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47: Seeking Balance (ft. Koji Pereira) May 18, 2024

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Transcript Jesse: I’m Jesse James Garrett, Peter: and I’m Peter Merholz. Jesse: And we’re finding our way, Peter: Navigating the opportunities Jesse: and challenges Peter: of design and design leadership, Jesse: On today’s show, Koji Pereira, Chief Design Officer for Brazilian fintech Neon, joins us to talk about his career journey from Brazil to Silicon Valley and back again, finding the balance between speed and quality, and strategies for making the design team and the design process more inclusive. Peter: Thank you so much for joining us, Koji. I think where we’d like to begin is just to get a better sense of your story. Who are you? What are you about? Where are you from? And what are you up to? Koji: Awesome. Well, first of all, thanks a lot for having me, Peter and Jesse. I’m very happy to be here. I’ve been following the podcast and you’re doing a great work. Thanks for that. Koji’s story Koji: I am originally from Brazil and I think my story began on design with graphic design. I was on graphic design for a pretty short period of time, starting doing posters for bands. I had my own band back in 1997 and then the internet was becoming a thing in Brazil and, you know, I was an early adopter. Before, I had a BBS, a bulletin board system where people could, you know, call my BBS and access pretty much like a website on DOS, which was crazy. So when the internet began, I was like, this is interesting, because to me, there’s a potential here for design to become something interactive and something with motion. And, you know, I started doing websites for companies and small businesses. And then around the year 2000, I joined another person who was building this website where people could order food from, and it was desktop internet back then, people would open a website, turn on their computers, that would take a lot of time anyways, then dial up to internet connection, open a website, and then, let’s say, 15 minutes later, they have a website where they can order pizza from. And I had a server connected to a facsimile. And we had a software that would send orders to the pizza place. Then the pizza place would deliver the pizza, they would get the money in cash. And that was our business model. Basically we were like a white list or yellow list for pizza. And we had this small service that run in the background. So that was my first experience with web design back then. And because of this company, we ended up selling this and I joined Google to work on Orkut. I don’t know if you all recall was the biggest Peter: I’ve met Orkut. Koji: You met Orkut? Okay, cool. So you’re very familiar, but for people who don’t know, Orkut was the biggest social network in Brazil and India. In U.S. I think was most of the time the second, losing for MySpace at some point and for, I think, was Friendster before. Jesse: Yeah. Koji: And of course, like Google was a totally different world for me back then. Working in tech Koji: The typical corporate job was very different from what it is today, and especially in Brazil, even more different. And for me coming from like a very, you know, half neighborhood in Brazil and going to this world, working at Google and even in Brazil was so, so different for me and kind of opened my eye to a lot of different stuff. So I think that’s pretty much how I began back in my career with product design, UX slash web design at that time. Peter: Tell us a little bit about kind of how you’ve evolved as a designer and design leader. Koji: Right. So I stay at Google for almost 10 years, and the reason why I stay 10 years is because with Google you have so many options, right? Like you can move from one team to another team, and there’s always these smaller teams trying to build something new. And those are the teams that I liked the most. You know, I was never really excited about the teams that were kind of, you know, keeping things going in a bigger scale. I was more interested on, like, teams are building something from scratch, zero to one products. And the last team that I joined was a team that I enjoyed the most, which was Next Billion Users. And to me, it was full circle because we’re trying to create products for emerging markets. Back then, we did a lot of research in India, Brazil, China, too, and Africa, and we build a product called Files. And what Files did was help people to free up space in their phones by looking at their storage. And for us here in the U.S. might not be an issue, but when you look at the population in the world, like 80 percent of people are using, at that time, Android. Most of the people are in phones that are under 300 dollars. So those are phones that, after three months, If you use WhatsApp a lot, then your phone is fully blocked with things and there’s nothing you can do with that. So with that team, we build Files and we help people to free up space and became like a one billion users app; from zero to one billion. And it became the default file manager for Android right? So that’s when I decided to, okay, like now I built something from scratch at Google, became very successful, I want to go and work in totally different fields, smaller companies. And that’s when I joined Lyft and Lyft to me was this interesting mix of service design, product design. You know, it’s a marketplace with multiple types of users. You have the social interaction and the, real life business model going on behind that, which is something that Google was not really working at the space that Lyft is right now. And that’s where I learned a lot because when I joined Lyft, I saw that the way that Lyft thought about design was super, super different from the way we thought about design at Google. And then like I joined Twitter later, it was all about coming back to social and working in a product that was more established in the social space. And that was pretty interesting area to be for me because I was able to use some of the learnings that I had back at Google, but in a product that was already kind of established and have more users in the end of the day. To where I am now, where again, I feel like it’s all the circles that come back and forth now working for Brazil remotely here in US. It’s a company called Neon. So it’s a fintech banking company, which for many might not be known, but banking and digital banking in Brazil is one of the biggest space for fintech companies in the world right now. Jesse: So I’d like to rewind to that moment early in your career where you got started doing web design for the Brazilian market and then Orkut, you find yourself thrown into a different context, different kinds of design challenges. And especially designing for a much broader and more diverse audience than you had before. And then I notice as you were talking that this seems to be this recurring theme for you of trying to address these very large scale challenges for very large scale audiences that are potentially very different from you. And I’m curious about how that’s informed how you approach design as a design leader. Koji: That’s a great question. So Google was not interested in building something specific to one group of users. When we talk about like, what’s your target? At Google, we’re pretty much saying like, our target is everyone. We want to build something that works for everyone. And in one hand, this is almost, you know, impossible because, of course, like, in the world, you have so many different people and different cultures and different interests and different even perception of aesthetics, in a sense of visual design. On the other hand, if you build something that really tackles a pain very well in one place, and then you’re able to figure out how to adapt that solution to other realities, then you’re likely be able to build something that will be more successful than if you start building something that are meant to be for everyone from the beginning. If you think about even Facebook, right? Like when they started, they started as a niche kind of product for universities and then they slowly grow to what they are now. So, same thing for Google. I felt like when the products that I worked on where we try to really build something huge from the beginning, some of them, I don’t think they really worked, because we’re trying to embrace the world from the beginning. Whereas for Files, because, and I will take WhatsApp as an example too. Because WhatsApp started with a very specific pain in a very specific market that helped them to grow and scale to other markets because they’re kind of solving a pain that only existed in certain parts of the world with certain parts of users, where they lack, you know, very fast connection or the connection was laggy. And because of that, they built a very good messaging system that works pretty well, even if you’re hiking in Yosemite and the internet is not working. Whenever you go back and you have your connection back, all the messages are keyed and they will be sent. Right now, all the messaging apps, most of the messaging apps do this type of resilience over laggy connection, but back, I don’t know, three years ago, Whatsapp was a pioneer on that. And, you know, pretty much every single messaging app kind of followed that lead. Company-specific design Jesse: Another thing that you touched on in here is the difference that you noticed in the way that different companies think about and approach design. There’s a strong sense, I think, among people who work outside the Valley, that the Valley is really kind of strongly unified in its approach to product development, and they’re sometimes surprised to hear that Lyft might have a different approach to design than Google has. What did you notice there? Koji: So many things, but I’ll start with craft, the focus on craft, quality, versus speed or the balance between speed and quality. I think that changes from company to company and for certain companies, it’s part of the DNA, right? Like if you think about Apple, I’m pretty sure that Apple is not afraid of delaying things, even to an extent of being the second or the third in market. We see that with Vision Pro. In a way for them to be able to then work in something that is more finished and more refined. And you see companies like Lyft and Airbnb that maybe sits in the mid range of the scale. I think Figma probably will also fall in that category where they, have a better balance of quality versus speeds of the market. And then you have other companies which are more all about speed and it’s not that it’s wrong. You see that many of those companies are very successful and they’re able to evolve their designs over time, whenever they launch the MVP, whatever, but it just becomes part of their DNA, right? Like it’s hard to change that once established, once it’s like, two or three years old of practice. And to me, that’s the trickiest part when I join as a design leader in an organization, like, what is our way of doing design? What is quality and what is good design for us? And of course, like, that to me is connected to all the, umbrellas of design. It’s not just visual. It’s not just interaction. It’s also research. It’s also, how do we make decisions. It’s also, how do we operate with other teams. It’s also, how do we connect the go-to-market strategies to the design strategy. Like, what are the things that we care about? What are the things that we are open to make tradeoffs in terms of speed, to make sure that we deliver something that it’s on the bar that we believe our company is set to do. Peter: To the question Jesse asked earlier, there’s this assumption of kind of a monolith when it comes to Silicon Valley and tech companies. And clearly they’re different. But also I find that a lot of designers and design leaders want to think that the businesses they work for are rational, right? And they’re making decisions based on some clear framework, rational framework, that’s driven by some concept of business value. But, if that were true, then every company, well, maybe not, but I was about to say, maybe every company would work the same, right? ‘Cause if there is a rational way of running a business, then everyone should approach that business similarly in order to maximize their returns. But clearly that’s not how it works. And so I’m wondering, kind of, what you’ve unpacked in terms of these different corporate cultures, different environments, different contexts that suggest where these bars are set for design and craft and quality. Make sure it’s a fit Koji: Mm hmm. Yeah, that’s an amazing question. It’s, first of all, it’s very hard. And that’s something that when I mentor, other people, I tend to say, like, the most important thing for you when you’re interviewing is to find the right place for you. It’s not just, you know, getting hired in the end of the day. One, because you can become miserable very quickly. Second, because if it’s not a fit, then, it won’t work for you, mid, long term. So, yeah. There is a few things that I learned so far. First of all, you can’t like really think that the CEO won’t make a difference, right? Like a CEO makes a lot of difference. Like how does CEO think about design makes a lot of difference. Does the CEO really care about quality in the way that you care about. I think that will be the first fit question to me. And maybe you’re not, you know, responding to the CEO directly, but if you’re just talking with the company, you can just go to YouTube and see some interviews and podcasts with that CEO. And that will give you a lot of hints of how the CEO thinks about quality, and I would not even say design, but quality in general. Then the second thing to me is just looking at the product itself, because when you look at the product, I think that’s a classical thing, right, at this point already where you can look at a product and say this is created by, you know, this team and this is created by another team and those teams clearly don’t talk to each other, right? Like that’s one thing that you can clearly identify when you look at a product. Second thing is, you know, is this product really run in a way that things are being pushed to promote things, promote specific areas or specific features. We all remember, like, the web news portals back then where they have a lot of pop ups and ads. I think those are things that you can really identify when you look at a product where teams are kind of just pushing their products in the whatever home screen or the most important part of the UI versus a product that really coordinate those things and create something that is a scalable. So those teams get their exposure, but at the same time it’s not disjoint, right? So I would say CEO and the product will tell you a lot about those things. There’s other things that I kind of feel that maybe give you the hint sometimes, but there’s so many times that I got it wrong by looking at, I don’t know, let’s say the principles, right? Like, which is beautiful to see, but then how many times you see like a company that has perfect principles or even design principles and then you join or you talk with someone who works there and they say like, Oh, no, this is just to put in a wall. That’s not real. Jesse: This issue of speed versus quality is one that I hear a lot about from my coaching clients and in a lot of cases, the way that they frame this challenge is as one of culture change. That they find themselves in a culture that tips that balance toward speed and away from quality. And they see it as their role as the design leader to advocate for a different culture and to try to drive a different culture. I’m wondering, listening to what you’re saying, whether from your perspective, that kind of culture change is even really possible. What do you think? Koji: I mean, it’s nuanced to me, because it really depends. I mean, like, let’s be clear here. Perfect to me is when you have a balance, right? It’s…

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46: Leading with Clarity (ft. Vuokko Aro) May 05, 2024

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Transcript This transcript is auto-generated and lightly edited. Some errors may remain. Jesse: I’m Jesse James Garrett, Peter: and I’m Peter Merholz. Jesse: And we’re finding our way, Peter: Navigating the opportunities Jesse: and challenges Peter: of design and design leadership, Jesse: On today’s show, Vuokko Aro, VP of Design for the UK’s popular digital-only bank Monzo, joins us. We’ll talk about shifting your design approach as your company scales, building a true peer relationship with product leadership, and creating a sense of togetherness for remote and embedded teams. Peter: Hi Vuokko, thank you so much for joining us. Vuokko: Hi guys. Thanks for inviting me. Peter: We’re going to start where we always start which is to learn a little bit more about you. So, who are you? What do you do? What’s your role? Give us a little background. Vuokko: Absolutely. So I’m Vuokko VP design at Monzo, which is a digital-only bank. It’s a scale-up based in London. And I’ve been on this startup scale-up journey since the early days and have scaled myself with the company. And before this, I was at other startups in London, New York. I have a kind of a strange background, where I have a master’s in design, but before that I actually studied economics. I have an MBA, which used to be a fun fact about me. No one would ever know, but actually as I’ve progressed in my career, especially the startup that took off being a bank, it has become pretty useful. I would say that I can, I can help lead the company without adult supervision. Peter: You, got your MBA before your design degree. Vuokko: I did. Yes. Peter: That’s the reverse of many of the design leaders we talked to. Vuokko: Yes. Why design? Jesse: I’m curious about the pivot for you. What drew you to design? Vuokko: Mm, yes. It’s a good question. Well, I’m one of those people who’ve always done creative things since like a young age, just drawing and designing things and, I don’t know, high school, someone needed a hoodie, I would design it. At my school of economics, if we needed to make a magazine, I would do the layout in InDesign. So I guess it was just always a calling. But earlier on at the time when I was starting to choose a career, it didn’t seem like a real one yet, at least if you ask my parents. I think I chose something more traditional and then ended up drifting to it anyways. I worked as a journalist, a copywriter, concept designer, drifted into full time design when the, actually when the iPhone was released and touch devices became a thing and that was very exciting that you could touch these things and actually people would feel things through those. So that’s how I made the leap. Peter: Interesting. I hadn’t realized just how much of your journey was also Monzo’s journey, and I think kind of charting that path could be interesting. But to set a little bit more context, you mentioned Monzo’s a digital-only bank. How many people use it, and in what parts of the world is it used? Vuokko: Yes. We’re mainly UK-only now. We’re starting to work on our US product as well, but it’s very early days. But in the UK we are a household brand. People are very passionate about it. It’s the kind of thing, it’s funny. Outside the UK, people have not heard of Monzo, and in the UK, you can’t tell anyone you work at Monzo without hearing so much love and excitement about it, and we have this, like, iconic, hot coral, we call the color hot coral, debit card, and everyone knows it, so we’ve got a big consumer brand. We’re also a social network, in my opinion, because every Monzo customer has 37 contacts on Monzo to send payments to and so forth. When I joined, we were a prepaid card. That’s how we got going just to build the product out in the open. The original team, which I’m not part of the original team. I just joined early. The original team started applying for a banking license, but already started building the product to learn from customers and to like start finding product-market fit early on. And then we got the banking license and then built the bank app on top of that. So the earliest version of the product was kind of like a Venmo. But for the past five, six years, more than six now, we’ve built loans and overdrafts and investments now. The goal is not just a bank, but, the interface to all your money, basically, which is a lot of complexity for us to handle and make simple for our customers. Design’s journey at Monzo Jesse: So you mentioned you were not part of the founding team. Where were they on their journey when you joined the company? Did design already exist as a function or were you the first designer or like how did that go when you were stepping into this? Vuokko: Mm hmm. Design already existed and, the first few designers were amazing, so they had set a really strong foundation already. There were three designers when I joined, and I came from other startups, I had designed other consumer apps, so came in to build a delightful consumer experience and looked across the whole app and things have scaled from there, so started managing every other designer who came after me, and introducing design critiques and design culture and all that good stuff. So taken from there, we were less than a hundred people in the company when I joined. Maybe a hundred thousand users. There had been hockey stick growth just before I joined, and a nice funding round so they could hire me and some other people. Jesse: Did they bring you in in a leadership role? Vuokko: No, I joined as a lead product designer, I think. Although the company was very flat at the time, there were no leadership roles other than the founders, really. Jesse: Yeah, so they needed to create a leadership role for you at some point. How did that come about? Vuokko: Yep. So we had our original head of design, Hugo, who’s amazing. And he was the first designer. And then I joined and did my thing and have been on a journey from that time when we didn’t really have any titles or no one cared, to, as we scaled up, created a director level and that became me and then VP. Jesse: Mm. That’s been, six, seven years. Peter: When you were director level, was that the senior most role? As things have scaled, have you been scaling kind of on top with that? Vuokko: No, Hugo, the original designer, was VP design for a while, maybe a year, two. But before he left, I became VP and then that’s been the last however many years. Peter: Couple of years according to LinkedIn. Jesse: Was that previous VP one of the founders? Vuokko: No, but he was there from day one. Jesse: What was it like to step in as the, kind of, the second leader? You know, like you’re inheriting something, but it’s not yet what it needs to be? What was that like? Vuokko: Yeah. I didn’t think about it too much at the time, to be honest. It was one of those times in a startup where everyone’s doing everything from, like, jumping on customer support if there’s a problem, or packing cards in the office if a lot of signups happened the previous day, so we were just doing things together, but I think I also had the privilege of learning with him and he was out there on the frontier and I could watch what he did and learn very quickly as well. I think I was at the right point in my career where I had enough maturity to watch and learn quickly and then do whatever was needed. That’s the thing in scale-ups. I think there’s a lot of opportunity for anyone to take a lot of responsibility, but it’s not always the right time for different people. It’s a high level of discomfort when you don’t know what you’re doing and you have to figure out the next step and the next step. So I guess you have to be ready for it to put in the work. No victim mentality Peter: You mentioned Hugo kind of being out in front, what were some of the things that you learned that you saw that maybe were, eye-opening for you as he was operating, and maybe that you’ve adopted in your leadership? Vuokko: Great question. I think one thing that I always respected about Hugo was he didn’t have any kind of victim mentality about design is not respected, or design needs to sit at the table. He was very grown up about it and just showed people what the impact of design had been to the success of a feature or a phase in our story, and kind of took it apart and explained like this is how it works. It’s not just magic that happened. We put in this effort and then this was the outcome of it. So I think I’ve learned that a lot, now that I represent design in rooms where I’m the only designer and other people don’t have my background, is to not be preachy about it or complain-y, but just… people love learning about this stuff anyway, it’s fascinating. I think I learned that kind of open mindedness about just being excited, about teaching, about design and you kind of can’t overdo it. There’s always more for all of us to understand and learn. Jesse: Mm hmm. So you’ve referred a couple of times to this business as a scale-up opposed to a startup. So implying that it’s gotten to a phase in its evolution where growth really, really matters. And I’m curious about what you see as the difference between design’s role in the startup phase versus design’s role in the scale-up phase of a new business. Vuokko: Yes. A lot of differences, a lot of similarities. I suppose early on it’s much more about creating new things and not everything’s going to be good. And now we’re getting to a phase where the brand is very valuable and we can’t risk just destroying it overnight. For example, where in the past we would do a lot of things and just see what works, and now we’re in a phase where we’re really defining what it is, who we are, and maturing a lot of things. Which is different, but still we’re clearly not at a phase where we’ve stagnated. We’re still creating new things just with a more careful approach, but still need to move fast and be bold about it. I think we used to take massive leaps and now we still take leaps, but I think that’s my biggest fear as well, that one day we slow down to a crawl and stop innovating, but that’s not. I can’t believe I used the word innovate, but you know what I mean. Yeah, so still creating, but with like knowing that all of this is actually very valuable. Product *and* brand design Vuokko: Now one thing about my role that I forgot to say is I look after product design, user research and brand design. So I think about the customer experience in a very wide sense. So thinking about the app, if… when we redesign it…I’ve done that a few times now… obviously breaking metrics and taking a leap into the unknown, those are huge things, but also changing the brand and the visual brand, for example, like refreshing it, and how will this change the sentiment of people who interact with all of these things. I’ve been on many startups before, but I’ve never gotten to this phase before where we have to be this careful. Which is, I’m not saying that as a bad thing, it’s actually, it’s what a privilege. Jesse: Yeah. Peter: Had you done brand design, marketing design before, or is this new for you in this role? Vuokko: I’ve done it before. I think I’ve actually gravitated towards startups where brand and product are very intertwined. So, just before this I was at Citymapper, which is another London startup which is huge here. Less so… It exists in the US, so maybe some people will know it. But also very much a strong brand and charismatic product, kind of intertwined. And I suppose I’m old enough to have worked in design when there wasn’t that much of a separation yet between brand and product, as there is now with younger people coming into the industry only having, for example, studied product design and worked in very tightly developed and matured roles, I think. At some point I was quite drawn to early stage work where you do everything. Peter: What I see that’s unfortunately common is, as companies scale, design, which had product and brand together, ends up getting separated because some new marketing leader comes in and that marketing leader wants the design team to report to them. Have there been any of those kinds of conversations or has it been recognized that design is more powerful when it’s all together? How have you navigated those discussions? Vuokko: We have had that discussion. It was a few years ago, actually, that that did come up and I… it was the first time I very forcefully put my foot down in what I believe we should do. And it was a discussion for a while, but ultimately I think we have enough proof points at Monzo, just the power of, I would say design is our moat, or at least one of the strong moats we have as a business, where it’s kind of not disputable that design is what draws people to use the product, to work at our company, all of these things. And it’s not just how easy the product is to use, or the card and the visual brand, but all of it, how it works together. I just look towards examples of where that worked and where the risks would be to separate it. I do very strongly believe that the way we build the product and the way we market it should feel like one fluid experience, and should feel like it’s made by one hand, even though we’re a large team now. But, it’s not been discussed since. So the last few years we’ve settled into this model and I actually proactively brought this up because we hired a new CPO a year and a bit ago. And when we were interviewing candidates, I made it very clear to everyone involved that It’s absolutely not personal towards anyone, but before we even get started, I don’t want to report into a CPO either, because I believe that design is wider than just product. I look after the product experience, but also the brand and the way we talk to customers in our app, our cards or the carrier letters, everything. So to me, design being a part of product is more narrowly focused than how I see it. So that’s been the way, and I think, obviously, it always comes down to personal relationships, but I work closely with all our execs and it’s gone well. I’m very collaborative and everything, but this is the way I prefer the team to be set up. Peter: So where is design situated in the organization? Vuokko: So I report into our COO. Which I thought was like a once in a lifetime setup for design, but I listened to an older episode of yours and you had someone else on from Instacart, I think, who had the same model. And that’s been really, very fruitful relationship for me, I have to say. But it’s, I suppose, it comes down to individuals as well. Our COO is a amazing business leader who I learn a lot from. And also I’ve gotten to teach non-design execs and non-product execs about the power of design and customer centricity in ways that they might not have heard about before, so. I prefer just reporting to a business leader. Who’s also an amazing person. Jesse: So you mentioned that there are a lot of people in the industry now who have spent their entire careers solely in the realm of product design and have never been exposed to kind of this broader field of brand and graphic and identity and all of these other forms of design that come into play for you. What do you think those folks are missing? What advice or direction would you give to somebody who has a lot of depth in product, but no experience with brand, like how can they level themselves up here? Vuokko: I love that question. I think when you work in just one medium, let’s call it, you do end up solving a lot of problems over and over, a similar framing and similar problems, and it can limit your thinking. I think of what are we even doing here as a designer, or what are we solving for? So I think, thinking widely about the brand, it’s more about storytelling and really simplifying a message so that it resonates with the customer so that they notice it in like the busy life that they’re leading and they don’t really have more than two seconds for us. And I think it’s…

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45: The Phase Shift Apr 24, 2024

Show notes

Transcript This transcript is auto-generated, and then hand-edited. It may contain some errors. Jesse: I’m Jesse James Garrett, Peter: and I’m Peter Merholz. Jesse: And we’re finding our way, Peter: Navigating the opportunities Jesse: and challenges Peter: of design and design leadership, Jesse: On today’s show, design leaders are feeling some major shifts in the landscape these days. In the wake of COVID and sweeping industry layoffs, leaders are facing difficult questions about the value of design, both from inside and outside the field, while new technologies and a chaotic job market make the future of the work harder to see than ever. Peter and I take some time to explore what’s going on with design leadership here in the spring of 2024 today on Finding Our Way. Hello, Peter. Peter: Hi, Jesse. How are you? Jesse: Welcome to the show. Peter: I’ve been here. So we’ve been having a lot of really rich conversations with a variety of different design leaders about their challenges. And those have been really great. But there is something larger going on out there in the world of design leadership. And I wonder if we can take some time today to try to put a name to it and kind of define the parameters of the elephant in the room here. Peter: Name it to tame it. What’s going on with leaders these days? Jesse: Yeah. So what’s going on with design leaders these days? Peter: Oh, you know uh, the usual. What’s going on with design leaders? So many things. I found myself, in the last six months, part of a number of conversations around the state of the industry, where things are going, whether it’s on LinkedIn or these recorded conversations. A lot of them have taken as a jumping off point. Robert Fabricant’s article on the big design shakeup that he wrote for Fast Company, reflecting on what he’s seeing as some step change that’s occurring, and the struggles that design leaders are having with figuring out, like, what to hold on to, to take them to what’s next. And I think what’s going on with design leaders is there’s a recognition that what we’ve been doing for the past 20 to 25 years… Jesse: Mm-hmm. Peter: You know, I’m thinking about around the time we started Adaptive Path, maybe a little bit before then, there was an evolution,, a curve, at times gentle, at times quite bumpy, but, you could draw a line between 1997 or 8 and 2022, in terms of what was going on with design and thus design leadership. And it feels like something in the last two years has broken such that we can no longer rely on that trend just to continue to carry us forward. But it’s not clear what the new thing is to hold on to, and so design leaders are struggling with their relationship of, like, what’s next? What’s expected of me? How do I show up? Because it’s not clear for many people, not even just in design. I, think we’re seeing this… I listened to a podcast interview that Lenny Ratchitsky did with Marty Cagan. And one of my takeaways from that is that product management is in a similar vein of disruption. Jesse: Oh, it’s just as bad on that side. Yeah, absolutely. Peter: I think we’re in this phase shift. And we’re in this middle of it, but you can’t really be in the middle of a phase shift, right? You’re either in one state or another, but we’re no longer in the prior state. We don’t know what the next state is. And I think a lot of the tsuris, a lot of the agita, the anxiety that we’re sensing out there is because we’re in this uncomfortable middle space. The value proposition of design Jesse: Hmm. You know, as I think about trying to describe the shift that’s happened in the last few years, and I think it goes back more than the last two, but definitely in the last five years, I feel like there has been a real shift in the way that business has framed the value proposition of design. And for this generation of design leaders, they’re very attached to a particular value proposition of design that has to do with product discovery. It has to do with customer insight. It has to do with experiential exploration as a way of discovering new product opportunities in the market. The value proposition there has paid off in a very inconsistent fashion over the last 25 years. And there are now quite a lot of, because of the growth of the field, because of the hockey stick curve that we’ve been on, there are now a lot of organizations that are finding plenty of value in the market without ever engaging with any of these practices, which then has their competitors looking at it and going, why are we investing in this stuff when we’re getting incrementally better results? Peter: Yes, I think this, actually, also leads to one of those parallel conversations happening in product management, because if you read you know, Marty Cagan and you have this view of the world of product managers as, you know, empowered leaders who, given an outcome to realize, have the autonomy to figure out how to get there…right? Jesse: Mm-hmm. Mm hmm. Peter: And that’s this kind of common conception from your product management thought leaders, your Marty Cagan’s, your Perri’s, of how product management works, but then, this came up on the Lenny Ratchitsky show, there’s this recognition, most product managers, like, well into the majority, 70%, 80 percent, maybe more, are operating in what would be called a feature factory environment, where they’re not empowered, where someone else has said, this is what you’re going to build, you can figure out how you want to build it. Sure. But this is what we’re doing. Those decisions have been made outside of that team. And, I forget who wrote it, but there was a product thought leader who was like, yeah, feature factory PMing is fine. That is right for some contexts, similar to this conversation, where mediocre-ish design is fine in some contexts, not necessarily every business will benefit from superlative design. And that’s a tough pill to swallow, I think, for a lot of leaders. Jesse: Or at the very least the threshold of diminishing returns kicks in way sooner for some businesses… Peter: right, right, right. Jesse: …than for others. Peter: Erika Hall talks a lot about exchange of value, right, between the business and customers, and the source of that value exchange might not be rooted in something that user experience design has a meaningful impact beyond a very basic, like, functionality threshold. Jesse: Hmm. You know, when I think about when we started Adaptive Path and the value proposition that we were putting forward into the market, I’m reminded of the arguments that we had internally, the seven founders, about whether to call what we did design, even, because, you know, truth be told, our deliverables at that time didn’t look like design deliverables A wireframe was an exotic, strange thing. If anybody had in-house designers, they were working in Photoshop. We at Adaptive Path literally had no one with those skills. So we were trying to define user experience as something that was little bit different from, and a little bit distinct from a traditional design discipline. Over the years, , the value proposition that emerged there was that the same practices of customer insight the same practices of experiential exploration that are a normal part of a design process could also benefit business processes as well. And that’s where the whole design thinking methodology comes from, among other things. That value proposition was a strong one during a time when there was a lot to be discovered, when there were not a lot of best practices to draw on, when nobody really knew what a lot of this stuff was going to look like, and we had to make it all up. That’s simply not where we are anymore. And those processes and practices, that value proposition, has a lot less potency in most product categories these days because the exploration and the discovery has been done. The best practices are there. There’s no need to reimagine the shopping cart. We’ve had 25 years 30 years of shopping carts. Peter: Yeah. So let me start with where you are and then I want to pull it broader. We’ve had 30 years of shopping carts. That is not an interesting problem to solve. Much like onboarding a new customer is not an interesting problem to solve. They fill out their name and password. They put in some information, they give you some money, whatever. But, we still treat onboarding flows as if they’re some source of innovation or some opportunity for innovation. And one of the things that you’re touching on that I think reflects the discombobulation that we’re feeling in design is, especially for those of us who’ve been doing it for 20-some years, is we haven’t taken into account that we came in where all of it was interesting. We published a report in 2002 on how to design a registration flow right? Because like, it was an interesting problem to solve, but we also recognized, like, 20 years ago, like, let’s just solve it once and everybody just use this thing. At this point, that stuff is basically done. Commodification of UI design Peter: And I think what design leaders have trouble recognizing is just how much of, I’m going to say this intentionally, UI design is commodified, is not strategic, is not interesting anymore. Much like… I tend to draw an analogy to residential architecture. Plumbing is commodified. Electrician work is commodified. Your basic contracting is, roofing is commodified. It’s not that it’s not important, but there’s a way to do it. You do it the same way. There’s standards and practices and codes. Just follow it and done. We still want to treat it like it’s a source of inspiration and new thinking. And so learning to let go of that, I think, has been a challenge for design leaders. There’s an opportunity that we as a community are missing of building a workforce of UI designers, highly trained UI designers who can design to code, who could come out of programs, like, in a community college. You know, you should be able to get an associate’s degree in software UI design. Instead what we’re doing is we’re asking people with 10 to 15 years experience to design onboarding flows. ‘Cause that’s, who we have around. We’re not staffed appropriately. Let me finish with one last thought though, which is reflecting on one of the conversations we had, which was with Rebecca Nordstroem from LEGO. She was this first UX designer on this manufacturing and supply chain team. And they realized, oh yeah, we’ve got some software, so we should have a UX designer on it. So she showed up and she did some UX design. And then she asked, what are your other problems? And they said what their other problems were. And she’s like, I think I can help with those too. And they weren’t UX screen based design problems, right? They were more systemic, more procedural challenges throughout supply chain and manufacturing that she realized, Oh, I can apply my UX design abilities to all kinds of problems that would not be considered standard UX challenges. And what I like about that is she didn’t define herself by her medium. She defined herself by… I am a capable problem solver with a set of tools, sic me at your problems and I can help you resolve those. And I think that shift is one that a lot of design leaders have not made. They’re too rooted in the media and material of their practice and not in the opportunity of their practice. Jesse: I can see that. I can see that. I can also see those opportunities being pretty tightly constrained by the environments that they’re in, and the mandates that they’re given, and the way that their roles are framed. You know, a lot of the fear and anxiety that I’m hearing out there comes from the fact that these design leadership roles, which used to be positioned as pretty highly strategic roles, influencing product strategy, product direction, product roadmaps, that kind of thing, are now being recast and reframed as operational delivery style management roles. The disjunction Jesse: And there’s this significant disjunction for people with what they thought their value proposition was, what they thought they could offer. And they haven’t been able to get the traction that Rebecca was able to get in demonstrating value in small ways that opens up those larger opportunities because nobody’s even giving them the small opportunities because they’re like, you’re our pixel factory; why do you care about all this other stuff? Peter: I imagine … this didn’t come up, that Rebecca might’ve been met with some of that resistance. I suspect… This speaks to how you and I interface with different audiences in our practices, because what you’re saying in terms of the strategic alignment of the senior most designers getting taken away and, retrenchment to production, I am not seeing that with the audiences that I’m working with. There is still a desire. I’m working with companies hiring sometimes their first design executive because they want a design leader in those discussions. Jesse: I’m not disputing that aspect of it. I’m definitely seeing that part too. Peter: I guess then it’s lumpy. Jesse: Yeah, it is lumpy. It absolutely is. It continues to be the best of times and the worst of times. Peter: A concept I’ve been recommunicating a lot over the past year is the Leadership Ceiling. Our conversation with Tim Kieschnick a few years ago now. And, there are folks who are hitting a ceiling that they can’t move above. But what the Rebecca story said to me is that I think too often designers make their own ceilings. They are so wedded to a particular space and way of working that when even given those opportunities they don’t engage them. They think that’s not what they do. Designers getting in their own way Peter: They don’t recognize it as an opportunity. I am generally far more critical, and have been for 25 years, of designers being the primary constraint on their own ability to have an impact, than anyone else in the organization. Because what I see elsewhere in the organization is people looking for someone with answers. People are looking for someone to show up with confidence, and if you can show up with confidence, you can make more change than you think you can. And I think designers lack that confidence often in new contexts. Jesse: That’s interesting because you’re suggesting that there is a cultural thread within design itself that holds it back. What you identified as this kind of reflexive passivity, this learned helplessness on the part of designers, or on the part of design leaders, such that they can’t see themselves as being bigger than what they’ve always been. Peter: Something you and I discussed a few days ago… In order to evolve, the need for ego death, right? They need to recognize that who they have been for 10 to 20 years is not serving who they could be and the impact they could have, and they might have to let go of what they thought were core aspects of their identity, say in craft, in some particular part of the practice, and be, you know what, I don’t define myself by my ability to model difficult interactive systems well, because that only was going to get me so far. I am needing to let go of that part of my identity and embrace a new identity in whatever that opportunity is that’s in front of you, whether as a leader or solving new kinds of problems. And, I mean, ego death is hard. That’s why it’s called death. If it was trivial, we would just be like putting on a new hat and be like, Hey, I’m a new person now. These identity shifts are challenging. Jesse: Yeah. Yeah. And certainly, if you have spent your career mastering a craft and advancing in your career by proving your value by demonstrating your mastery of that craft, it can be very, very difficult to let go of that mastery as being the source of your value. I think that for a lot of these design leaders, there is kind of a choice that you have to make, as to whether you’re going to take a more kind of operational stance where you are goi…

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44: The Mindful Executive (ft. Christina Goldschmidt) Mar 25, 2024

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Transcript Jesse: I’m Jesse James Garrett, Peter: and I’m Peter Merholz. Jesse: And we’re finding our way, Peter: Navigating the opportunities Jesse: and challenges Peter: of design and design leadership, Jesse: On today’s show, in a conversation recorded in November 2023, Christina Goldschmidt reflects on her first 60 days on the job as the newly appointed VP of product design for the music industry giant Warner Music Group. She offers thoughts on getting up to speed and finding early success as an incoming leader, profiling your stakeholders as if they were users, the leadership power of personal vulnerability. Peter: Christina. Thank you so much for joining us. Christina: Thanks so much for having me. I’m so happy to be here. Peter: As, usual for us want to start out just by getting a better sense of who you are and what you’re up to. I know you’re in a new role, so if you could just share kind of your professional affiliation and, what are you doing now? Christina: Yeah. Yeah. Thanks. So I have been in the field of digital design for over 25 years and that’s been many twists and turns. And I just started a new role as the VP of Product Design at Warner Music Group. And I’m just a few days shy of hitting my 60 day mark And so it’s a very, very interesting time to have a chat about that. And my role there is that I lead product design, which is both user experience design and visual design, but also working to build out our user research practice. Also, our brand new content design team, design operations, and making sure that we are just a fully functioning working product design team. Also adding things like design systems, things like that. Starting a new role Peter: It sounds like you’re introducing a lot of. new elements into the organization. Was that something that they knew they needed and were looking for the leader to bring it? Or was that part of a conversation you were having with them as they were talking to you? Like, oh, this is, this is what I would want to do if you were to bring me in. How did that conversation go? Christina: Yeah. So one of the things that’s really interesting is that my entire hiring cycle was three weeks and I’ve never actually had a job, I think that was that quick, except for maybe 25 years ago. And so that was a real testament to them knowing a lot of what they wanted in a leader, but also trusting in me to be able to come in and diagnose everything that needed to happen. And so we would have conversations along the way of maybe we need this, maybe we need that. So, halfway through the conversation saying, Oh, you know, we don’t have content here, so think about that. You know, that would be the kind of aspect of the conversation, but larger things like design systems the larger structure of how to build out research, adding design operations, those are things that they’re trusting me to really bring, diagnose and decide how to structure. Peter: What group are you in? Are you reporting up to a product leader or are you in a different kind of organization? Christina: Yeah. So, because Warner Music Group is a music company, I report to the president of technology. And so it’s very different than, say, my last job at Etsy, where we were a technology company and I used to report to the chief product officer. I’m still one away from the CEO, but I am in this interesting new space where our entire organization is the technology organization. So now my immediate peers are engineering, product management, and something called product solutions, which is really our liaisons with the various labels and business, business partners. Jesse: So you described this three-week sprint of a hiring cycle and, that just feels like this whirlwind where you have absolutely no time to prepare, no time to even really get your head around how you want to show up, who you want to be, who you need to engage with, how you want to engage. It feels like you had to hit the ground running and make it up as you went along. How did you start figuring out how to engage this brand new organization? A very different kind of a problem, different kind of context than you were used to. Christina: Well, I think that hiring process was sort of a, in a sense, a preview of what the job might be in the first year. Jesse: In a good way, I hope. Christina: In all honesty, right? Like, it’s a two-way street every single time you’re in a hiring process. And the concept is, is that it’s a startup within an enterprise company. And so being able to actually intelligently show up in a super fast hiring process, diagnose what they need so that I can show myself in my best light to them, shows that I can have basically a bunch of things thrown at me every single day and be able to diagnose that and move it forward. It’s not for everyone, we’ll just say that, right? This was not a role that was for everyone. Yeah. Peter: You know, one thing I’ve noticed, just following you on LinkedIn, is, and you mentioned it earlier, expanding the organization. Something else I also know about you is that you went and got an MBA at one point, so you know how to do math in spreadsheet form. Christina: Yes, Yes, I do. Peter: I’m sure your PowerPoint game is on point. But I’m wondering, what, if any, business case did you have to make around expanding your team? Was that something they had done the work to realize there’s some broader expansion and, we’ve already assumed it, or were you needing to argue for, may not be the right language, but help them understand the potential and opportunity and, thus do business casing. Like, how did you free up the resources for headcount? Christina: When you’re undertaking something like this, that’s the first thing you ask. Especially in such a short cycle you want to understand how open they are to design, how much they value it, what they think the role of design will be and therefore my role. I was actually very happy and pleased to hear right out of the bat that they were already planning and had already started to put budgets in, that were very appropriate for things that I would want to need. And so I did not have to actually make the business case. When I got in the door, there was definitely finagling, horse trading, and things like that. I will say that immediately from day one, I had to prove value, and have to make sure that I’m not going to lose those heads, right? But at least they understood and they value design and they see how important it is to build a really great product arm and that they had actually already allocated significant amount of head count to design. And that they left it up to me as to how to carve out that headcount. Jesse: I think one of the biggest challenges for leaders who are new to an organization, trying to figure out how to deliver some kind of short term value, is the fact that they just don’t know anything yet. They don’t know anything about the context. They don’t know anything about what people really care about. They don’t know what their priorities ought to be, really, in terms of value delivery. And so I wonder, how did you go about learning the landscape in order to figure out where you could start delivering value right away? Christina: Hmm. Yeah, so let’s be clear I don’t know anything. But I know just enough to be a little bit dangerous, right? One of the things that’s interesting about Warner is that their fiscal year starts in October. Planning was basically close to being done when I was walking in the door. And so, that was a really important time for me to understand where things were really important. By knowing what their major focus areas were, and getting involved to help them make a better PowerPoint, to present that to the executive leadership team to the CEO so that we could convey that story, I was able to then say, Okay, I now understand this because I’ve helped to better visualize it and help us tell that story better Jesse: Hmm. Christina: And then understanding what that is, talking more deeply of… what does this mean, and having basically weekly prioritization conversations every week to say, I could choose to do 1000 things this week. Which do we think are the top three, five that matter this week? And that kind of triage is really important. Jesse: Who are you having those conversations with. Whose opinions really matter here? Christina: Yeah, so it happens with my boss, the president of technology, and you know, I’m four in a box, right, with my other three peers. And it, oddly, is not happening all together. I’m having them as sort of more one-off conversations than triangulating it myself. But it actually is pretty consistent. They’re just nuances that come with it when you have it as individual conversations. And I actually think in our environment, it’s working very well because it allows me to be that filter as opposed to us trying to work very hard to get in a consensus mode, which, If I was trying to facilitate that, it would take us much longer than if I’m taking in quick information and then choosing it for myself. Jesse: Hmm. Peter: The speed with which they moved suggested they had a, and I think you said this, like a pretty decent idea of what it was they wanted. And I’m wondering, what was it about you that landed? What were those qualities or characteristics, and then perhaps related, how clear was your mandate upon arrival? Or is that something you’re having to tell them? Sometimes we hear from leaders who, their first three months is to figure out what their mandate should be. And other times, when they come in, there’s a pretty clear idea of what’s expected of them. Christina: Yeah. I can only report what they’ve parroted back to me, right? So there could be other things that I don’t know about why and how they chose me. But the question that they asked me for my case study was to present to the most complex project I’ve ever worked on. And they also were like, and it doesn’t matter if it’s like song and dance beautiful, just show up with some work. That was their instructions. That’s a very different sort of prep sheet than other jobs that I’ve seen and things like that. And I think that that really shows to me sort of how they think and what they value. Telling a transformation story Christina: And what I gathered was a massive transformation story that I had done previously in the insurance space, where I had taken extremely legacy systems, you know, things that are on green screens, things that look like they’re Windows 98, variety of legacy old systems where there are three different systems, systems that had stories about people needing over a year to get trained on how to use them, systems like that, and showing them how relatively quickly was able to diagnose, was able to prove that the system that my team was working on was actually going to be better without having A/B testing or statistical results. That I could actually leverage both quant and qual in a much smaller in-house pool as opposed to, what I might do at Etsy, which is A/B test very quickly at scale and be able to prove that with metrics and be able to make something that is simple, usable, beautiful out of something that was previously none of those things, you know, cause I think I have that idea that because we all have really stunning cell phones in our pockets now, right? These mobile devices, that no matter how deep into enterprise software or workhorse software that you’re in, everyone has a mental model of really beautiful, simple, elegant interface design now. And so there’s no reason for any tool to not take the, like, deep, really thoughtful customer experience into mind there. I think that philosophy also really was exciting for them, too, that I also had had experience bringing that kind of consumer facing interface design and simplified user experience to actually enterprise-based software and it was for, actually, business improvement, right? Things like reducing training, improving time on task, that is also always about making the experience better, making tangible metrics better, being able to prove that value. I think that that was a big part of that story for me. And that I was able to show them that case study that they were like, Oh, this is exactly our problem here. You get it and you’ve done it. After, you know, one 30-minute conversation with the hiring leader and one, 30-minute conversation with the in-house recruiter. So being able to pull that out, I think made it look like a good fit. And then the other thing that I think was helpful was that they were signaling that this is a hands-on role and you know, my last job was very much at scale. Very much where I was primarily doing operations and improving the way my team worked. Yes, I would have regular weekly reviews. Yes, I would think about the holistic customer experience, but my job was not day to day in our products and making them better and leading designers day to day. I had an entire, you know, hierarchy of managers and directors underneath me who I deeply trusted in order to do that on a day to day basis. Here we’re a much smaller organization, where my ability to still give day to day design decisions is actually important. My ability to still be able to do that and to show that I could still do that, learn and talk about the work and not be just at a pure operations level, I think was also helpful. And, to understand, I think, part of the larger value proposition to go to your second question They didn’t fully articulate this to me, but I could see it immediately when I walked in the door, is that you know, there are three major, like, music companies out there, right? And we’re one of those, and it’s a great time in the music industry where there’s all this growth and really learning how to leverage streaming to make the business better. It’s a time for great innovation. But not all of the experiences are really, truly human centric and don’t actually meet the mental models of the users or the customers that use them. And so to be able to actually bring innovation, to bring the tools of the trade of helping the team use more modern design techniques, really upping their game, so that we can look at design as a center of innovation, so that we are more competitive, that we can produce software that will gain us more business, that kind of aspect is definitely an aspect of my job. That it will be a competitive differentiator that the experiences that we make and the software that we ship will actually help us improve our business. What does it mean to be ‘hands-on’? Jesse: So you raised the question in here of how close you actually get to the work as part of your role. And for a lot of the people that I talk to, stepping from a highly leveraged operational oversight kind of a role into a role where you are closer to the design work, you’re kind of sleeves rolled up in it, for a lot of people that raises this fear that they’re not actually progressing as leaders, that this represents some sort of backsliding toward craft and away from leverage. And so I wonder what it was like for you to step back into craft and how that has affected how you see yourself as a leader. Christina: I think one of the things that design leaders have is craft and that it’s our, not to reuse this term again, but it is our competitive differentiation as a field. Jesse: Mm. Christina: That there’s lots of overlap with the people that we work with every day, right? There’s this Venn diagram of, oh, we can set strategy together. Oh, we can determine technical feasibility together. But the craft is the thing that we do and that we own. And so as a leader, when I had an organization at scale, I never actually hired managers who did not come from craft. You know, there is a school of design leaders who are wonderful and design managers who are wonderful and are great managers. But there can be a lack of credibility with them if they actually have never done the work t…

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43: Leading Enterprise UX for LEGO Group (ft. Rebecca Nordstrom) Mar 09, 2024

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Transcript [This transcript is auto-generated and lightly edited. Please forgive any copy errors.] Jesse: I’m Jesse James Garrett, Peter: and I’m Peter Merholz. Jesse: And we’re finding our way, Peter: Navigating the opportunities Jesse: and challenges Peter: of design and design leadership, Jesse: On today’s show, one of the largest scale and highest precision plastics manufacturing operations in the world belongs to Denmark’s LEGO Group. LEGO’s Rebecca Nordstrom leads the team designing the software they use to produce those billions of little bricks. She joins us today to talk about bringing UX to the factory floor, measuring success when user adoption is mandatory, and the differences between leading design in North America and in Europe. Peter: Thank you so much, Rebecca, for joining us today. Rebecca: Thank you for having me. Peter: Typically we start our conversations with a very easy question, which is: who are you and what do you do? What’s your job? What’s your role? Tell us a little bit about yourself. Rebecca: Yep. So I am the head of digital product design for our area inside of digital technology inside of the larger LEGO Group. So, LEGO Group is a little bit of an onion organization, if you will, and inside that we have digital technology, which is responsible for all of the external digital tools that our customers and play experiences support, but also we have a lot of internal. And then I am in charge of a digital product design team of around 20 folks and we are primarily supporting internal-facing applications. So, these are supply chain and manufacturing. So it’s a little bit of a different flavor. And I hope that listeners are not disappointed that we’re not going to talk about the fun LEGO play experience. But I think we really do some fabulous work where it is focusing on enterprise design work, supporting folks in the factories, folks in supply chain, and it’s a lot of really tricky, complex problems. But we also get to deal with a lot of kind of cutting edge technology and the things that we interact with, which is really fun. Peter: You mentioned the factory and supply chain, like I’m assuming there’s like internal design and development. What’s your relationship to that, if anything? Rebecca: Yeah. So for the internal design and development, we have product teams, and my team is the design resource into those product teams. And then we have product managers, which sit on the business side. And then we’ve got engineers inside those product teams as well, which sit kind of in the same area as me in digital technology. So, the product teams straddle both sides of the organization, if you will, and then they are dedicated into kind of user group areas within LEGO. So we have a product team, for example, all around packing. And so that is supporting all of the packing functions that help produce the finished LEGO good that leaves. Yep. I don’t know, I feel like, I feel like the stuff that happens behind the scenes in large organizations like LEGO is like this hidden gem that nobody really ever talks about or looks at, but there’s so much interesting things and like fantastic work happening there. Design for Internal Tools Peter: What’s the top thing that no one knows about that you wish they did? Rebecca: I think one is that we, we strive to create those play experiences for our internal employees inside LEGO as well. So even the factory workers should get that fun, enjoyable experience because we have that people promise to them. So we are creating, you know, polished end products, even with like the little microinteractions and animations and all of those things into it, for the factory workers. And I think that’s something that, unless you really, like, pull back the cover, you would never know that about LEGO. And we do that in a lot of organizations, actually, not just LEGO, but I think we have a high promise to our employees in that way. Jesse: it’s fascinating to think about the tension between playful experiences and supply chain and manufacturing logistics. And so I am curious about how products even get conceptualized in an environment like that. I feel like a traditional, kind of, requirements definition approach is not going to quite capture it for you guys, right? Rebecca: Yep, so typically we are approached with a business problem that needs solving. Either that we need to cut down the cost for manufacturing the finished good, that’s the one that we are constantly kind of battling year over year, because we always need to drive down cost, right? And so then what we do is we work with business. So the designers will go out and start researching with business on the processes that they’re involved in and start to identify different areas where we can change the process, and so, in that way, a lot of time, we’re not doing kind of traditional digital design in that way, but it’s really looking at end to end process, and how do we redesign the entire process and experience that we’re supporting in the shop floor. And how can digital tools play a role in that, and then working together with business to kind of tear that apart and put it back together. Jesse: I imagine that entails a different kind of a partnership with the business than you might see in other places. Because you need that deep process expertise at the table, right? Rebecca: Yep, so we have designers embedded into the product team. So they’re not, we don’t work as a agency or consulting centralized team. We’re embedded into the product teams, and in those then the designers over time are getting those relationships with all of the stakeholders in the business, but they’re also getting a lot of domain knowledge in there. So you can go in and talk to the designer that’s working in the molding area and ask her about all of the different settings and all of the processes to do with like molding and manufacturing. And by the way, LEGO is the largest producer of tires in the world. If you don’t know that. So like we are, we are a massive manufacturing company actually, and that’s kind of at heart of what everything does. And so the designers really deeply know those areas and those processes, and they are experts in their own way of that. But also you need that expertise to be able to talk to business about it too, because it’s not, it’s not an app for buying a cup of coffee where it’s super relatable, Jesse: Mm hmm. Rebecca: it’s getting into these really complex and engineering-focused processes. And so you have to be able to speak a bit of the language with the users for them to trust you and to open up. Peter: Nothing against apps for buying cups of coffee. Rebecca: No, those are, those are wonderful too, but I think, I think it’s like a totally different end of the spectrum of like what we deal with. Yeah. Peter: I’m wondering then, as you’re looking to build your team, right? Because you’ve had looking at your LinkedIn, I’ve seen you’ve had jobs in corporate America. I don’t know exactly… I saw Capital Group and Kaiser Permanente, so large legacy organizations. Then you’re now at LEGO. You’re working in this really specialized environment, like, like an uncommon one. Hiring for specialized environments Peter: Not that many people are probably working on the design of manufacturing and supply chains. And I’m wondering how that, that has caused you to shift how you approach recruiting and hiring, or your orientation on skills. Like what is it you’re looking for in building your team that might’ve been different than the kinds of things you were considering in the past. Rebecca: Yeah, I think one is, people that really fall in love with the problem, right? So it’s not people that are super focused on the solution all the time, but that can really fall in love with the problem. So they are willing to spend time investigating that problem, spend time understanding it, and really understand all of the, the nuances and edges to the problem. So we get these like really crazy wicked problems of… you have all of these VPs and stuff and they’re looking at it and they’re like, we don’t know what to do. And then we get some of the design team in there. And so they need to fall in love with that problem as number one and really enjoy that it is complex. And you’ve got some really amazing designers that that is their sweet spot. They don’t, they don’t want the, the easy showy stuff. They want the stuff where they know this is going to take a bunch of iterations to really smooth this out and understand where the places that we can move and where are the places that we can’t move. So I think it’s, it’s that problem that’s number one and then the other one is just really strong collaboration skills, because part of what we also face on a regular basis is the change management portion of design as well. So for like consumer-facing things, you can kind of release it. And then the adoption of it as a proof point that you’ve made something of value to the consumer-facing audience. That’s not really true when you talk about internal applications, because it’s a mandated use of those applications, and so the adoption of it and the change management of that is a totally different beast, right? Where you need to be working with the training organizations to understand what are their obstacles around the change that you’re proposing, working with all of the different local teams that should be adopting it to also understand what’s their point of view because they adopt, like, local practices towards their work as well. So it’s kind of the problem, and the stakeholder management, and collaboration and the ability to kind of lean into those things. So it’s, it’s maybe less of a traditional design role where you’d get a brief and then get to kind of rock and roll and create something that’s really, really fun in that aspect, but enjoying the other types of problems in there. Jesse: And in your role as leader, how close do you get to these problems? Rebecca: So when I joined LEGO Group five years ago, I was actually an individual contributor in a team. And I was the first designer that they hired in to my area inside LEGO Group. So at that point I was kind of acting as individual contributor. And then over the last five years, we formed a team of 20 people and I’m head of this larger department. And so I’m more triage for some of these things and to be the glue between all of the different applications that we work on as well. So when we have supply chain and manufacturing, all of those pieces need to kind of flow together this bigger system design. And so my role now is kind of to look across and to spot where we need teams to be collaborating, where do we need designers to be collaborating, and then encourage as much as possible for our designers to steal from each other with pride. Like don’t, don’t keep reinventing something. Like we have our Figma files completely open and people should be in each other’s Figma files. They should be copying each other’s work. They should be leaving comments and asking questions and trying to, to bridge it so that it is cohesive across. Jesse: Well, it’s this interesting balance that you have to strike because you have this need for deep specialization and expertise, kind of team by team. But then you need something that’s going to hold all of them together in some way. How do you do that? Rebecca: I think one is, so I’m partnering with the heads of product in that way to create kind of the bigger picture of those larger cross-product initiatives that need to happen. And part of that is also the vision and they’re calling it roadmap. And I really cringe at the word roadmap usually, but, so they call it roadmap of where manufacturing should be going. So part of it is to see, okay, in, you know, 3, 5 years, what is the ambition from the LEGO Group of where they want to bring supply chain and manufacturing, and from the knowledge that I know about the product teams, how does that piece together to move towards that, and then we have a lot of recurring sessions together with the heads of product and engineering and the product teams to then review what they’re planning to work on and get it there. So I think it’s more in that trio function, I’m playing at kind of like that leadership level to then steer the direction of the product teams and help coach the designers to support that bigger vision. Jesse: Mm hmm. Rebecca: But it’s, it’s chaos, honestly, right? Like it’s, you know, it sounds all good and it sounds like we have a nice plan and a path there, but it is constantly things popping up and it is a bit chaotic, but that’s part of the fun. Peter: Chaotic because you’re responding to what? Rebecca: Chaotic because we have 30 product teams and 600 plus applications inside those 30 product teams. And then we’ve got 5 factories, soon to be 7 factories around the world that each have their own set of stakeholders and want to have a say in what’s going on? So it’s, it’s a big communication game sometimes. Jesse: And are you also operating in that trio mode when you’re engaging the stakeholders? Rebecca: Yep. So we try to have the trio within the product team. So with one of the designers in the product team, the product manager, and one of the more senior engineers, and then we also have the trio at the leadership level. So head of design, head of engineering, head of products working together and this kind of trio at the leadership level. That’s the one that is engaging with a lot of the different stakeholders across the factories and across the supply chain, because they also have those kind of leadership hierarchies and are trying to put together plans at these wheel levels or leadership levels. Yeah. The intersection of physical and digital Peter: And you’re… I’m curious. You’re the head of digital product design. So your team is largely building software or designing software. And that’s what these groups are doing. But I, I’m imagining there’s a need for integration between your software stuff and some form of hardware physical manufacture… like when I think manufacturing I’m thinking giant robot arms moving things around, and so like, where does your design end? Where does other design begin? How do you coordinate and integrate with teams to make sure that it’s all coming together? Given what you said about the chaos, I can imagine part of the chaos is all these different modalities and kind of ways of working. Rebecca: Yeah, no, you’re totally right about that. I think with the integration with the hardware that’s in the shop floors and the factories, that is a different team. So there’s a operations technology team that handles the purchase and design of that hardware, but by and large, it’s off the shelf purchases for that. So that team is kind of screening which hardware we should purchase. And then it would come into ours to deal with, okay, how does somebody actually interact with that hardware now? And more and more we’re learning that that decision, when they’re purchasing the hardware, needs to start engaging with the design team as well, because we see that we purchase a lot of hardware where there’s built-in interfaces that are completely unusable, or there’s clashes between the way that the hardware operates and the process of how the user actually needs to interact with that hardware. So, I think more and more, we’ve kind of learned our lesson that it needs to be this holistic approach where we have the design team, the product team, and this operation technology, all looking at the tools that we’re buying, both in terms of software, but also hardware, to make sure that it actually works together. And we have a couple more collaborative initiatives that we’ve been running more recently where that’s been really successful. And it has been a nice kind of proof of concept of that collaboration. But I think the integration with the hardware is really like a fun thing for the tea…

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42: Leading From Trust (ft. Cynthia Savard Saucier) Feb 23, 2024

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Transcript [This transcript is auto-generated and lightly edited. Please forgive any copy errors.] Jesse: I’m Jesse James Garrett, Peter: And I’m Peter Merholz. Both: And we’re finding our way, Peter: Navigating the opportunities Jesse: and challenges Peter: of design and design leadership, Jesse: On today’s show, Cynthia Savard Saucier, co-author of the book Tragic Design and VP of UX for the Canadian e-commerce giant Shopify, joins us to talk about what’s worth fighting for and what’s not, sharpening the business acumen of her teams, and the strategic value of kindness. Peter: Hi, Cynthia. Thank you so much for joining us. Cynthia: Hi. Thank you for having me. Peter: So, if you could share with us what your role is, and I’m curious, because I know you’ve been there for a little while, how your role has evolved. Cynthia: Oh, yeah. One answer is faster than the second. So my role is four letters: VP UX. I like it. It’s very short and easy to reply. I’m vice president of user experience at Shopify. At Shopify, we use UX as a overarching word for content design, research, and design as well. So I lead all of those disciplines. In the past, I’ve had other roles at Shopify. So I started there almost nine years ago now when it was a much smaller company. I started as a designer, IC on the team. I was leading a smaller team at an agency before that, but I chose to join a tech company as an IC, and then I grew from designing the thing to leading one person and then the Montreal team, and then eventually becoming a director and then eventually leading the whole discipline at Shopify. And then recently I just made a bit of a horizontal shift where I chose to focus on the product. So now I am VP of UX for core. So I directly manage a team of around 200 people-ish in UX for core. Core is the core offering of Shopify. So it’s mainly the admin experience for our merchants. So that’s how I went from IC to VP in nine easy steps. Peter: Thinking about the organization, I know Shopify has gone from having a centralized UX org to a federated UX org. Did it then go back to centralized and now it’s federated again? Cynthia: It’s a bit of both, actually. So we had a chief design officer that was the co-founder of Shopify. So he had been there from the beginning. And when I joined Shopify, I was actually reporting into Daniel, who was the co-founder. However, as the team grew, we then went into product lines. So the whole organization got split into like a bunch of, I think, seven groups. After a while, we just reached the edges. Like we were, we were, like the seams were cracking from these groups or organizations, and then we reorg-ed the company into two larger groups. So there is core and merchant services. And now all of UX reports into UX into core and all of UX reports into UX into merchant services. So it is somewhat functionally reporting. All the way up to me and Andrea Manini, who is the VP of UX in merchant services. But under that, if you are a UX or you report into a UX leader all the way to me basically. So it’s federated and functional at same time. Peter: Andrea doesn’t report to you. She has a different… Cynthia: Exactly. So we both report into the leaders of these groups, basically. They both happen to be from product, but it’s not that UX reports into product. It’s that we happen to report into the person that also leads product. Peter: And given that you have these two UX teams, is there anything that’s holding the center of user experience at Shopify, or is Andrea able to kind of “do whatever you want,” and maybe it starts to diverge, or how do you make sure this stays aligned across your orgs? Jesse: Well, even beyond that, I want to ask, is it actually all that necessary for the two teams to be aligned or are you really separate worlds entirely? Cynthia: I mean, we are separated in many ways. However, we are touching very common user experiences. So for example, the core, the admin of the product. While I own the scope of the majority of it, there are still a lot of services that merchant services, the other organization, is responsible for bringing to life, and this does get introduced into core. So we do need to be very tightly aligned, but ideally loosely coupled. And this is why we have different leadership structures. There’s many ways we create, like, a centralized organization, like a centralized culture, centralized discipline, hiring practices. Leading The Discipline, Maintaining Coherence Cynthia: So this is through discipline work. So that was a role I used to have, which was leading the discipline of UX. Leading the discipline doesn’t mean everyone reports into you. It’s more like all of these horizontal tasks. So you can think of design, or UX ops, recruitment, hiring the big goals of the organization as well. What’s the makeup of the discipline? How many people? How should it grow? So now this is something that Andrea does. The discipline is horizontal, so we look at it across all the teams. However, the ownership of the user experience and, like, really how that transpires into the product, this is reporting into both of us basically. And the way we achieve unity or cohesiveness to a certain extent, well, first of all, we have a design system. So we have Polaris, who’s a open source design system. It’s, it’s a really good design system, actually. Peter: It’s one of the OG design systems. It’s been around forever. Cynthia: It’s one of the OG ones, yes, yes. But it’s still very well maintained. We’re at v12, that was just released, not too long ago. So the design system is one of the way that we achieve like some sort of alignment. But overall we have design principles, we have design values, and really we work with each other as much as possible. Like this whole idea of like providing a lot of feedback, getting really involved, not being afraid of going into details as well, is definitely one of the tools that we utilize to make sure the experience just works together. The whole principle of, like, not shipping the org chart is very important to us, and our merchants are using our admin without any understanding that the organization might be organized a certain way or not. So it’s very important for us not to let that bleed through. Jesse: You know, when I hear stories about these kind of horizontal leadership models where, and correct me if I’ve got this wrong, but, a case where people are driving outcomes across teams that don’t report to them… Cynthia: mm hmm. Jesse: …and they are, attempting to influence the organization on a broader scale than the reporting structure itself actually provides or allows. And what I hear from folks in a lot of these cases is that this is a recipe for frustration, disappointment, and disempowerment. And so I wonder. If it’s working for you guys, what do you think is making it work here? Cynthia: Yeah I mean it requires a few things but first and foremost like it’s a set of tradeoffs. Like there’s no magic answers. You could have everyone report into a single person, and that would be good for certain things but really bad for other things, such as the decoupling of decision making, or it is impossible for any one person to have context on every single piece of the organization of the product. Really, the product is really complex, but also, like, I fundamentally believe that different organization makes decisions differently. But that’s a feature, not a bug. We want the growth team to be a little bit more gutsy. We want the growth team to be more aggressive with the features that they’re willing to test out. And at the same time, we want and we need the core team to be a little bit more resistant to creating a lot of quick iteration. We want it to be more foundational. And that is also part of how we achieve good results. So to me, like this is a trade off that we are making, but one that works for us. I have been in this situation before where I had, like, to influence without the authority, which is what you’re referring to. And yes, there are pieces that can be frustrating, but like, I think I’m an eternal optimistic. Like, I, I can recognize that something can be frustrating without being frustrated about it. And this is what I try to tell people as well, that like, hey, the disempowerment that someone might feel is actually just a misreading of the priorities, because in the end, our CEO actually really, really believes in the importance of UX as a discipline. Like I don’t need to sit down in a room with Tobi and explain like, “Oh no, UX is important, Tobi, please remember that it needs to exist.” We don’t have to fight for that. It’s a given. It’s actually like our CEO has to remind us sometimes like, “Hey, fight for yourself,” because we don’t have to do it naturally. And because Shopify doesn’t have to fight for UX most leaders that have grown at Shopify were not selected because of their ability to fight for UX, if that makes sense. So. I mean, we do have the classical executive sponsorship, so this is not something that at the discipline level you need to convince up and down. It’s just about convincing down and bringing people together. And then when you are that person that is trying to create that cohesive experience or culture, of course, like some people are motivated to ship their thing and you might get in the way of doing that. So there’s a lot of negotiation, there’s a lot of conversation that needs to happen, relationship building as well, like only through trust can you achieve anything really when you don’t have authority. But I operate from a place of, you know, I have a trust bank and then sometimes I need to make withdrawals, and sometimes I put back trust in the bank, and this is how I achieve anything basically. Accountability for UX Peter: I’m curious how you are held accountable as the head of UX for core products. Like does your boss have a set of things that are expected of you, to deliver outcomes, impact, anything like that, that is somehow specific to UX separate from the work of the product team. Cynthia: Yes, the answer is absolutely yes. My boss, my manager, Glenn, basically leads core, will absolutely come to me if an experience is broken, if something is suboptimal, if something is not as good as it should be, if there is a visual bug, but sometimes other types of bugs as well. So I think it’s hard to really define precisely what my role is. Like, we always say, like, aim, achieve and assemble is the framework we use, but I don’t think it does a great job of explaining everything that I’m expected to do. But mainly, I could not do anything about the discipline. As long as I have the right impact on the quality of the user experience, I’m doing my job at Shopify. Like we are very product-impact-driven and, like, what that means for me is ensuring that our product gets better every day. If I do this, I do my job. Everything else are tools that I set for myself to achieve that role better. So my boss doesn’t care about what culture I’m creating on the team. My boss does not care about what tool I’m putting in place, or systems or processes or any of that, as long as I have the right incentive structures in place for my team so that we achieve great UX. That’s all that he cares about, but he certainly cares about it and will hold me accountable for the quality of the UX, of anything shipping under my scope and sometimes outside of my scope as well, as he rightfully should. So if something ships from a different team that happens to touch a surface area that I own, and I didn’t pay close enough attention, I wasn’t curious enough, I didn’t get involved enough, that is on me, because in the end, our merchant don’t care. If I’m the boss or not, like they are using a page and if it doesn’t work appropriately, I don’t get to say it’s not my fault, it’s this other team. That’s something that we really don’t ever want to say at Shopify. The Trust Bank Jesse: So this shift into taking more responsibility for the outcomes was a natural result of your moving from a position of influence without authority to a position of authority, and you mentioned that when you were trying to wield that influence without authority, it all relied on what you described as the trust bank. And I love that that metaphor for it. You know, a lot of leaders, as they are moving into these executive levels for the first time, they might not have a trust bank to work with yet. And I’m curious about, now that you’re in this role where you do have the authority, how does the trust bank still play into how you do your job, and how can someone who’s stepping into that role go about building that trust bank for themselves? Cynthia: I really like that question, because it is unfair for me to assume that everyone has been at a company for 10 years. And I have, I’ve grown and I’ve been in every position, so I have a really good idea of, like, the context and the people and the organization, and it’s not true that everyone comes in with that, so that’s actually a great question. Trust plays a role that people misunderstand sometimes. They believe that the exchange currency between an employee and a manager is money. But really, that’s not the case. Money is a currency between the company, the employer, and the employee. A manager, an employee, the only currency is trust. And if I want my team to achieve anything, I cannot just use authority because they can choose to not listen to me and that’s it. It’s about trust. It’s trusting that I will say the thing and if they achieve the thing that I have said, they will be properly rewarded for that thing. It’s believing that the thing I say is closer to the end result than if I didn’t say that thing. It’s trusting that I understand enough about the craft that I’m not going to send them in a crazy goose chase, trying to find solutions that don’t exist. So that’s a trust that I need to build even with people that are reporting to me. Trust is multiple things and you don’t just have it by magic. It’s three things. So, it’s interpersonal trust, it’s disposable trust, and institutional trust. So disposable trust is, as a person, how likely am I to trust? This can be influenced by like, have I been scammed in the past? Were my parents trustworthy? So this is very individual. This is hard to influence. And you have to recognize that you are interacting with people. They have their own ability to trust, and this is something that is hard to navigate. However, if you know that you’re with someone that is less likely to trust, you just need to build a lot more trusting moment, because trust is built. In order to build trust, you go through interpersonal trust. And that is basically, like, how credible are you? How knowledgeable are you? How likely are you to do the thing that you said you were gonna do? Do you have a lot of experience achieving the thing you said you were going to do? So, if I need to do something with someone that I know is not trustworthy, I will say a lot of small steps, like I will say a thing and then do the thing. And then I will request for them to do the same thing. And this builds mutual trust together, until we are in that stage of like, they know they can trust me. I know we have to create smaller trust steps, if that makes sense, instead of just pointing at the mountain over there. There’s also institutional trust, and that is really hard, because the institution is really anything that is supporting the trust relationship. So that can be the organization, the company, but it can also be like the banking system, or technology, or the stock exchange, you know? It’s all of these institutions that are underlying the trust relationship. And again, this is really hard to build on that trust. But if the person doesn’t trust the institution, if I have an employee that doesn’t trust Shopify, there’s very little that I can do as a manager to change their mind. I can try to explain better certain st…

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41: Leading Experience Design for the Military (ft. Colt Whittall) Feb 05, 2024

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Transcript What follows is a lightly edited transcript produced by our podcast software. It may retain some textual glitchiness. Jesse: I’m Jesse James Garrett, Peter: And I’m Peter Merholz. Jesse: And we’re finding our way, Peter: Navigating the opportunities Jesse: and challenges Peter: of design and design leadership. Jesse: On today’s show, “mission critical” takes on a whole new meaning when you’re the Chief Experience Officer for the United States Air Force. The first person to take on that role, Colt Whittall, joins us to talk about getting things done when you have more influence than authority, finding meaning and purpose in government service, and taking risks in an environment where failure is not an option. Peter: So Colt, what I’m curious about is, I think this is a new role, right? This role didn’t exist before. I don’t know if it was created for you or if someone had the idea and then found you. But why were you the right person to be the first Chief Experience Officer at the Air Force? Colt: So, great question. First of all, yes, this was a brand new role. Well, let me just tell you how it was created, and then we’ll talk about, why was I picked to do it? So it was, it was really created because the Air Force knew we had a user experience problem, primarily with IT but also with software. We had a lot of complaints. And this has been going on for years, and I think there was a general sense that maybe things were getting worse and not better. And so the CIO at the time knew he had an issue. He also had an understanding of the importance of software, which, the CIO role is a little different in DoD, their control of enterprise IT is fairly direct, but their control of applications is less direct as in a corporate environment. There’s generally control of those that’s spread out amongst a bunch of different organizations. He knew he had an issue. He had some authority over it and wanted to create this role. Then why me? I came out of about a 20, 25 year career in the digital agency space, digital consultancies. I was at Deloitte in the nineties, built one website after another and mobile app and so on from. 2000 to 2018 with a digital agency that we spun out of Deloitte and did a lot of fantastic work in a variety of industries, media, health care, wellness, travel, hospitality, financial services, and some federal government. And Bill Marion, the CIO, had been a client of mine at one point. And so I had a, probably a fairly typical background for people that listen to your podcast, right? A mix of digital strategy and user experience and customer experience. And by 2018, I was at the equity partner level, practice lead kind of level. And we sold the company and we were looking to get out. And so that’s what I did. And took a little time off. I had always had an interest in federal government and user experience and technology in the federal government. And when I was in graduate school I pursued it a couple of different ways and kind of built on that. Did internships in DC. One of them had to do with high definition television. I worked on the high definition television project for AT&T, interacted a lot with their government affairs group with Bell Labs up in Summit Hill, New Jersey. And then I did an internship with the FCC. It was set up by my thesis advisor, who’s named Dale Hatfield. And worked on the first ever narrowband PCS auctions. This whole idea of the intersection of technology and government’s always been a big passion of mine. And so after a career in the digital agency space , I happen to know some people in government. I approached Bill Marion, Bill Marion had a problem. He knew me, didn’t know a lot about me, but he, he knew enough about me. That on LinkedIn , I basically just said, “Hey, Bill, I’m thinking about going to work for the government for a while.” In my mind, I’m thinking US Digital Services or something like that, which you may have heard of. I wanted to talk to Bill because I knew him and I need a little advice. Like, how would I even go about this? , I don’t want to just go looking for, jobs on USA Jobs and just start submitting resumes. I’m like, there has to be a better way. And Bill responds on LinkedIn five minutes later, says, “meet me at the Pentagon on Tuesday.” That’s literally what he said. And I flew up and I met with Bill and we started talking about the challenge of user experience and performance across IT and the Air Force. And I think we began to formulate what this role could look like and that’s really it. Most of my background, as you just heard, is more in the software and application, and more consumer and outward facing. However, a lot of the tools we need to fix our problem internally for airmen– which is what I focus on, I barely touch the external facing web stuff at all– but a lot of the same tools apply internally for the applications and systems and IT that airman use. The Scope of the Chief Experience Officer Jesse: So I think it might be a little challenging for folks to conceptualize what those needs might be inside the Air Force. Why you would need a chief experience officer. I would love to hear a little bit about, to the extent that you can without committing treason, the communities that you serve, a little bit the broad use cases that you’ve served just to get a sense of the scope of the challenge that you’re really talking about here. Colt: Sure. The scope is huge. I mean, first of all, think about all the missions that we do, right? You know, first of all, we’re the, air force and the space force. Jesse: Right. Colt: Delta Airlines has, I want to say eight or 900 planes. We have over 6, 000. All right. So it’s huge. And we have a vastly wider range of aircraft, right? Both fixed wing, rotor, drone, all of it. Right. Plus we have the space force. We fly satellites. We work with contractors that launch us into space. We do all of that. Right. Then we have land base missiles. We have air defense type stuff and radar installations of all types. All of that it, all of those systems have an IT component to it. All of them, right? Just one, for example, we’re replacing the Minuteman missiles that sit in ground based silos. It’s a program called Sentinel. That will have big deadlines coming up over the next few years because we have certain timelines that we have to hit. But there are 10, 20, I don’t even know what the latest number is, there’s a number of systems that support all of that. Everything from the logistics to the control, to all of it, right? All of that has to be designed and built. So we have, you know, I was talking with the CTO of a major, well, I’ll just say it was Coca-Cola, several years ago, and he was telling me about the number of systems they have. First of all, they have more than I would have thought or a global organization, right? I thought there’s a lot of duplication, right? They’ve acquired a lot of companies over the years. Yada, yada, yada. We have many, many times more than that, right. Jesse: Mm Colt: It’s a big complex. Okay. Now, so you got all these we have, let’s call it 700,000 total airman contractor. That’s active duty guard, reserve, civilian, and contractors that are like on our networks in our systems. Call it 700,000 plus or minus. And they are interacting with, call it, there’s maybe 40 systems that have more than 50,000 accounts, quite a few of those over 500,000 accounts. And then there’s this long tail of systems that go all the way out to very tactical things, some of which are extremely mission important, that might only have a few dozen or a few hundred accounts, right. And they’re doing everything imaginable, right? They’re flying satellites, they’re handling logistics, all of it, right? They’re putting together schedules of flights and sorties and getting fuel on planes and recording the hours of pilots and crews and making sure it’s scheduling of all of the above. And then you’ve got really mundane things like getting people paid on time and dealing with health care and booking their flights. It’s everything that a typical large organization does, plus all of these other long tail of missions. And then on top of that, just to make it even more complicated, we are literally around the world and supporting a lot of hardware out there. Across Levels of Security Colt: And then we’re doing it at multiple different information security levels, which if you’ve never dealt with information security in this kind of an organization, it gets a little crazy, right? Because you’ve got completely public information, right? Then there’s unclassified and essentially public, like the public could have it. And then there’s controlled unclassified information, which is just things that aren’t publicly releasable, but they’re not classified. And then there’s secret, top secret, and various flavors and things above that, So, it’s a complicated environment. And these systems, think about it, some live at one level, some live at another level, some live at the other level. So it, it is a complex environment. It’s not unique to the air force and space force, right? This is across all of DoD. Developing an Agenda Peter: Given this complexity, I would imagine a big challenge in your role is maintaining focus, figuring out what, what to work on. And I’m wondering, when you joined and then maybe over your time there, something that we heard from prior heads of design was the importance of some vision. Not necessarily destination, but generally a direction they were trying to move things towards. And I’m wondering, did you have something like that when you joined? Or what did it take for you, because it sounds like this was probably a new environment, to realize this is what I’m here to do. This is my personal North Star. And then how did that help you make sense of this complexity, where it would be very easy to get overwhelmed by all the things you could do, and you needed to focus on the things that actually advanced your agenda toward that vision. Colt: So we definitely have a vision now. But it took a little while to evolve. It’s not that the vision evolved. The way that I talk about it got clearer and clearer. And it can probably be clearer still. When I took this role it was June of 2019 and like any kind of incoming executive, I kind of set the expectation there was going to be about a 90 day sort of study transition kind of plan, and then I’ll come back with an approach. And the good news is, after that meeting at the Pentagon with Bill, I had about six months while they were creating the job, and I had a pretty good idea that I was going to get the job. So I had a lot of time to prepare. And it was a little bit my sabbatical, or you know, I call it my gap year. So I had a lot of time to prep. So I came in with a lot of preparation. Then I had my 90 day transition. I booked a lot of plane tickets. I visited a lot of places. I talked to a million people. I looked at a lot of data. I’m a career professional consultant. So I came back with a nice, big, thick document. And I thought it was very well- structured and clear. And , like a good senior executive in the federal government, my boss said, “Love it. On board. This is exactly what you need to do, but it’d be better if you could put it in a placemat.” And I’m like, okay, can do. Put it in a placemat. And did a lot of talks and you can actually go out and you can go on YouTube and you can actually find videos of me presenting my placemat in public events and the placemat was helpful, but it wasn’t clear enough. Colt: And so not long after that, people were asking me, Colt, okay, love the placemat, but what’s our strategy? And we needed something that applied to both enterprise IT and software that people can understand very quickly. And so essentially the strategy is, we’re going to treat airmen like they’re customers. Which is a big shift in mentality in a government organization. So we’re gonna treat our airmen like they’re customers. As if we’re a major IT services company, like a Microsoft or Google or somebody else, right? And so we treat airmen like customers, and then we’re going to measure the experience from their perspective. And then we’re going to track that over time, figure out how to make it better and manage service levels. Fundamentally, that’s a strategy. So it’s an outside-in type of user-centric approach focused heavily on measuring experience, because that’s something that we can do at scale. I mean, think about the scale of the organization I described earlier. I can’t think of another way to do it. Well, there’s many challenges with user experience, but one of the challenges with user experience is, at the end of the day, it improves system by system, application by application, user journey by user journey. And so we needed a way to kind of say, okay, how do we go set the bar, measure the bar, figure out where the bar is, and then start trying to get the entire culture to move the bar up. We needed a clearer, more succinct strategy and that’s when I got down to, okay, here, the strategy is fairly concise: treat airmen like customers, as if we are basically a big IT services company, and measure user experience from their perspective as they’re doing the mission. There’s implications to all those things, and then track it over time and manage service levels, you know, to improve them. And that is fundamentally the strategy. People seem to be able to understand that very easily at all levels. I talked to general officers, totally get that because they apply similar techniques everywhere. You know, the organization understands all aspects of that. They understand about measuring service levels and managing service levels. Once you start putting user experience into those terms, an organization as big as with these kinds of missions can grab on to it and say, yeah, that’s a good way to do it. Jesse: This is fascinating because it feels like such a shift for you, away from consulting work, which I know that you’ve done for many years. And I’m curious because it feels like there’s an element of consulting, which is about get in, make the strategic impact, get out and move on to the next thing. And this is about, getting in and going deeper and deeper and deeper and getting sort of more into it. And I wonder, what was attractive to you about the shift to this context? And what did you discover when you actually got to the other side? Colt: You know, you’re right. Career professional consultant going from project to project. And we had a very good run. I mean, I was with essentially the same organization the entire time, right? I was with Deloitte, we spun a company out, we sold it so I was essentially with one organization the whole time. But never really got to see a lot through in the way of our client work. I even had accounts for years, one account 7, 8 years, so saw a lot of things through, but not like this. So my goal was, let’s see if we can move the needle in a massive way for an organization this big. And I was fairly convinced that we could, but that was what was really attractive to me is, let’s attempt to measure user experience in a way that’s meaningful and relevant to airmen doing the mission, and their mission. And then let’s track it over time. And then let’s figure out what levers we need to pull in order to move the metrics and deliver a better service level. And have everybody agreed that we did it. I mean, fundamentally, that was what I wanted to do. That’s what attracted me to doing this. And I went in fairly convinced that we could do it. I didn’t know exactly how we were going to do it. But I had a lot of ideas on how we could do it. But you’re going to go look for what are the biggest levers you can find to shift how airmen perceive the service level though they’re getting from IT and focus on those areas. Peter: I want to unpack a couple of terms just to make sure that we’re all usin…

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40: The Cross-Trained Design Leader (ft. Rajat Shail) Jan 19, 2024

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Transcript Jesse: I’m Jesse James Garrett, Peter: And I’m Peter Merholz. Jesse: And we’re finding our way, Peter: navigating the opportunities Jesse: and challenges Peter: of design and design leadership. Jesse: Hardware design, software design, package design, experience design. Rajat Shail oversees all of it for home automation company Vivint. Rajat joins us to share what he’s learned about managing design as a holistic function, the benefits and pitfalls of using design thinking training to engage executives, and what to do when your mandate is broader than your boss’s. Peter: Rajat, thank you so much for joining us today. Rajat: Thanks, Peter. Thanks for the invite. It’s good to see you and Jesse. Peter: So we’re just going to start at the top, which is to better understand: who are you, what you do, current role, responsibilities, what it is that you’re up to these days. Rajat: Great. I’ll give you a quick synopsis. I am currently leading the design team, user experience team, and the industrial design team and working very closely with the research and insights team here at Vivint, which is a home automation company, which recently got acquired by a Fortune 120 company called NRG, which is focused on delivering great energy solutions. So we’re really looking at what we call a category of one where we’re looking at home automation along with energy combined, could be a really nice foray into how people live in the future in smart homes. A little bit about me. I started my design journey in India, I did my undergrad and masters in India in design. Worked there for a short time, moved to this country about 20 years ago, and went on a journey working for different companies like Motorola, Whirlpool, Honeywell, Resideo, Bose, and then most recently at Vivint. My journey has been starting from being an industrial designer to getting to Institute of Design, Chicago, and focusing more on design methods and frameworks and strategy. Not practicing it as much because you know, when you just start, you’re at a certain elevation where you can’t really influence thought leadership at a very high level, but you can use those frameworks in your work and projects. But as I grew in my career, I not only started to focus more on training, you know, the VP/GMs on design thinking, but also started to, over a decade last decade, I started to make a transition into the digital space because there is no such thing as, you know, hardware design, digital design, it’s the end to end experience. So, in order to be more holistic in creating a great customer value, I had to learn on the job from some of the best digital designers UI, UX. And for the last 10 years, I’ve focused more on digital, less on hardware, even though I manage hardware teams and I’m very familiar with that. So that’s been my journey. Spanning the physical and digital Jesse: What was the biggest shift in mindset for you as you made that transition from the focus on hardware into the digital? Rajat: That’s a really great question, Jesse. I think I asked myself that question a lot, right? Like what, what makes me special? The biggest shift was starting with imposter syndrome, saying, “Oh, I’m trying to play digital designer when I’m not really traditionally trained as one,” to starting to figure out that there are things I bring to the table as a traditionally hardware designer, which make me more adept at understanding things differently, which was, basically, in industrial design, people are looking at form and function together, right? And in digital, I noticed that there were a lot of subcategories around interaction design, visual design, usability, which was not something we typically divorce in hardware. So for me, when I started to look at interaction design, when I started to look at UI, UX, I was looking at the visual design and the interaction, mental models and the information architecture with the, holistic lens. And I found myself to be good at that because I could look at something that potentially looked complex, could be simplified with better visual design and vice versa, right? So to me, I felt like I was realizing in meetings that there was something there that I brought to the table, which everyone doesn’t naturally have, because they’re so specialized, and of course, it was a journey and learning from the best interaction designers and visual designers to really understand the realization has also been that it’s not about digital or physical design. It’s about what is the best way to solve a problem, right? And digital design, hardware design, just enablers in the journey to solve that. We focus a lot on touch points, but it’s really about the experience, the end experience and the most acute realization for me has been as little design as possible and sometimes really forcing myself not to design a piece of hardware and not to design a feature on a, product in a, like an app, which is not needed. Peter: So a big reason we were interested in having you join us is that, as we’ve been talking with design leaders, they’re often purely software, maybe software and service, but you’re distinct in that you’ve maintained this connection with hardware, industrial design in I think for your last three jobs, right: Honeywell, Bose, and now Vivint. You know, we’ve talked to other former industrial designers who have kind of let go of that. I work with one, a different design leader at an enterprise SaaS company who was trained in industrial design, but now works primarily in software and service. And I’m wondering how you’ve been able to maintain a career at this intersection of hardware and software. And, were you motivated specifically to stay there or did it just happen? Rajat: Yeah. Again, you’re asking me questions that I’ve asked myself a lot. Honestly, it would have been easier to move into digital in its entirety because of its complexity, but to be able to manage teams which are very hardware focused, which work still in a very very waterfall approach versus digital teams, which are working with very different set of engineers in a more agile approach, it would have been easier to focus on one, but I continue to realize that design is holistic. It’s integrated, right? Today’s experiences are physical. They are physical and digital coming together. If you do not look at this holistically, you start to see a disconnect in the work. And it’s, apparent, like there are cases where I’ve seen the hardware is great, and I actually work for those companies, but the software is very poor; or the software is very robust, but the hardware touch point, the first point of delight of holding something in your hand which delivers additional experience, is just weak. You cannot not look at these together. And of course my heart is in both the places. So it’s become something more of a natural approach for me now to switch on and off between the two teams and how they think. And I’ve also come to see that both sets of designers slightly look at design differently, right? Their approach is different. And it always makes me chuckle when I see that fine difference on how an interaction designer solves a problem versus an industrial designer solves a problem. I sometimes feel really, really fortunate that I can see from both those sides and almost to the extent now that I’m able to see it from a mechanical engineer’s perspective as well as a software developer’s perspective very clearly. Peter: You are leading design and I’m wondering what it means to lead these two flavors of design and how you maybe, do you need to show up differently with the digital side than you do with the hardware and industrial design side, or are you showing up the same and trying to help them understand that they have more in common than they thought? But like, how does it affect how you lead when you have these teams that you’re responsible for that have different perspectives, preconceptions, different kind of starting points themselves. Rajat: Yeah there is a difference both in the engineering development as well as the product leadership within both teams, right? There is a stark difference. One is focused on getting the word that I like the least, which is minimum viable product, into the market. The other one is rabidly idealistic about creating the greatest hardware and tools. Neither one is wrong, because in digital it’s easier to go back and refine. In hardware, once you cut the tools, it’s very difficult to go back and make those continued improvements and refinements. So, that being said, I also like to believe in any product development, once you launch something, the followup becomes an afterthought, right? And, and so I like to use the word minimum lovable product as we use here at Vivint. What is the best experience that we can give and then build on longterm value on that? So, changing this mindset, that let’s not just focus on the speed, but let’s focus on the quality of the experience which is loved, and at both those touch points is what’s been very different for me within the teams. Jesse: You know, it’s interesting because what I’ve seen and what I’ve heard in a lot of organizations that are in the hardware business fundamentally, is that the software design is almost never actually unified with hardware design in this respect. In a lot of cases, I hear from people on the software side who wish they had more interaction with, who wish they had more engagement with the industrial design side. Apple famously tried to organize all of design under Jonny Ive on both the hardware and the software sides before deciding that that unification didn’t work. What do you think makes this unification work in these contexts that you’ve seen that other people are finding so challenging? Rajat: They’re finding it challenging because the natural order of things is to create focus and speed, which frankly is achieved through a siloed approach. When you are in your lane and you’re moving fast, you’re not looking around. You achieve the speed that you need, but it also leads to a level of compromise on the quality, Jesse. Building a culture of just ‘design’ Rajat: I don’t know how it played out at Apple. It was very interesting to hear Jonny Ive when he took over the interaction design team. What I’ve learned to do is, I think it starts from ground up, right? You really have to build a culture where designers are not calling themselves UX designers or industrial design. They’re just calling themselves designers or design thinkers. I would extend that all the way to engineering and product because we train product folks to do good design thinking, right? So we need to be very, very open to anyone who is thinking creatively, thinking from a user-centered point of view to be addressed as a designer, right? It comes down to very small, ground-up changes, making people sit together, okay? So they look over the shoulder and understand and learn every day from each other. Start to find these nice synergies and wonderful moments where they find that if I did this thing slightly different, the person who is connected to this experience can alter their design. So I’m finding those magical moments by forcing people to listen to each other. It’s very easy for an industrial designer to switch off during a design review with the UX. And it’s very easy for a UX designer to switch off during industrial design. I often ask questions to people so they stay a little bit more aware. That’s at a design level. At a leadership level, and this is a practice we started at Honeywell and I gained a lot from that, we don’t like to review designs. We like to review experiences. So let’s say you’re designing a soundbar, okay, for a home entertainment system. You don’t want to review the hardware of the soundbar, the industrial design or the UX. You want to review the end to end experience. How is someone going to buy this? What is that? How is someone going to find out about the soundbar? And what is it about it that’s so unique? How are they going to purchase it? What is that purchase experience? And how is it better than everything else out there? How are they going to get it shipped to them? What does their out of box experience feel like and then what does their first time user experience of setting it up feel like and then part of that is the hardware, part of that is the software install flow, and then finally how does it feel like when they start to use it for the first time and 60 days and what does long term value? So we kind of lay this out in a long table, almost 20 feet long and we build all these touch points and prototypes and have our leadership go through it to say this is the product. The product is not what you’re holding in your hand. The product is that entire journey that customer is going to go through. Which, frankly, Apple, I mean, I was trying to avoid using the Apple word, but Apple set the ground rules for it, right? Really well for us. And they’ve shown us the map and it’s shame on us if we don’t follow that, a good customer journey is what people enjoy more. For the longest time, people struggled that Apple’s features are not as good as maybe some Android phones. That’s not the reason why people are buying Apple phones. People are buying Apple phones for the consistency of the ecosystem and knowing that they just need to learn once and rinse and repeat, right? At different touch points, whether they’re in the Apple store or the Apple website or on the help desk, right? So I think that approach is what I am forcing leadership to look at holistically. And then you, you get a lot of help from different functions, because when you bring so many minds together people come up with newer ideas, which a traditional UX person would not have thought of, which a traditional marketing person would not have thought of, right? The power of forcing functions Jesse: A few times now you’ve used the word “forcing” to describe the way that you engage different parts of the organization with new ideas. Forcing the designers to see things in different ways, forcing the executives to see things in different ways. Forcing is some pretty strong language to use, and I wonder, you know, does it have to be a fight? Rajat: I don’t say that in a pejorative way. It’s not forcing as a fight, but more like, in big corporations, speed and cost are the defining factors, right? People want to get things out and the natural order of things is the path of least resistance, is the shortest path, but it’s not the best path. It’s often the minefield also, people like to focus on their function, whether it’s the finance person, whether it’s the, even the CEO or the salesperson in what they are good at. They do not have the time to understand the other functions and see how well they can integrate their thinking with that. When a designer is designing something, they look at solving problems. They look at understanding the value proposition. A salesperson can gain a lot from that. In defining what the sales and marketing approach, go-to-market strategy is. So forcing I say because… let me put it this way. There is a really great practice that’s happening at Amazon right now, which Mr Bezos describes as forcing function, which is they don’t allow any PowerPoints. They say when a product person is going to present their product plan for a new product, we’re going to have all the cross functional people sit down together around a table, including the executives because the executives have attention of a gnat, right? Attention span of a gnat. We tell them to keep their phones away. They sit down and they are going to read the six-pager. Everybody in the room is sitting quietly for an awkward 35 40 minutes reading the six pager. And understanding they’re not looking at quick slides and taking key points. They’re reading the story, the value prop, the go-to-market strategy, the experiences. It’s well articulated. It’s w…

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39: Reflections on the State of Design Leadership (Season 3 finale) May 31, 2023

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Jesse and Peter drink a “Warp Core Breach” at the Star Trek Experience, 2007. Photo by Leisa Reichelt. In this episode, Peter and Jesse reflect on the conversations they had with senior design leaders, the themes that emerged, the challenges facing design leaders today, and our hope for a brighter future. Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, Together: And we’re finding our way… Peter: …navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, for our season finale, Peter and I take a look back at our recent conversations with design executives to explore some of the emergent themes we’ve heard, including how to make sure you’re set up for success as a leader, the personal qualities such as resilience and pragmatism that help leaders thrive under pressure, and how to succeed as a design leader by being truer to yourself. Design leadership as change management Peter: So probably kind of most obvious place for me to start when thinking about the conversations we had was this thing I wrote at the beginning of the year where after the first five discussions we had with design executives, I went back, I analyzed the conversations we were having, I tried to pull out themes and topics, and as I went through my process, I hit upon what struck me as an an overarching emergent theme, which was around change management, how four of the five design leaders we spoke with very intentionally approached their job as a change management initiative. and Katrina, the very first person we spoke with, said that right out of the gate, at the start of our interview with her, that design leaders have to be change agents because businesses still don’t really know what to do with this function. Jesse: Right. Peter: And that was an interesting start because then Greg, whether or not they said change management, Kaaren’s approach was a change management approach, Greg Petroff’s approach was a change management approach, Rachel Kobetz’ approach was a change management approach, in terms of an intentionality of taking not just their team, but the function of design wherever they found it when they got there, to some new place and a set of activities that they were going to use to get them there. Jesse: Right, right, right. Yeah, it’s a really interesting thing, because if you think about the different kinds of change that a leader could potentially make, you could definitely see how in a more mature organizational function, something that has a more robustly defined value proposition than product design currently has, that has better entrenched practices and ways of talking and thinking about that value proposition, you can see in a lot of those kinds of functions where change management wouldn’t really be part of the job. There isn’t a lot of change to be made if you’re a CMO, for example. I’m sure there are people out there who would disagree with me. But for design where it is in its maturity, on its trajectory, there is still a lot that is not understood or not widely understood about what the value proposition of design as a function to an organization that creates digital products actually is. And what we see across this range of leaders that we’ve spoken with are a bunch of different frames for that value proposition. But in any case, they all have bridges to cross with their partners, with the business, to help them fully appreciate that value proposition. Because that understanding is going to be discontinuous through an organization. Not everybody’s going to get it. Because of the level of maturity of digital product design as a practice, because of the breadth of understanding of it beyond people who have engaged directly with design processes. So there’s a lot of evangelism, education and, really, shifting people’s mindsets, that’s necessary in order for these leaders to deliver on the promise that they see as there. Peter: Totally agreed. Even before these conversations, when people would ask me, well, how is a VP of design different than any other VP… Jesse: mm-hmm. Peter: … it’s because they have to spend so much time educating and evangelizing and increasing organizational maturity or awareness around the design function, which is Jesse: Yeah, Peter: understood for engineering, for sales, for marketing. Jesse: Exactly. Right, right. But I then I think that for the design leader, it’s a question of how far do they want to take that? How far do they want to go? You wanna level the product up to, you know, to be something more than it was, to take the design to someplace that it hasn’t gone before. Do you wanna level your team up in terms of expanding the capabilities of design, changing the shape of that value proposition of design as a function within the organization? Do you wanna change the organization beyond design? Are you interested in seeding, you know, for want of a better term, design thinking beyond design functions in the organization? Like these kinds of ambitions are all part of the balance that you have to strike as an executive design leader. The importance of clarity of vision Peter: One of the leaders that we spoke with, Kaaren, had the most clarity in terms of, like, ultimately where she was trying to head, and she used this phrase, “one freaking experience,” right? So she’s responsible for the consumer bank for Chase, JP Morgan Chase. And she saw kind of ultimately her vision is how do we create one experience for customers across the suite of products and services that Chase offers consumers. And when you do that, when you have that kind of clarity of vision, it ends up that gives you the almost marching orders to address the questions you were asking. Is it about the product, is it about the team? Is it about the broader organization? I mean, the short answer is, it’s all of those things, ’cause in order to deliver one freaking experience, she has to figure out how do we get these different internal lines of business aligned, the credit card business with the home mortgage business, with the basic banking business. And so that can’t be just something happening within design. You need to figure out how to weave it into the broader organization. But… Jesse: mm-hmm. Peter: … something else that she talked about when we spoke with her, that I’ve used since in, conversations with other design leaders is, where to begin? And in order to deliver on that one freaking experience, she saw where she needed to begin was with her team. She talked about the very first thing she did was establish or work to establish a world-class team, right. That that was gonna be the foundation upon which everything else rests. And as someone who’s been supporting her for the past year and a half, I’ve seen some remarkable hiring at all levels, but particularly at a design leadership level, as that initial step towards that greater vision. Organizational maturity Jesse: Mm-hmm. And you know, it’s interesting, too, because I think there is the question of, to what extent does design, by definition, regardless of the maturity of the organization, regardless of the maturity of the design team itself, to what extent does design necessitate organizational change if design is actually going to deliver on its value? And I think that for a lot of these leaders, they feel that if we’re just delivering better product over and over again, that’s not going far enough because we haven’t gotten into the roots of the culture of the organization. And one of the things that has come up a few times in these conversations is the notion of how much permission does the culture allow design as a function to have to push the boundaries of its value proposition to offer new ways of delivering value to the organization. And those experiences are wildly inconsistent based on the specific cultures of those organizations that those design leaders are stepping into. Peter: I like this frame. The companies that would hire people, like the folks that we interviewed are likely more permissive…. Have a greater maturity around these things, or they wouldn’t be hiring someone to lead a team of 400, 800 people, like, there’s some investment in it that suggests a greater permission. But I like the permission frame because I think something that a lot of design leaders don’t do, but need to do, when they enter into that new role, is assess, measure, understand where the, where that organizational maturity is at. Jesse: Mm-hmm. Mm-hmm. Peter: And permission is going to be caused, by that company’s maturity around design. Jesse: Mm-hmm. Peter: And, and that was an insight. Another one that I’ve dined out on since we’ve spoken with him uh, came from and, wow, that was an unintentional almost pun because it’s with Jehad, who’s Chief Design Officer at Toast. You know, we had spoken with these other design leaders, and they would talk about impact and they’d talk about co-defining outcomes, and it was from a place of greater maturity. And Jehad pointed out that, at least in his growth, he had to dial in his conversation to meet the maturity of the organization he was part of. And so it might not start with impact because your company might not be ready to hear about the impact that user experience or design has. They might not be mature enough to take advantage of that. And so he used a frame that I’ve, again, employed often since then, around “show your worth,” because your worth might be just understood relatively in the environment you happen to be in. It might have very little to do with the impact the metrics of the products that your team is building. And it might be around, Do your peers like working with you and your team? And, and measured through some internal pulse survey or whatever. And that in an immature organization that is actually a legitimate measurement when you don’t have anything else to go on. And, and that really got me to be thinking about how important it is for a design leader to tune their message, their engagement with where the organization currently is, not where they hope it will be. Jesse: Right, yeah. It’s huge. It’s huge. This comes up with my coaching clients all the time. The way that I talk about this with them is that the problem space at any given moment is the intersection of the trajectory of the larger organization and its maturity as it relates to design practice, the trajectory of the design team itself and its capabilities and its maturity, and the trajectory of the leader, what their past experiences have prepared them for and what new challenges they are well-suited to take on. And when you put those three things together, then you start to be able to define the shape of what the role actually is in that context. Peter: The maturity cube. Jesse: Sure, sure. Peter: Well, yeah, and I’m curious how you help your clients manage through this, ’cause one of the things that inevitably leads to is frustration, because I think the design leaders often feel like they are ready for a more mature organization. Or they’re ready for the organization to be more mature, to take advantage of what they have to offer. And so then they’re frustrated because when they try to push that, it doesn’t go anywhere. How are you helping your clients manage their own sense of… not trajectory, but, cadence and, traction to dial it in with what’s organizationally appropriate and not get defeated in that process. Resilience Jesse: Right, right, right, right. So part of it is about resilience, right? How do you maintain the emotional resilience day to day, week to week, to keep having the same conversation, keep fighting the same fight, keep having the same argument, right? The persistence that’s required there and the patience, and this is another thing that new leaders frequently don’t really get, is how long it takes to create cultural change. It’s one of the slowest -changing elements of an entire organization. You can turn a team over really fast. You can turn processes over, you know, pretty quickly. Cultural change is the slow-moving deep currents of the organization. And what that takes is, it takes persistence, it takes patience. It takes a dedication. A dedication to repetition. It requires the ability to ride it out for a while and know that you might not see any significant impact of this culture-shifting mindset, shifting work for a long time before it starts to actually pay off, because you’re laying the foundation, you’re building that foundation of credibility and trust for design as a function within the organization that’s gonna enable you to expand that value proposition. Peter: Well, and this gets to something you’ve written about recently on a post on LinkedIn, which is the job is bigger than the person. A design executive’s job is going to be bigger than any individual. It’s just by nature there’s more work to be done than any one person can do. And so, how then are you helping your clients navigate that, figure out, given all the things they could be working on, do I work on these long-term culture things, ’cause that’s ultimately what I want to drive. Do I work on near-term quick wins? Just to get some traction. Do I work on, building my team? Do I work on managing my relationships? Like how are you helping them navigate all that opportunity or all that potential activity so that they’re not feeling like they have to work 60 to 80 hour weeks in order to… Jesse: Right, Peter: …get it done. Jesse: Right, right. Well, it’s an interesting thing because, first of all, those three trajectories are a huge influence on how I help leaders set those priorities, to be able to assess where to invest their energy. ‘Cause you’re absolutely right, the job is just too big. So you have to choose that selective focus of your attention and how you set those priorities. A lot of leaders get into trouble by not having an agenda of their own for their priorities. They’re receiving priorities from the business, they’re receiving, you know, requests or sometimes demands from their teams and they see their role as mediator, negotiator, reconciler of everybody else’s point of view about what’s needed. And they don’t bring their own point of view. And the irony in this is that often what’s needed in order to narrow your focus of attention is to take your focus off of everything for a minute and reset and reflect. And that’s one of the big things that I help my clients with is, you know, whether we’re doing some reflection live in session, or I’m helping them create the patterns that create that space for reflection so that they can engage more strategically, so that they can get out of these reactive loops where the first thing that they do is they open their email and they’re immediately fighting fires to start their day. Peter: Kind of related to this, what I drew from those discussions with design executives was, in order to make sense of how to spend your time, what you’re calling reflection, to me, it feels aligned with just that recognition of having a vision, like, what is it, what ultimately is it that you’re trying to get done? And, and how can you use that as some internal orienting point, north star, that helps you make decisions about how you are spending your time? And then how you’re spending your team’s time, ’cause you wanna focus yours and your team’s time on work that moves you toward whatever that point on the horizon is that you’ve identified. But you need to take the time. You need to make sure you’ve given yourself some time to just figure out, What is that thing that I want? Jesse: Right, Peter: And you’re allowed to have, you’re allowed to have that desire. When I did my analysis and did the change management, that was clear. That each of these folks, part of their success is they had vision for where they wanted to take things, that they weren’t reactive. None of them showed up and were just like, what do you need? They all showed up with some s…

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38: The Craft-led Design Executive (ft. Tim Allen) Apr 12, 2023

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Transcript Peter: I’m Peter Merholz. Jesse: And I’m Jesse James Garrett, And we’re finding our way Peter: navigating the opportunities and challenges of design and design leadership. Jesse: On today’s show, we are talking with Tim Allen, Global Head of Design and Research for Instacart, about the leader’s relationship to the craft of design, the balance between creative and operational leadership, and how growing up as a Black child in rural Japan has shaped his thinking about inclusion in design. Peter: Well, Tim, we’re so excited to have you with us today to talk about all kinds of things to do with design, design leadership. I think where it’ll be great to start, though, is just to get a sense of like, who you are today. What do you do? What’s your role, what are you accountable for? Set some context for us here. Tim: I mean, well, first, thanks for having me Peter, Jesse, it’s great to be here. My name’s Tim Allen. I, I lead design and research at Instacart. And I spend my entire day looking after a community of designers, researchers, writers, operations folks, and specialists focused on providing access to food that people love, and hopefully giving them back time so that they can enjoy that food as well. Peter: You mentioned looking after a community. One of the things that we’ve been probing in these conversations with design executives, and I’m curious your take on it, is how much time is spent with your team, managing this organization of however many folks, and how much time is spent being an executive, being with the “first team”, being with the C-suite, and your cross-functional peers? How do you navigate? Figuring out where to focus time and energy Tim: Yeah, I think, well it varies according to the time, the fiscal calendar, as well as the development cycle of any one of our, like four, we’re a four-sided marketplace. You have four product ecosystems. One is, you know, our Instacart consumer app, which, you know, most people are aware of. But most, a lot of people don’t understand that there’s a whole product and service ecosystem around shoppers fulfilling these these orders as well. So there’s a ecosystem designed for them as well. Then you have our retailer segment as well, which is, you know, how do we empower retailers and provide a technology platform for them. And then we have an advertising ecosystem as well. So brands that would like to showcase, you know, what they have for, for customers as well on the platform. So yeah, so depending on where we’re at within each one of those segments, I could be spending more time at the C-suite just in terms of, like, strategic conversations, setting visions roadmapping and so forth, down into like, where I like to spend a lot of my time, which is inspiring–… You know, we mentioned the word community a bit. I try to reserve the lion’s share of my time in empowering the community, setting the conditions for the design team, especially to do the best design work they possibly can. And, you know, be a part in their development and transformation into, you know, wherever they, they want to be. Of course that involves the product as well. So, you know, my approach to the product is to be down, you know, have hands on and eyes on, like down to the pixel, down to the comma, as much as possible. So very sort of detail-oriented there without, you know, micromanaging. But I do want to understand insights that led to decisions that led to pixels moving, that led to, you know, commas being placed and so forth. Jesse: How do you walk that line with people that you want to give, you know, authority and autonomy to, to dig into those design problems, understand them deeply and make the best possible choices there, while also providing an appropriate level of oversight over those detail-level decisions from your perspective as an executive? Leading through craft Tim: Yeah, it involves, like, setting expectations of —we’re all peers before the object. And we’re all trying to make it as best as it can possibly be, and so we’re all on the same team. And sometimes that involves and necessitates a lot of autonomy, especially when, you know, there’s domain expertise involved and there’s you know, a keen understanding of the customer involved and so forth. And then at a, at a certain level, especially during reviews and crit, there’s just craft involved and typically that’s where I want to get involved the most, along with you know, sort of envisioning and setting the vision of things. So like I’ll, I’ll come in, usually it’s, you know, you have this sort of divergence and convergence across the development cycle and I set the expectation that I’ll probably be most hands-on when we’re diverging. And then sort of definitely as we start to make the final convergence towards the end. Peter: I’m curious and, and Jesse actually just wrote something about this on LinkedIn, because you’re mentioning craft and you mentioned the pixel or the comma. How selective do you have to be in terms of your attention? ‘Cause I’m assuming you can’t be at that level of detail across all four sides of the marketplace and all the experiences you’re offering each of them. And so how do you navigate that? So that you’re not, I don’t know, overwhelmed or that you’re spending all your time in these details, like there’s so much surface area… Tim: Yeah, definitely. I make those decisions based on just business priority. So, you know, in one quarter I may solely be focused on shoppers and fulfillment. And, and another quarter may be sort of like distributed across all four segments. It’s based on business priorities, what I would say. And usually that forces a level of focus. Peter: I’m looking at Jesse ’cause one of the contentions in his article, and it’s something I’m aligned with, is, as you grow in your career, right, as you develop in your career, as you become more senior, it becomes less about craft and those details, and more about setting up an organization that can execute on the details. And so, but it sounds like you consider it important to maintain a pretty tight connection with details as needed. And so how do you navigate, like building the engine, focusing on, on the mechanics that enable success versus knowing when to dive in and get to those specific points. Tim: Yeah, well, one, and you know, there’s a light and a shadow to this. One, I can’t help myself. I love design and I love the craft of design. And so early on in my career traditionally you have this paradigm where the higher you go, the farther you get from the craft. And I never enjoyed that so much so that I almost wanted to stunt my own sort of career growth. And RGA was one place where the closer you got to the craft and the client and the work and the better that work became, and, and, and the more you use that work to influence the team and so forth, to empower them, like through the work, the, the more you are rewarded and the business thrives and so forth. So I really, really clung to that. And what was the icing on the cake? Just most recently was, you know, and at Airbnb where, you know, the CEO is a designer as well, and he is directly related to, you know, the pixels and, and the commas at the highest level of, of the company. That where I was like, oh, okay, this is, it’s rare, definitely, but this is the type of leadership that I want to emulate. I’m not saying that one way is better than the other. I think there’s pros and cons each way, but I, I can’t help myself from doing that. And I was just like, is that okay to do? And like, how can I mitigate the issues and concerns that that does raise? Jesse: Yeah. I think that question of is it okay to do is an important one because I think a lot of it, you mentioned RGA, you mentioned Airbnb. These are companies that have very design-centric cultures historically. And… there is a question of, like, how much cultural permission you get to go deep on craft. And I wonder about how you manage the expectations of your cross-functional peers when you decide to go deep on design. Do they feel… are they okay with that? Do you have to negotiate something to create that space, to get that permission to go deep? Tim: Well, at some point it just all comes down to, like, output. I’ve been in situations, I, I maybe even dare to say recently where, you know, that approach wasn’t expected. And people like you could see the, like, why, why are you doing this? Like, you were very close. And, and as the output evolves you know, the design community in, in addition to cross-functional partners, start to understand, oh, this is a different way of approaching it, but like, I see the value. Where it’s not based on like control or power or anything like that. It’s truly based on like contribution to making… Jesse: mm. Tim: … better products and just different levels of, of contribution. Learning through making mistakes Peter: When you were mentioning your, your leadership approach, you used the word “mitigate” to suggest that in order for you to have this detail orientation, at least at times you recognize that there needs to be something to kind of balance that out. And I’m, I’m curious, over your career, what have those mitigations been? How, what have you done as you’ve established your leadership practices and as you’ve built teams, what have you found you’ve needed to do, organizationally, to support your desire to get into those details? Tim: Yeah. Yes. Mainly just made a lot of mistakes, Peter: That’s how we learn! Tim: And learn… exactly, and learn from them, which is, you know, leaning in too hard. You know, I’ve leaned in too hard at some times and I’ve also pulled back too far at times. And so I’ve had to understand, like, as I’m giving direction, how can I give it in a way that allows people the flexibility to interpret it and also bring their own creative spirit to it and, and make that direction better. You know, I, early on, I must say I was probably spoiled by so much talent at like, places like RGA where just a little bit of direction comes back with a ton of improvement. And, you know, as I got into other spaces where that wasn’t necessarily the case, it was really about refining that approach. Refining, like, reviews and crits and like, I feel like, you know, workshops or crits of work are where the magic kind of really happens, I think. And, and really setting those up so people feel accountable for one, but then also like fearless and creative too. Jesse: How do you avoid being a bottleneck as you are engaging in these processes? Are people automatically expecting you to be engaged, or are you negotiating a different scale of engagement with that process of critique? Tim: Yeah. I think it’s easy to become a bottleneck. Yeah. And that’s, and that’s also one of the mistakes that I’ve made in the past as well at least for priority projects. And, you know I think the team’s only as fast as, like, their leader. So that is very front of mind, we talked about mitigation, but concern, I’m, I’m always having, like, am I responding quick enough so that I am not a bottleneck? I do in high priority business programs want to be a part of decisions and understanding like what insights are coming in, how are we interpreting data, how is that translating into design decisions, and so forth. And so I, what I’m trying to do is like limit, you know, speaking, speaking tactically, limit the amount of preparation needed for my involvement, too. So, you know, in some cases what I’ve learned in the past through my own, again, mistakes is not understanding that some people can interpret presenting to people at my level as like, “Hey, we gotta circle the wagons and, and put as much thought into this presentation as we did into the work.” And then sometimes more. And so that’s completely not the case. So I’m, I’m, I’m setting the expectation of, yes, we’re talking about sausage-making. So show the appropriate level of fidelity for the moment in time we are in the development cycle. The importance of safety in creative work Jesse: So it seems like a lot of this is about the expectations that you’re setting and the relationship that you’re creating with your team to get them to trust you, that it’s okay to be messy, and for the work to be a little unrefined and a little unpolished. What are some of the ways in which you create permission within your team for people to be messy when they know that you’re gonna be looking at their work? Tim: Well, I think that’s where the safety comes in, I, I relate safety to like, fearlessness. You know, I think, like, we do best work when we’re not afraid. And, and that’s just hopefully establishing that, like, great ideas are just great ideas no matter what the fidelity is. Jesse: Hmm. Tim: So what’s the least amount of fidelity you can give to an idea that allows people to understand that it’s a great idea, you know? And, and in some cases it’s gonna be a functional prototype, so you’re gonna have to spend a lot of time on it because like, you can talk about, I don’t know, like swipe gestures and so forth and, you know, 10 different people will interpret that 10 different ways. Or it could be like a whiteboard sketch or, you know or maybe even a document. So I think the expression of ideas is what I try to encourage the, the team to understand. Like, the tool set is very varied that you can use to express in an idea, and it’s up to you on, on how to do it. Peter: How do you set expectations for quality? How do folks understand what you’re expecting of them in terms of what the quality bar is? What have you done to define that? Tim: Principally, in terms of, like, principles, like we need you to do the best work of your life, like just straight up. So, but that can be interpreted a couple different ways, but that’s the, in, in terms of principles, that’s, like, what we’re trying to do, and it’s on us or, myself as a leader, to set those conditions so that that can happen. But the expectation is for you to be doing the best work of your career. And so, so what does that actually mean? I think it means just being world class at solving customers problems, and that that means falling in love with the customers and their goals and their needs, you know, thinking deeply about them. And, you know, I interpret falling in love with problems as also thinking orthogonally about the solutions as well, right? So, you know, going down blind alleys which, you know, sometimes can be dangerous. Again, connecting disparate thoughts. And also because you’ve fallen in love with so many different people, with different contexts and so forth, you can start connecting them in different ways as well. I had the privilege of working with Jonny Ive at Airbnb and I, there’s many things fascinating about that individual, but one of the things I was completely blown away with was, like, the connections he was making, just like organically between, cultures and ways of seeing the world and perspectives, because he’s fallen in love, literally, with so many different types of people and contexts and so forth. And so he has this like library he’s drawing on to make these connections. Just really truly stepping outside of yourself into other contexts. Making space for a design Peter: Airbnb and Apple are often held up as paragons of good design, but they’re also really weird companies, in part because of this. Because of this willingness to embrace design in, in such a elevated, robust, exploratory fashion. You’ve operated in environments, you’re possibly in one now, where design wasn’t that highest order bit the way it was at a place like Apple and Airbnb. And I’m wondering what you’ve had to do to make space, say at a place like Instacart, for your team to take this really rich approach to practicing design in a context that maybe before you were there, didn’t necessarily enable it, right? I look at the people I work with in other types of product-led, maybe even engineeri…

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