number of things during that week as a way to do things we wouldn’t normally do, and just have fun. It was very much getting together and just working intensely alongside someone. [Which] was, and honestly still is really fun, [but] was hard to replicate with the tools at the time.
Mark: I think that holds to this day, this idea that the meetup should be a social event as well because you’ve got the entire rest of the year, and you have all of these tools in which you can organize and communicate and brainstorm. And so really pinpointing the specific things that you can only do in person together — and that’s also building relationships and building trust with each other — that you can then go back and be honest on Slack and P2.
Matt: Exactly. Those meetup projects ended up creating a lot of things that became very crucial to Automattic today. So it evolved what first was called Prologue, which was the early version of a theme for WordPress, which put the posting on the home screen, so again, very much like a Twitter built on WordPress that looked a lot like what early Twitter looked like at the time, which was just a box and a list of posts.
And then that evolved at a later meetup into what we call P2, which basically took Prologue and made it real-time, so that as things were posted they would show up without you having to reload the page to get new comments or anything. So that was the evolution of what became what was and still is to this day the most important communication tool inside Automattic.
Mark: It’s an interesting segue to today because you’ve got P2 that are now hundreds of P2s, team and project P2 websites across the entire company. And then we have this global search tool in which people can search across every one of these websites. We also have a field guide which is more evergreen pages of documentation.
But the P2 is where most of the deep communication is. And I’m raising this as a segue to today because seeing your original “Finishing up meetings” post and then seeing a post just the other day from Nick Momrik on our HR team, about the growing word counts of our P2 posts [laughter] as a trend, I think we can see that P2 has not fundamentally changed but how we use it has changed, especially once we started to embrace something like Slack.
Matt: Let me paint a picture of P2 so people listening can know what it’s like. So imagine on, kind of like a website, with a main area and a sidebar, and in the main area there is a post box at the top so you can type in there and click “post” and it shows up immediately, much like a Twitter or a Facebook. Below that is something that can be a post of any length but all the comments are in-line, so all the conversation happening next to a post, which again, doesn’t need a title, can be right there, and they pop up in real time.
And on the right, on the sidebar, can be widgets that allow you to search, might have a list of people on the team, could have a schedule, could have notes, could have links to things, to resources, could have target launch dates or a countdown timer. And so the sidebar — it becomes kind of like your ultra-customizable home page for your team or project.
The key for us was, as you mentioned — transparency was our default for most of our communication. The one thing that didn’t really work for that was email. So we’d email each other ideas and threads and brainstorms but then if someone new joined the team they had no way to catch up to those emails. And there was all this intelligence and data and wisdom being lost in people’s inboxes.
Also, our email was busy at the time because support was all done through email and “support@” was just an alias for “everyone@.” So every support thread we got would go to everyone in the company and whoever replied first would claim that email or that ticket.
So P2, Prologue, this internal blog, became a way for us to eliminate email. So anything that I would normally email, let’s say “Hey Mark, I’ve got this idea for a podcast, I think it should be X, Y, Z.” I would just post that as a blog post and you could see it whenever, and you still got that general intelligence that anyone else could see it and choose to interact with it or add their two cents to it, which is both a blessing and a curse. [laughs] It’s a blessing when you want the two cents and it’s a curse when you’re crushed under a sea of pennies.
Mark: I want to go back to today. One could argue, at least from my experience — I joined, just for the record, in 2014 — but one could argue the past two years at Automattic have seen some of the most dramatic changes since you’ve started organizationally. We’ve grown very quickly. We’re now at 900 employees. And where we once were a strictly flat organization — we made up our own titles — we now have executive roles, product roles, and actual hierarchy. Can you talk about what’s changing and why at this stage and why it’s important?
Matt: Sure. A common misperception about Automattic was that we were non-traditional infrastructure. And that probably stems [from] — I avoided creating any hierarchy or really teams or normal company structure until we were maybe 50 or 60 people, and it became really, really necessary. So that’s where that comes from. But really since then, which is, by the way, the time chronicled in Scott Berkun’s book “A Year Without Pants,” which was — he was joining partially because I was like “Oh we need someone who’s done this before to help us create these teams,” but ever since then we’ve had a completely normal org chart, a completely normal hierarchy.
Although I’m a strong believer in how we work being non-traditional, distributed, it’s still really important for lines of accountability and for people to know where they fit and have one-on-ones and all those sorts of things. So that part of Automattic has always looked kind of normal.
Mark: Essentially we’ve got team structures, which are — teams can be, what, eight to 10 people per team and they’ve got a specific focus? What is the ideal team size?
Matt: How we have approached Automattic is in a fractal way. So the idea is that if you zoom in or zoom out of Automattic it looks like the structure that is self-similar in many ways. So when Automattic was ten people, we had a designer, a businessperson, a bunch of engineers and we’d all work together to iterate on our area.
So our team structure inside Automattic is very much modeled on that cross-functional idea where you get everyone together and you just — it’s that classic idea, a two-pizza team or whatever you want to call it. Get people working together with the autonomy and all the know-how that they need to ship and iterate with users, ideally as frequently as possible. Then when that gets too large, much like cell division, you split it into two identical teams and now you have two teams of, let’s say five doing cross functional work.
As that grew, we eventually had divisions and now business units that are made up of divisions. Our largest business unit probably has two hundred and sixty people in both product and engineering and design. But still, if you zoomed in on one of those teams it would look very much like the teams that we had a decade ago.
Mark: And the tools too look very similar. So we still have the P2, as we’ve gone over, we use Zoom for video conferencing, as you and I are doing right here, then of course Slack came into the picture. That was shortly after I joined the company and that very much started with you, right? I feel like we were experimenting with it and then you decided let’s go all in.
Matt: I appreciate the credit. [laughter] With many things at Automattic, we give the teams a lot of autonomy. So we tried to adopt HipChat before other things that were a little better than IRC. It just didn’t take. I want to say probably the mobile team or there was some team inside Automattic that adopted Slack and then it was optional for people to get on it. Many, many did and we utilized their free version.
I also knew Stewart from his Flickr days and so I knew a lot of the people involved with it. And in fact, a very early Automattician joined Slack pretty early on. I think she was one of the first 20 or 30 there. So we had that connection as well.
It just got so good. And my decree was more that we still had a chunk of the company that was really holding out on IRC and didn’t want to sign into Slack. And for communication tools it’s really, really important to have everyone on the same thing. And we were going through a lot of growing pains. Our non-IRC was mostly through Skype, or if IRC would go down we’d use Skype and that was just really awkward because then you would have to add everyone who joined the company manually. So it was just a very weird process.
And so Slack, everyone being on there, the directory, all the things that everyone knows and loves about it, it was just so darn convenient. It really seemed like a better version of IRC. And, in fact, a lot of the conventions in Slack are directly modeled after IRC, like the reason why public channels have a hash in front of it. That is taken directly from how most IRC clients work. So it was pretty natural and, just for communication standardization, seemed important. So that was what I think eventually got our Systems team onto Slack.
Mark: I think it fundamentally changed how we even used our other tools, like P2. Whereas P2 maybe was more of a conversational tool in the past, now it’s a little more announcement-focused or this is our plan-focused [tool]. What would your take be on how P2 has evolved in the world of Slack?
Matt: It totally depends on the team. I would say this is one of the things that has changed most. I don’t know if it’s for the better but I’ll observe it in a neutral way. That as we hired more and more people that then come from the online collaboration or open source space — which, to be honest, there’s only so many people who have worked in an open source project or things like that. [laughs] They brought an approach to P2 that was a little bit more like announcements, like you said, and more meeting-centric, so needing more of that kind of synchronous real time communication and get everyone on the same page.
And I think that coincided a bit with Zoom, which honestly makes meetings a lot easier than they’ve ever been and more pleasant than anything we’ve done in the past. So I think also people just wanted to connect better. We have a lot of psychological diversity in the company. I would say early on [we were] very much composed of introverts, including myself, for whom text was really our first choice of communication. And as the company grew, a lot more extroverts, or people who wanted to use voice or see each other as they converse. And so it was hugely controversial early on, even the idea that we’d have an audio-only meeting was widely debated for why that’s needed, if for nothing else than it’d be inconvenient for everyone not in a couple time zones.
But teams can choose their own way. So as more and more teams had more and more people that were maybe composed of these or that wanted the real time synchronous communication and the tools got better, we started to use that more. And so on a team-to-team basis it varies a lot.
I love, for example, our VIP team — that’s the enterprise part of Automattic — uses P2 I think the best of any team or division within the company. They put really everything through it. Their Slack is still busy but they really put a lot of thought and their P2 is great to read. It’s funny, it has GIFs, it’s fast, everyone has it pretty dialed in there.
Other teams have gone to where they might only make a few P2 posts a month, which if you’re doing that you’re not using it for daily communication, you’re not using it for real-time saying what you’re doing and keeping people up to date. You’re using it more like one-way announcements.
Mark: This raises the question of what skills are necessary to succeed inside of Automattic? Because I think there is a little bit of a — with P2 being so central and with written communication being so central and the fact that WordPress.com is a website and a blog hosting platform — that a lot of the most successful elements come around being able to blog internally as well. Do you believe that’s true?
Matt: I try to be pretty active on P2s. Call it an average of maybe a hundred posted comments per month. And my total word counts, I think it’s over a million words now that have been posted to these internal sites. And it’s really one of the richest treasures I have in my time in Automattic because everything is archived, everything is searchable, everything is there. And if I need to remember what I was thinking in 2012 when we made X, Y, Z decision, hopefully that decision is documented and the debate around it, and it becomes this huge source of wisdom, which I think allows the company to evolve in a more informed way. We try to only make new mistakes in having that entire history of the discussions and the collaboration that led to where we are today on these internal blogs. I think it allows us to move faster, smarter and better as we blaze a new trail.
Mark: It raises some other questions about talent. And one of the great promises of distributed work has been the idea that we can find talented people all over the world. But there are also trade-offs to what skills and talents this culture prizes versus, say, an in-office culture that’s more extrovert-focused or verbally-focused. What would you say the major trade-offs are and are they worth it?
Matt: As I said, different teams work different ways. So there are teams that do very little written communication and communicate mostly through Zoom or audio or things. And so a nice thing about Automattic is whatever your work style is, you can generally find a team that matches that. If you want to be on a team that uses IRC and then basically never has any Zoom meetings, we got that. If you want to be on the team that has daily stand-ups, we got that too. And so by switching teams or divisions within Automattic you can get what might — you might need at a different company to switch companies to find your ideal work and collaboration style.
Q: You have mentioned here if a team wants to experiment with something — what are the experiments that you have maybe heard about recently that we haven’t tried inside of Automattic that you think we really should prioritize and try?
Matt: One that has come up is Invision, which is a distributed company, actually has everyone work East Coast hours. I don’t think that would be right for our entire company. We’re already too distributed for that, but it would be interesting if a team which was largely American-based agreed to overlap the exact same hours, if they would find that beneficial or just inconvenient.
So that’s how I would want to approach any of these experiments is, say, find a team, at least 10 people, 15 people, who want to try something out, and see how it goes and have them do it for a fixed time period. Do a pre-mortem, do a post-mortem, see what are the learnings from it, and then what are the next actions we want to take from those learnings.
Q: Is there enough creative tension or friction in a distributed company that maybe some form of self-censorship takes over, or we’re too polite with each other and we don’t raise the questions we need to raise? Do you think that is a valid concern?
Matt: This is why I have become relatively recently obsessed with the idea of an idea meritocracy. Have you read the book “Principles” by Ray Dalio yet? It’s a really impactful one in that you’re not going to agree with it but it will make you think differently. And one of the things he emphasizes is even in their in-office culture that the comfort that people have with challenging ideas and the openness people have to their ideas being challenged is crucial to getting the best outcome.
Because if either of those is missing you get sub par outcomes. And because when you’re communicating on text it can be so easily misread, people hold back. I do think that’s 100 percent true. It’s less bad on audio or video but definitely in text communication you just don’t have that nuance. All the emoji in the world can’t recreate the kind of timbre and tone of voice and all the additional data we get when we’re actually talking or seeing each other.
I think a lot about that, and I’ve been thinking a lot about how to foster that. Google talks about psychological safety being key to the high performance of teams. How to foster that where we think that good ideas can come from anywhere and everyone is comfortable presenting and defending vigorously anything they believe in.
Mark: One other thing I’d like to do real quick is just a quick speed round in equipment breakdown. Tell me a little bit about your workspace. Now you travel a lot; you’re in a lot of different cities, tell me a little bit about your must-have items?
Matt: [laughs] Yeah, check out the What’s In My Bag post for the kinds of things I use every single day. It’s the 15-inch MacBook, it’s the cables, it’s the Sennheiser headset for being on calls. I find audio quality is far more important than video quality for creating a great meeting. At home to me that’s the ultimately luxury. [laughs]
My favorite part from being distributed is when I am able to work from home, which is probably a minority of the year, but I love it because you can have your music you like. I like having a candle on the desk. [laughs] I like the temperature to be a little bit warmer because when I work my hands and feet tend to get extremely cold for some reason. Normally they’re fine but for some reason when I’m on the computer they get ultra cold. I recently installed the instant hot water thing at home. So in my sink I can get near boiling water and make tea. On my desk I always have a notebook. I love paper notebooks for writing things down, I find it’s a lot less distracting than trying to type things out.
For a while I used to try to have desktops, like an iMac, and in fact the new iMac Pro is — I still have one of those in Houston. But I’ve really gone to where I like a great monitor, [and plugging] it into the 15-inch is the easiest. And I love these new ultra wide monitors. LG makes them. I think I have one that’s 34-inch and one that’s ginormous, 38 inches wide and curved. And using that, it feels like a panoramic experience.
I knew that I was spending too much time on Google Sheets when I was like, “Oh my goodness” and I stretched out the sheet all the way to the 38 inches of this ultra wide monitor. I was like, “I can see everything!” It felt almost omniscient. But I was like, “I’m in spreadsheets too much.” [laughs] I need to load up some JavaScript.
When I’m at home, I use a Logitech BRIO camera, which is a high-end, 4K-webcam that they have. I find it has a much better aperture so it creates better colors and light in low-light situations, which is often where it is. If I don’t have good natural light wherever I am, I have some desk lamps — just soft light that I can put there so I don’t look weird or back-lit [laughs] wherever I am. If I’m on video I try to — I actually think of it probably much like a webcam YouTuber would. Like, “What’s the lighting like, what’s the audio, how can I present well there in a professional manner?” And I actually see a lot of folks at Automattic curate their background, having things they like in their background. Because you actually end up looking at yourself, what’s behind you, a fair amount when you’re on Zoom or Hangouts or one of these things.
Mark: A couple quick speed round items. Phone calls, love them or hate them?
Matt: It’s actually a resolution of mine to pick up the phone more. I don’t really receive phone calls because it’s all spam now but I love all the non-phone things, like Facetime audio, Zoom, Slack Audio is actually really good. And one thing I’m trying to do more is actually switch mediums. So if I’m finding I’m having a long text conversation with folks, I try to balance the audio.
And it’s also nice in that some folks — my mom is getting older and sometimes it’s hard for her to read the text. So it’s always really nice to hop onto that. Video is really nice too. I got my mom one of these Google home devices that had a built-in camera. So you can use Google Duo — that’s actually the only reason you would ever use Google Duo to make a video call — to her and it lights up this device that’s by where she usually hangs out. So I’ve found that’s actually been really, really lovely as a way to drop in and stay connected with a loved one who I don’t see as often as I would like.
Mark: Final question. Twenty years from now, what percentage of jobs will be distributed?
Matt: You’re turning my questions back on me. I am going to say… Well, I kind of don’t want to say so that future guests can answer this without knowing my answer. I do believe there is a window where distributed companies have a real advantage for recruiting, retention, and everything. That window is probably three to five years before the incumbents really embrace this.
I then think that job seekers are going to learn to ask more sophisticated questions. So they won’t just say can I work from home or not, they really dive in to where do decisions get made, where the center of gravity for the organization is, can their career advance as much being not where the headquarters is or in a distributed fashion as it would if they were say in Mountain View, at Google.
And those types of more subtle questions will be the things that — as the internet giants embrace the surface of distributed work but perhaps not the deep spirit — all the things that are currently bundled with that — and startups like Automattic or Invision or UpWork — I guess are we still a startup? But companies like that. The bar will change. I’m looking forward to that happening.
Mark: Thank you, Matt.
Matt: It’s been fun chatting.
Mark: That was Matt Mullenweg. Thanks again, Matt, for taking the time to speak with us about the past, present and future of Automattic. If you want to read more from Matt, you can always go to his blog ma.tt, and he is also Photomatt on Twitter. Thanks for listening.
VC Arianna Simpson on Distributed Work and the Blockchain
Jun 13, 2019
When venture capitalist Arianna Simpson tweeted this opinion, she never could have guessed the massive response she would receive. In this episode, Arianna has a chance to clarify her thoughts on remote work. Then she explains how “programmable money” on the blockchain could lead to a new world of smart contracts and distributed work arrangements.
The full episode transcript is below.
***
MATT MULLENWEG: Back in March, Arianna Simpson tweeted an offhand remark that went crazy viral.
“Unpopular Opinion: Remote work is mostly bullshit.”
Arianna had no idea that thousands of people would like the tweet, and hundreds would weigh in with their thoughts, some pushing back, others hailing the blunt honesty of her “unpopular opinion.” As a true believer in distributed work, I naturally had to get in touch with Arianna when I saw the tweet.
Arianna is an early stage investor, with close to 40 investments to date, many of which deal with the blockchain and cryptocurrency projects. I wanted to find out: How is it that someone, who knows so much about distributed software that’s created among globally-distributed teams, has such a pessimistic view of distributed work?
It turns out, as it often does, that Arianna’s thoughts on distributed work are more nuanced than her tweet might lead you to believe. We discuss her reservations with remote work, we cover some of the things that traditional office arrangements are really good at providing workers, and we explore how companies can give their employees the best of both worlds with a hybrid model.
But things really get cooking when we started talking about how the blockchain could one day be used by distributed companies to pay workers in far-flung locations with stablecoins that are pegged to a traditional currency. When money becomes programmable, all kinds of interesting contracts and financial arrangements open up, making it easier than ever for the distributed company of the future to partner with workers all over the world.
ARIANNA SIMPSON: My name is Arianna Simpson and I run a fund called ASP. I’ve been an investor for the past several years, first general VC, and now running a crypto-specific fund.
Matt: So you’re into distributed systems.
Arianna: I am.
Matt: One of the reasons I really appreciate you coming on — and a goal of this podcast is — I wanna have the very best versions of why people should be in the same place, as well as making the case for distributed work. We are obviously in the same place right now.
Arianna: Yes, we are.
Matt: We are in a tiny studio in New York City, and this is nice, right? Because we’re having a higher-fidelity communication.
Arianna: Mhm.
Matt: This all started in a tweet. Do you remember the tweet?
Arianna: The tweet heard round the world! Oh yes, it was kind of Paul Revere-ish in its quality in that sense.
Matt: Do you want to read it?
Arianna: Sure. “Unpopular opinion, remote work is mostly bullshit. Way more gets done when you’re all in the same office.” [laughter]
Matt: So are you normally this popular on Twitter?
Arianna: Well, it’s funny because I tweeted that, and it’s definitely an idea I’ve held for a while. But I definitely didn’t expect it to have such a strong reaction from people, both in the positive and the negative. It got close to 5,000 retweets and hundreds of comments, and I was frankly shocked at how personally [people] took the comment. So I think it was an interesting way of seeing just how strongly people feel about the topic.
Matt: What were some of the comments you got back?
Arianna: People took it very personally to some extent because they saw it as a personal attack, which it really wasn’t meant to be. And I think a lot of nuance is obviously lost on Twitter. [laughter] Yeah, shocker, right? So I then went on and kind of explained what I meant.
So for example, some of the caveats that I think are important to make [are] — I was referring to basically…traditional, venture backable, early-stage tech startups. There are lots of other kinds of businesses — lifestyle businesses and other things — that can run perfectly well, and probably even better in some cases, with distributed teams. But I think there is something to be said for having people in the same place at the same time when you’re driving towards a common goal and that was really what I was trying to allude to.
But yeah, I think having people come and interrupt you every 25 seconds, as is often the case in open floor plans, is definitely not the most productive situation. So the model I’ve seen work well, or the model I lean towards, is having an office where people are working from, but having private offices or spaces where people can plug in their headphones and just do work alone while still being in the same place as, hopefully, all of their colleagues.
Matt: I’m actually always struck when I visit friends at Dropbox or Airbnb — beautiful offices that I actually get jealous of because they’re so exceptional. Stripe has a beautiful office. How many people have headphones in and are looking at their computers?
Arianna: Mhm.
Matt: I’m like, well you could do that anywhere in the world.
Arianna: Yes and no. So I think — say you have to sit down and write some code or write a blog post or something like that where you need to focus on one task and don’t want to be distracted.
Matt: I call that work.
Arianna: Sure, I agree, and that’s actually part of work. One thing I’ve noticed about startups that end up being very successful is often there is this really strong sense of shared mission and shared energy, and that I find very difficult to replicate if you have people in different locations because you don’t have the same sense of camaraderie, the same sense of “You know what, this sucks but we’re gonna stay here until 10 PM and pound it out until we’re done ’cause we’ve gotta get this release out” or whatever it is. So that is a really difficult intangible that’s hard to replicate if you have people in different time zones or in different locations. It’s hard to muster up the same level of enthusiasm.
Matt: It’s interesting you mention time zones. There [are] some distributed companies, like InVision, that actually ask everyone to work essentially New York hours. So they’ll hire you wherever you are in the world, but they say “This is our window and we’re all gonna be working at the same time,” probably for some of that collaboration-overlap benefit.
Arianna: Yeah, yeah absolutely. I’ve seen companies — sometimes they’re small, they’re 15 or 20 people, and they have eight time zones. And I honestly don’t know how you manage to get anything done, because even just internal scheduling can become such a time suck and such an added complex issue, that really shouldn’t be one, that it can easily become a drain on resources and time.
Matt: Often Twitter is for hot takes and reactions to things. So was this in reaction to any particular moment or experience?
Arianna: No, honestly, not so much. I think it was just a general reaction to the trend I’ve been seeing, which is in the direction of more teams being distributed or remote. And my seeing that I’m still not totally convinced that that’s the most productive model for most — of the kinds of companies at least that I’m interested in investing in. It’s important to point out that there are certainly counter-examples and there are a number of companies that have been distributed from day one and have done very well. I would pose the devil’s advocate perspective that they might be —
Matt: Would they be bigger?
Arianna: Exactly.
Matt: Yeah, what’s the opportunity cost.
Arianna: Exactly. And I think it’s incredibly hard to measure that and so I can’t say that I’m right and they can’t prove that I’m wrong. So we’re stuck on that point.
Matt: Do you find in your own portfolio [that] some of the standouts, or ones furthest along in their journey, have tended to be these more in-office ones?
Arianna: I would say — obviously my portfolio is too small to be a generalizable subset, but at this point it’s north of 50 companies so it’s not three. [laughs]
Matt: That’s sizeable, yeah.
Arianna: Yeah.
Matt: And to invest in those fifty you’ve met with five thousand?
Arianna: Thousands, yeah, yeah.
Matt: Yeah, thousands. People sometimes don’t realize just how many different companies investors see before they make investments.
Arianna: Oh yeah, oh yeah.
Matt: It’s kind of incredible. And a really good data input.
Arianna: Mhm. Obviously as someone who tries to be pretty analytical, you have to say correlation, causation — there are so many issues that go into making a startup successful or not that just being like, oh well there are plenty of startups that fail and they were all right in the same room. So that is definitely not a sufficient attribute. But I would say in general there is something to be said for, at least in the earliest days, having that central locus of cohesion.
Matt: That was such a reasonable thought. It would never fit on Twitter. [laughter]
Arianna: Yeah, right?
Matt: So I’m going to try to summarize. You’ve seen in the past and you expect in the future more companies, especially in their early stages, to do better when they’re all in the same room because the value of that collaboration is really high.
Arianna: Yes.
Matt: You’re open-minded to counter examples, but maybe those are the exceptions that prove the rule?
Arianna: Yeah I would say that’s true. And I think one thing that I’m [advocating] is a hybrid model as well. So for example, some companies in my portfolio have the business HQ in San Francisco, and I see this typically if the founder is from somewhere that’s not the U.S., but they tend to still have a pretty strong presence in the Bay Area, and even when they’re distributed it’s a couple of hubs, not individual people all over the map.
Matt: The easiest thing in the world is everyone around a table, that two-pizza team. It works for a reason.
Arianna: [laughs] Mhm.
Matt: You can maintain all the connections, it’s easy to communicate, etcetera. I think fully distributed also works really well. In between what’s really hard is multi-office because then you often have distinct cultures growing up.
Arianna: Yes.
Matt: A lot of the companies you see as more traditional are almost all multi-office. It’s physically impossible sometimes to get a certain size in a single building. And I would argue as soon as you’re on multiple floors, even, you’re essentially distributed, you might just not be doing the work. But the other one, this hybrid, it’s really hard. And it’s just hard to have them at equal footing to the rest unless the in-person team works really hard to make sure everything is documented; that the conversations are accessible.
And even then there’s just things that happen naturally. We’ll have something when we’re walking to the coffee shop. That might be an important discussion. That might influence how we both think about how this widget is going to evolve. And unless we really put in the work to document that, to catch everyone else up, they might see the end of that decision and not the beginning. And that’s challenging, especially when you’re creating things in the early stages.
Arianna: Yeah, I think that’s totally true and I’ve seen that happen a lot where the employees who are not in the main office often end up getting passed over for promotions or they just feel really disconnected, and so often have higher churn and end up deciding to leave because they’re in a silo. And everybody wants to feel connected to their team and to their work, and it’s hard to maintain that connection if you’re not on the same physical playing field as most of the team.
Matt: I think churn is actually an interesting trailer indicator of how well you’re doing at this.
Arianna: Mhm.
Matt: We’ve observed in other successful distributed companies that the churn is actually way lower than any in-office companies we know. And that multiplies in the Bay Area. And I think that’s a function of — well, one, if you’re at the place where everyone is being poached to every other place, you’ll naturally have some higher churn.
Arianna: Yeah, sure.
Matt: Two, I think being in an office in general — you’re asking someone to do that work to get to and from the office everyday. And that commute and that scheduling — all of that can be challenging. Even companies that are very progressive and might say sure, if you want to leave at 3 PM to pick your kids up, that’s fine, and you can come back and work an extra 30 minutes or something. Meetings are still going to get scheduled then.
Arianna: Yeah.
Matt: And to be honest, I do get jealous when I visit some offices — like, I have a little bit of FOMO because I really love my colleagues and I really love spending time with them. But I think in our personal lives, when we make the decision to live with someone, to cohabitate, whether that’s a roommate or a partner or whatever, that’s a very considered decision and we take into effect a lot of things — their eating style, their music, their habits of all sorts, and we enter that in a deliberate fashion. But during a third of our lives, eight hours a day, traditional offices thrust us —
Arianna: Oh yeah.
Matt: — in sometimes tight quarters, depending on how fast the start up is growing, with people who we did not necessarily screen for those things.
Arianna: I didn’t sign up for this, yeah. [laughter] Totally.
Matt: And it’s funny, my friends who work at offices, sometimes their complaints — the things that really, really, really bother them — might be the temperature in the room, or there’s someone who calls their mom everyday and it’s an annoying conversation, or the person who brings in a really strong curry three times a week. You’ve probably had examples of this yourself that you think — like, you don’t like open offices for example. That’s a pretty specific taste.
Arianna: Yeah. Well I mean that — I think the most egregious example of this was when I was working at Facebook. I was right in the middle of basically the main walkway to everything. So if you wanted to get to the door you went by my desk, in order to get to the cafeteria, the bathroom, literally anywhere, you had to walk by my desk. And so this was an office of, at that point in time, three hundred people and —
Matt: So you knew most of them probably, yeah.
Arianna: Yeah, because I tend to be pretty social and again — small team. But I couldn’t get anything done because I was literally in the middle of everything and everyone would be like oh hey, how’s your weekend… And I’d be like, oh my god, six hours later and I’ve accomplished nothing.
So then what I started doing was barricading myself. I was booking conference rooms, which technically you weren’t supposed to do, but whoops, [laughs] to just go in there and work. So that’s where I realized okay, actually what I like is having other people around and the ability to go and talk to my colleague if I need to, be present in meetings, and all these sorts of things — but also an independent workspace where I can just be alone and think — that’s where my preference on that emerged personally.
Matt: And how much of your day then would you say was like work [where you] needed to talk to other people, versus work where you needed to be in that grind mode?
Arianna: For me, I was in that — they call it Global Marketing Solutions, aka Sales. So for me, I had a lot of time talking to people both internally and externally, and I was working in a somewhat cross-functional role, so I had to triangulate with engineering and design sometimes in addition to the client. So there was definitely a lot of active collaboration that I was doing. So I would say maybe two to three hours a day I needed to be alone, just answering emails or things like that, and the rest of the day was a little bit more interactive.
Matt: That’s a high percentage, that’s 40 percent of a normal workday.
Arianna: Yeah.
Matt: And that definitely varies per role, of course. If you’re an engineer, maybe that’s higher, a writer — I feel like a lot of engineers and writers replied to your tweet.
Arianna: Yeah, definitely. But I think even with engineering, it depends. What are you doing? Because if you are just executing on something then yeah, I agree, but so much of what, for example, my portfolio of companies [is] doing is not just like, “Oh, write the code to do the thing,” it’s “Figure out what are we writing code to do. What is the product that we’re building to begin with, how should it be built?” And a lot of that is much more collaborative than just going off and writing code in a silo.
Because what happens — and again this is par for the course in terms of companies I see — if you just focus on going off and writing all the code rather than thinking about “oh, what are we building, what do our customers actually need?” it’s easy to just spend a lot of time writing code that doesn’t actually solve the problem you were trying to solve for. So I think especially, again, particularly in the very early days of the company when you’re trying to figure out product-market fit, you need to be talking to your team, and you need to be talking to your customers, and a lot of that is less silo work and more collaborative.
Matt: So if you were going to fish in a pool and put everyone in the same office, then you want to fish in the biggest pool possible. And the hubs are probably better for that.
Arianna: Mhm.
Matt: Historically we’ve said that’s ’cause of the universities and the previous companies there. What changed is now people can learn the skills to be amazing at these things all over. They can follow your Twitter, they can read Fred Wilson’s blog, they can — the resources are really going online in an amazing way. And so when you multiply that, and if you assume talent and intelligence is equally distributed but opportunity wasn’t historically, but is becoming more equally distributed with the internet, there’s just a lot of good people out there, and so there’s an arbitrage opportunity in that they might not have — the 5,000 thousand companies that are in the Bay Area that are interesting to work at. So the 100 interesting distributed companies have a lot more access to what I would call an ocean versus a pool of talent.
Arianna: Yeah I think that’s true, and that is why I think, at least in part, we are seeing a trend in that direction. But I will push back on the idea that all of this can be learned online. There is definitely a lot that can be learned online and I have learned — I studied nothing related to anything investment-related, so everything I’ve learned in that category has been through a combination of reading stuff online, but also learning from peers. And that’s true both if you’re an operator and if you’re an investor. And the highest concentration of that is going to be where? Probably the Bay Area.
Matt: I totally agree peer and other mentorship is super important, but I definitely have people I’m very, very close to that I might only see once every year or two. You can just build really great relationships mediated through the internet. And then you run into each other at a conference, which is, by the way, neither of your cities you’re normally in —
Arianna: Sure.
Matt: And that can be the in-person spark. There is one place where I think we agree one hundred and a million percent, which is the importance of that in-person interaction — and something I really recommend — that distributed companies do meetups.
Arianna: Yup.
Matt: Because there is a level of trust. I call it the breaking-bread moment. If we were to share a meal, there’s just something built into us, a trust is engendered there that then increases the bandwidth and our ability to connect when we’re not physically collocated.
So our policy is the whole company comes together once a year. We call it the Grand Meetup. And the individual teams, which are anywhere from five to fifteen people, get together two or three times a year outside of that. So we tell people when they join Automattic, it’s just about four weeks of travel per year and then the other forty-eight weeks, be wherever you want. Which is the reverse where most in-office companies say, “Be here forty-eight weeks a year, the other four weeks you can do whatever you want.”
Arianna: Yeah, definitely.
Matt: We just try to flip that. But that in-person time is what makes the whole thing work. Text is the toughest, right? Because I think it’s very easy to misunderstand. There’s usually a charitable way and a non-charitable way to read any message. And it’s almost like in a tone of voice that —
Arianna: Like how would this person say this?
Matt: Yeah.
Arianna: Yeah and if you know them and you trust them…
Matt: [reciting in various intonations] Did you get to that report? Did you get to that report? Like, did you get to that report..?
Arianna: Yeah.
Matt: [There are] so many variations in how it could be said. And we bring our own biases into that. When I read something you’ve sent me, if I’m nervous about how you’re feeling about me, I might read it in a way that you’re judging me or something. So that’s the hardest thing. Humor doesn’t always come through in text. But once you meet someone…
Arianna: Sarcasm. [laughs]
Matt: Yeah, you can kinda hear their voice and like it’s kinda uncanny.
Arianna: Yeah I agree. And I think that’s why, especially at the beginning of a working relationship, I think it’s really helpful to spend time in person. Now that may or may not always be possible but it does really help set the tone for how you will be perceiving interactions with that person.
Matt: Yeah. I mean everything you said and everything you’ve observed, I believe.
Arianna: [laughs] Well look at that! Twitter, a little bit lost in context. Yeah.
Matt: Well there’s some things that I think you might be missing, some other advantages, especially if you go whole hog on the distributed approach. But if anyone’s listening to this, whether you’re doing one or the other, I would say that all the things you raised are things that distributed companies need to compensate for.
Arianna: Yup.
Matt: And collaboration is really, really important. And that brainstorming — you know there’s now tools that make it better. InVision, actually, which is a distributed company, makes a pretty good one. Zoom is really good. [There are] all these things that are doing really well. But there is something about being around a table.
Arianna: Yeah.
Matt: One thing I do see though is that some of the most successful startups I’ve seen or invested in have been very thoughtful about how they work together, whether they’re in-person or distributed. They actually devote a lot of engineering resources, a lot of thought, the founders spend a lot of time on the mission, the documents, repeating it, getting everyone on the same page. Sometimes I liken it — I’m not a baseball guy but I’m gonna make a sports analogy. You know when they go up before they’re about to bat and they have like three bats and they swing that a few times so it’s a little harder?
Arianna: Yeah, yeah.
Matt: But then when they have the one bat, I guess it makes it easier, I don’t actually know. I think that first 15 people is kind of like that. If you’re distributed, you have to work harder for those first 15 people. But it makes that 15 to 150 way easier. You run into the problems of — how do we document and get everyone on the same page — earlier.
Arianna: Right, so if you can do it at that scale — yeah yeah, totally.
Matt: One of the biggest issues I see in in-person groups is when you have that meeting and you think everyone agrees and they don’t really, right?
Arianna: Hmm… yeah.
Matt: We’ve all been in those meetings.
Arianna: Totally.
Matt: We’ve all seen that. And it didn’t matter that we were all in the same room and had a white board and spent an hour, hour and a half together.
Arianna: Yeah, everyone says “Yeah, yeah,” and then everyone leaves and they’re like “Did you think that was good?” and the other person’s like, “No.” [laughs] And it’s like, what did we just do for an hour?
Matt: Right? Or even if we all agreed emphatically in the meeting, we might’ve had a different definition of what we were agreeing on.
Arianna: Yeah.
Matt: That’s the most common one I see. That’s why notes are such valuable things in meetings. I think note-taker is the most powerful position to be in.
Arianna: Hmm, interesting, yeah.
Matt: It’s kind of like the first draft of history, it’s journalism.
Arianna: Right, right, yeah, it’s true.
Matt: And that’s where you really see — Did we all agree and think about the same thing?
Arianna: Mhm, yeah it’s actually been interesting a few times to see somebody else’s notes and be like, “Is that what you got? Because that was not what I got.” So it’s — even in person there can certainly be a lot lost in translation.
Matt: A common pattern that I really like about distributed meetings — let’s say meetings on Zoom — is you’ve got the Zoom here and then you have a shared Google Doc in the other, and someone’s the designated note-taker but you can read what they’re writing as they’re writing. And then again it leads to that clarity because we’re actually writing down — we’re agreeing on words that represent what we thought this meeting represented or the decision it came to.
Arianna: No, it’s true, but I think, for example, I get much more distracted if I’m having a conversation with you and we can look at each other, I’m generally much better able to be there. Whereas if it’s a screen it’s like oh, can I open this window behind this window so I can do this other thing at the same time.
Matt: Mhmmm.
Arianna: It becomes — my phone goes off.
Matt: It takes practice, for sure.
Arianna: Yeah, things that I wouldn’t do if you and I are chatting unless we’re really good friends and I’m expecting something important. I wouldn’t take out my phone and be messaging on it. It’s just easier to get distracted by that sort of thing if the person’s not there in real life.
Matt: In a distributed company it’s one of the personal development things that people really have to work on is how to go into that mode where things aren’t popping in. I definitely have to close all windows ’cause if I see a chat message come in or something…
Arianna: It’s like, oh what’s that? Yeah…
Matt: I have most of the bubbles, the number bubbles, turned off on my computer. There’s apps like Focus and things that will actually shut down access to other websites.
Arianna: Yeah. But I find even my brain, even if there’s no external notifications, my brain will just go off. [laughs]
Matt: Yeah. I would argue that’s practice.
Arianna: Mm. Okay. Yeah, maybe.
Matt: Yeah it’s one of those habit things.
Arianna: Maybe I just need to meditate more still. [laughs]
Matt: I don’t know about meditating but I definitely do it sometimes where if I find myself getting really distracted at my desk, I’ll take my laptop to some place else just to get that practice in.
It’d be a waste if we [had] a blockchain expert on here and [didn’t] talk about blockchain a little bit. Do you think there’s any interactions between — and I will say the mental incongruity of this massively distributed ledger system and the in-office bias — but does blockchain fit into future of work at all?
Arianna: Yeah.
Matt: Anything you’ve seen?
Arianna: Yeah I think it’s a great point. And it’s funny because I definitely think a lot of the promise has been “Ah, everything is distributed, decentralized, blah, blah, blah.” And in reality what I think teams are realizing is that especially in the early days of something, it’s very hard to build a network or a project if you don’t have a tight-knit group of people working on the thing. So physical centralization is one facet of that, there are many other kinds of —
Matt: Kind of shortcut to get that alignment.
Arianna: Yeah, mhm, exactly. But I think in general teams are saying “We’re gonna start out pretty centralized.” And I mean that both in physical location but also in — how do we make decisions. So is it the core team that’s making decisions or is it the community? Can the community vote on certain proposals and how the protocol should evolve, for example? Then, from there, as the network becomes bigger and more mature, more stable, then they move towards a more decentralized model. I think that’s both in terms of how they make decisions and how the protocol is governed, as well as where [the team is] and the people who are contributing to things.
I think crypto has definitely been more distributed than most other kinds of companies or projects. But I still see a very strong concentration of teams in, for example, the Bay Area and to some extent New York, particularly ones that are working on financial infrastructure. Because again, where is a high concentration of engineers? It turns out the Bay Area, New York also. And particularly ones who have the relevant backgrounds and interest oftentimes to be building some of these things. So I would say it’s more distributed but it’s still actually — we’re still definitely seeing strong hubs in, for example, those two places.
Matt: I wonder as well by hypothesis — which you can agree or disagree with — that the hype around blockchain attracted a lot of folks for a while there. And so I mean — I remember you said lifestyle business earlier. Maybe a lot of people who weren’t fully in it or didn’t fully understand what a startup required —
Arianna: Yeah.
Matt: And those teams might’ve coincided with some of the more distributed ones or ones where they didn’t do the work to get together.
Arianna: Oh yeah, definitely.
Matt: You might’ve seen more than most investors, a higher percentage of really just terrible…
Arianna: Oh for sure. And one of the things about prices having come down significantly since, for example, 2017, is just the fact that there’s so much less garbage to wade through.
Matt: It’s cleared it out a lot, right?
Arianna: Yeah, a hundred percent. So the people who are starting teams now are much more dedicated. I would say the volume of deals has gone down significantly but the quality has increased dramatically, which is actually a really good sign. So from my perspective now it’s a great time to be investing in the space because it’s still pre-hype. I think we’ll probably have another crazy bull run at some point but we’re before that and the people who are starting teams now, distributed or not, are much more legitimate and committed to whatever it is they’re building.
Matt: A big challenge for distributed companies is payroll and payments. Like I said, we have people in sixty-five countries. Are you seeing anything there?
Arianna: Yeah. Well, I think stablecoins are super important for that point in particular and —
Matt: Just for people who might not know…
Arianna: Yeah, sure. There’s a few different models but the main idea is that you have a digital asset that is in some ways like Bitcoin but rather than fluctuating in price it holds a peg, presumably to one dollar, let’s say. And so what that allows for is basically you avoid the issue of volatility. So I don’t have to be worried that my next month’s salary could be four dollars or it could be 50,000 dollars, which is an exaggerated version of what might happen today if you were being paid your salary in Bitcoin. Which, by the way, some people still opt to do, especially teams who have folks who are in other parts of the world. In many cases they have opted to do crypto-payments because it’s just easier. But in general the volatility is a problem because you have to pay your rent and your rent is not fluctuating, your rent is stable.
Matt: By the way, this is also why we pay people in local currencies. I remember very distinctly, I think it was a colleague in Ireland coming to me, he’s like “Hey, my paycheck is going down every month and my bills are the same. So this is gonna cross at some point and I’m gonna — it’s getting tighter and tighter.”
Arianna: This is a problem.
Matt: And so I realized, oh yeah, it makes perfect sense, you should be paid in whatever your costs are denominated in.
Arianna: Yeah, absolutely.
Matt: And the company can absorb [those] swings a little easier than a person can.
Arianna: An individual, mhm, yeah. The idea with a stablecoin is that you could be paid in cryptocurrency but it wouldn’t need to be fluctuating in value. And so I think that was a big gating factor for a lot of teams or companies that wanted to pay in crypto. Now I’m not saying that all [of] the sudden everyone’s going to want to be paid in crypto, but now that stablecoins are in existence — like Dai is one of the most popular ones.
Matt: How do you spell that?
Arianna: D-A-I.
Matt: Okay, okay.
Arianna: Yeah, yeah. It’s — sorry, I get deep in my crypto rabbit hole, it’s —
Matt: I don’t mind asking dumb questions.
Arianna: No, no it’s a perfectly reasonable question. [laughter]
Matt: Weren’t there some stablecoins that there were some allegations around that it wasn’t all there or they weren’t fully backed?
Arianna: Yes, so you’re probably referring to Tether. The issue there is, in some cases, these things are not easy to audit. There’s different models for stablecoins. So [there are] ones that are basically — give us a dollar, we’ll give you a digital dollar. And then there are ones that are more regulated by smart contracts. So a piece of computer code that executes some sort of function, for example —
Matt: Like if this then that?
Arianna: Kind of, yeah, at the most basic level. And so you could say, if this person dies, then release their Bitcoin to this other Bitcoin address. The good thing about it is it doesn’t require me to trust you necessarily. Obviously I have to trust that the code is valid but it allows me to basically interact with a machine rather than an individual. And you can bake in lots of rules to basically create money that is programmable, which has a lot of different sorts of applications.
Matt: And Ether is the most popular there? Ethereum?
Arianna: Yeah I would say… Mhm. Yeah, Ethereum is definitely the most used platform for that sort of thing.
Matt: So some of these stablecoins are built on smart contracts?
Arianna: Mhm.
Matt: So how does that work?
Arianna: So let’s use an example to make it concrete. I just referred to Dai, which is the — basically pegged to a dollar, stable currency of the Maker system. And Maker, by the way, is built on top of Ethereum. So the way Maker works is basically — let’s say I have $150 worth of Ether but I need to pay my bills, or I want to lever up on my Ether position because I’m a trader. So I don’t want to sell my Ether but I want dollars, basically, what can I do?
I can create — it’s called a CDP, collateralized debt position, with Maker. So I send to this smart contract, I send it a $150 worth of Ether. So what it does is it sends me back $100 worth of Dai. So I still own my original collateral but I have this stablecoin available now to me in a smaller percentage. And that can be used again for a number of different things. I can go buy more Ether with it so I have exposure to more than my original position, or I could use that to pay off my loans. I don’t know. [There are] a number of things that you could do with it obviously.
But that is pretty incredible because, if I have a bunch of Ether, how else can I get some sort of stable U.S. currency from that? I’d either have to sell it or — a bank is not gonna accept that as collateral. So we’re starting to see this emergence of very interesting new financial ecosystems and having the ability to have a crypto version of a dollar is a very important part of that and —
Matt: It’s a programmable dollar. That’s so useful.
Arianna: Exactly, yeah, yeah. So I am super excited about that whole category of things.
Matt: Speaking of smart contracts, and this is where we’ll end, I’ve heard pitches where smart contracts can be used for massively distributed work arrangements. Where you and I — there’s no company, the company is just a series of smart contracts. Plausible, implausible? Any companies you’ve seen that seem cool like that?
Arianna: Yeah. DAOs or Decentralized Autonomous Organizations definitely play off that idea and want to implement that model in a whole variety of ways. And this is not a new idea, by the way.
Matt: It popped up in journalism the other day, right? Like there was some journalist saying “I don’t get paid as a freelancer all the time,” and there was something, some platform saying that this would be like a smart contract; when the writing is delivered, the payment gets delivered.
Arianna: We’re gonna see more of that. There is definitely a lot of complexity because in reality you’re still involving people in a lot of these processes and people are complicated and messy and there’s regulation and there’s compliance and [there are] all these other things where people are like, “Oh you can make a decentralized Airbnb.” And I’m like, “Yeah okay, but who’s gonna pick up the phone if there’s a problem? [There are] all these trust and safety considerations. A lot of this stuff is not gonna be fully automatable for hundreds of years.
Matt: Hundreds? Wow.
Arianna: I mean, before we eliminate the need for people in that context I think — I mean who knows, I might be wrong, but I think it’ll be a while.
Matt: If you eliminate the people who needs the Airbnb then?
Arianna: Right, exactly. [laughter] Yeah, just get rid of them from the process entirely. Yeah I think [there are] a lot of human elements and challenges that come into the picture. But for example, I think these platform systems of smart contracts can be really interesting for fundraising as well, and that’s how Ether rose to be well known — was being used as a platform for aggregating capital. And that’s, again, a system of smart contracts.
Matt: If you were to look maybe not 200 years in the future but 20, what percentage of jobs do you think will be primarily distributed, not working in a central office?
Arianna: I still think it’ll be fairly low, like probably under 25 percent.
Matt: Oh. That’s higher than some people who believe in distributed work say, so…
Arianna: Yeah no that’s fair.
Matt: So that’s not bad.
Arianna: Yeah.
Matt: Well we’ll see in twenty years.
Arianna: We will, we will.
Matt: Until then, thank you so much Arianna for coming on. I really loved the conversation and really appreciate it.
Arianna: Thank you.
Matt: That was Arianna Simpson. You can find her on Twitter at @ariannasimpson—that’s A-R-I-A-N-N-A Simpson—or at her personal site, ariannasimpson.com.
I was glad to have the opportunity to speak with folks like Arianna, who are challenging my own beliefs when it comes to the future of work. There are some real hurdles—hurdles that we consciously work through every day at Automattic—and it’s important to understand them and fix them.
On the other hand, how encouraging is it to hear about the promise of payroll on the blockchain? If stablecoins can overcome the volatility problems that plague bitcoin, it will become easier than ever for distributed companies to sprout across the globe, in the places we least expect it.
After leading PopCap Games to a successful exit, cofounder John Vechey started Pluto VR to help humanity transcend physical location through a virtual reality chat app. In this episode, John explains how VR might be used in distributed workplaces to enable people to have high fidelity meetings that capture the nuances of human conversations.
The full episode transcript is below.
***
Matt Mullenweg: We’ve been hearing about virtual reality since the late ’80s, but this technology still hasn’t yet leapt from the pages of science fiction into our universe—at least not into the mainstream. The VR revolution seems to be always just around the corner, but some people believe that we really are on the verge of something that’s going to change everyone’s lives.
John Vechey, cofounder of Pluto VR, is one of those people. He’s specifically interested in how VR is going to change the way we communicate. John found success as the founder of PopCap Games–you may know them as the folks behind your favorite mobile games like Bejeweled or Plants vs. Zombies. After selling PopCap, he transitioned into virtual communications.
I wanted to speak with John because he’s got some big ideas about how VR will one day be used for work.
Pluto VR is building a communication platform that will allow people with VR headsets to talk to each other in a way that feels far more immersive than a phone call or a video chat. His goal is to seamlessly recreate the experience of speaking with someone face-to-face, with shared presence and context. He wants remote conversations to have more fidelity, so they can capture the nuances and subtleties of communication that humans are used to experiencing.
If distributed work is going to take off, we’re going to need really good communication tools. But how realistic is it to assume that we can have virtual offices that are so lifelike and useful that they replace physical ones? Are we really anywhere near this dream?
Matt:Hello, this is Matt Mullenweg, we are on the Distributed.blog podcast and I’m talking to John Vechey, who I’ve known for a few years now. John, tell us a little bit about your early career so we know how to catch up to where you are now.
John Vechey: So in 2000, I started a company with some friends called PopCap Games. And at the time, PopCap was like, we’re gonna make some games, but instead of for games, which at the time was pretty much sixteen to twenty-five year old males, we’re gonna make games that everyone can play. Our first game was a game called Bejeweled.
Matt: I love Bejeweled! I played it on the Palm Pilot.
John: Nice. And that was like the original, like, great format for it with the touch of that stylus.
Matt: With the pen, yeah.
John: Yeah. Bejeweled, Plants vs. Zombies, Peggle, we started as a web game company, transitioned to a downloadable game company and then a multi-platform company and then eventually a mobile company. So over the course of like fourteen years there was a lot of different phases of PopCap.
Matt: Of those, which did people get most obsessed about?
John: Of our games, like, Bejeweled and Plants vs. Zombies were our most popular. And people got obsessed about them in different ways. In Bejeweled 2 we put a Zen mode in so you couldn’t even lose. All you could do is just play. Like, it would never hit a losing condition and there was just points that would rack up. And it was one of those things where I realized that there were people that had spent over a year’s worth of hours playing that mode.
Matt: Wow.
John: Right?
Matt: Last night I told friends I was coming here to Seattle to do this interview and Plants vs. Zombies came up, and it turns out both of them had taken a whole Thanksgiving where they just got obsessed with it and went through every possible level.
John: Yeah. And I think that’s the Plants vs. Zombies story ’cause it had a linear aspect to it that Bejeweled didn’t have. Bejeweled was more like an arcade game and Plants vs. Zombies was like an exploration and collection game. And so you’d hear stories about people like yeah, we went on this vacation and we just beat Plants vs. Zombies, that’s what we did for a vacation. [laughter] I’m like, that’s cool.
Matt: No I totally get it. So PopCap sold to Electronic Arts, right?
John: Yeah, in 2011. We were around four hundred people.
Matt: And was PopCap all in one office?
John: We had a joke at some point that the sun never set on PopCap. So we had offices in Seattle, San Francisco, San Carlos, Vancouver, Dublin… period, I think that’s it. [laughter] So we had a lot of offices and all offices were pretty — I mean they were all kind of doing a mix of regional work and game development so it was definitely a lot of travel.
Matt: So you were a multi-office?
John: We were multi-office, yeah.
Matt: Most of the people working there went into some office somewhere in the world everyday.
John: One of the weird things about PopCap was one of the cofounders, Jason, who was the creative director, he was always remote.
Matt: Wow.
John: So we had this really weird thing where one person was distributed and that actually shaped our culture of game development.
Matt: Where was he?
John: He was up first in Vancouver Canada and then he moved to Vancouver Island. The core of what we were was always distributed. And he came down quite a bit but in some ways it was frustrating for him because he’s like, well, I can come down and not get work done or I can just stay up and get work done.
Matt: You’ve been running companies and doing highly creative and successful development with games for a long time. Why don’t you introduce us to what you’re working on now?
John: I left EA in 2014 maybe, after working there for three years. I knew I didn’t want to make games anymore and so I started looking around at what was happening and I went to D.I.C.E, a gaming conference, and saw Palmer Luckey talk. And he talked about what virtual reality was doing and how it was closer than anyone realized and —
Matt: Say who Palmer was.
John: Palmer was the founder of Oculus. It’s a VR headset and it was bought by Facebook. And I saw this presentation, and I was like, wow, this could be really world changing.
Matt: It must have been a good presentation.
John: There was a lot of passion behind it. And it was like, I wonder if any of this is real. But it was. It was real enough to at least be like, hey I wonder if there’s something there. And so I started just going around town being like, hey let’s say I want to do this type of thing or that type of thing in VR, does anyone know anyone I should talk to? How would I do that, right? I wasn’t an expert in VR.
And I met two co-founders, Jarrod and Forest, who had this startup called Impossible Object. I head up north into the far Seattle suburbs into this studio they had, where they had this high-end professional motion capture set up, and then an Oculus development kit. And their first words were like, take your pants off and put this suit on. So I had to like, put this motion capture suit on.
And I had experienced a bunch of different experiments that they had done where I could like walk around the room, I could look at my own body, I could manipulate things with my hands — things that weren’t possible with the current consumer VR hardware. And so I was like, that was amazing, what are you doing with this? What’s your plan? And they were like, well we’re not thinking that anyone’s gonna buy this forty-thousand dollar motion capture system, but we think this is where VR is going, so we’re trying to learn as much as we can about the future five years from now, instead of trying to think about how to develop for the world right now, which is gonna rapidly change.
Matt: And those are your co-founders at Pluto?
John: Yup. And then with another person that I was friends with.
Matt: How do you go from this mixed reality thing to thinking about work and how people collaborate together using these technologies?
John: I had come from games and I didn’t want to make games. Jonathan, one of the other co-founders, had come from animation, didn’t wanna —
Matt: Why didn’t you want to make games?
John: I was just done with it. You know, you do something for fourteen years and you just want a break maybe.
Matt: So one of your co-founders also was done with games.
John: Well he had been in animation. He came from Disney Animation for fourteen years.
Matt: Wow.
John: Yeah. So his career was interesting ’cause he started with Lion King and ended with Frozen and he’s like — and everything in between was very different than either of those extremes. [laughter] He was like, it was like a long walk down and then a looong walk back up.
Matt: Interesting.
John: And I think I was sitting there being like, well I really don’t want to get into VR and then start a game company. So for us, what was important about coming together was that there was something that existed above us and above any kind of decision-making power structure, even ownership structure. Our purpose was to help humanity transcend physical location. So that was important, and that we could align ourselves around that was the second thing.
And then the third thing, what was it? So really we felt that the power of what was happening with virtual reality at the time wasn’t just that you could go to a place, but that you could go to a place with someone else.
Matt: Hmm.
John: It wasn’t just like cool, I can essentially take a drug and space out, it was more about like, well what can we do together? And we took it even farther, like what if right now we’re so tied to our physical location, right? Like just today alone I got up, I went to an office, then I went to go have a meeting in one part of town. I came back to the office to have lunch, went over here, right? I’ve already done more trips than I would care to do. It’s nice to be in a car for a little bit, it’s nice to be on a bus for a little bit, but it’s not really serving my life. I could’ve been more present working on something, reading, or just sitting out in the sun.
Matt: Help humanity transcend physical location.
John: And we spend a lot of time on each word.
Matt: Help humanity, as opposed to robots.
John: I think you can actually break it down literally one word at a time. Like “help,” what does that mean? It’s like, to aid, to be a part of, to make something possible that wasn’t possible or make it easier for other people. So I think that the help part really for us came down to — we don’t need to own the solution, we just need to be part of creating something bigger than us and helping other people do something. Like, we are in service of other people.
And then “humanity” is like, who is it? It’s humanity. It’s not companies, it’s not tech bros, it’s not Americans, it’s everybody. Every choice we make we need to think how is this helping all of humanity, right?
Matt: At a global level.
John: At a global level, at an able-ness level, at a gender level. Really being like hey, we need something that serves and can help everybody. And then “transcend,” right, that’s like a — we spent a lot of time on that word.
Matt: [laughs] That’s a big word.
John: It is. And so for us it’s about moving beyond, making something thoughtless. So if you think about things that have transcended something before in our society, you can certainly say commerce has transcended physical, I think would be a pretty fair thing to say. What else has transcended?
Matt: ‘Cause now we have credit cards and…
John: Yeah, how much do you touch physical money, much less prioritize your life around it?
Matt: Yeah.
John: It’s pretty rare that you’re like, oh I’ve really gotta go to the bank to do this large financial transaction with physical currency, right?
Matt: Yeah, almost never. Are there technologies in the past that you feel like helped humanity transcend location that you find inspiring? ‘Cause that was actually one of my first thoughts is like, from the telegram to the phone to email, you know, all these sorts of things. Like, we are more connected than ever and I think it’s the primary thing responsible for our progress. So in theory, if your mission is successful, and this new technology brings humanity closer together, it’s just like upgrading the routers and ethernet between a data center. Like, it’ll get faster and better and we’ll be able to create better things.
John: So there’s been this history of community of making the physical limitations smaller to communicate over a longer distance and then at the same time there is a higher quality of communication. And so you think about the telegram to the telephone to the mobile telephone, but then you pretty much get to audio chat and then you add some video — and we’ll talk about video in a second — but then that’s it. And then it’s in-person, but there’s this giant gulf between what it means to be in-person and what means to use video chat or talk on the telephone.
There is all this information you get from in-person that you don’t get from those other mediums. And that information is what is fundamental to what we’re trying to do and it’s fundamental to our purpose. Because you can’t just say we’re making a better video chat. Great, humanity has transcended physical location. You’ve gotta do something that we can’t even imagine right now. The closest we can get is a high def video of you but you’re never watching a video being like, I feel like I’m in the same space as you.
Matt: So what is Pluto today?
John: What Pluto is today is the start of a new form of communication. We call it shared presence and this idea that you can share our presence with someone and feel present. And so we have an alpha version of an IOS client right now that we’re working on. So IOS to IOS, one to one.
Matt: But that has to be a flat screen, right?
John: Yes, it has to be a flat screen but it doesn’t have to feel like a flat screen.
Matt: What does that mean? Mind blown. [laughter]
John: It’s like imagine if you were looking through a portal.
Matt: So I would be holding up my iPhone and then on the screen I’d see you sitting in a chair across from me?
John: And instead of it feeling like you’re looking at video of me, you’re feeling like you’re looking like — think like a magic portal, right? So it’s just a portal in space and you’re just like, oh yeah, I’m holding my hands up like a little rectangle, I’m still looking at you. And it just happens to be that we’re in the same physical space and I’m doing this, but what happens if it’s like, oh, it’s like a magical portal and you can be anywhere?
Matt: So for our listeners, John was just holding up his fingers right in front of his eyes. Now if my phone were there though, the camera would only be showing you like my eyebrow and eye, one eye.
John: Correct, if I –
Matt: So it seems like we normally position these things for the sake of the person on the other side.
John: Right. And so what happens is when you’re communicating with a shared presence and Pluto’s product, there’s a mutualism —
Matt: To position it so you see my face, I need to hold it farther away, right?
John: Yeah. So you can’t just do a small segment of it. And it’s one of those things where it’s like, there’s things you can do on video chat that you can’t use Pluto for. Pluto is really bad for walking. ‘Cause just imagine you’re walking backwards and I’m walking forwards and we’re still trying to talk, like it doesn’t — that’s not how walking communication works.
So like Facetime, for example, or video chat, is really, really good for that type of communication. But if you’re in a long distance relationship and you really wanna connect with someone, Pluto is way better, right? You sit the device up on a stand or on a table or something and it’s like that portal and you can really look at each other. It’s like we’re talking like real human things, like you feel more present.
Matt: What am I seeing on the screen?
John: You’re seeing something that could look like video but doesn’t feel like video.
Matt: What does that mean?
John: One of the challenges that we’ve learned over the past four years of Pluto is it’s really hard to describe what we’re doing in a way that is satisfying.
Matt: Better to experience?
John: But when you experience it you’re like aha, that’s it.
Matt: So you’re working on a beta ISP app.
John: Yes.
Matt: You have something on Steam, right?
John: Yeah it’s alpha software.
Matt: And you’ve got something on Steam, right?
John: Yeah. So a year ago we released an alpha on Steam and that’s the VR client. So that’s more of an avatar-based human representation. But you have your full screen view and so it’s great for ten person conversations super natural, you have a body language because when you’re using the motion controllers and you’ve got your head movements, like, you feel like oh that’s a person.
So there’s this weird mental thing where if we’re in VR and you look just like you and you’re moving around while you’re talking and then you left, you changed your human representation to be nothing at all like you, and you came back, my mind would so quickly pick up that it’s you.
Matt: Because of the way I move?
John: The way you move, the way you time your movements with your voice. It wouldn’t take longer than a couple minutes for my mind to replace what I was seeing visually with the feeling of you.
Matt: So how this enhances what we would get over a Zoom call, for example — ’cause we have a sense of location, we’d have some way where I’m getting a higher bandwidth sense of your presence…
John: Yeah.
Matt: We’re on just a 2D kind of camera based video call.
John: Yeah.
Matt: Anything else people should be thinking about?
John: I mean, that’s the fundamentals right now. So we actually think there’s three key elements to the communication service we’re building. One is the shred presence. That’s like, when you’re in a conversation, what’s the quality? The other two elements are shared context. So in real life you have all kinds of information to know when and how to engage in a conversation and what’s appropriate or not. Like, [when] we’re all in the same physical office building, you treat it differently than if you randomly run into a coworker in a coffee shop, which is different than if your coworker randomly showed up at your house, right? So there’s all this content you have about physical location that gives you insight and control over when and how to engage.
Matt: Am I in this Pluto virtual room all day and you kind of come and knock on the door, or do we schedule it like a call?
John: Right now it works like a call. But I think, when I talk about context, there might be like, oh drop in, if I’m in the work hours, like, John can just drop in and be like hey, whattcha doin,’ right? It could also be like, oh, we schedule a call and as soon as we’re both available for that call we just automatically see each other.
Matt: Hmm, huh.
John: So let’s just take — you’re on [a] three-person call, right? So fundamentally in video chat you can see each other’s video, you can hear each other’s audio, there is no sense of space for audio and there’s no sense of space for video. There is no correlation between what someone is looking at and what your think they’re looking at.
On Pluto, on a three-person video chat, you would hear everyone spatially. So where their mouths were is where the sound would come from.
Matt: And then so everyone would turn in that direction?
John: I mean if that was appropriate. Like you don’t—
Matt: But then I would need a camera wherever I’m turning to, right?
John: And that’s the thing. So certainly right now we’ve done a three-person experiment and on an iPad Pro it works. So when you get a small screen it’s harder, but in iPad you have the depth of a three-person conversation so that you see enough so that when you look at me, the other person, the third person, knows that you’re looking at me.
Matt: So let’s say we’re a three person meeting, myself and let’s call Joe over there is talking —
John: Hi Joe.
Matt: — and Joe says something and then I look at you like…
John: Can you believe this crap?
Matt: That would be a very strong signal to everyone.
John: Right, right. And Joe would see that. And I would know you —
Matt: But today if we’re all on a Zoom you can’t do that.
John: Correct.
Matt: I have to send a backchat or something.
John: Right, that’s a perfect example and that’s something you get in real life that you don’t get in video chat right now. We believe in the medium term, right, in the next like three years, there’s gonna be this moment, like the iPhone moment where there’s gonna be a piece of spatial computing hardware —
Matt: What’s spatial computing?
John: So spatial computing at the fundamental level is when computing understands the physical three-dimensional world, it’s also when it can display things to humans in a way that’s more natural to the three dimensional world that we experience.
Matt: So we perceive it in 3D as well?
John: We’ll perceive it in 3D, right. So that can be virtual reality where you put goggles over your eyes and all you’re seeing are pixels, you think they’re 3D and you can move around and use your hands with a controller. And then you’ve got HoloLens or Magic Leap, which are like mixed reality devices, and those are ones where you have a lens over your eyes and you’re mostly seeing the physical world but then it can project digital objects as if they’re mixed with the physical world.
And then if you think about mobile computing in 2000, it wasn’t one device. Mobile computing was your GPS, your Game Boy, your PDA, your cellular phone. And then over the course of time, there was this time where the iPhone came out.
Matt: It started to coalesce into one.
John: Yeah, this is one thing.
Matt: So you feel like spatial computing is going through a similar coalescence?
John: I think it’s gonna happen in a very similar way, where you’re gonna see all these different things that don’t seem related to each other or they seem like they’re competing with each other and then at some point someone’s gonna release a piece of hardware that has some attributes — like it’s gonna be wearable, it’s gonna be always on or always with you. So either you can always walk around with these glasses or you just — they’re easy to pull off and put on, kinda like the phone. You’re not technically always using it but it’s always kind of on, it’s really accessible to start it, it’s gonna be able to do a virtual reality mode and a mixed reality mode. That inflection point is somewhere in the future, call it two to four years, if you will.
Matt: How does Pluto use spatial computing?
John: Starting with our purpose, it’s like, help humanity transcend physical location. What we’re kind of doing strategically is looking at the different areas of spatial computing, and then asking ourselves, how can we best transcend physical location in that form of spatial computing? So we’re looking at virtual reality and we’re saying, how can we do that in just VR? And then we’re looking at augmented reality, like on the iPhone Xs — what is transcending physical location as a communications product look like there? And then we’re gonna do the same on mixed reality, like the Magic Leap or the HoloLens.
And then what we’re doing is saying okay, those all have different strengths and different weaknesses but we need to make sure that that’s creating one communication service and so that you could essentially say we’ll be ready for the inflection point hardware, when we can have all these different devices that seem very different at an experience level but they all interoperate and they can all create the same communication experience no matter which ones you’re on in any direction.
So you could be on an iPhone talking to someone in virtual reality and you should feel like I’m physically present with them. You should also feel that from an iPhone to an iPhone or an iPhone to a HoloLens.
Matt: Help me understand the problem that’s being solved. One of the reasons I like Zoom is they have what I call the Brady Bunch view. You can see a bunch of small videos all next to each other. So I’m on a meeting with six of my colleagues, we’re all on video, we have good headsets, the audio is good, it’s a really good experience.
John: Yeah.
Matt: We’re communicating, we’re talking, it’s not perfect. People are looking at their camera, which isn’t necessarily aligned with where the people are… What’s the problem there that we need to improve [upon]?
John: So if you could instantly be in the same room with those group[s] of people for that same conversation, and then instantly not be in the room with those same group[s] of people, would you choose that over Zoom? So you’re gonna have an hour long meeting —
Matt: What would be the advantage of being in the room?
John: The quality of communication that you can have in the room, the body cues, the visual cues, the pace of the conversation, the empathetic experience you can get in person is very different than you can get even on the best that video chat can provide. And it’s because video chat — It’s like, you don’t have a “video,” that’s not a human centered concept, it’s a very computer centered concept. And so it isn’t how you experience people. And so if you had those same six people and they were just all holograms around the room and they were indistinguishable from them in the physical world…
Matt: So there must be something location wise, right? Because I feel like video gets you maybe eighty percent of the way there. You can hear inflections in voice way better than text, we can all agree there, right? You can see someone’s mood, you can get some idea of how present they are there. So is there something about where we’re located relative to each other as opposed to this flat plane that makes it better?
John: Yeah so there’s where you’re located, there’s how you experience each other — So right now we’ve got these microphones in front of us and these headphones on. We don’t actually have positional audio. So if you close your eyes and you hear my voice, where is it coming from? You can’t really point to it, it’s like a nebulous —
Matt: It’s kind of coming from both sides of me, yeah.
John: Yeah. But if we didn’t have the set up of the podcast, you could point to me.
Matt: I could locate you, yeah.
John: Yeah, you could point. And if I moved around the room, with your eyes closed, you could point to me. So on video chat, you don’t really have that choice. But on Pluto, for example, that’s a choice that you do have. How are you physically related to each other in space? It’s a core part of connecting with people is that spatial awareness.
Matt: One of the nice things — we talked about screen sharing but one of the nice things about some of these is that they are multi modal. So we’re sharing links, we’re chatting as well as having the kind of — there’s different layers that the communications happen on, including some of these backchannels.
John: We don’t believe that like you’re gonna run the Pluto app and then you’re gonna be in the Pluto app all day. We think that’s ludicrous. It’s like you’re gonna be running hundreds of applications. And so it does happen like that where you’re on the call and you drop a little note to your Slack channel when you’re [in an] in-person meeting and then maybe get a response back. It might be lower in-person but you’re still, it’s still a common thing.
Matt: I don’t know if this is the ultimate thing but it seems like people are just going to use this to check Facebook while they’re on meetings.
John: Which would break presence. And so a lot of what’s important about presence, shared presence, is like an integrity to the interactions. Right? It’s like, my eyes are where my eyes are, you see where my eyes are looking. And so we’d probably say right now with everything that we know, with all the experiments and research we have done, is that it’s okay to do that but we have to, we’d want to signal that your attention was elsewhere. You might not want to share with me what you’re doing but in real life, you know, like if you’re checking Facebook while we’re talking I have some signals, we might want to retain those ’cause it makes better communication.
Matt: I think that’s the downside of conference calls today. There was probably a point when conference calls were good, maybe when the internet was boring, VR is always right around the corner. I remember playing a Virtual Boy, did you ever do that?
John: Yeah.
Matt: But it’s still not mainstream yet. How many people have all the headsets, millions?
John: Yeah, tens of millions.
Matt: Maybe tens?
John: Yeah, so like —
Matt: But not a hundred yet?
John: No probably not a hundred.
Matt: And active usage is probably a lot lower?
John: It’s definitely a lot lower. I mean, so like —
Matt: I think I own one but I don’t —
John: Yeah, like Steam VR, for example, which is probably, for PCVR, is the number one channel, has probably fifty — a hundred thousand DAU, daily active users, who use VR and do something in VR. That is not an exact number but it’s — they’ll have ten, twenty thousand simultaneous users. So it could be a couple hundred thousand daily users. So we’re still doing a lot of learning about what does it mean to transcend physical location, how do we do things, what technologies enable our use case. We don’t have that many ways to communicate. And what we’re doing is saying we’ll have a new one.
Matt: What’s the matter with that? We seem to be getting along pretty well.
John: That’s a interesting take on the world, Matt. [laughter] One could say there is a little bit more war and suffering and destruction than we maybe need.
Matt: So you’re not part of the Steven Pinker camp that things are maybe better than they have ever been?
John: Not necessarily, no. I think that there are ways that things are better and then there are ways that it’s easy, especially in a western country and especially as a white dude, to be like, oh things are great, things are so much better than they have ever been, and to be missing how bad things are for people and how that’s a societal choice we make, not a limit of constraint.
Matt: And you think this is caused by our mediums?
John: I think — I mean I don’t know — I don’t think it’s caused by that, but I do think communication mediums are tools and like all tools they cut both ways. And I’m definitely not of the “technology for technology’s sake” is an answer to our woes — it’s like, hey, it’s just more tools. You need to take a look at social networking, it’s provided a lot of good and it’s provided a lot of bad. What we have to do as a society, we have to somehow make sure that the technology we’re making is serving humanity.
Matt: I’ve heard a lot of non-profits actually starting to do VR experiences ’cause they say that people can really experience in a visual sense, much in the same way you and I went to Ethiopia to experience some of what was going on there, they can get that thing without having to fly halfway across the world. That also worries me though because we have gotten very good at sort of inciting human emotions.
John: Yeah.
Matt: And we’re not rational beings. And so if I was hooked up to this Pluto ten years from now, amazing system, what is the advertising in that that detects my exact mood and tailors a message exactly to that?
John: That’s a good question. I mean that’s part of the reason why we’re really focused on communication. And so like we’re not trying to create the meta verse.
Matt: Say what the metaverse is.
John: So the metaverse is the idea that like there’s a universe that has — It’s all digital and you go into this world and in this world you can do anything. So if you think about Snow Crash, how that started, I think that coined the term metaverse.
Matt: Which is a novel by Neal Stephenson.
John: Thank you, Neal Stephenson. You take a look at like Ready Player One. So in those cases they’re metaverses. In each case they’re like, oh the people are plugging into these worlds.
Matt: In Ready Player One he has a 360 treadmill so he can walk, a suit, and the suit exercises him, right?
John: Yeah, and then he —
Matt: He can lift weights with it and —
John: Yeah and he puts goggles on his face.
Matt: Goggles on. So he can essentially have total freedom of movement and is moving around in this virtual world.
[clip of movie plays]
John: So much so that almost all of his life is existing in that virtual world, such that that is more of his world than the physical world where he’s living in a stack of trailer parks.
Matt: Which some people might define their internet experience as that today, like their friends or connections already transcend their physical space.
John: Oh yeah. I mean one of my closest friends is someone I play this board game with online and I’ve never met him. He lives in France, but we play this game a couple times a month and we always spend half the time talking as we do playing. So it’s like he’s just as much my friend as someone else is.
Matt: You’ve said you felt like we’re two or three years away. What give you that kind of confidence? ‘Cause you’re not a guy who says those things lightly.
John: There’s movements happening and starting with like OpenXR, which is an open standards body — participation in that and that they’ve got the provisional specification that — they just announced it at a game developers conference. So things like that are now saying hey, what if, as an application developer, you could just do a spatial application and that could run anywhere? So concepts like that — Like right now, if you want to make an application, if you want to make an iPhone Air application, it’s completely different than doing an Oculus Rift application, which is different than a Magic Leap application. But with OpenXR spec it’s really exciting because, as that gets adopted and more run time supported, you’ll just be able to make a spatial application and it’ll be able to work anywhere.
Matt: Tell me a little bit about Pluto the company, just as we start to wrap up. How many people is it today?
John: We’re about twenty people.
Matt: And how do you work together? Do you have some sort of futuristic — Do you all wear VR headsets all day?
John: Yes. So all of our stand ups are in VR.
Matt: Say what a stand up is.
John: A stand up is where like they — everyday all the engineers get into VR — actually they’re often sitting — and then they just go around the room and so I do a check in, here’s what I did yesterday, and here’s what I’m getting done today and there’s some live troubleshooting of issues if need be.
Matt: So everyone is in the same time zone or do you have people all over the world?
John: Right now everyone at this moment is in the same time zone.
Matt: It helps a lot, yeah.
John: Yeah, we’re still very collocated because what we’ve done is made the choice to have an in-person culture and then we’re now slowly eroding at that, just to create a more distributed layer on top of that that leverages Pluto.
Matt: So the Pluto office somewhere that everyone goes into everyday.
John: Yes, we have a Pluto office. But then I spent thirty days working from Venice Beach, California. And especially — ’cause like hey we’re about to launch the IOS version, we need to use it a lot. And so I’m like, great, I’m —
Matt: So you took one for the team in Venice Beach?
John: Well what was cool is that it seemed like that. But then I’m like well I’m more connected with people, probably ’cause I’m talking to them more, but we could really maintain a connection, so much so that we had two employees start while I was gone and I had two meetings with one, three meetings with the other, and there’s this moment where you’re like wow, I feel like I’m with you, when I saw them in person it wasn’t like, nice to meet you, it was like, oh we’ve been hanging out.
Matt: Do you imagine a day some day where no one goes into the office at Pluto?
John: Yes. So we’re actually actively working on kind of the Pluto 2.0 phase. And that is one where we will be office optional. So we do have a need for an office because we do have a lot of cutting edge new hardware.
Matt: I bet, yeah.
John: We have a laboratory type thing and that does require physical space. But we are moving towards a world where what it means to be a full time Pluto isn’t tied to where you’re physically located. So it’s really — this year is the year of how do we live our purpose? We’re at the forefront of that, not at the backend of that.
Matt: Twenty years from now, what percentage of jobs do you think will be distributed?
John: Oh I think it’s gonna be like eighty percent, ninety percent. I think it’s gonna be a huge percentage.
Matt: Thank you again.
John: Yeah, thank you, Matt.
Matt: This was John Vechey. I really appreciate you coming by.
John: Yeah.
Matt: Looking forward to seeing more of Pluto in the future.
John: Thanks for having me.
Matt: That was John Vechey. You can find him on Twitter at @johnvechey, that’s J-O-H-N, V-E-C-H-E-Y, and check out Pluto VR at plutovr.com.
When I was playing around with my janky Virtual Boy headset in 1995, I never could have imagined that one day there would be hundreds of millions of people using VR. But that future is already here, so it feels pretty safe to assume that a lot of us will do work in VR very soon. Distributed employees work best with a wide range of communication technologies, but there’s something special about face-to-face communication in 3D space. Here’s to folks like John who are trying to bring that experience to people who are communicating across oceans and beyond.
“The American Dream is Broken, and I think we have a shot at fixing it.”
Stephane Kasriel, the CEO of Upwork, thinks that most work, as we think of it today, is in need of an overhaul. In this episode, Stephane explains how changing the way we think about work can simultaneously give workers freedom and flexibility, enable companies to operate more efficiently, and revitalize local economies all over the world. He also shares tips on how companies can make smart moves toward a distributed work model.
The full episode transcript is below.
***
Matt: To start off, say your name and how long you’ve been here, just so people have a sense of you. And then we’ll talk.
Stephane: Sure. So my name is Stephane Kasriel, I’m the CEO of Upwork. I joined the company close to seven years ago. Initially I was running product management and design and then when our head of engineering left, I became the head of product management, design and engineering. And then a couple years later, when the CEO left, I got promoted and became the CEO of the company. And that was about four years ago.
Matt: Awesome. How big is Upwork? How should people think of it?
Stephane: You know, that’s a great question, how big it is it depends if you define it by employees or everybody in the workforce. There’s about fifteen hundred people who work at the company, about four hundred of them are full time employees of Upwork Inc., the company, and they mostly work in one of our three offices in the U.S. We have an office in Chicago, we have an office in the South Bay — in Mountain View, and then we have an office in San Francisco.
But then we have another eleven hundred or so people that are what we would call freelancers and they work from home — they work from about five hundred different cities in the world, which is pretty impressive.
Matt: That’s a lot of cities.
Stephane: I’m not sure I can name five hundred cities in the world, so that’s a pretty big part of the world. And part of the reason why we call them freelancers is because that doesn’t have a legal meaning. And so some of them are full time employees of Upwork but they just happen to work remotely. Some of them are independent contractors or whatever is the equivalent in that particular country. And then some of them are essentially what the U.S. would call leased employees, meaning they get a W2 but they get a W2 from something called Upwork Payroll, which is our product.
So as you can imagine, we use our own product to manage our entire remote workforce. And so depending on the employment law and all of the other considerations that are embedded in the product, they end up being classified differently. And because this whole discussion was pretty long, we call them freelancers.
Matt: [laughs] And Upwork is now a public company.
Stephane: Mhm, yeah.
Matt: Tell me about that.
Stephane: Yeah we took the company public in October of last year, which is something that we had wanted to do for a long time. The reason being, you know, a lot of companies go public because they need to raise a lot more money. In our case, we’ve been cash flow positive or break even for many, many years, so we did not need to raise the money. What we really needed was to raise the awareness.
And I think the labor market is obviously one of the biggest markets in the world, like a hundred trillion dollars or so, of which remote work can be a very substantial part of it, and I think Upwork can play a role in trying to create a better future of work. Like I think the current present of the labor market is pretty messy — and we can talk about that if you want — but it’s pretty broken for a lot of people in the world. And we think we can be a driving force in creating a better future but we need a big, big loudspeaker in order to be able to influence people. And being a public company just allows us to have a lot more visibility, a lot more credibility, than what we used to have. And that’s been the main driver for doing this.
Matt: And that also means all your numbers are public. So what’s the rough size of the business now?
Stephane: Yeah so this year we’re going to do on the order of about one point seven billion dollars.
Matt: Wow.
Stephane: And it’s growing pretty nicely so it’s going to be much more than that next year.
Matt: That’s super cool.
Stephane: Mhm. And I should mention that’s the amount of business that is done on the site, what we call gross services volume, or GSV — we looked at the financials of the business, gap revenue is… about fourteen point something percent of that one point seven billion. So the gap revenue in 2018 is on the order of two hundred and fifty million dollars.
Matt: That’s incredible.
Stephane: But what I really care about, to be honest —
Matt: Is the gross.
Stephane: Is the gross. Because that’s how much money we give in the freelancer’s pockets. Fundamentally our mission at this company is to create economic opportunity so people have better lives. And the way we measure that is the amount of money that goes into people’s pockets. So revenue is how much we get to keep, we are a for-profit company, we need to make money too, we need to hire all these people and continue to build the business and all that stuff.
But the real reason why this company exists is for the GSV, right? It’s the money that goes and allows people to be more free, be more flexible, live anywhere in the world that they choose to live in and be able to have access to jobs that they would not be able to get otherwise.
Matt: Would you call that number your north star metric?
Stephane: Yeah. I mean the one number — like, when I look at our all-hands and what we talk about all the time, we don’t talk about revenue, we don’t talk about EBITDA. I mean obviously we have a finance team and we have an accounting team and they really care deeply about this stuff but I would say the reason why people join this company either as full time employees or as freelancers and either in an office or remote, is because they get to create jobs for lots of people. And the proxy for that is how much money goes into the freelancer’s pockets.
Matt: You mentioned earlier that work was a little broken.
Stephane: Mhm. Very broken.
Matt: Tell me more about that.
Stephane: Well I think we’re in a place right now where if you live in San Francisco, for instance, where, ya know, we are based here, you have — If you are highly skilled you have access to amazing economic opportunities, great jobs, working for some of the most amazing companies in the world.
But the cost of living has been rising faster than your salary. The average rent in San Francisco has been growing by about seven percent per year for the last forty-five years, so you compound that, it’s become outrageously expensive. What we see is that young people, young college graduates, when they move to the Bay Area, spend close to seventy percent of their disposable income on rent. And that’s despite the fact that they have a pretty lousy apartment and they typically have roommates. And that is more than twice as much as the overall U.S. market right now, right?
So you’ve got a place where [there are] great jobs, great environment, very international, very dynamic, all that stuff, but completely unaffordable to live in. And then meanwhile you just go a couple hundred miles away from here, you go to Stockton, you go to Modesto, you go to Fresno, you go to Sacramento, let alone going in the Midwest of the country, and you have places where it’s extremely affordable to live in and frankly it’s actually very nice to live in. There’s plenty of beautiful places outside of the Bay Area where you really want to live but there’s no jobs.
So fundamentally we are in this economy where if you’re a young person in particular and you don’t already have real estate that belongs to you and you might even have a ton of college debt to get started, you have this catch 22, where if you live in the middle of the country you don’t have a job and if you live in the big cities in the U.S. you have a job but you have no money, and either way it seems like a pretty bad outcome. And it doesn’t need to be that way.
It’s the last evolution where we missed — we missed a turn. The first industrial revolution you had to move people from the farms where they used to be working to the assembly line because physically we were manufacturing our goods and you had to be on site and the whole nine-to-five was because the machine was gonna run from nine-to-five and so you had to work when the machine was gonna run because frankly at the time machines were expensive and humans were pretty cheap and so it made sense that way, right?
But you fast forward to the fifties where manufacturing started to slow down in the U.S. and a big part of the western world and the service industry knowledge work became a big thing. And increasingly a bigger part of it was done in office towers and cube farms. And if you think about it, that was — I would say — a bad metaphor.
The cube farm is the modern version of the assembly line except that none of the work that you do in the cube farm actually has to be done on the cube farm. And increasingly work can be done from anywhere, and increasingly it doesn’t need to be done from nine-to-five, increasingly it doesn’t need to be this long term, one-on-one relationship between an employer and an employee. But somehow we missed the transition and we are continuing to operate as if work had to be done the same way.
And you could say so what’s the big deal? Let’s keep doing it. But the reason why it’s a big deal is like — not to get into politics or something — but there is increasingly, in the Western world, a group of, a part of the population that is saying this system is not working for us. And you have the myth of the American dream, the idea that if you’re highly skilled and working hard, you should be able to be successful increasingly depends on where you were born or where you live or how much wealth your parents have and whether you’ve been able to go to college or not as a result. And that is not what — I’m an immigrant in this country, I signed up for the American dream. And I think it’s pretty broken right now and I think we’ve got a shot at fixing it.
Matt: When I moved from Houston to San Francisco my rent went from eight fifty per month, which I paid half, to twenty-seven hundred dollars a month. And this was 2005.
Stephane: Yeah. It’s gotten worse since then.
Matt: So compound that by seven percent per year since then.
Stephane: It’s bad.
Matt: For a similarly sized place, ya know? A little bit of an upgrade. Yeah. How about you? Do you remember your old rent when you lived in France?
Stephane: Well I moved here in ’97 and I remember when I moved here people were saying don’t buy a house, it’s crazy, some of these houses are worth a million dollars. There is no way this is going to last. And of course the same houses now are probably three or four times that. You know, eighty percent of houses in San Francisco cost more than a million dollars.
Matt: Eighty percent?
Stephane: Eighty percent. There’s not a ton of people in the world, even if you work for a tech company — like the amount of money you need to save in order to have a down payment to be able to afford a million dollar house and then you pay, you know, one point something percent of property tax. I mean it’s really hard to afford a good life in the Bay Area right now, even if you are a data scientist working at Facebook. If you are not in tech and you’re just an average worker trying to get by, it’s a real struggle.
Matt: It’s kind of amazing as well. We think of the Bay Area as this engine of innovation but the percent of the economic activity that just goes to landlords is astounding.
Stephane: Yes. Historically there have been more billionaires coming from real estate than from tech in the Bay Area. [laughter] Little known fact.
Matt: You have so many cool stats about the Bay Area. [laughter]
Stephane: Twenty years of doing this. But you know the thing is, it doesn’t need to be that way. And I think this whole distributed company, remote workforce, whatever you want to call it movement is finally the awakening by the tech industry [to the reality] that we are part of the problem. Part of the reason why jobs have been destroyed in plenty of places in the country while all of the new jobs were created in a small number of areas is because of tech.
And overall it’s a good thing. Right? Increasing productivity makes people richer. We need innovation, we need automation. By the way, we don’t make as many kids as we used to so we need more robots to actually help us grow the economy — like, all these things are true. But the problem is the jobs that are being displaced are not in the same location and don’t need the same skills as the jobs being created and the displacement of the jobs comes from us, the tech industry, right?
And so I think increasingly there is both a practicality of — as a small start up you just can’t hire good developers in San Francisco because if they are really good, they are paid so much more money by the big tech companies that you can’t possibly attract them. So there’s a very down-to-earth, like, you-don’t-have-a-choice type of approach to this.
But I think increasingly there’s also a bigger social calling for realizing that hey, there’s some really great developers and great marketers and great everything else over there, and we can really help these people get a better life by giving them a job instead of trying to poach people from Google who will then poach them back. This very zero sum game, red ocean type of approach of the war for talent, the way it’s conducted in the Bay Area.
Matt: If we allow the economic opportunity to be world wide, won’t that just mean more accumulation of capital by the companies themselves? So Google has to pay their employees very high salaries because they’re in this competitive market.
Stephane: Mhm.
Matt: If the global average was much lower than that, let’s say a third of what it was in the Bay Area, the extra profit would just go to Google shareholders or the company itself.
Stephane: Well I think it’s — the economy is not a zero sum game, right? In an ideal world workers are better off and companies are better off. I mean that makes it much more attractive than if it’s a win-lose where yeah Google is worse off but Google’s employees are better off. I mean that’s going to be how to convince the CEO to then convince their board, to then convince their shareholders, right?
So in an ideal world you get to a place where — and that’s what we tried to do at Upwork, right? We tried to make sure that the companies are better off because they get access to talent that they would struggle to get otherwise. They don’t necessarily need the talent full time and so they can pay by the hour or by the task. And frankly they may not be that attractive to the workers in the first place because, if you’re a highly skilled worker in today’s economy, your skills are in high demand and you get to choose where you work.
Matt: Yeah.
Stephane: And for most companies, they really struggle. Not everybody is not attractive to workers as much as they’d like to [be]. And so sometimes — so, on the company side, some of it is driven by cost savings. For some companies, in particular very small companies that are bootstrapped and before they get VC funding and what have you, the ability to pay developers less than what they would pay locally can be a driver.
But for the most part it is just accessing the talent and being able to work with people on demand. And that is not incompatible with the fact that people are better off because they get to have more flexibility in their life, work on their own terms, and frankly potentially move to a part of the country where the cost of living is lower.
Matt: They could leverage that income way more.
Stephane: Yeah. For years we have had way more people signing up to become freelancers on Upwork than we’ve had companies signing up to post jobs on Upwork. I mean we have huge demand constraint, meaning we don’t have enough jobs for people. And that to me is an indication that people are ready for this.
The reason why people do this is because there’s really little not to like about being a successful freelancer on a platform like Upwork. You have the freedom and the flexibility and you make more money than whatever your local job market is, which might still be less money than if you lived in the Bay Area but then you don’t have the cost of living of the Bay Area.
Matt: Yeah and actually after we first met, Automatic became a much bigger client of Upwork.
Stephane: Thank you. Good.
Matt: So I’ll put in the plug here that we’ve been a happy customer. And if you’re listening to this and you’re constrained in some way, Upwork has lots of people who can help you. So. But you did say earlier that you didn’t love the wealth going to landlords.
Stephane: Mhm.
Matt: Yet we are in an office right now.
Stephane: Yes.
Matt: Tell me about why you’re paying a landlord for this space.
Stephane: You know, that’s a fun debate. In particular, this office here belongs to Google, like everything else in Mountain View. Google has notified us that at the end of our lease they are not going to renew. And so as a result we are about to sign a new lease in another office space. And there was a real debate as to whether we go and spend millions of dollars a year again on yet another office space, or whether we just do what you guys did, which is close the offices and have everybody work from home.
And you know, it’s a tradeoff. I think, like, here’s my selfish point of view on this. So we are in a small — describing it for the listeners here, right? We are in a small conference room where there is a big TV with a webcam on it. The reason is because most of the work we do here is going to be with people that are remote.
There’s about a hundred and fifty people in this office, there’s about fifteen hundred people in the entire company, so ninety plus percent of the people that you’re gonna be engaging with are unlikely to be in this office, which means ninety percent of the time you’re gonna be on video conferencing. And the average time of commuting to this office for our employees is about forty-five minutes each way.
Matt: Really?
Stephane: Yes.
Matt: Wow.
Stephane: Traffic in the Bay Area.. By the way, that’s another thing that’s broken is congestion in all of these cities that were never designed for the level of density that we have today. And so people are going to spend an hour and a half every day to come to a place where ninety percent of the people they need to talk to are not physically present, plus this costs us millions of dollars a year. There is an argument for shutting it down.
I think, you know, if we had started as a fully distributed company, which a lot of companies are doing today, right? I mean some of the companies that you are talking to never had an office and they started from day one being distributed. I don’t think we would have ever signed up to get an office at some point.
Some people here in this company have been working in this office for a decade and when we told them hey you might have to work from home, a lot of people were not very excited about it. So we decided, you know, in the grand scheme of things it’s not philosophically aligned with what we want to do as a business. But in the grand scheme of things it doesn’t cost that much money, right? I mean the entire budget for this company is in the hundreds of millions of dollars a year so a relatively small percentage of that goes into office space.
And ultimately, we care deeply about employee satisfaction and people really loving their job. And so we had enough people saying look, we have always operated this way, we totally embrace remote work — like, we fully realize that ninety percent of the people at this company work from home, but we, the people in Mountain View, don’t, and we’d like to keep it that way. [laughter] So you know, like…
Matt: So will the new office be bigger, will it be nicer? Can you make the office worse so people don’t want to come in?
Stephane: It’s actually not gonna be much bigger partly because generally I would say we’re expanding outside of the Bay Area more than we’re expanding in the Bay Area. I mean philosophically what we tell people is hire the best people you can find anywhere in the world with one caveat, which is time zones.
We want to make sure that if people are gonna have a good work/life balance, they need to have time zones that are somewhat aligned. So you don’t want to have somebody from India, somebody from Australia, somebody from France, and somebody from the U.S. having to be on the same agile development team, ’cause then somebody, at least one of the people does not sleep, ever, and that’s really, really painful for everybody.
Matt: Yeah.
Stephane: So we try to align people by time zone. But other than that, if you find an amazing developer in Chile and a great salesperson in Greece, great. You know, like, why on earth would you force yourself to hire them just in the neighborhood? So the U.S. is only about five percent of the global population or whatever the latest number is, but roughly that number. So the odds of having ninety-five percent of your workforce in the U.S., let alone ninety five percent of your work force in the Bay Area, which is a tiny, tiny population, is pretty low.
Matt: Yeah. Although by that argument, isn’t more than half the world’s population in non-U.S. and European time zones?
Stephane: Yes. So one thing that I think is gonna change over the next decades, and this is a very risky prediction that I’m making because I might still be alive…
Matt: [laughs] Hopefully you are.
Stephane: But if you think about how the world is organized today, it’s very much organized by — and I always get them confused — latitudes, horizontally. The northern hemisphere tends to work with the northern hemisphere, and the southern hemisphere — and that’s due to climate and it’s due to the days when we were farmers. Right?
Matt: Yeah.
Stephane: I mean agriculture in France is very similar to agriculture in the U.S., very different from Nigeria. But in a knowledge economy what really matters is not physical resources, it’s intellectual resources. And what really matters is time zone alignment. So this idea that the U.S. is outsourcing IT to India and outsourcing BPO to the Philippines from a time zone standpoint, except for a few things like QA where maybe the follow the sun model where the developers in the U.S. write code during the day and the QA team in India contest it during the night, which is day there. But if you are trying to be doing more like synchronous, agile type of development, time zones are a real issue.
So I think the real prediction would be that there is a lot more alignment between North America and South America. And that if you’re going to be offshoring software development, and you are based in the U.S., you should be doing it much more in Chile or in Argentina than you should be doing it in India. And for that reason, to your point about the southern hemisphere, if you look at Europe, the real alignment should be with Africa, right?
Like, if you look at France and Morocco, it’s already happening. A lot of call centers for French companies are happening in Morocco and that’s historical because [there are] former colonies where people still speak French. But there is also Mauritius, which speaks English. I mean there is a lot more alignment from a time zone standpoint, north and south, than there is east and west.
Matt: I think we need to go to Mauritius for some research.
Stephane: I totally should be doing [that]. A great place for kitesurfing.
Matt: It’s actually on my bucket list.
Stephane: Yeah it’s awesome, beautiful place.
Matt: So you talked about investing a few million dollars to have this office, to really serve the people here. From your point of view as a CEO, what are other investments you’re making in employee productivity and happiness?
Stephane: Oh there’s plenty. But I would say let’s start by the office itself. So we want to make the office be as remote friendly as possible because the one thing that really doesn’t work is if people in the office think that they are more important than people outside of the office.
And I think in our case, we have so many more people outside of the office, and it’s a norm in the company, and we train people, and it’s a big value part of the company. So I think people are just generally very aware of making sure that the remote people get preferential treatment over the onsite people. But it’s harder to do it when you have ninety percent — when it’s reversed. Most companies have ninety percent of people in the office and ten percent of people that are telecommuting or remote working or what have you.
And establishing the right technology. The video conferencing equipment, really good audio. And then cultural norms. Like understanding that the person who is on the video conference call can interrupt and, in fact, you want them to interrupt, because it’s harder for them to indicate with body language that it’s their turn to talk. So having the tools and the training and the norms to be able to make sure that remote people are really successful and, in particular, how that happens in the office.
Matt: What are some tools? You mentioned audio.
Stephane: Yeah, just buy good equipment. When people, like back in the days, and I’m not gonna mention old tools, but there used to be tools which would take fifteen minutes before you could get started. I would start with the obvious — it’s always the video. So when people are just on [a] phone call, you hundred percent lose the body language. By the way, when you don’t see people, they also tend to be doing something else at the same time, nobody is listening to anybody, and the conversation tends to be extremely ineffective. So always do video unless there is a very good reason why that can’t be done.
Matt: Although I do like when I’m on audio calls and I can walk around my room or like sometimes I do little stretches.
Stephane: Yeah well ya know…
Matt: On video it’s a little awkward to do that.
Stephane: I mean there are some very legitimate reasons why some people — there’s also some people that just don’t want to be seen for very legitimate reasons and that’s okay. And I think you also need to be culturally sensitive to some of these things. My point is there is a real value in seeing eye contact and the body language and all that stuff that you lose if you just do phone calls.
So generally I would say do video whenever you can. I would say have the level of empathy for the people that are remote, that make sure that you don’t have the water cooler discussions with the people that are in the office that are essentially making it harder for the remote people to know what’s going on.
Invest in face to face meetings. So we do regular meetups. Usually the teams that need to work together hire a freelancer on Upwork who is kind of a virtual assistant/travel agent who figures out where everybody is based, and based on that, what are some reasonable cost flights that would take them all to a nice place.
Matt: Oh cool.
Stephane: And then they rent a bunch of Airbnb’s, they stay there for a couple of weeks, there is a lot of working together during the day and I’m sure there is a lot of drinking together during the evening. And so there’s this more informal social connection that frankly gets lost over video conferencing. It’s hard to have a beer with someone.
You know, companies try to have the more informal stuff but every once in a while, having people meet face to face. And by the way, usually after two weeks what we hear from, especially from the developers, is “Enough of this whole social thing,” like, “I feel like I’ve spent too much time with the PMs and the designers and I want to go back and do my thing.” [laughter] And so quite often after ten days also everybody is happy to go back.
Matt: To go back, yeah.
Stephane: And then after that, the level of interaction, the ability for people to have conflict — it’s easier to disagree with somebody that you have a personal relationship with. And conflict is important. If everybody always agrees and nobody ever dissents, then you typically don’t have a really good outcome. So building these social ties really helps in having a more productive working relationship moving forward. So it’s an investment, it’s not cheap to travel people around the world.
It’s also a big perk. You know, some of the people who work at this company have never traveled abroad before and when they know that one year they’re gonna be in Bulgaria and another year they are going to be in Sicily — the person sitting next to me had a trip in Bali a couple of years ago, which out of all places doesn’t seem central but apparently I hear that that was pretty good.
Matt: Somehow that was the most central thing for that team, yeah.
Stephane: Exactly, very essential to go spend time in Bali. But it’s a great perk for people and I think generally it’s something that is hard to measure the ROI but I think it’s probably the right thing to do for the company as well.
Matt: So I want you to put on your Upwork advocacy hat for a second. There are some people listening to this that are probably in fully office-based companies.
Stephane: Sure.
Matt: How should they start to explore shifting that?
Stephane: Yes. So I think you shift — first of all it’s a change process, so you find people that are excited about the change and not people that are resisting the change. You know, if you want to prove that it doesn’t work, you know, — ot to give names of companies that we all know that stopped allowing remote work — like, if you want to make it fail, you can make it fail. Generally if you want to make anything fail you’re gonna make it fail, right? So start with people that are excited about embracing the change.
I would say ideally start with allowing well established people that already know the company in and out and allow them to go work remotely. One of our customers, the way they started is they had a developer who was from China and who decided to move back to China. And he was one of their earliest developers, he knew how things got done, he knew the code really well, he knew everybody back in the Bay Area. And he progressively started building a remote workforce that was partly in China, partly everywhere else, from there and they became pretty big Upwork customers.
I think it’s easier if you start with somebody who really understands how things get done. And then if your first remote person is also so remote that they don’t know anybody in the company, it’s just putting them at a disadvantage. If you do start with people outside of the office, I would say at least for the first few, have some form of on-campus training for them where you bring them into the company, have them spend a few weeks with people just to build that social connect, understand how things get done, and then you allow them to go back and work remotely.
But I think after that, you need to go big. You know, the thing that doesn’t work is if ninety-nine point nine percent of your workforce is sitting in the office and zero point one percent of your workforce is remote, they are always going to be at a disadvantage because they’re never gonna be top of mind.
Matt: They’ll be second class citizens, yeah.
Stephane: Right, exactly. Like, I mean the water cooler to me is the perfect example, right? If most of the conversations happen in a way that is excluding the remote people and is favoring the local people then they are never going to be successful in the long run.
Matt: So how do you go big?
Stephane: Well I think you start by looking at which parts of your company are growing. I mean hopefully you’re a growth company. If you’re a shrinking company it’s a different problem that you might be solving. But if you’re a growth company, figure out where you’re gonna be hiring a lot of people and that’s a very logical place to say we want X percent of these people, ideally more than fifty percent, to be anywhere in the U.S. or anywhere in the world. And because you’re going to be hiring a lot of people pretty quickly, it’s going to get momentum in the company.
But I would say I think what people need to watch for is the sense of isolation that the remote people are going to have, right? For them to be successful, you need to go out of your way to help them be successful. If people feel like they don’t belong, then they are not gonna stay.
One of the frankly biggest benefits of distributed teams that I don’t think people talk about so much is how much longer remote people stay in your company compared to Silicon Valley based people.
Matt: Tell me about that. Do you have any stats there?
Stephane: I mean I can tell you. Of the first fifteen engineers that this company hired, and this was fifteen years ago, twelve of them are still at the company. There [are] not a ton of fifteen year old companies in the Bay Area that still have their first early employees. And the reason is because like one of them lives in the middle of Siberia.
Matt: Literally Siberia?
Stephane: Literally. [laughter] In a place that, from what I hear, used to be kind of owned by the KGB and used to not be on U.S. maps. [laughter] I think he is loyal to us because he loves what we do and because we pay him really well and all that stuff. But partly also because frankly I don’t think there’s a ton of other jobs in the middle of Siberia right now.
Matt: Yeah. [laughs]
Stephane: So there is definitely like a — I would say a social contract for those types of workers that is very different. And I would say for instance, one thing we have started to do a few years ago is we allow people to de-locate. So a lot of companies relocate people, they do college recruiting elsewhere in the U.S., try to bring them to Silicon Valley, which adds even more to the drama that I was talking about earlier.
I think what makes a lot more sense is to do the opposite. Some people just say “Look, I have kids and I want them to grow up in a different environment,” or “I have my parents are getting older and I want to go live…” whatever the reason is. But a lot of people say I would love to keep this job, but I’d love to go work somewhere else.
Matt: I was actually one of those. I was [in the] Bay Area and as my parents started to get older, I wanted to go back to Houston so I de-located.
Stephane: There you go. But in your case, you had started your own company so you get to choose to do it however you want it. I think for a lot of employees, they ask permission from the employer and the employer says, “Well too bad, you need to leave the company.”
Matt: As a CEO, you know, you have to be where the people are. So if we had had an in-office culture, I couldn’t be not there.
Stephane: It would have been harder, yes.
Matt: Yea, it would’ve been, I think, impossible actually.
Stephane: Yeah, yeah.
Matt: So because we were distributed, that’s what allowed me to be in different places.
Stephane: Yes.
Matt: I will also confirm that Automatic as well has really off the charts retention. And I attribute that partially to the distributed model. Now correlation and causation — like, do we also do other things — do Upwork and Automatic both do things maybe other ways that make people want to stay that happens to be highly correlated with the distributed first approach?
Stephane: Sure. I mean there’s a bunch of things, right? I mean we have people who work on Upwork either for us or for some of our clients for whom there is just no traditional job that would work for them. We run this study every year called “Freelancing in America,” and in the later study we were asking people, like, “Would you ever take a full time job?” And for a few years we’ve been asking this question, which is, “How much money would a traditional employer have to pay you to convince you to take a full time job?” And every year it’s come back with fifty percent of freelancers saying “No amount of money.”
Matt: Wow.
Stephane: And you’ve gotta wonder, like, well that seems like a big, I mean that’s a big number — no amount of money — right? [laughter] So there’s something there and we need to dig a little bit deeper.
So this year we asked additional questions to understand like, why are you saying this? And it turns out that forty-two percent of full time freelancers, and these are not Upwork freelancers, these are freelancers in the U.S. in general, forty-two percent of freelancers said they either have a physical or mental disability too that makes it hard for them to travel to an office or to be in an office — veterans with PTSD and people with Asperger’s — like, all sorts of physical or mental reasons why the traditional labor market does not work for them.
There is another bracket of people that are saying, “I have care duties, I have young children, I have a sick spouse, I have elderly parents,” but for whatever reason, the whole nine-to-five grind, plus the two hours of commute, just does not work with my life.
And then the third bracket of these forty-two percent of freelancers was essentially saying “I live in a part of the country where there are no jobs.” And this is in the U.S. right now, this is a U.S.-based study, and there’s just tons of people that say “I’m college educated” or “I’m highly skilled, I want to work hard but I just happen to live in a part of the country where there’s no jobs and for any kind of reason, I just can’t move.”
And by the way, mobility in the U.S. keeps declining every year. So people are less and less inclined to move, especially across states. And in fact, what’s been happening in the last few years is the reverse to what’s happened historically. Historically it’s the gold rush, people go from the Dust Bowl to California because that’s where all the opportunities are. And increasingly people are not moving at all and when they do, they do the opposite because they just can’t afford to live in the coastal areas anymore. And they go back to their more economically-depressed parts of the country not because they think they’re gonna get great jobs, but just because they are being chased away from the rising costs of living.
Matt: There is a — and this might be related to this — but a lot of companies might consider certain roles being better for being distributed or not.
Stephane: Mhm.
Matt: When I walked into this office a few hours ago I was greeted by not a physical receptionist but a virtual one.
Stephane: Sure.
Matt: So tell us about that. I would say office receptionist is probably an area that almost everyone with an office would assume you need someone there.
Stephane: Sure, yeah, I mean I think generally everybody assumes a lot of things about — this job has to be on site. And I would just allow people to challenge themselves and really — the five whys. Like, why does it need to be on site? [laughter] No, but seriously, why does it need to be on site? And if you ask the question five times, maybe you’ll say “Yes, it has to be on site,” right?
I mean clearly there are some jobs, you know, there are people here that clean the office, clearly at least with the current state of technology there are no remote controlled robots that they can move around to vacuum and all that stuff so some jobs surely need to be done on site. But I would say most of these environments, they are an exception, not the rule.
To the example of the receptionist, it’s a little bit tongue in cheek, it’s a good branding exercise, but it’s also a great job opportunity. The two women that do this, they have two shifts, they live — one lives near Detroit and the other one lives in the very far suburbs of Chicago and, you know, if you asked them, they would say yeah, this is by far the best job that I could ever get.
So the reality is, I think in our case it’s aligned with our brand and so visitors get excited about the idea that they have a remote person greeting them in the office. Maybe in a more traditional company this would come out as being a little bit weird but it works pretty well. So they are on the screen and they have an ability to open up the door and they can ping us through our messaging system, which obviously is part of the Upwork product. And you know, we go and greet people.
And Faith, I don’t know which one you saw, but Faith has been with us for —
Matt: Faith welcomed me. It was an awesome experience.
Stephane: Yeah, I think she’s been with us for like eight years and if you ask her, she loves her job. I met her for the first time last year, she actually came to one of our all hands and I had never met her before and we had a — it was very emotional and it was great to meet with her physically. But I see her multiple times a day over video conference.
Matt: And I got the sense as well that people would come, which is what happens at normal offices, by the way, like, you go, you talk to the receptionist and then someone comes to meet you.
Stephane: Mhm.
Matt: Especially Silicon Valley offices. I got the sense that people coming to meet, ’cause I saw a few of that while I was waiting, had a real relationship with Faith. Like she knew their names, they knew her.
Stephane: Of course, yeah.
Matt: Like, it was pretty neat.
Stephane: Yeah, she’s actually a real human being, she just happens to be living a few hundred miles away from here but you know she cares about us and we care about her and she’s part of the team.
Matt: And do those two people cover all three offices or are there two per office?
Stephane: They cover two offices. I think we’re trying to figure out the whole Chicago thing. Like I’m not sure if — which is ironic ’cause Faith lives close to Chicago. But I think there’s a couple of other people doing Chicago. But yes, technically — actually there’s two entrances in this building so she covers both entrances and one in Chicago. So she has three screens in front of her, which, by the way, purely from a cost savings standpoint makes sense. Right? We probably pay her less than she would get paid in the Bay Area and she can do multiple offices, which she couldn’t do if she was physically present.
So to your earlier question about can it be a win-win, we do something that’s right for the economy, right for her, we save money and she has a better job and makes more money than she would make otherwise.
Matt: And the money she makes goes into that local community.
Stephane: Well yeah, that’s another thing that economists have been studying for a while. They call it the local multiplier effect. And so the idea is if you have a highly skilled, highly paid person in an economically depressed part of the country, on average they create another four jobs. So what happens is they make a sufficient amount of money and they need to go to the dentist, they need to go to the movie theater, they are going to consume goods locally and so that’s gonna create jobs for the baristas and create jobs for the local retail shops and what have you.
Matt: That’s one job, you also run — I forget the percentage but let’s call it the vast majority of the company — in kind of a distributed fashion.
Stephane: Mhm.
Matt: How do you manage, as a CEO, productivity and performance across that, especially as a public market CEO?
Stephane: Yeah well I think I get that, from what I can tell, productivity for remote people is at least as high and probably a little bit controversially higher than it is for local people.
Matt: [laughs] If you were going to theorize why it might be higher for people not in the office, what would that be?
Stephane: Just, there’s fewer interruptions, for one thing. I mean the culture of — I can turn around and tell you, ask you a question — well for a lot of jobs it takes you awhile to get back in the zone. You know, definitely as a developer, having the sales person or the designer constantly distract you while you’re trying to write code and then it takes you thirty minutes to just get back into what it is that you are trying to do, and by the way, you have introduced a bug along the way because you don’t really remember what you were doing. So that’s part of it.
Part of it is that you don’t have to commute to work. It’s just like whatever time you’re going to be spending for work is gonna be spent for work, it’s not gonna be two hours a day spent in a car that ultimately either eats [into] your personal life, which means it becomes a grind and you don’t stay as long in the company because you get burnt out, or it comes from your working hours, in which case you don’t work as many hours and you don’t get as much done.
I think the down side, the thing that I hear a lot from people — like the two biggest objections I hear — like this can’t possibly work for us — one is culture. This can’t be good for our culture, like, how could people feel like they belong? Which is not true, but we can talk about that.
And then the second thing is oh, but we need to brainstorm, we need to ideate, we need to move fast and like — collaboration over video conferencing and Slack and whatever tools you use is not as good as it is on the white board. And I think that’s actually true. I actually think that when you are truly trying to figure it out and you are in the initial early phases of a project — that’s why we do these meetups, right? If you really don’t know what you’re doing and you’re really trying to hash it out, then working synchronously rather than over messenger, you know — higher throughput, higher level of interaction —
Matt: Yeah, bandwidth.
Stephane: Bandwidth does help. So yeah, go fly across the country and go meet physically together for a couple of weeks while you figure it out.
Guess what, for most jobs that is a very small percentage of the time. Most of the time, especially if you’re a slightly later stage company and you’re iterating on the nth time on your payments infrastructure or what have you, it tends to be a little bit more programmatic. We have three month quarterly roadmap cycles and people have relatively clear roles and we are relying on strategy and all that stuff. And for the most part the dispatching of tasks using Jira and the clarification using Slack — I mean we use our own version of Slack, which is embedded in Upwork, but whatever people want to use, and then when you need to [have] a quick sync up meeting, as a daily stand up, over video conferencing or what have you, it works pretty well.
And I think there is also this — what I hear a lot of people is comparing the ideal scenario, which is, boy, if I could have exactly all the same people, paid exactly the same amount of money and be as loyal to me and stay for as long of a time and it could all be local to me, then that would be even better than my current situation. And it’s like yeah but that’s not the choice.
The two options you have is deal with local talent who, by definition, [are] not as strong as global talent because it’s a tiny subset, pay them the local rates, which are tied to the cost of living, which is always going to be higher than the global rate, have them not stay with you for nearly as long because they’re going to get poached by somebody else sooner rather than later, and by the way, in the agile world where we document a lot less than we used to and a lot more is in people’s brains when they leave, it’s really, really painful for everybody. Right?
So that’s the real tradeoff. It’s the distributed model versus the lots-of-compromises model. And I think that’s what’s quite often missed in the conversation.
Matt: Are we recreating these problems? So before maybe the person in the cubicle next to me could interrupt. But now everyone in the company can interrupt me on messaging or Slack. So what are we recreating and what should we try to keep?
Stephane: Yeah I would say, like, people need to recreate norms in general and think about what makes sense and what doesn’t. I would say it’s easier to ignore a synchronous text message than it was to ignore the person who is desperately trying to wave at you and attract your attention.
Matt: [laughs] It was a little awkward to do that before.
Stephane: Yeah, but you know, like, at the end of the day it’s a cultural norm. If you as a CEO impose the norm of as soon as you get a dash — sorry, Dash is our internal tool — as soon as you get a Skype message or a Slack message or what have you, you have to respond within the next five seconds, then yeah all you’ve done is replicate in a virtual way the same type of behaviors that people used to have in the office.
If you’re allowing people to work more asynchronously and in particular when you have multiple time zones, the respect of saying “It’s ten p.m., unless it’s really, really urgent, I probably don’t need that person to respond to me until tomorrow morning.” Like, that level of tolerance for synchronous work I think will end up leading to better productivity for the most part.
You know, one of the things we tell our developers is you should not get blocked for multiple hours but you also should not get help after two minutes of trying. [laughter] Right? So there is a window and — I don’t remember where [the window is] today — but I think we tell people, “Like, try for fifteen minutes and then ask for help.” And I think when you ask for help, help will come fast because people know that you’ve given it a fair shot.
But at the same time you don’t get blocked for four hours, wasting your time, because somebody probably has the answer. And its finding the right level of tolerance for when you should be interrupting somebody else versus when you are so stuck by yourself that you should be interrupting somebody else.
Matt: Yeah. And CEO to CEO, something I have been learning as well is that because of the power dynamics of where you are in the company, or where I am, if I send that message, even if I don’t need a response till tomorrow, if someone sees it at 10 p.m., even if they’re not responding, they’re stressed out about it, things like that.
So I’ve actually started batching things. I keep a text file using Simple Note that I keep all my questions that occur to me in the hours where they often occur to me, which is usually off hours, or I’m traveling or something, and then try to batch those at more work appropriate times. Just because of that dynamic, people would respond, even if they know — even if I say it’s not urgent. [laughs] They’re thinking about it.
Stephane: Yeah. If the CEO does not follow the cultural norms of the company then the cultural norms won’t happen. My previous assistant is on maternity leave right now and when we decided to hire somebody new I was getting a lot of push back that the person had to be in the office. And I said no, she doesn’t have to be in the office. And people were like, no of course she has to be in the office, she needs to greet your visitors and all that stuff. And I’m like frankly I can greet my own visitors. [laughter] I’m pretty sure I can do that.
So we hired somebody through Upwork a few weeks ago. And she’s not far, she’s in Half Moon Bay, but she’s far enough that she works from home and she takes care of her horses and doesn’t want to come to the office.
Matt: Horses?
Stephane: Horses. Yes, she’s on a farm. And it works just fine, you know? And so I think part of it is — model your own behaviors. Like if you expect the company to be a very distributed company, then I should do the same thing.
Like one of my direct reports is based in Chicago. She’s like semi-local but remote. And generally I would say we are all spread, the leadership team of this company is spread between this office, the Chicago office, the San Francisco office and then people having to travel for all sorts of reasons. And so most of our meetings are also fairly distributed. So I think us modeling the behavior makes it more credible when we also tell other people to do the same.
Matt: You literally wrote a book about distributed work and engineering teams.
Stephane: Mhm.
Matt: Tell me what you learned about different types of teams working together in a distributed fashion.
Stephane: So I wrote this book many years ago. Thank you for reminding me, I had totally forgotten about it. But I wrote it —
Matt: Oh [laughs] it was — part of my prep was checkin’ it out.
Stephane: Thank you. But I wrote it at a time when we had switched from doing traditional waterfall type of development, which was still big in the early 2000s, to doing agile. And as part of the transition we had said “Hey, even though most of us have done some form of agile development at some previous company before, [there are] a lot of people that haven’t gotten the training and we should hire trainers from the outside.”
So we interviewed a bunch of consultants that were doing agile training and all of them told us you can’t do agile and be distributed. Agile means physically co-located. And I was like, “Well that’s bullshit.” [laughter] I don’t think that’s true at all. Like, I think there is absolutely no reason why that’s the case, but clearly you are not qualified to [be] training us on this because you don’t believe it can be done.
And so we decided to start essentially documenting how we thought agile should be done in a distributed environment and then we practiced it for a while and then I ended up documenting it for other people because, frankly, I was talking to all of these startup founders and they were asking me how do you guys operate an engineering team at scale in a distributed way. And I just thought okay well this is — rather than me repeating myself a hundred times, let’s just write it down and describe how it works once and for all.
Matt: Cool. Tell me a bit about your exec team and the org structure of Upwork.
Stephane: Yeah, I think we are organized I would say in a relatively traditional way for a tech company. It’s very functional. And so there is somebody who runs marketing, somebody who runs engineering, somebody who runs product, somebody who runs legal, HR, finance, sales and operations, and they all report to me directly, and then they each have team members, some of whom are employees, some of them are freelancers, some are remote, some are local, and it’s organized that way.
I would say there is one specific part of our organization that — you and I had this discussion a little bit earlier, off the mic. We also do a lot of managed services for our clients. So we have clients where we deliver the work for them. And of course we, with a quote, [have] freelancers. And so we have freelancers that are on Upwork that work for Upwork. We have freelancers on Upwork that work for a client but essentially for Upwork who then subcontract it to the freelancers. And then of course we have hundreds of thousands of freelancers that work directly with the client.
So there’s an interesting continuum of — when you say who works for whom, it’s almost, like, not so super clear. You know what I was telling you earlier, like, we have enterprise clients who regularly ask us, like, can you please do this for us? And I’m like, sure, “we,” quote/unquote, will do it for you but the “we” is a freelancer.
And so whether the freelancer works for us and we pay for them, or they work for us but we cross charge them to the client, or they work for the client who hired them and pays them directly, these things are almost very fuzzy, if you will. Like, ultimately it’s human [beings] that do work for a specific company through an agreed-upon engagement in a remote way and it’s very fluid how this happens.
Matt: That is pretty fluid. What would be a typical day for you? One on ones, direct reports, meetings?
Stephane: I would say I wish they were perfectly structured and very typical. I would say I spend as much time as I can with customers. Because we try to be a very customer driven company. So I talk with freelancers, I speak with agencies, I speak with our enterprise customers, we do dinners with customers, all that stuff. Then I have weekly one-on-ones with all of my direct reports. We have regular, I would say, updates on some of the key initiatives, like just before this I was chatting with our legal team about a potential new thing that we’re going to offer to our enterprise customers that they need to finalize.
And then, you know, increasingly I also spend time with investors. And that’s the pluses and the minuses of being a public company is that we used to have a very stable base of investors historically as a private company and now that our stock is open for the public I run a second marketplace, which is in addition to running the Upwork marketplace, I run the marketplace for the Upwork stock. And so there is also supply and demand. The more I can get demand for the stock, the more the price is going to go up.
Matt: What is the biggest misconception of those public investors that they have about Upwork?
Stephane: Oh, misconceptions about Upwork? I think we have tried really hard to make sure they don’t have misconceptions about us. Yeah, I’m not sure. I would say the biggest misconception in our world in general is this idea that work needs to be done on site, but I wouldn’t say it’s with investors. I think it’s…
The thing that frankly keeps me up at night and the thing that constrains our ability to completely fulfill our mission is the fact that there are so many people looking for work everyday on Upwork than there are jobs available. Every day [there are] over ten thousand people who apply to join Upwork, we only have jobs for about two hundred of them.
Matt: Wow.
Stephane: So literally we are going to turn down, every single day, ninety eight percent of the people who sign up. And it’s not a happy message, right? We are going to say you might be amazingly qualified but we just don’t have enough work for you. And so workers are convinced — like, people want to do this and the thing that’s really blocking — the complete unlock of doing this at a much bigger scale than we do today is convincing companies to change how they operate.
And so that’s why I spend an inordinate amount of my time on working with enterprise clients, working with SMBs and really trying to get to the point of — now this does not need to be done on site and no you don’t need to quote/unquote “own” the worker, which is a complete misnomer anyway. Like the idea that you own your employees and you don’t own the freelancers. Like, nobody owns anybody, we are all human beings here and we are free to go where we choose to. And the way you retain people is you give them meaningful, exciting things to work on and you treat them the way you’d like to be treated. It’s not based on whether they get a 1099 or a W2 and they are on site or what have you. But there is a lot of, just, misconception about how work gets organized in corporate America that we are really trying to change.
Matt: You made a very good case for the practical reasons to go more distributed. Is there a moral reason?
Stephane: Yeah, I think the moral reason is what I said earlier. Forty two percent of freelancers have a physical or mental disability, have care duties, live in the wrong part of the world, wrong being defined by the norms of the traditional labor market. You can have an impact, you can create opportunities for these people.
You know, when the Bureau of Labor Statistics in the U.S. says that the unemployment rate in the U.S. right now is three percent or whatever the latest number exactly is, it misses a big part, which they also report on, but nobody ever talks about. It’s called labor participation rate. That is the percentage of adults between — so they have different trenches but let’s say between eighteen and fifty-something that participate in either — they are either employed or they are unemployed. And that number is about sixty percent.
So there’s essentially a real unemployment rate of about forty percent. And of course they are not unemployed, many of them are freelancers, but for many of these people, they just can’t participate in the traditional job market the way it’s defined. So yes, there is a social aspect to this. Yes, you can increase the diversity of your work pool.
People in the Bay Area are complaining that they don’t have enough of X, Y, Z type of workers, African Americans being an example. You know what, [there are] a ton of really, really highly qualified African American developers in Atlanta but if you just hire them in Silicon Valley and you force people to relocate — like, [there are] a lot of them that just don’t want to relocate and they won’t.
And so if you open up the aperture of what you do and you are willing to hire people that are super hard working, probably more dedicated to you than any of your traditional workers will ever be because you’ve massive changed their life, you can have much more diversity, you can have much more social impact, and you can frankly do something good for your company at the same time. It’s not either/or.
Matt: What percentage of jobs would you say are distributed today or remote?
Stephane: I think it’s still very small. What the U.S. government tracks is telecommuters.
Matt: [laughter] That’s such a funny term.
Stephane: And I don’t remember the latest number, you know, but like telecommuter typically means you’re local, you just don’t go into the office everyday because you’re somewhat far away and your traffic kind of sucks. And that’s great. I mean obviously if somebody lives fifty miles away it’s probably nice that you allow them to work from home a couple of days a week, but it’s still, like, you’re still stuck in a suburb of Chicago or the suburb of New York or what have you.
If you’re truly looking at a fully distributed workforce, I think it’s still a pretty small number. Now if you’re looking at freelancers, not just looking at full time employees, it’s a much bigger number, right? So the estimate we’ve had for a number of years — you know, we track this number of freelancers in the U.S. through our annual survey and it’s about thirty five percent of the U.S. workforce that’s doing some amount of freelancing. And increasingly — and they made, through freelancing last year they made about one point five trillion, so that’s about seven percent of U.S. GDP.
Matt: That’s a good amount.
Stephane: So it’s a pretty substantial amount. And it’s back to my point about —
Matt: A lot of room for Upwork to grow too.
Stephane: Well yes, it means we are a very, very small part of a much bigger pie. People tend to obsess about this whole gig economy, [or] on demand economy. Like us and Uber and TaskRabbit and whoever else, if you add all of us up we are like, [a] single digit percentage of the true freelance economy. Like, most of it is done in a fairly traditional way where, as a freelancer, you have your own professional network and you re-engage with clients, and it’s highly inefficient.
I mean the idea that as a small business I’m supposed to figure out who the best independent lawyers and the independent recruiters and independent designers are by looking at the yellow pages or wherever it is that you find them. And then on the other side, as a freelancer, you spend an inordinate amount of time on business development, networking, trying to find the next gig.
Matt: Billing.
Stephane: Billing, getting paid, like, nobody ever pays you on time if it’s not done electronically through a platform. And so that’s the stuff that we are trying to fix through Upwork is basically streamlining all of that stuff so that as a freelancer you can spend less time on business development and administrative tasks and more time on what you actually like to do, which is being a great designer or a great developer or whatever it is that you do as a specialty.
Matt: It reminds me of commerce in the US. Like, we think ecommerce is so huge because we always have Amazon boxes in front of our house. That’s still like single digit percentages, all retail and commerce that happens just in the U.S., not even globally.
Stephane: Yeah. I mean the reality of having a really, really big market is that it takes a very long time to get to a big percentage of it. So e-commerce, twenty plus years in, is about ten percent of U.S. retail. Upwork type of platform based freelance work is definitely in the low single digits of the freelance economy, let alone the other labor markets.
Matt: Wow. So let’s fast forward as the final question. Twenty years from now, what percentage of jobs do you think will be distributed?
Stephane: Oh, I think the jobs that can be distributed — because there’s always gonna be local jobs — it’s gonna be the majority.
Matt: The majority? Wow.
Stephane: Yeah. I mean I think like the — first of all, there’s a generational cut of this. So we study both the supply side, so the freelancer side, through our Freelancing in America study, we also study the buyer side of this through what we call the Future Workforce Report, which is coming out right now. And I can give you — the highlight of it is that the young generation, so managers on the buying side of the equation, managers that are gen z and millennials are much, much more likely to leverage freelancers and allow remote work than the baby boomers.
And what’s happening is the baby boomers are fast exiting the workforce. I mean they were there on the manager side, right, they were the managers. Until recently the typical director, VP and, let alone CEO and other execs of a company, was a baby boomer. And they are not digital natives and there is still a lot of managing by facetime and a lot of very traditional conceptions of how work should be organized and how management should work. They are very fast exiting the workforce and they are increasingly getting replaced by millennials. The oldest millennials are thirty-eight now. They’re not exactly kids anymore, right?
Matt: I’m close to that actually.
Stephane: Yeah, yeah.
Matt: I think I’m one of the older millennials.
Stephane: Well exactly but you’re a digital native and you have a totally different behavior towards work and towards collaboration than what my generation had, let alone the one before. And so what’s happening — part of the reason why it’s gonna be fifty percent and it’s relatively easy to predict is that it’s already fifty percent in that generation.
So what’s happening is the baby boomers are exiting the workforce — by the way, they are coming back as freelancers, they are coming back as entrepreneurs, and when they do they suddenly awaken to the idea that, hey, maybe this “digital online” thing actually works. But they are no longer the CEOs and the CHOs of companies and they are being replaced by younger people for whom it’s totally obvious that this should be how it gets organized.
So I think [it will be] the social, economic, [and] political pressures, along with the generation replacement, along with technology that keeps getting better and better. You know, when we started this company, I wasn’t there, but when the founders started the company, the idea of remote work done over an expensive landline and a fax machine — [laughter] It was crazy. Like visionary way too early, right?
Matt: Yeah it’s changed.
Stephane: And you look today, like broadband is fairly ubiquitous in many parts of the country and many parts of the world. A lot of the tools we use are in the cloud, you can do video conferencing pretty much for free. Like, every device you have has a webcam. And so it’s already gotten a lot better. And I think you’ll see the next wave of technology, whether it’s augmented reality, it’s much better chat tools — I mean there’s gonna be all sorts of things that make the location so much less relevant. Fundamentally if everybody is using AR goggles in order to do 3D modeling of a product, we are all watching the same thing virtually, so whether we sit next to each other or we are far away from each other, it matters a lot less.
I think the only thing that will stay probably forever is time zones. So like I don’t think we’re gonna fix the fact that when it’s the middle of the night for you, you probably don’t want to be at work. And that’s why I think the world will be much more organized vertically and much less organized horizontally.
Matt: Longitude versus latitude.
Stephane: Whichever way that is, yes. [laughs]
Matt: Well we could obviously talk a lot more but thank you so much for this time. Also, thank you for the leadership that Upwork has in this — what I think of as a revolution of distributed work. I’m really looking forward to the story getting more out there and hopefully we can chat again sometime.
Stephane: Of course, thank you for having me.
Matt: Of course. Appreciate it, man.
A new podcast, 15 years in the making.
May 15, 2019
Matt Mullenweg, cofounder of WordPress and CEO of Automattic, embarks on a journey to understand the future of work. Having built his own 850-person company with no offices and employees scattered across 68 countries, Mullenweg examines the benefits and challenges of distributed work and recruiting talented people around the globe.
Produced by Mark Armstrong and the team at Charts & Leisure: Jason Oberholtzer, Whitney Donaldson, Cole Stryker, and Michael Simonelli. Theme music by Jason Oberholtzer. Cover art by Matt Avery.
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