Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft)

1. 0:00 – 4:47

   Katie’s background

   1. KDKatie Dill0:00

      ... the use of the word beauty in, in books that have been digitized by Google has decreased, like pretty dramatically. And it, it's aligned with this idea of like, well, functionality is king. Functionality is what matters. And as if people think about functionality as b- and beauty as, like two opposite things. Like, no, they're not two opposite things. You know, functionality is important. And actually beauty enhances functionality because it does make things easier to use, more approachable, uh, more compelling to use. And the other piece of it that is not talked about in business as often is just the importance of how people feel. Things that are more beautiful increase trust. They, you, you see that, like we've put painstaking detail into this and we care about the details of how something works, and that gives you assurance that we care about other details that you can't see too.

   2. LRLenny Rachitsky0:52

      (instrumental music) Today my guest is Katie Dill. Katie is head of design at Stripe where she oversees product design, brand and marketing creative, web presence, user research, content strategy, and design ops. Katie was previously head of design at Lyft and head of experience design at Airbnb. She's built and led design teams at three different hyper-growth companies, seen the team scale at least 10X, and two of which, Airbnb and Stripe, are some of the biggest and fastest growing companies in the world, and also the best-designed products. In our conversation, Katie shares stories of trials and tribulations of leading large design teams, processes she's put in place for operationalizing quality, how she thinks about quality and beauty very practically, how design can directly lead to growth, and examples of this that led to big lift in conversion at Stripe, plus a math formula she uses to increase team performance, how she suggests organizing your design and product teams, what to look for in design hires, and so much more. I was really lucky to get to work with Katie while at Airbnb and I am so excited to have her on this podcast. With that, I bring you Katie Dill after a short word from our sponsors. This episode is brought to you by Sidebar. Are you looking to land your next big career move or start your own thing? One of the most effective ways to create a big leap in your career, and something that worked really well for me a few years ago, is to create a personal board of directors, a trusted peer group where you can discuss challenges you're having, get career advice, and just kind of gut check how you're thinking about your work, your career, and your life. This has been a big trajectory changer for me, but it's hard to build this trusted group. With Sidebar, senior leaders are matched with highly vetted, private, supportive peer groups to lean on for unbiased opinions, diverse perspectives, and raw feedback. Everyone has their own zone of genius, so together we're better prepared to navigate professional pitfalls, leading to more responsibility, faster promotions, and bigger impact. Guided by world-class programming and facilitation, Sidebar enables you to get focused, tactical feedback at every step of your journey. If you're a listener of this podcast, you're likely already driven and committed to growth. A Sidebar personal board of directors is the missing piece to catalyze that journey. Why spend a decade finding your people when you can meet them at Sidebar today? Jump the growing wait list of thousands of leaders from top tech companies by visiting sidebar.com/lenny to learn more. That's sidebar.com/lenny. You fell in love with building products for a reason, but sometimes the day-to-day reality is a little different than you imagined. Instead of dreaming up big ideas, talking to customers, and crafting a strategy, you're drowning in spreadsheets and roadmap updates and you're spending your days basically putting out fires. A better way is possible. Introducing Jira Product Discovery, the new prioritization and road mapping tool built for product teams by Atlassian. With Jira Product Discovery, you can gather all your product ideas and insights in one place and prioritize confidently, finally replacing those endless spreadsheets. Create and share custom product roadmaps with any stakeholder in seconds, and it's all built on Jira, where your engineering teams are already working, so true collaboration is finally possible. Great products are built by great teams, not just engineers. Sales, support, leadership, even Greg from finance. Anyone that you want can contribute ideas, feedback, and insights in Jira Product Discovery for free. No catch. And it's only $10 a month for you. Say goodbye to your spreadsheets and the never-ending alignment efforts. The old way of doing product management is over. Rediscover what's possible with Jira Product Discovery. Try it for free at atlassian.com/lenny. That's atlassian.com/lenny.

2. 4:47 – 10:55

   Katie’s pivotal leadership moment at Airbnb

   1. LRLenny Rachitsky4:48

      Katie, thank you so much for being here. Welcome to the podcast.

   2. KDKatie Dill4:52

      Thanks for having me. Good to be here.

   3. LRLenny Rachitsky4:54

      It's absolutely my pleasure. So as we were preparing for this podcast, you hinted at a story that you had from your time at Airbnb where the design team staged an intervention with you, which I had no idea about because I was there during this time and, uh, did not know this was happening. I am so curious to hear the story. Can you, can you share what happened?

   4. KDKatie Dill5:15

      Uh-huh. Sta- starting with the easy questions, I see.

   5. LRLenny Rachitsky5:18

      (laughs) .

   6. KDKatie Dill5:18

      All right, all right.

   7. LRLenny Rachitsky5:19

      Right into it.

   8. KDKatie Dill5:20

      Um, yeah. No, I'm happy to talk about it because frankly it was the biggest learning experience of my leadership career, or at least that happened in one moment. And it happened in my early days at Airbnb. So I was hired to take on the design organization, or the, the experience design organization. That's basically the product design team, uh, which was 10 people at the time. And so they had been reporting directly to one of the founders, and they were gonna start reporting to me. And during my interview process, I learned a lot about what was working and what wasn't working and some of the, you know, trials and tribulations with the, the design organization and its collaboration with others. So it seemed like there was room for improvement in how engineering, product management, and design all worked together. And there was also really low engagement scores in the design team. And so...... I kind of came in (snaps fingers) ready to go and, you know, excited to try to help make some change based on all the things that I had learned, uh, from various leaders and people across the company. And I, you know, came in swinging, ready to go. And then about a month into my time there, I got a meeting on my calendar, Thursday, 8:30 AM, it was an hour and a half, with, uh, half of the design team, so that was five people, and our HR partner.

   9. LRLenny Rachitsky6:37

      Oh, no.

   10. KDKatie Dill6:37

       It's not usually a good sign.

   11. LRLenny Rachitsky6:38

       That's never a good sign.

   12. KDKatie Dill6:40

       Yeah. Uh, and I, I remember this so vividly. I remember walking into the office and, you know, all the rooms in Airbnb's office are very unique spaces that look like Airbnb's. But of course this was the one (laughs) room with like all white walls and just like a gray, you know, flat rectangle table. And I walked into the room and there were five of them seated around the table, and they had a pack of papers in front of them, and they went on taking turns, you know, quietly reading from the papers all the things that they w- saw that I was doing wrong and all the things that they didn't like about me. And, you know, (laughs) it was a really hard moment, you know, there. I, I went through all the usual kind of like stages of grief when one hears feedback, which is this like, you know, immediate want to like respond, to be like, "No," like, you know, "Well, there was a good reason for that," and like, "That's not how it actually was," and, "This is why I did that." But luckily I had, you know, (laughs) thank goodness I had the sense to just like listen and not respond in that way. I mean, clearly what they were telling me is that, you know, that was one of the things that was missing. And so I, I heard them out and, you know, took it all in and, you know, regardless of each individual thing, what was very clear was that, you know, the missing piece, the theme that was across all of that is that I hadn't earned their trust. So, you know, whether, you know, how right or how wrong what I was doing was is like the key piece is that I wasn't bringing the team along with me. They had no idea that they could trust in, you know, what I was trying to build and what I was trying to shape and that I, I cared about them and that I had, you know, their best interest and shared goals at heart. And that was absolutely my fault. And in retrospect, you know, as, as hard as that was, I'm like very grateful and very amazed that, you know, that they could kind of come together and, and, and share that with me. Uh, it's, it can be hard to, you know, bring, you know, feedback forward like that. And so it was an e- extremely valuable learning experience, and I took from that to then ch- immediately shift how I was operating, and really a key part in building trust was to, to listen, to hear out, you know, what, you know, the individuals on the team were, you know, setting out to do, what they cared about, uh, and what motivated them. And so I started to make pretty fast change, and still moving in the direction that, you know, was necessary for the org to make like the, you know, the really large impact in how we were operating, but bringing folks along with me. 'Cause you can inflict change on people, but if you want to do it with them, you, you really, you know, trust is the, the key element there. And then, you know, a couple months later we had the best engagement scores in the company. So like it-

   13. LRLenny Rachitsky9:20

       Oh, wow.

   14. KDKatie Dill9:20

       ... actually like, you know, it did i- objectively improve the situation. And I've, I've, you know, since then taken that on into next steps in other companies that I've joined, and just think about like instead of coming and swinging, you know, come in listening, so that you can really, you know, set out to make change that actually has like true positive impact on, on the folks around you and that you bring along with you.

   15. LRLenny Rachitsky9:42

       Wow. Uh, I was there during this. I did not know this was happening. Is this the time when all the designers were all always in one room together in Thayer? Is that that period?

   16. KDKatie Dill9:52

       Before I got there, I think there was a little of like, you know, design is just gonna sit with design and not necessarily like-

   17. LRLenny Rachitsky9:57

       Right.

   18. KDKatie Dill9:58

       ... work in, in close proximity with engineers and product managers, et cetera. And one of the things that I believe as, you know, a necessary part of building a high functioning organization is that, one, you know, building together is important. So like having engineers and product managers and designers be together, have shared goals, and align on that and like be able to just like look over each other's shoulder and talk about things is important. So sitting together is important. However, that Thayer thing that you're talking about actually like was something that I was very devoted to, which is bringing design together at key moments multiple times throughout the week to also build the community in design. You know, like Joe Bott at, at Airbnb once said, it's like, "Well, what T-shirt are you, do you wear? Like what team are you on?" And I was like, "You wear two T-shirt, you have two T-shirts. You have the design T-shirt and you have the like marketplace T-shirt," or whatever, you know, cross-disciplinary team that you work on, uh, because both are really important communities to build for slightly different reasons. So yeah, Thayer was a good

3. 10:55 – 16:07

   Advocating for design ROI

   1. KDKatie Dill10:55

      spot for that.

   2. LRLenny Rachitsky10:55

      Zooming out a little bit, I think the elephant in the room a lot of times with design is this idea that I'd say most PMs, most founders intellectually understand the value of design, understand the value of high quality, but day-to-day it's often not actually prioritized versus new features, new product launches. And partly because the ROI is just really unclear. If we spend another month making this more awesome and making this even more amazing design-wise, experience-wise, why, what is that gonna get us? Clearly at Airbnb, design was highly prioritized. At Stripe from an outsider's perspective it clearly is. I'm just curious what you've learned about how to make the case for the ROI of design and just how Stripe and Airbnb and, and Lyft have done that.

   3. KDKatie Dill11:39

      It's a great question, and I think this is like an age-old question that I, I don't know if will ever go away. And, you know, probably because, you know, the, the quality bar, you know, keeps evolving and keeps rising. But I think like, you know, first to like kind of level set before we, you know, kind of dive into that, I, I would say that there are levels of quality, right? There is the like does the thing work? Does it provide some sort of value proposition that like executes on its job? Like that's like baseline quality. Next is that like does it do it, you know, exceedingly well? Is it like error-free? Actually, I mean, that's not even exceedingly well, but just like error-free and it actually works in a well-rounded way. And then beyond that, like level three, level four to level five, is it, does it exceed expectations and it do, does something that you weren't even in- seeking for as a user?And I do think like the levels of quality should be based on user expectations. I don't believe that there are disciplines that just don't care about quality. I think it's more about that prioritization and kind of like what you talked about, is just like is it really worth getting something to that exceedingly well state, or is it, you know, what about just like another feature? You know, and getting that, being seduced by the chase of another feature versus actually, you know, taking your features to a level of being great. That is hard. And I get it when, you know, you look at your user base and they're all shouting from the rooftops for this additional feature, uh, you know, of course you're going to want to prioritize that over something they've never asked for. And then the other thing would be, you know, you end up with like you've got three things that you could possibly do to make perhaps, you know, the next stage in your product development. Two of them you know you can measure and they're going to line up to business goals, and one of them you can't. Like, of course that's going to be enchanting to want to go after the things that you can actually measure and you know that they're going to have that impact. But the companies that, you know, know that quality is non-negotiable, it is, you know, a long term necessary aspect of what they build, don't play that numbers game. Or that they, you know, what they do is they recognize that it's in, it is absolutely functionality, but the quality of those features that is actually going to get to great usability, desirability in their product. And actually I think it, it's kind of like an analogy for going to the gym or working out. Like I don't know about you, but literally every time I, I think to do this, there's like a fight in my head of like, "Ah, do I really need to work out today?" You know? "Is this one day, you know, gonna give me six pack abs?" Like, of course not. So like, why, why, why go? Why, why not just like skip it today? But of course like then at some point, hopefully, I realize that it's like, "Well if I skip it today, what's to stop me from skipping it another day?" And really in the belief of that these things can, you know, inten- it really does add up to better outcome in the end, and so you know a longer, healthier life. And so hopefully I can get myself together and, and go to the gym. Uh, and I do think some of the best companies in the wor- on the planet think that way. And I, I recognize that our customers don't always ask for it. I mean, you might see it in, you know, support cases, for example. Like clearly they don't know how to use this next step, and that is probably a quality issue. Um, and that, you know, they might be asking for, you know, more improved features. Uh, but some of the levels of quality that, you know, the level two and three and four, you know, you might not get direct asked for. But I guess I'll, you know, give you another analogy. Like if you don't have competition, that's fine, right? Like if you think about the first car, I am sure that wheel was really hard to turn, and I'm sure that seat was not comfortable, and you know, you could have any color you want as long as it's black, right? But like there was no competition. The competition was a horse. So, you know, no big deal. For, you know, cars today, it's like the stitching, the, you know, the choice of the leather, the sound of the door, like these distinguish, you know, a mm, okay car to a high end special car with higher value. And this is very much by understanding, you know, that, how the details matter and how execution of quality will take it to the next level. And, you know, lastly I'll just say that like I know there's this saying of like it's growth versus quality, but like quality is growth. And if you think about how you can make your product easier to use and more understandable, you know, that will of course drive people to use it and use more of it and, and take, you know, have a better experience with it that they'll, you know, want to talk about with others.

4. 16:07 – 17:50

   Stripe’s quality focus

   1. KDKatie Dill16:07

      You know, in fact at Stripe our growth team I would say is like pretty much maniacally focused on building better experiences because we've seen it tie directly to our business metrics. We have things that we've improved on in, you know, our onboarding flow, for example, to make it easier to understand the products, understand how they work for your different use cases, such that then we have seen activations increase because we've made these quality improvements that are just directly tied to growth. You know, one of the biggest examples that I've seen of business impact through quality is actually in the checkout experience.

   2. LRLenny Rachitsky16:46

      Mm-hmm.

   3. KDKatie Dill16:46

      So we've done research on the checkout experience in some of the top sites, e-commerce sites, and we found that 99% of the top e-commerce sites have errors in their checkout flow that actually hinder a more impactful, more, you know, seamless, quicker checkout, and therefore higher conversion with their customers. And these small things, it really, like they're quality issues. They're just that if you really understand what a consumer is trying to get out of the experience, then you can make it better. And so we have been, you know, maniacally focused on that over many years, trying to make the checkout experience so much better for businesses and their consumers. So by improving the quality of the checkout experience through details small and large, we have seen a 10.5% increase in businesses' revenue from that, you know, an older form of checkout to a newer form of checkout. And those little details matter to have such a material impact

5. 17:50 – 18:45

   Stripe’s vast scope

   1. KDKatie Dill17:50

      on one's revenue.

   2. LRLenny Rachitsky17:51

      You mentioned this before we started recording, but you guys power the checkout flow for some very big sites. Can you mention a few of these? 'Cause it'll give people a sense of like, holy moly.

   3. KDKatie Dill18:00

      Yeah. Stripe is used by millions of businesses globally, small and large, from, you know, early stage startups to SMBs, larger organizations and enterprises like Amazon and Hertz, Shopify, Spotify, X, which I believe you use.

   4. LRLenny Rachitsky18:15

      Mm-hmm.

   5. KDKatie Dill18:16

      Uh, and-You know, the, the work that we do i- ranges. We have checkout flows, so when, you know, someone's paying online or in-person. Or we also provide a, a suite of financial automation tools so that you can run, uh, your subscriptions business and recognize your revenue and receive tax and essentially, you know, manage the complexity of the financial space, uh, through, you know, powerful tools that hope to make your job easier so you don't have to sweat the details of how these

6. 18:45 – 21:39

   How design enhances utility

   1. KDKatie Dill18:45

      things work.

   2. LRLenny Rachitsky18:46

      I just want to follow this thread a little bit. You talked about these opportunities to improve the checkout flow through a design lens. You could also think of it from like... Like as a product manager I'd be like, "Oh, wow, let's just find all the things that people get stuck on and fix them." How is it that you see that from the, the quality design perspective versus like, "Oh, there's this... Let's just move this metric and here's all the things that are stopping people?" What would you say is the designer's lens on that, if there's anything there?

   3. KDKatie Dill19:12

      I... Honestly, a, a pet peeve of mine is this way of talking about things is there's business goals and there's design goals. Because, you know, I think maybe the first conversation, you know, one should have is that, you know, like, "W- what are we trying to build towards?" And I would think that folks that want to create, you know, really impactful products, they want to create quality products, and that they want to create things that actually serve their customers in a, you know, positive and beneficial way because they know that will build a stronger business in the long run. And so yes, there may be, you know, slight prioritization details, uh, different through the process where, you know, a designer might be thinking, you know, more about the emotional experience and how somebody feels because that's, you know, o- oftentimes how they're wired and that is an important lens to bring on it. Whereas, you know, somebody else might just be like, "Well, you know, just make the button bigger and they'll, they'll click it more often," and, you know, that's wha- what the outcome that we seek. So this is again why I was talking about how important it is to have multidisciplinary teams that work closely together because sometimes we are, you know, the checks and balances in the conversation. But I do think if, if, uh, we can align on what are we trying to build, are we trying to build something great, then, you know, we can, you know, recognize the fact that, like, it isn't just the... You know, utility is an incredible important part of that. But so is usability and so is desirability because these things together make something truly great. And so, you know, beauty is an important part of that, uh, because it does make things more useful, it does make m- things more, uh, accessible. And that with these things kind of coming together you can, you know, build towards something better. I think that, you know, beauty on its own or just, you know, like craft on its own without utility, I mean, that's like... I don't know, that's like Blu-ray or (laughs) or Path, right? Like it... That, that does a- does not lead to a high-quality product so it is like the combination of these things, uh, and so it's like stepping towards that. But if you really want your, you know, product, those features to be utilized for all that they're worth and, like, to actually, you know, gain such, you know, esteem and, uh, respect and reuse, taking it to that next level and thinking about, you know, how do I make this actually, you know, an enjoyable use and that it really feels like it's, you know, meant for me and it maps to my mental model, uh, that craft and that quality of, you know, the execution of those details is gonna be paramount.

7. 21:39 – 26:19

   Defining beauty and its role in product growth

   1. KDKatie Dill21:39

   2. LRLenny Rachitsky21:39

      You mentioned this word beauty and I wanted to follow on this a little bit of just... This is a big question but just, like, what i- what is great design? What is beauty? Is there, like, a objective definition where if designers are like, "This is great design," is they're just like, "Yes, that is true," or is it just an opinion? How do you think about it? What is great design? What is beauty, Katie Dill? (laughs)

   3. KDKatie Dill21:59

      I, I love that we're talking about this because I feel like there's probably some people listening that are, like, squirming in their seats of like, you know, like, "Beauty? We're talking about business here." Um, and I mean that's which is great and the, um... Actually there's a fun fact. Uh, Stefan Sagmeister and Jessica Walsh have a book called Beauty, and it is... I would highly recommend it. Very, very worth the read. But one of the first things they talk about in the book is that from the 1800s to the 2000s, the use of the word beauty in, in books that have been digitized by Google has decreased, like, pretty dramatically. And it, it's aligned with this idea of, like, well, functionality is king. Functionality is what matters. And as if people think about functionality as be-... And beauty as, like, two opposite things. But what the whole book talks about is that, like, no, they're not two opposite things. You know, functionality is important and actually beauty enhances functionality because it does make things easier to use, more approachable, uh, more compelling to use, and there is actually some objectivity to whether or not beauty enhances things. But if you ask, you know, p-... A, a wide audience, you know, what color do they like more or what, you know, version of things do they like more, like, they, they tend to say the same thing because there is this, like, shared understanding. And, you know, the other piece of it that, you know, yes, I w- I can imagine is not talked about in business as often is just the importance of how people feel and, uh, you know, and a good example of how something looks and how something is, is structured and how that can, uh, translate to that also from the, the book Beauty, they mentioned that they studied the tweets that came from people that were traveling through Penn Station versus Grand Central (laughs) and if, and if you've been to those places I'm sure you know where I'm going with this, which is just like the, the... People tweeting from Penn Station was just, like, more negative than the people that were tweeting from Grand Central Station that hend- tended to be much more positive and optimistic. And so, you know, the things that you create have this impact and if you're thinking about, like, "I want people to enjoy using my product. I want them to feel, you know, at home in our product," of course beauty is a part of it. You know, and, and this matters deeply to us and I know, you know, as a financial infrastructure company in the B2B space, you know, some may assume that that-... doesn't matter as much, but it's actually a key priority for us because number one, things that are more beautiful increase trust. You, you see that, like, we've put painstaking detail into this and we care about the details of how something works, and that gives you assurance that we care about other details that you can't see too. And then secondly, it is easier to use, as I've mentioned. It gives better user outcomes. You know, what we're trying to do is we're trying to equip businesses to make the right decisions to be more successful at what they do. And by, you know, bringing a interface or, you know, our invoices or whatever it might be to be more beautiful and more easy to use and more trustworthy, that will lead them to better outcomes. Thirdly, I, uh, strongly believe beauty begets beauty. And so when, you know, our business users or the consumers see, you know, the, the beauty and the, the care and the creativity that we put into things we deliver, then, you know, that again reassures them of, you know, the, just like the care that we put into them. And actually a perfect example of this, have you seen the show The Bear?

   4. LRLenny Rachitsky25:23

      I have. Yes.

   5. KDKatie Dill25:24

      Okay.

   6. LRLenny Rachitsky25:24

      Great example of-

   7. KDKatie Dill25:25

      All right. I don't want to... No spoilers, but, like, all I have to say is peeling mushrooms. Do you know what I mean?

   8. LRLenny Rachitsky25:29

      Mm-hmm.

   9. KDKatie Dill25:30

      Yeah.

   10. LRLenny Rachitsky25:30

       Yeah.

   11. KDKatie Dill25:30

       Yeah. Such a good example. Such a good example.

   12. LRLenny Rachitsky25:32

       Yeah. That... Someone just mentioned that same episode, uh, on a-

   13. KDKatie Dill25:35

       Ah.

   14. LRLenny Rachitsky25:35

       ... recent podcast episode.

   15. KDKatie Dill25:36

       Okay. All right. Well, it's that good. It's that good.

   16. LRLenny Rachitsky25:38

       Yeah.

   17. KDKatie Dill25:38

       And I wish I could remember which episode that was, but who... It was seven? I forget. But anyway.

   18. LRLenny Rachitsky25:43

       Yeah. That's exactly right. That's exactly right.

   19. KDKatie Dill25:44

       Oh, nice. Okay. All right. Well, and then lastly, it... You know, quality is a matter of pride. Beauty is a matter of pride. I- if we put that in, you know, kind of care into our work, more people will want to work with us because they want to see, you know, their time spent in the care for their craft recognized and utilized and, and see that that can, can be, you know, put together into something really impactful. And so you know, we really put that on a pedestal, you know, because we know how much it matters to our users and then how much it matters to the people that work with us. Um, beauty, beauty is an important part

8. 26:19 – 28:44

   Operationalizing quality

   1. KDKatie Dill26:19

      of it all.

   2. LRLenny Rachitsky26:20

      Amazing. Speaking of beauty, I think, when I think of Stripe and beautiful, I think of your website and some of the specific landing pages you have, which are just incredibly nice. I'm just curious how you decide it's time to redesign your website and how much time and thought you put into a new website, 'cause that feels like a, a common question founders have. Like, should we redo our website? And it feels like you guys really think deeply about that. So I guess is there anything there that you, you can share?

   3. KDKatie Dill26:45

      Yeah. There's definitely a couple things we could talk about in terms of like operationalizing quality because... I mean, the gravitational pull is to mediocrity, right? Like, you know, it is, it is very easy to fall into a path of a baseline where what is required to go to that next level where something feels truly great is, is certainly a lot of effort and it's a concerted effort. And I will definitely say like we are a work in progress. You know, we have not nailed, nailed all the things. Uh, and it is an ongoing pursuit of, of excellence. And so the, the way that we build the website is that, you know, we, we certainly do, you know, put a lot of care into what we're putting out into the world and we view it as a articulation of, you know, how we care about our users and, and all that we provide for them. So, we take that very seriously. We try to kind of meld art and science, so it's the creativity of the work but it's also just like the technical kind of power of the, the way that we show it. How we've actually operationalized the way we do that is that we have design and engineering and our product partners and product marketing work really, really closely on this. And actually, it's one of the, the few teams where all of these things report... Well, not all of them, but most of those functions report into one place. So engineering and design actually all report up into the design organization when they work on the website. And together they, like quite literally as we were talking about earlier, you know, if we were physically together, they would be sitting side by side and, you know, they're batting ideas back and forth. Because, you know, the engineer on the team, you know, has a great idea for how we could go about executing on it, and the designer on the team has another idea how to, you know, push that a little further. And so that kind of rapid cycle of iteration is really, really powerful, especially when we're, you know, trying to move quickly but at an extremely high standard.

9. 28:44 – 34:47

   Katie’s insights from dialogues with diverse organizations

   1. KDKatie Dill28:44

   2. LRLenny Rachitsky28:44

      That's super interesting. Is there anything else that you've found to be really helpful in just operationalizing great design, craft, beauty? Any processes, systems, frameworks?

   3. KDKatie Dill28:54

      Yeah. I would love to tell you about something that we've actually rolled out, you know, pretty recently that I'm extremely excited about the, the positive impact on.

   4. LRLenny Rachitsky29:02

      Awesome.

   5. KDKatie Dill29:02

      But before I get into that, uh, one of the things that, you know, kind of has been driving a little bit of this process and the way that I've been, you know, thinking about how, you know, we can build better things, uh, at Stripe is actually I've been just talking to people. Talking to different, you know, design leaders, product leaders, engineer, engineer leaders at different organizations and trying to understand, you know, how they go about it, and there are a couple of themes that are clearly coming through. You know, number one is that quality is definitely a group effort. You know, you're sunk if you think that like you can just like hire some incredibly talented person and then like, and they'll do it, that'll be fine. You know, the rest of us will do what we're doing and they'll do it. Um, or that it's just like one organization that's gonna look out for quality or, you know, QA is gonna solve it all for you. Uh, it really does need to be, you know, an organizational and a group effort. And if you think about like, you know, the way that you run, you know, the, the internal functions is go- is gonna show up in the outside and like how clear you all are and how you're talking about it and the standards that you set inside and you're constantly reminding people of in the way that you communicate inside will then eventually show up outside. So take... You know, of course keeping your talent bar high and then thinking about how those things, you know, really need to be cared for and that shared care across the organization is, is number one.Number two is that, you know, there needs to be some amount of vision and alignment. So, you know, if you hire all the best people in the world and you just, like, set them out to, like, go and do their thing, what are the chances that they're all gonna end up with something that actually aligns pretty well? Right? Like, even if they all have incredible taste and they're very good at what they do, you know, th- there is subjectivity to every decision in some part, and so that they might end up with some things that are really great but don't fit together as a really nice whole. Like, the (laughs) perfect example would be building a house, right? So you have, like, the person that works on the roof and the person that works on the deck and the person that does the siding, et cetera, et cetera, et cetera. And a house is arguably far less complex than most of the technical products that we all know. And yet there, like, is painstaking effort put into, you know, having, you know, the plans and having, you know, a drawing of what the final thing is gonna look like. There's a GC, there's an architect. And these people are helping to make sure that all those pieces fit together. And we should have that same care when we're trying to build products together. And so I- I think a big pair on that is then the next piece, which is editing. And, you know, you might call that your- your GC or your architect or somebody that, you know, kind of sees how all these things fit together and then has, you know, an ability to kind of help narrow and- and reduce and remove the things that don't fit. And so, like, at Airbnb, you know, Brian Chesky is, like, the editor of all the things that, you know, come together. At The Economist, you know, there's a chief editor. But, you know, other organizations they might decentralize that approach, which is, you know, certainly possible and, but, you know, challenging because you do need somebody to help them, like, see these things come together. And that pairs with the next piece, which is about courage. Like, the ability to actually, like, say, you know, "No. This isn't good enough." Like, to have the resolve to just be like, "Mm, almost, but no." Which is, like, one of the hardest decisions I think leaders can make and certainly I've had to ever make in my career too, is just, like, you know, a team puts, like, all this care and effort into something and then you're gonna say, like, actually it's just, like, un- unfortunately, like, we're just not there yet and let's try again. And that is, I think, you know, incredibly important part of getting there, uh, and building that, you know, the kind of the fitness of what you do. And then lastly, the other thing that I've learned that will lead me to w- the- the example that you were asking about is that in order to build quality, you really do need to understand it also from the user perspective, which kind of gets me into, you know, my fixation (laughs) with journeys.

   6. LRLenny Rachitsky32:44

      Mm.

   7. KDKatie Dill32:45

      Because that is how a user sees it. The user very, very, very rarely just, like, deals with any aspect of what you build in isolation. There has to be a moment where they learn about it, there has to be a moment where they get to know it, and then there's a moment where they actually decide to use it, and then, oh, something just changed and now they need to n- use the a- uh, that product in some other way. And so you have to understand it from that point of view to really understand whether or not the quality is there. And I think that's a critical piece of building teams that have empathy for their users. So we have been operationalizing that. You know?

   8. LRLenny Rachitsky33:18

      Mm-hmm.

   9. KDKatie Dill33:18

      A- all of the things that I just mentioned, but, like, one of the- the key pieces is to, you know, kind of bring that approach to understanding the quality of the product. And so our goal was to set out to try to solve the fact that, you know, products can be shipped and they could be at the- their highest gain when you ship 'em. Like, you- they go through all the processes i- internally to be, you know, a high quality thing. And then it gets out into the world, and then over time the quality regresses. And some of the reasons for that is that, you know, other things are being shipped. And it's kind of like again back to an analogy of a house. Like, imagine you have one room where you redo the molding, uh, and, you know, you paint the little aspects and you put, like, new plates on the lights. Now all of a sudden that room is great, but it makes everything else (laughs) look worse (laughs) .

   10. LRLenny Rachitsky34:07

       (laughs)

   11. KDKatie Dill34:07

       And the whole composite is worse. And so that is, you know, something that can happen to products is actually they, you know, kind of get worse over time. And then you organize a company oftentimes in, you know, parts to be able to focus on their key business areas. That's a very good thing, because they get focused and they know what they're, you know, building towards and they get expertise and they're, you know, laser focused on that, and so that ideally they move faster. But what also happens is that they get so focused on that they forget about that piece of the journey and how it all fits together, and not recognizing that, you know, part of their product experience is intimately tied to another. So what we did was we set out to,

10. 34:47 – 44:35

    15 Essential Journeys: Stripe’s method for holistic UX understanding and unified vision

    1. KDKatie Dill34:47

       number one, increase the, you know, kind of awareness and accountability of leaders to own their journeys. And so what we have established are, you know, we- we started with 15 of our most important user journeys. 15 is, you know, somewhat of an arbitrary number. It's a number that we can kind of keep track of but also, you know, has pretty good breadth but is certainly not comprehensive of all the most important things. But 15 of our, you know, critical user journeys, the things that we know matter so deeply to our users that we must get right at the highest level of quality possible. And so those 15 things then each have engineering product and design leaders that are responsible for the quality of those products, and they review these journeys, wh- what we call walk the store, where they review them as if they're, you know, walking the floor of their store on a regular cadence. And they friction log what they experience, which I know David Singleton talked about on your podcast.

    2. LRLenny Rachitsky35:43

       Mm-hmm. Mm-hmm.

    3. KDKatie Dill35:44

       And they will write, you know, what they have seen, what's working, what's not working, and they're- they're viewing this from, you know, they're trying to put themselves in the shoes of their user. This is- of course doesn't replace user research, but it, you know, kind of substitutes it and it adds to that. And so they go through the experience and- and noting, you know, what's working and what's not working. And very critically it's a journey, so a lot of times, you know, it starts from internet search, it starts on, you know, Google trying to understand something, goes to the website, you know, they end up on docs, they end up in the dashboard. And they're seeing it as a user might, and with that they're be- they're able to find, you know, the- the entailments of, you know, the experience that may or may not be working, and they lo- jot that down-... they file bugs, they reach out to the teams that may own the different spar- parts of this experience, and then they score it. And then on a, again a- a regular cadence we come together in almost like a calibration, where we meet and we talk about the score of their work. And it- it kind of relates to performance reviews, right? Like, you know, performance reviews, managers are assessing an individual's performance. Which is hard, right? Like, it's like there's some subjectivity to it, just like understanding quality can be. But what we do as managers is we calibrate. We come together and we talk about like, "Okay, how well is this, you know, of, uh, is our interpretation of our ladders document, and you know, how well does that performance align, and are we doing it, you know, consistently across the rest of the organization?" And so we do something very similar. We- we calibrate, you know, these scores because what we're really trying to do is not just, you know, the 15 essential journeys and the- the owners of those. We want to actually like up-level, um, and- and bring more, you know, shared understanding of our quality bar across the company. And so these moments of calibration kind of start that. And then having leaders do this, you know, kind of like creates this like, you know, number one, it like cascades this idea of the importance of owning your journey, and then also has upstream impact. Because when people see the state of products in the wild as a user would, they learn a lot about, you know, what are, you know, some of the bigger opportunities that we can make to make the product better? What are some of the things that maybe we want to change in our process to make sure that we have, you know, even better things coming into the wild? And, you know, one of the best parts of this is since then, we've learned that, you know, folks, you know, have seen that like, "Oh my goodness, our SEO for this particular product, you know, or, you know, the way we're articulating it doesn't align to actually how we want people to understand it later on in the journey. So if we improve this over here, we're going to improve outcomes later on." And so they're seeing that and, you know, they're- they're now, you know, like able to make that happen even, you know, faster to make some of the changes there. And then my, you know, real favorite part is that we're hearing from folks that maybe at first didn't see this as- as necessary, uh, that, you know, maybe in different functions that are, you know, just like, "Oh, you know, I- I was so very focused on executing, you know, the technical ability of what I do on this thing, but I, you know, hadn't seen it from this lens before." And now they are like actually like converts of like, "Yes, this is a really important part of it." And that goes back to the point of like, it's a group effort. Like, y- you don't want just one function looking out for the quality of the product. So having engineers and product managers and people of different disciplines kind of walking the store, seeing the experience, feeling it first hand, I think will lead to better care in, you know, all of the details that will align to better craft in the end.

    4. LRLenny Rachitsky39:12

       Oh man, what an awesome process. I have a million questions I want to ask to better understand how you operationalize this. I'll try to ask just a few. But one thing that stood out about this process is I think people kind of don't trust their own judgment when they're looking at their own product. They kind of, well especially product managers, almost have to like, feel like they have to rely on user research-

    5. KDKatie Dill39:32

       Mm-hmm.

    6. LRLenny Rachitsky39:32

       ... or data to like know a thing. Versus like, "I just see this and it feels bad to me." And I think I've learned over time more and more that you should really trust that. Because you're s- you're spending your energy trying to use this thing, you're not that different from a potential user. So it just, I love that this actually relies on your personal judgment trying to use a thing, which I think people undervalue.

    7. KDKatie Dill39:53

       Yeah.

    8. LRLenny Rachitsky39:54

       A couple of just very tactical questions. Uh, how often roughly does this happen? Is it like once a quarter?

    9. KDKatie Dill39:59

       Yeah. And it, yeah, to your first point, 100%. Like, they're all just forms of input. Like, I'm def- definitely not saying like, "Do this instead of user research. Do this instead of data." It's like, you know, these things in an additional sense. And I- I do think what's so powerful about doing it first hand is that although I am like the biggest supporter of user research, even hearing somebody talk about an experience, while that is like really, really powerful, feeling the pain first hand (laughs) is just like this next level of visceral understanding of like, "Oh, this could be better." And your users, you know, they might not always say what's m- missing or what's wrong, or maybe they don't, you know, they don't know that certain aspects of it could be better. So yeah, having your, you know, point of view on that in addition to the user research and what you've heard from them directly is really, really important. But, you asked about how often. Uh, we have, you know, as I've mentioned, we are, you know, constantly looking at our processes and trying to figure out how we can, you know, make them better and better. You know, as an o- organization, you know, as we've grown, you know, things, you know, need to adjust. We today are doing it quarterly, and the quarterly aspect of like walking the store is by no means meant to be like that's the only time people do it, but that is the time where, you know, we're looking for like update your scorecard and, you know, share the information in a dashboard where, you know, everybody can see. And that is feeling right now to be the right cadence because there, it's enough time that, you know, there can be, you know, material differences made, and so you can see and kind of like the scores evolve over time. But also frequently enough that, you know, you're not missing that perhaps, you know, there's been a setback since. But of course, my real hope is that these happen, you know, they're happening weekly, just perhaps in different parts of the organization.

    10. LRLenny Rachitsky41:46

        I want to ask a couple more questions so that folks can try this at home. I was just thinking like, this podcast is the opposite of don't try this at home. It's like, "Here, do, try this at home."

    11. KDKatie Dill41:54

        Try it at home. (laughs)

    12. LRLenny Rachitsky41:55

        Yeah. So I want to try to give people w- a few more answers to questions when they're probably going to try to do this themselves. So, um, who's in these meetings? Like, do you join these walk-throughs? Does like David join? What do you suggest there?

    13. KDKatie Dill42:07

        Yeah. And so what we're, for, what we're doing for each team is they do them th- themselves together. So, uh, y- you know, at bare minimum it should be the engineer, product manager, and designer doing it together. And the reason why we like to see it happen together is, again, as we've talked about before is that like people bring a different perspective to something. And so let's say, you know, somebody in the room might be like, "Oh my goodness, you know, that, like..."... that the load time didn't feel really good there. And like, oh, whoa, that like, the way we're stating this is not consistent per page. Um, and ah, that's not on our design system. Uh, so, you know, it is really powerful to have folks, like, come together and do it. And in fact, David Singleton, who you mentioned, he and I do these things very regularly too. Like, this is, like, kind of outside the Essential Journeys program, but like, he and I walk the store, and we'll just pick random flows and go through it together. And, you know, I can't code, but he can, and so he'll, like, he'll do the code part and I'll be, you know, sitting there being, "What? You know, do they really do that?" Like, you know, "C- can we, you know, how can we make that better for them?"

    14. LRLenny Rachitsky43:07

        Mm-hmm.

    15. KDKatie Dill43:07

        Uh, and so it's, I, I really loves the multidisciplinary approach. But then when we do the calibration after the team has done-

    16. LRLenny Rachitsky43:15

        Mm-hmm.

    17. KDKatie Dill43:15

        ... these walkthroughs and they've kind of gotten their own perspective and they, you know, fill out the scorecard based on our rubric for quality, uh, we will come together in what we call a PQR, p- product quality review, and they will take us through what they have, you know-

    18. LRLenny Rachitsky43:29

        Mm-hmm.

    19. KDKatie Dill43:29

        ... experienced and then they'll talk about like, and so this is why we've scored this a yellow or a yellow-green and, uh, and then we might have a, you know, conversation about that. It's like, "Well, actually, like, that felt a little worse than, you know, you've described it, and actually, like, I think that, you know, we probably need to put more urgency on solving that." Or, in some cases, it's like, "Actually, like, that was pretty great," you know, if you think about, you know, what we're, we're trying to, you know, help somebody achieve at this moment, like, that actually is, is really, you know, hitting the mark. And so we will debate that there and in those meetings you'll have, yes, myself, David Singleton, um, uh, Will Gabrick, um, who, you know, leads product and business, and then various leaders from the organization that might be relevant to that area. We are trying to give people kind of like insight to what's happening across, so, uh, again, it's a multidisciplinary room. I'm trying to keep it, you know, not too, too large because obviously it can be, you know, hard to have discussion, uh, but it is, you know, very valuable to make sure, again, that we have, you know, the perspective of product marketing and the perspective of engineering and the perspective of p- product in the room as we discuss what our

11. 44:35 – 46:25

    Stripe’s PQR quality review

    1. KDKatie Dill44:35

       quality bar is.

    2. LRLenny Rachitsky44:36

       Awesome. Okay. That makes a lot of sense. In terms of scoring, are you scoring individual steps of these journeys or is it yellow for, like, segments? What are you scoring?

    3. KDKatie Dill44:44

       The way the rubric works is so that... And, and we, we have a template for the friction log. So people fill out a friction log and it'll be like screenshots and then what they experienced, and then there is a, you know, kind of a tool to tag for each kind of moment. It's like, "Oh, that was a nice touch," or, "Ooh, that is, you know, not great, we should consider a fix," or different levels of kind of severity of like, "Oh my gosh, P zero bug, we need to fix this right now." So they'll, they'll tag for different moments in the journey, and then there is a summary score at the end which is based on a rubric that we have that talks about, you know, the importance of quality from the point of view of usability, utility, desirability, um, and, you know, actually going to that next level of surprisingly great. And then we'll ask them to score on a whole what they felt of these things and then that c- adds up to a summary score, which we have also talked about the different ways of scoring. You know, is it a number based system? Is it a letter based system? Like, A-, B.

    4. LRLenny Rachitsky45:40

       Shirt sizes.

    5. KDKatie Dill45:42

       Uh, yeah. Uh, we have so far we have landed on c- a color system because honestly I think people can get a little tied around the axle on how you're measuring it, and like, to your point, as, like, especially in subjective things and it's just like, "Oh," you know, it's like, "Well, is it really a six or is it a seven?" And, you know-

    6. LRLenny Rachitsky45:59

       Mm-hmm. Mm-hmm.

    7. KDKatie Dill45:59

       ... we didn't want people to get a little too, you know, too worried about, you know, how does... Like, it's not meant to be an objective quality- uh, quantitative score. It is qualitative. It is judgment. We hire people for judgment, you know, so we want, you know, th- them to bring that to the conversation. And so that's, you know, how we chose to score because we felt that would actually lead to, you know, quicker but, like, straightforward, uh, opinions and decisions.

12. 46:25 – 48:29

    Stripe’s prioritization philosophy

    1. KDKatie Dill46:25

    2. LRLenny Rachitsky46:25

       At a lot of companies, you have these reviews and the founders, like, share all this, like, "Oh, this is broken, this is busted," and as a product team you're like, "Goddammit, we have these goals we got to hit, we have this roadmap, and now we're going to get 100 things that the founder's like, 'You got to fix this.'" I'm curious just how you tell teams to take this stuff and prioritize it amongst all the other things they're going to do. Is it just up to them? Is there, like, need to fix this? Anything you can share there about just, like, how to actually operationalize taking this feedback and doing something with it?

    3. KDKatie Dill46:54

       Yes.

    4. LRLenny Rachitsky46:55

       (laughs)

    5. KDKatie Dill46:56

       Yeah, I've seen some organizations talk about, you know, when they're doing planning, you know, you do your OKRs quarterly or half year or year or whatever, you know, recommendations of like y- you know, 10% of your time should be spent on, you know, fixing things and 20% on growing things and the rest on, you know, keeping the lights on, whatever it might be. So yes, I've seen different companies, you know, build a recommendation based on certain percentages of how they think teams should be spending their time. And we, uh, at Stripe think that, you know, first and foremost is that, you know, we have to make sure that folks are, number one, you know, hired with the fact that they have great judgment and care for what they build and they take pride in it. Like, you know, that's like number one. And then, you know, you can give a lot of trust to people based on that kind of commitment to building great things that they will use that in their decision-making. And then, of course, it, it needs to be very clearly, you know, advocated for at the highest levels of the company. And with that, I think that kind of like fuels people's thinking as they're building their plans. But there is iteration in the plans and we do have multi- multidisciplinary people, you know, making the plans together. So it's like, "Oh, okay, are we advancing these features? Are we, are we going to be building growths? And, you know, is that, you know, improving the quality as well?" Uh, and so I think that's how we kind of together get to it. But we don't have, like... There's no formula

13. 48:29 – 50:28

    Measuring impact beyond metrics

    1. KDKatie Dill48:29

       that we ask people to follow.

    2. LRLenny Rachitsky48:30

       So basically what I'm hearing is it's a cultural kind of just everyone... People are hired with this expectation, "We are gonna focus on quality."... and we'll prioritize things even though they may not move metrics, because we know that this will generally improve and help grow the business.

    3. KDKatie Dill48:43

       Part of it though is showing how it moves metrics.

    4. LRLenny Rachitsky48:46

       Mm.

    5. KDKatie Dill48:46

       Because I, I think that is a dangerous belief that is absolutely out there as we, we talked about earlier. But that actual quality improvements do increase growth. They do improve the bottom line, right? that like, you know, for example, we, you know, saw that folks were reaching out to support because they didn't know the state of, uh, how, you know, one of their invoices was performing. And what we, when we dig in we realize it's like, well, we had a button that like looked nice but it wasn't super clear.

    6. LRLenny Rachitsky49:18

       Mm.

    7. KDKatie Dill49:18

       And so they didn't know how to access the thing that they were trying to do. And so by improving that, we decrease the need for them to have to reach out which is clearly not their, you know, want. Uh, to have to, like, call somebody to, you know, find the answer to their problem. And so with that we made an improvement and we of course improved the bottom line because of that. So I actually think that maybe, you know, one of the steps that somebody should consider in their organization is just like, you have those examples, like every company does, where, you know, quality leads to better business outcomes and to talk about those and make them known. Because I, I think it's actually a false belief that, you know, it's like one or the other. It's like are we going to work on quality and it doesn't move the metrics, and, and, and where we do. You know, some of them are, you know, longer term and so you have to look out for a w- a while to see that change in, you know, the beliefs of your customers or, you know, how often they're, they're sharing your product or how often they're succeeding in what they're trying to do. But some of them are short-term, uh, impacts, and that is an important thing for people to be aware of because it will give them ideas of like, "Oh, we could do this in our team too. We could have a higher quality product and actually move the business metrics."

14. 50:28 – 54:09

    Performance = potential – interference

    1. KDKatie Dill50:28

    2. LRLenny Rachitsky50:28

       Is there anything you do in how you evaluate performance of teams that helps prioritize this sort of thing? So, generally it's just like, cool- ... this team moved this metric by a ton. They're doing great. I guess is there anything that you bake into performance evaluations at Stripe especially for product teams that help them understand and prioritize some of these things that may not obviously move metrics other than just broadly we believe great experiences are going to improve growth?

    3. KDKatie Dill50:53

       Yeah. Well, I think one part is being clear on what impact means.

    4. LRLenny Rachitsky50:58

       Mm-hmm.

    5. KDKatie Dill50:59

       Because I do think that in some companies, you know, impact just like, "Okay, how, you know, what business metric did I move and how much?" And there are, you know, certainly really important impact projects that folks can have that maybe they're multi-quarter or, you know, multi-year, and so, you know, maybe you didn't move, you know, this incredibly important business metric in one quarter, but actually, like, the work that you are doing is instrumental to the success of the business. Uh, so there's that. And then like you said, you know, there are perhaps, you know, quality efforts that are harder to measure or they're longer term, uh, but they are still impactful. So, I think number one is that, you know, when you're thinking about how to come up with a rubric for how you're going to judge performance is just like really honing in on what, what does impact mean? And, and then a, a lot kind of comes from that and being able to, you know, celebrate and recognize great work happening even when, you know, it's not necessarily materially moving that number. Um, the other part of it is, you know, we have a levels and ladders system, so it's a, a document that's not meant to, like, lay out, like, here's the checklist of all the things you need to do. But it's, you know, kind of a guide for this is what is expected in your role and at this level. And in these documents we talk about the importance of things like quality-

    6. LRLenny Rachitsky52:19

       Mm-hmm.

    7. KDKatie Dill52:19

       ... uh, and that the, you know, what we pursue is, is building these, you know, things that are, are great. And another part of that is also the operating principles which is kind of like the, the thing that we align on underneath all of these kinds of levels and ladders systems that we have. And our operating principles include meticulous craft. Um, it is one of the things that is really important to us as an organization, is just like having that meticulous care for all that you do, like whether it's like you're, you know, designing the space that we work within or that you're creating the API or that you're building the interface or that you're, you know, talking to people on support calls. Like the meticulous craft is something that, you know, is actually expected of everybody.

    8. LRLenny Rachitsky53:02

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15. 54:09 – 1:01:46

    Building and managing large teams

    1. LRLenny Rachitsky54:09

       I'm going to shift to a different topic, and this is just the last area I want to spend some time on, which is team building, leadership, that sort of thing. So you've led design at three hyper growth companies. Two of them, Airbnb and Stripe, are like two of the biggest companies in the world and also just known for great design. And I'm just going to ask a broad question. What have you learned about building, leading, managing, scaling large teams? Are there lessons that stick with you? Anything come to mind when I ask that broad question?

    2. KDKatie Dill54:40

       One of the things that has stuck with me, and, you know, through all the, the trials and tribulations of leading and s- as I've already laid out for you in the very beginning of this call, haven't always got it right, uh, but one of the things that has, like, been a clarifying force as I think about growing and leading teams, uh, is actually something I learned at Airbnb when we were there together, it's a formula, uh, sort of. Uh, so performance equals potential minus interference.

    3. LRLenny Rachitsky55:09

       Mm. I love that.

    4. KDKatie Dill55:10

       And I really like this, it's pretty simple, but, like, is a good reminder that, you know, as a leader, one of the things that you are, you know, of course driving towards is trying to get better performance. Uh, you know, better performance so that, you know, your team feels, you know, more purpose and motivation and is excited about their work and that you're building greater things for, you know, your customers and you're having more business effect, of course, performance. But the key pieces of that are, of course, is potential, so thinking about how you increase potential, which would be, of course, hiring really well, developing the talent and helping them grow and, and increase their own potential to do better and greater things. And then, uh, paired to that though, of course, is decreasing the interferences, which could be that, like, kind of lead weight on top of great talent. 'Cause you can hire the best people in the world, but like a muscle atrophying underneath a cast, if, you know, there are interferences that are holding them back from doing great work, you know, they're gonna burn out, they're not gonna enjoy the work, they're not gonna be as successful and you will not get as strong of performance from it. And so I really do think of this constantly as to, like, "How can I increase potential? How can I decrease interferences?" And over time, especially as your company grows, you know, you're gonna have to keep doing that. Like, you know, the, the design work is never done in designing a team because th- the more people you bring in, you know, the more it puts your processes in a, in a faulty state. Um, we, you know come f- intentionally or I, I have intentionally, you know, run teams where, you know, you get to a point where, like, it's kind of like running hot, right? It's just like, okay, like we've outgrown our processes. And that's okay because then you can learn as to, like, "Okay, this is how people are actually trying to work and this is how we actually c- you know, can improve it." So, you know, making those changes a- as needed, you know, helps to make them, you know, more sought after and, you know, more, uh, informed in terms of as you improve the processes. Uh, one of the things that I've been working on since I worked back at Airbnb was this idea of improving awareness of the things that are happening. What happens in a lot of companies, especially as they grow, is people lose touch with what's happening in different parts of the organization and, you know, everybody's got, like, a doc that, you know, their PRD where they've written down what they've done and it's got, like, tons of, you know, words that nobody really understands (laughs) and, you know, keywords for the different projects, and that isn't, you know, the best way to lead to clarity. And I'm a strong believer that a picture tells a thousand words and a prototype tells, you know, saves a thousand meetings. And what we do, and have been doing it for the last, uh, I don't know, you know, decade or more, is having people within the design team share as a screenshot or a prototype of what they are working on in a shared deck. And so they add this to a slide in Google Slide Decks every couple of weeks and we get to see what's happening across the design team, and this is really important for all the designers because they can see, you know, whether or not they're a team of 10 or 170 or whatever it might be, what is happening and they can say, like, "Oh my gosh, like, you're working on that surface? Like, so am I and let's talk about it." Or, "Oh, that's an interesting pattern. Like, you know, maybe we could use this in more places." And we send it to the product managers and the engineer leaders and the leaders in the company because it is also a really great way for them to understand what's happening and what are we building together, 'cause going earlier as I've talked about, the importance of thinking about things as a journey, so, like, what's happening in the marketing side, what's happening in the, you know, this aspect of the product and seeing how all these pieces really fit together. That has been, you know, absolutely, like, one of the things I will take where, you know, wherever I go, whatever I do because it has just been, like, very, very useful tool.

    5. LRLenny Rachitsky58:51

       I remember that at Airbnb and I... there's nothing more fun than just looking through a bunch of awesome designs and products that are in motion and in a deck form is so handy. You just flip through, "What's going on around the company?" And like, "Oh wow, look at this thing. That's amazing." And it's interesting that ends up in a deck, like, feels like Figma would be really good for that too but, but somehow decks are still really, really handy for simple things like that.

    6. KDKatie Dill59:11

       One of the key pieces is just, like, keeping it really low maintenance. Uh, yes, you know, the, the design team would definitely prefer that it would be in Figma-

    7. LRLenny Rachitsky59:20

       Mm. (laughs)

    8. KDKatie Dill59:20

       ... but I, you know, critically I, I want all functions to be able to look at it, uh, and, you know, if not everybody is on Figma and they, you know, if they were that would be great too but if they are not, you know, it's just like flipping through, really easy, touch of a button, you know, you can just, like, send it off. Um, it's behaviors that people are really used to, commenting, but yeah, maybe one day Figma.

    9. LRLenny Rachitsky59:42

       (laughs) And the way you do that is it's just, like, a scheduled call for all designers, "Add your stuff to this deck," and then you email it out every two weeks I think you said?

    10. KDKatie Dill59:48

        Yeah. Yeah, we, and we experiment with, like, how often we ask folks to share and also, like, you know, the granularity of what they're doing. Like, it is not meant to be a status check. We're not asking everyone, like, "Show us what you're doing." It's more of, like, "What are the projects that are happening?"

    11. LRLenny Rachitsky1:00:02

        Mm-hmm.

    12. KDKatie Dill1:00:02

        And, you know, we might ask, like, "Well, show us, like, the medium and large projects," you know, if there's not just too much going on and all of a sudden it's, like, a 200 page deck and no one's gonna flip through it. So we have experimented and evolved that depending on the team size, uh, and I think right now we're at monthly, uh, sharing of it, and that seems to be working pretty well. Um, it used to be biweekly, which I loved because I really love looking through it, but it, it adds up, you know...... if it's, you know, feels like it's an arduous task, um, then you know, it's not succeeding.

    13. LRLenny Rachitsky1:00:31

        Yeah, and especially knowing designers, they want to make sure it's the best version of what they've done and then it takes all this extra time to like, "Okay, we've got to make this beautiful mock-"

    14. KDKatie Dill1:00:38

        Yeah.

    15. LRLenny Rachitsky1:00:38

        "... to show everything we're working on."

    16. KDKatie Dill1:00:38

        You know, and that's actually another part of it that, you know, is another benefit of, you know, opening up the curtain a little bit, of like, we, you know, we do, you know, certainly we have to take things seriously in terms of like, you know, it's confidential work, it's work in progress, you know, it's not ready to go live. You know, we're not ready to, you know, critique all the details about this. Like, you know, we, we do need to make it very clear to folks that this is like work in progress, but also, you know, that it, it is really beneficial to bring the work out because what isn't great is that you get to the end of the project and people have worked tirelessly on it for some long stretch of time and then find out that like, "Oh my gosh, this is the same project that we're doing over here (laughs) and, you know, this can be completely redundant." Or like, "These two things are on a path to collide." So we want to know that sooner because it absolutely at the end of the day will make the work better, save time, uh, and so, you know, opening up that curtain and showing the work in progress, you know, it can feel hard at first, but I think people have started to see the benefits in doing that, and then, you know, usually that will lead to better outcomes in the long run in the culture too.

16. 1:01:46 – 1:06:10

    Removing interference at Lyft: a practical example of Katie’s leadership impact

    1. LRLenny Rachitsky1:01:46

       Going back to this formula you shared, which I love, performance equals potential minus interference, is there an example that comes to mind of helping with interference where you found that, "Oh, wow, this is really slowing things down." And you changed something?

    2. KDKatie Dill1:01:59

       It actually goes back to org design that we talked about earlier, um, and where people sit. So when I joined Lyft, uh, as I mentioned to you earlier, I was like, oh, I had learned from the experience that I had at Airbnb and I came in needing to transform the organization and was hopefully (laughs) much better at it because I had learned so much. Uh, what actually was going on there is that the way that the team was organized before I got there was that actually, you know, physically, the design team sat separately. They sat in a room that was just like beautifully designed, uh, separated from engineering and product and all the other functions by a locked door.

    3. LRLenny Rachitsky1:02:38

       Oh, no. (laughs)

    4. KDKatie Dill1:02:39

       And that was really interesting to see because, of course, there are a lot of benefits to it, which is that like design, you know, had this like very safe space for creative discovery and exploration and communication. There was, you know, work all over the walls. It was like wall-to-wall whiteboards and it was just like absolutely a place where, you know, creativity could thrive.

    5. LRLenny Rachitsky1:02:58

       That sounds exactly like the Airbnb situation, by the way.

    6. KDKatie Dill1:03:01

       The current Airbnb situation?

    7. LRLenny Rachitsky1:03:02

       The original.

    8. KDKatie Dill1:03:04

       Yes.

    9. LRLenny Rachitsky1:03:04

       The fair-

    10. KDKatie Dill1:03:04

        Oh. Yeah.

    11. LRLenny Rachitsky1:03:05

        ... fair times.

    12. KDKatie Dill1:03:06

        Yeah. Yeah. Yeah. And, you know, absolutely there are a lot of, like, tie-ins to, you know, what I had seen. And the, you know, interesting part about, like, how, you know, actually teams were working is that you, you would see that there was, like, a lot of wasted work and there was a lot of, like, misalignment in what we were trying to do because there was, you know, product managers and engineers that were sitting alongside each other making decisions and talking about the work and deciding things, and then designers were sitting over here in this other room and they were working on something and then they're like, you know, they'd meet up and it's like, "Ooh. That's not aligned." Like, you know, "That doesn't fit the goal." And like, "Ooh, why... You know, you went that way, we were supposed to go over this way." And so, you know, interference in the sense that it was like, it was wasted work, it wasn't actually aligned to the goals, it was slower, and, you know, there were definitely benefits, like, there was real reasons for doing this and I know there are companies, um, including Apple that have, you know, kind of like separation of these things. But I think if, if you're going into that kind of way of working, you know, there's probably a lot of other decisions you need to make too in terms of the way the teams work. And so what I was seeing there was just, you know, just kind of like the composite of all these, you know, aspects coming together that was not leading to, you know, more efficient and, and less interference. And so what we did was to evolve the way we were working and bring better alignment to the different functions, and again, you know, had done it with, you know, an approach about listening and, you know, came into that with a, you know, kind of better understanding of getting to know the team and getting to know engineering and product and, and see what our goals were together so that when we were making changes, we were making the changes together and we, you know, actually were aligned so that, like, on the day that we opened the doors and, you know, brought, you know, design and eng and product together and, and had, you know, spaces for folks to, like, work together and, like, they actually sat with each other, we still kept the creative space for, you know, "This is where we'll do crits. This is where we'll do working sessions. This is where the folks that don't work in an embedded fashion will sit." But we had, like, you know, the best of both worlds in that way. And so with that alignment of the way that the func- the teams were working together, there was much, like, faster kind of iteration cycles, better clarity on how the work was working, and we still kept and protected, you know, that room for creative space, like literally The Room and literally the room in terms of, like, figuratively speaking-

    13. LRLenny Rachitsky1:05:20

        Mm-hmm.

    14. KDKatie Dill1:05:20

        ... uh, for allowing for, you know, creative exploration but more aligned.

    15. LRLenny Rachitsky1:05:23

        And just so I understand, essentially you re-orged the teams and not just physically move people, but you kind of changed the way the product and design and eng team was even organized?

    16. KDKatie Dill1:05:34

        Yes. Yes. Like, literally and figuratively, we broke down the wall-

    17. LRLenny Rachitsky1:05:38

        (laughs)

    18. KDKatie Dill1:05:38

        ... and, you know, brought, you know, the teams physically together so that they would work together and then, you know, we had an org chart where it's like, "Okay. These designers are working on driver. These designers are working on rider. These designers are working on, you know, the, the safety team." And then they would sit with their respective engineers and product managers, uh, and then, you know, we would, as I talked about earlier, like, we would come together at key moments to make sure that we as a design function were still, you know, aligning on, you know, shared goals about, you know, the overall experience, but also making sure that we could work

17. 1:06:10 – 1:07:41

    Stripe’s physical workspace design

    1. KDKatie Dill1:06:10

       well with our partners.

    2. LRLenny Rachitsky1:06:11

       So interesting that that was a recurring pattern at the places you went. I imagine Stripe was not like that, there was not all designers sitting in a locked room.

    3. KDKatie Dill1:06:18

       ... not in a locked room. And when, when I joined Stripe it was a Zoom universe, so it's a-

    4. LRLenny Rachitsky1:06:22

       Mm-hmm.

    5. KDKatie Dill1:06:23

       ... it's a little bit different. Um...

    6. LRLenny Rachitsky1:06:24

       It was Zoom.

    7. KDKatie Dill1:06:25

       But, you know, we do even today we have, you know, a studio space, uh, where, you know, we have all the, the great, you know, tools of craft and when you do go into the offices, we do have places where, you know, designers sit together, especially in the functions that aren't embedded. So we do have, for example, we have brand and marketing creative-

    8. LRLenny Rachitsky1:06:44

       Mm-hmm.

    9. KDKatie Dill1:06:44

       ... we have the, the website team, um, and we have, you know, folks that work kind of across all of the things that we do. And so, you know, for sure there, there usually is some sort of creative space, which I actually think like having a physical space for creative discovery and exploration and, you know, having that up on the wall, like, you know, I, I love that so much and, you know, I, I go into the office about halftime now and, you know, I think over time we'll probably build that out more and more because it is really powerful, in addition to having teams, like, sit by the, the disciplines that they work with every day.

    10. LRLenny Rachitsky1:07:17

        It reminds me of a quote I have on my wall that I think I found in the Rick Rubin book, but it's by someone else, so I don't know exactly where I found it, but it's, uh, "The object isn't to make art, it's to be in that wonderful state which makes art inevitable."

    11. KDKatie Dill1:07:31

        Ooh, that's good. I like that very much.

    12. LRLenny Rachitsky1:07:34

        By, uh, Robert Henry.

    13. KDKatie Dill1:07:36

        Okay. By Robert Henry.

    14. LRLenny Rachitsky1:07:37

        That's what I try to do in this little podcast studio that we got here.

    15. KDKatie Dill1:07:40

        That's awesome.

    16. LRLenny Rachitsky1:07:40

        Um,

18. 1:07:41 – 1:11:07

    Embracing bold ideas

    1. LRLenny Rachitsky1:07:41

       is there anything else that you think would be useful to share, either from scaling design teams or broadly?

    2. KDKatie Dill1:07:50

       I think one of the other tendencies I see of companies at, you know, different stages of their growth is, you know, a fear of bold ideas. Um, what happens is that, you know, i- i- it can happen at small sizes and then it can happen at large sizes actually. It's just that, like, you know, a fear of kind of like, you know, shaking things up too much or, you know, big ideas with lots of things changing at once are really hard to measure, and so, like, actually, like, you know, if we just, like, make an incremental approach, it's very measured and we can, we know what the outcome is gonna be, it feels safer. You know, I can get it done in the quarter, and depending on how your performance is managed, that might be more attractive. And so that is a diff- dangerous tendency, because I think if we go back to, like, what quality means, you know, and you think about it as like, well, like, quality is really, you know, your users are the judge of that and the way that they experience things oftentimes are, like, across products, across surface, across time. If you just think about, you know, these, like, incremental approaches to the little s- you know, to the scope of whatever that is that you own, you are very likely not to, like, make the, the whole thing better. So I think we have to fight against that. And, you know, the way I look at it is, you know, the way I talk about it is, like, reach, reach for the stars and land on the moon. And what I mean by that is that vision work is really important, and I think, like, sometimes it can get a bad name because you can end up with some folks that are doing vision work that goes nowhere, and they make a beautiful deck and then it gets, like, seated on a shelf and nobody ever builds it. Like, that is not what I'm talking about here. That is not what I recommend. But actually, you know, vision work that absolutely does look at the c- you know, the entirety of the experience, a comprehensive approach, you know, a journey approach and thinks about how these things, you know, various things may come together to be better, and, like, sketch out the ideal version. And I think Brian Chesky talks about it, I think it was, like-

    3. LRLenny Rachitsky1:09:41

       Mm-hmm.

    4. KDKatie Dill1:09:41

       ... the 11-star experience, I think he once said. Um, so it's like-

    5. LRLenny Rachitsky1:09:44

       Plus, plus the Snow White stuff-

    6. KDKatie Dill1:09:45

       Yes, exactly.

    7. LRLenny Rachitsky1:09:46

       ... that we've talked about a couple times on this podcast. Yeah.

    8. KDKatie Dill1:09:47

       Exactly. Looking at it as a journey. Yeah, like, i- it's not the five-star approach, it's not the six-star approach, but, like, the 11-star approach. But show what that ideal version is, like, 'cause you, you, if you don't know what that is, like, w- what are the chances that you're gonna increment yourself to the right outcome in the end? And, you know, as I talked about before in, like, building the house, like, you wanna see what that picture looks like in the, you know, the, you know, how all these pieces come together. And I strongly recommend you want to see what it looks like in, you know, in an ideal form, 'cause you can always work back from that. And so it's like, okay, if this is what we want to get to, if this is what, like, our product is gonna look like in two years, how do we get there? And y- what very likely is, it's a team effort, and various parts of your organization are gonna have to own various parts and, you know, maybe we ship this piece first so that we can study it and learn and, and, you know, make sure that the data is good before we move to the next piece. Like, I'm not suggesting you have to ship the whole thing at once. But that, like, you know, kind of north star lays out the process in a way that I think allows for, you know, big risk-taking in a way that is measured and thoughtful and, um, you know, actually also feels like progress as you step towards that, versus, like, you know, trying to, like, get there, you know, day one and, you know, likely, you know, end up giving up.

    9. LRLenny Rachitsky1:11:02

       I love that. Reach for the stars, land on the moon. That could be a metaphor for so many things.

    10. KDKatie Dill1:11:06

        (laughs)

19. 1:11:07 – 1:15:15

    Qualities of great designers

    1. KDKatie Dill1:11:07

    2. LRLenny Rachitsky1:11:07

       Um, let me try to squeeze in one more tactical tip for people listening. If someone's hiring a designer, so someone that's not a designer, you know, just founder of product team, just, like, what should you look for that may be a red flag or something that you wanna look for, to kind of feel good that they're gonna be a good fit?

    3. KDKatie Dill1:11:23

       The key, I think, to keep in mind, uh, is, you know, i- it's easier to teach tools and process than it is taste and character. So I would certainly, you know, pay a lot of attention to that, you know, kind of like their hit rate for, you know, great judgment and, and great taste and how they've honed that, you know, even if, you know, they're not very experienced. Like, just to, like, see do they have that, you know, natural inclination, uh, for great things? The other piece of it is that, you know, certainly youwant to find somebody with great talent, for sure, a- and high craft, but you also want to find somebody that's humble, you know? And like ch- you know, folks that are really good at what they do aren't always, uh, but humility is a really important part. I mean, I think it's a really important part for anybody on a team because, you know, if you're working on a team, you know, you need to work together and it is important that they have that respect and empathy and understanding and, and, you know, enthusiasm for the folks around them, but also the users. So, you know, humility means that they're going to pay more attention to what the users are saying and hopefully be curious about what's working and what's not, and, you know, strive to, to-... navigate these things to make it better. And then I guess the last piece would just be, you know, hustle or, or chutzpah (laughs) . Um, I'm not sure exactly what's the right way to put it, but you know, the design and, you know, the creative functions is, you know, it's the act of creation and it's scary. You know, it's like to like cre- take a blank piece of paper and propose something that you think is better is, is scary. To, you know, have the courage to say, "This is not good enough, and we should do it again," is scary. And so having somebody that has, you know, that kind of like courage inside them to, you know, fight for great is pretty important. And that hustle to like try to execute on that, you know, rapidly is, of course, you know, essential as you're, you're hiring at, you know, really any stage of company. And I guess lastly, I think you, you were asking in particular like es- you know, especially with younger companies or startups-

Episode duration: 1:34:00