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    Distributed, with Matt Mullenweg

    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.

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    Copyright: © 2019, Matt Mullenweg

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    Latest Episodes:
    Episode 13: Attorney Lydia X. Z. Brown on Making Work More Accessible Oct 31, 2019
    Show notes

    Read more about Lydia X.Z. Brown in “Making Work Accessible, Wherever it Happens.” Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen. 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. *** 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 prioritizat…

    Full show notes at the publisher

    Episode 12: Toptal’s Taso Du Val on Finding the Top Distributed Talent Oct 17, 2019
    Show notes

    Read more about Taso Du Val in “Inside Toptal’s Distributed Screening Process.” Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen. 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…

    Full show notes at the publisher

    Stephen Wolfram on 28 Years of Remote Work Oct 03, 2019
    Show notes

    Read more about Stephen Wolfram in “The Machine that Turns Ideas into Real Things.” Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen. 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 go…

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    Automattic’s Sonal Gupta on Communication and Chaos Sep 19, 2019
    Show notes

    Read more about Sonal Gupta in “Welcome to the Chaos.” Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen. 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: Tha…

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    Author Scott Berkun on Managing Distributed Teams with Respect Sep 05, 2019
    Show notes

    Read more about Scott Berkun in “Observe, Don’t Surveil: Managing Distributed Teams with Respect.” Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen. 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…

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    Automattic’s Cate Huston on Building Distributed Engineering Teams Aug 22, 2019
    Show notes

    Read more about Cate Huston in “How to Build and Strengthen Distributed Engineering Teams.” Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen. 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. *** 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…

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    Leadership Coach Leo Widrich on Emotional Wellness for Distributed Workers Aug 08, 2019
    Show notes

    Read more about Leo Widrich in “How to Stay Connected in a Distributed World.” Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen. 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. *** 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 t…

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    Design leader John Maeda on how to foster creative collaboration on distributed teams Jul 25, 2019
    Show notes

    Read more about John Maeda in “Helping Creativity Happen from a Distance.” Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen. 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. *** 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…

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    Upwork’s Zoe Harte and Han Yuan on Managing People and Products in a Distributed Company Jul 11, 2019
    Show notes

    Read more about Zoe Harte in “How to do HR in a Blended Company” and about Han Yuan in “Engineering with Empathy.” Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen. 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…

    Full show notes at the publisher

    Automattic CEO Matt Mullenweg on building a fully distributed company Jun 27, 2019
    Show notes

    Read Matt’s history of Automattic: “On Building Automattic.” Subscribe to Distributed at Pocket Casts, Apple Podcasts, Spotify, RSS, or wherever you like to listen. 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. *** 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 we…

    Full show notes at the publisher

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