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

The use of the word beauty in books that have been digitized by Google has decreased, like pretty dramatically. And it's aligned with this idea of like, well, functionality is king. Functionality is what matters. And as if people think about functionality 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, 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. You see that 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.

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, seeing the teams 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 her 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 lifts 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 waitlist 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 roadmapping 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 team is 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 cash, 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. Re-discover what's possible with Jira Product Discovery. Try it for free at atlassian.com/lenny that's atlassian.com/lenny Katie, thank you so much for being here. Welcome to the podcast.

Thanks for having me. Good to be here.

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 did not know this was happening. I am so curious to hear the story. Can you share what happened?

Starting with the easy questions, I see. All right, right into it. 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 experience design organization. That's basically the product design team. which was 10 people at the time. They had been reporting directly to one of the founders, and they were going to start reporting to me. During my interview process, I learned a lot about what was working and what wasn't working, and some of the trials and tribulations with the design organization and its collaboration with others. It seemed like there was room for improvement in how engineering and product management and design all worked together. There was also really low engagement scores in the design team. And so I kind of came in ready to go and excited to try to help make some change based on all the things that I had learned from various leaders and people across the company. And I 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 a.m. was an hour and a half with half of the design team, so that was five people. and our HR partner.

Oh no.

Not usually.

That's never a good sign.

Yeah. And 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 Airbnbs. But of course, this was the one 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, quietly reading from the papers, all the things that they saw that I was doing wrong, and all the things that they didn't like about me.

And.

It was a really hard moment. I went through all the usual stages of grief when one hears feedback, which is just immediate want to respond, 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, 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 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 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 hard as that was, I'm like very grateful and very amazed that that they could kind of come together and share that with me. It can be hard to bring feedback forward like that. And so it was an extremely valuable learning experience. And I took from that to then immediately shift how I was operating. And really a key part in building trust was to listen, to hear out what the individuals on the team were setting out to do, what they cared about, what motivated them. And so I started to make pretty fast change and still moving in the direction that was necessary for the org to make the really large impact in how we were operating, but bringing folks along with me. You can inflict change on people, but if you want to do it with them, you really, trust is the key element there. And then a couple months later, we had the best engagement scores in the company. So it actually, it did, objectively improve the situation. And since then, taking that on into Next Steps and other companies that I've joined, and just think about instead of coming and swinging, come in listening so that you can really set out to make change that actually has true positive impact on the folks around you and you bring along with you.

Wow. 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?

Before I got there, I think there was a little of like, you know, design is just going to sit with design and not necessarily like work in close proximity with engineers and product managers, et cetera. And one of the things that I believe has, 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 was something that I was very devoted to, which is bringing design together at key moments multiple times throughout the week to also build a community in design. You know, like Joe Bot at Airbnb once said, it's like, well, what t-shirt do you wear? Like, what team are you on? And I was like, you, wear two t-shirts. You have two t-shirts. You have the design t-shirt and you have the marketplace t-shirt or whatever cross-disciplinary team that you work on. because both are really important communities to build for slightly different reasons. So yeah, Feynman was a good spot for that.

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 going to 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 Lyft have done that.

It's a great question and I think this is like an age-old question that I don't know if will ever go away and it, you know, probably because the quality bar keeps evolving and keeps rising. But I think first to level set before we dive into that, I would say that there are levels of quality, right? There is the, does the thing work? Does it provide some sort of value proposition? It executes on its job. That's baseline quality. Next, is it, does it do it exceedingly well? Is it error-free? Actually, maybe that's not even exceedingly well, but just error free and it actually works in a well rounded way. And then beyond that, like level three, level four, level five, does it exceed expectations? And it does something that you weren't even in seeking for as a user. And I do think 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. 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 end up with, like, you've got three things that you could possibly do to make perhaps 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. 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'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 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 ads? Like, of course not. So like, why? Why go? 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 in another day? And really in the belief of that these things can, you know, It really does add up to a better outcome in the end. And so, you know, a longer, healthier life. And so hopefully I get myself together and go to the gym. And I do think some of the best companies in the world and the planet thinks that way. And I recognize that our customers don't always ask for it. I mean, you might see it in support cases, for example. Like, clearly they don't know how to use this next step and that is probably a quality issue. And that, you know, they might be asking for, you know, more improved features. But some of the levels of quality, the level two and three and four, you might not get direct asked for. But I guess, give you another analogy. If you don't have competition, that's fine, right? If you think about the first car, I'm sure that wheel was really hard to turn. And I'm sure that seat was not comfortable. And you could have any color you want as long as it's black, right? But there was no competition. The competition was a horse, so 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, 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 take, you know, have a better experience with it that they'll, you know, want to talk about with others. 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 tied 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. 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 more impactful, more seamless, quicker checkout, and therefore higher conversion with their customers. And these small things, really, they're quality issues. They're just that if you really understand what a consumers trying to get out of the experience, then you can make it better. And so we have been 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 on one's revenue.

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 they'll give people a sense of like, holy moly.

Yeah, Stripe is used by millions of businesses globally, small and large, from early stage startups to SMBs, larger organizations and enterprises like Amazon and Hertz, Shopify, Spotify, X, which I believe you use. And the work that we do, it ranges. We have checkout flows, so when someone's paying online or in person, or we also provide a suite of financial automation tools so that you can run your subscriptions business and recognize your revenue and receive tax and essentially manage the complexity of the financial space through powerful tools that hope to make your job easier so you don't have The details of how these things work.

I just wanna 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 quality design perspective versus like, oh, there's just, let's just move this metric and here's all the things that are stopping people. What would you say is the designers lens on that if there's anything there.

I honestly, a pet peeve of mine is this way of talking about things as 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, 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 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, 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 click it more often. And, you know, that's 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 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 that, 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 because it does make things more useful. It does make things more 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 path, right? Like that does not lead to a high quality product. So it is like the combination of these things. And so it's like stepping towards that. But if you really want your product, those features to be utilized for all that they're worth and like to actually, you know, gain such, you know, esteem and respect and reuse, taking it to that next level and thinking about how do I make this actually an enjoyable use and that it really feels like it's meant for me and it maps to my mental model, that craft and that quality of the execution of those details is going to be paramount.

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 is great design? What is beauty? Is there like an objective definition where if designers like, this is great design, Is there 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. I love that we're talking about this because I feel like there's probably some people listening that are squirming in their seats of like, you know, like beauty. We're talking about business here. And I mean, that's, which is great. And the, actually there's a fun fact. Stefan Sagmeister and Jessica Walsh have a book called Beauty, and 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 books that have been digitized by Google has decreased, like pretty dramatically. And it's aligned with this idea of like, well, functionality is king. Functionality is what matters. And as if people think about functionality and beauty as two opposite things. But what the whole book talks about is that, no, they're not two opposite things. Functionality is important and actually beauty enhances functionality because it does make things easier to use, more approachable, more compelling to use. There is actually some objectivity to whether or not beauty enhances things. But if you ask a wide audience, what color do they like more or what version of things do they like more? They tend to say the same thing. because there is this shared understanding. And the other piece of it that, yes, I can imagine is not talked about in business as often is just the importance of how people feel and a good example of how something looks and how something is structured and how that can translate to that. Also from the book Beauty, they mentioned that they studied the tweets that came from people that were traveling through Penn Station versus Grand Central. if you've been to those places, I'm sure you know where I'm going with this, which is just like the people tweeting from Penn Station, it was just like more negative than the people that were tweeting from Grand Central Station that 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. and this matters deeply to us. And I know as a financial infrastructure company in the B2B space, 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 see that we've put painstaking detail into this and we care about the details of how something works. And that gives you assurance that we we care about other details that you can't see too. And 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 strongly believe beauty begets beauty. And so when, you know, our business users or the consumers see, you know, the beauty and the care and the creativity that we put into the 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?

I have. Yes, great example.

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

Such a good example. Such a good example. Someone just mentioned that same episode, recent podcast episode.

Okay, all right. Well, it's that good. It's that good. And I wish I could remember which.

Episode that was, but it was 7, I forget.

But that's exactly right. Oh, nice. Okay. All right. Well, and then lastly, quality is a matter of pride. Beauty is a matter of pride. If we put that in 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 see that that can can be, you know, put together into something really impactful. And so, you know, we really put that on the pedestal, you know, because we know how much it matters to our users and how much it matters to the people that work with us. Beauty is an important part of it all.

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, because that feels like 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 can share? Yeah, there's definitely a couple of things we could talk about in terms of 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 that we are a work in progress. You know, we have not nailed, nailed all the things. Uh, and it is an ongoing pursuit of excellence. And so the way that we build the website is that, you know, 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 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 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 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.

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

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

Awesome.

But before I get into that, one of the things that has been driving a little bit of this process and the way that I've been thinking about how we can build better things at Stripe is actually I've been just talking to people, talking to different design leaders, product leaders, engineer leaders at different organizations and trying to understand 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, or that it's just, like, one organization that's gonna look out for quality or, you know, QA is going to solve it all for you. 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 going to show up in the outside and 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, of course, keeping your talent bar high and then thinking about how those things really need to be cared for, that shared care across the organization is number one. Number two is that 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 go and do their thing, what are the chances that they're all going to 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, 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 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 a 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 the plans and having, you know, a drawing of what the final thing is going to 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 think a big pair on that is then the next piece, which is editing. And, you know, you might call that 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 reduce and remove the things that don't fit. And so, like, at Airbnb, 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 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 kind of 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, almost, but no, which is 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 going to say like, actually it's just like, and unfortunately, we're just not there yet. Let's try again. And that is, I think, an incredibly important part of getting there and building that kind of the fitness of what you do. And then lastly, the thing that I've learned that will lead me to 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 my fixation with Journeys, 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 use the app, 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, all the things that I just mentioned. But like one of 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 their highest game when you ship them. Like, they go through all the processes 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. Imagine you have one room where you redo the molding, and, you know, you paint the little aspects, and you put, like, new plates on the lights. Now, all of us in that room is great, but it makes everything else look worse. 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 focus 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, 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 started with 15 of our most important user journeys. 15 is somewhat of an arbitrary number. It's a number that we can kind of keep track of, but also has pretty good breadth, but it's certainly not comprehensive of all the most important things. But 15 of our 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, what we call Walk the Store, where they review them as if they're 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. And they will write, you know, what they have seen, what's working, what's not working, and their 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 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 able to find the entailments of the experience that may or may not be working, and they jot that down. They file bugs, they reach out to the teams that may own the different parts of this experience, and then they score it. And then on a, again, 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 kind of relates to performance reviews.

Right?

Like, you know, performance reviews, managers are assessing the 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, is our interpretation of our ladders document and, you know, how well does that performance align and are we doing it consistently across the rest of the organization? And so we do something very similar. We calibrate these scores because what we're really trying to do is not just the 15 essential journeys and the owners of those, we want to actually up level and bring more 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 kind of creates this 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 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 now, you know, like able to make that happen even, you know, faster to make some of the changes there. And then my real favorite part is that we're hearing from folks that maybe at first didn't see this as necessary, that maybe in different functions that are, you know, just like, oh, you know, 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're 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 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 firsthand, I think will lead to better care in, you know, all of the details that we're aligned to better craft in the end.

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, especially product managers almost have to like feel like they have to rely on user research 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 spending your energy trying to use this thing You're not that different from a potential user. So just, I love that this actually relies on your personal judgment trying to use a thing, which I think people undervalue.

Yeah.

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

Yeah.

And yeah, to your first point, 100%.

They're all just forms of input. Like I'm definitely not saying, like, do this instead of user research. Do this instead of data. It's like, you know, these things in additional sense. And I do think what's so powerful about doing it firsthand 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 firsthand 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 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 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, we have, as I've mentioned, we are constantly looking at our processes and trying to figure out how we can make them better and better. As an organization, as we've grown, things need to adjust. We today are doing it Quarterly and the quarterly aspect of like walking the stores 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 that's enough time that, you know, there can be material differences made. And so you can see in 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.

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. Try it at home.

Yeah.

So I want to try to give people a few more answers to questions when they're probably going to try to do this themselves. So who's in these meetings? Do you join these walkthroughs? Does David join? What do you suggest there?

Yeah. So what we're doing for each team is they do themselves together. So 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 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 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. And ah, that's not on our design system. So, you know, it is really powerful to have folks 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 do the code part and I'll be, you know, sitting there being, what? You know, do they really do that? Like, you know, can we, you know, how can we make that better for them? And so it's, I really love the multidisciplinary approach, but then when we do the calibration after the team has done 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, we will come together in what we call a PQR, product quality review, and they will take us through what they have experienced, and then they'll talk about, and so this is why we've scored this a yellow or a yellow-green. And then we might have a conversation about that. It's like, well, actually, that felt a little worse than you've described it. And actually, I think that we probably need to put more urgency on solving that. Or in some cases, it's like, actually, that was pretty great. If you think about what we're trying to help somebody achieve at this moment, that actually is really hitting the mark. And so we will debate that there. And in those meetings, you'll have, yes, myself, David Singleton, Will Gabrick, who leads product and business, and then various leaders from the organization that might be relevant to that area. We are trying to give people insight to what's happening across. So again, it's a multidisciplinary room. I'm trying to keep it not too large because obviously it can be hard to have discussion, but it is very valuable to make sure again that we have the perspective of product marketing and the perspective of engineering and the expected product in the room as we discuss what our quality bar is.

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 segments? What are you scoring?

The way the rubric works is so that, and 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 with a tag for each kind of moment. It's like, oh, that was a nice touch. Or, oh, that is, you know, not great. We should consider a fix or different levels of kind of severity of like, oh my gosh, P0 bug, we need to fix this right now. So 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, and 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 adds up to a summary score, which we have also talked about the different ways of scoring. Is it a number-based system? Is it a letter-based system? Like, can you imagine? Yeah, we have so far we have landed on 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 and 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, we didn't want people to get a little too worried about, you know, how does like, it's not meant to be an objective quality quantitative score. It is qualitative. It is judgment. We hire people for judgment, you know, so we want, you know, them to bring that to the conversation. And so, That's how we chose the score because we felt that would actually lead to quicker but straightforward opinions and decisions.

At a lot of companies, you have these reviews and the founders share all this, oh, this is broken, this is busted. And as a product team, you're like, God damn it, we have these goals we got to hit. We have this roadmap and now we're going to get a hundred things that the founders like, you got to fix this. I'm curious just how you tell teams to take this stuff and I 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, but just like how to actually operationalize taking this feedback and doing something with it?

Yes. 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 whatever, you know, recommendations of like, you know, 10% of your time should be spent on, you know, fixing things and 20% on growing things and the rest on keeping the lights on, whatever it might be. So yes, I've seen different companies build a recommendation based on certain percentages of how they think teams should be spending their time. And we at Stripe think that first and foremost is that we have to make sure that folks are number one hired with the fact that they have great judgment and care for what they build, and they take pride in it. That's like number one. And then 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 needs to be very clearly advocated for at the highest levels of the company. And with that, I think that kind of fuels people's thinking as they're building their plans. but there is iteration in the plans and we do have multi-disciplinary people making the plans together. So it's like, oh, okay, are we advancing these features? Are we going to be building growth? And is that improving the quality as well? And so I think that's how we kind of together get to it. But we don't have, there's no formula that we ask people.

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

Part of it, though, is showing how it moves metrics, because 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 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. 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 to have to call somebody to, you know, find the answer to their problem. And so with that, we made an improvement and we, of course, improve the bottom line because of that. So I actually think that maybe one of the steps that somebody should consider in the 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 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 where we do, you know, some of them are, you know, longer term. And so you have to look out for 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 and what they're trying to do. But some of them are short-term 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.

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.

Yeah. Well, I think one part is being clear on what impact means. because I do think that in some companies, you know, impact is 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, 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. So there's that. And then, like you said, there are perhaps quality efforts that are harder to measure or they're longer term, but they are still impactful. So I think number one is that when you're thinking about how to come up with the rubric for how you're going to judge performance is just really honing in on what does impact mean? And then a lot comes from that and being able to celebrate and recognize great work happening even when you know, it's not necessarily materially moving that number. And the other part of it is, you know, we have a levels and ladder system. So it's 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 in that, you know, what we pursue is building these, you know, things that are great. And another part of that is also the operating principles, which is kind of like 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. 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.

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

I love that.

And I really like this. It's pretty simple, but it's a good reminder that as a leader, one of the things that you are, of course, driving towards is trying to get better performance, better performance so that your team feels 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 impact, of course, performance. But the key pieces of that, 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 increase their own potential to do better and greater things. And then paired to that, though, of course, is decreasing the interferences, which could be that like kind of lead weight on top of great talent. because you can hire the best people in the world, but like a muscle atrophying underneath a cast, if there are interferences that are holding them back from doing great work, they're going to burn out, they're not going to enjoy the work, they're not going to 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 Gross, you know, you're going to have to keep doing that. Like, you know, the design work is never done in designing a team because the more people you bring in, you know, the more it puts your processes in a faulty state. We, you know, intentionally, or 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 can improve it. So making those changes as needed helps to make them more sought after and more informed in terms of as you improve the processes. 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 at a lot of companies, especially as they grow, as people lose touch with what's happening in different parts of the organization. And everybody's got a doc that, their PRD where they've written down what they've done. It's got tons of words that nobody really understands and keywords for the different projects. And that isn't the best way to lead to clarity. And I'm a strong believer that a picture tells a thousand words and a prototype saves a thousand meetings. What we do, and I've been doing it for the last, I don't 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 could 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, 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. Because going earlier, as I 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. 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 it feels like Figma would be really good for that too, but But somehow decks are still really, really handy for simple things like that.

One of the key pieces is just like keeping it really low maintenance. Yes, the design team would definitely prefer that it would be in Figma. But I, you know, critically, I want all functions to be able to look at it. And, you know, if not everybody is on Figma, and, 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. It's behaviors that people are really used to commenting, but yeah, maybe one day.

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. Yeah, yeah. 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? And, you know, we might ask, like, well, show us, like, the medium and large projects, you know, if there's such as too much going on and all of a sudden it's like a 200 page deck and no one's going to flip through it. So we have experimented and evolved that depending on the team size. And I think right now we're at monthly sharing of it, and that seems to be working pretty well. It used to be bi-weekly, which I loved because I really love looking through it, but it ends up, you if it feels like it's an arduous task, then it's not succeeding.

Yeah, and especially knowing designers, they'd 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 gotta make this beautiful mockup. Yeah.

And that's actually another part of it that is another benefit of opening up the curtain a little bit of like, we do, certainly we have to take things seriously in terms of confidential work, it's work in progress, it's not ready to go live, we're not ready to you know, critique all the details about this, like, you know, 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. 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 in the end of the day will make the work better, save time. 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.

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?

It actually goes back to org design that we talked about earlier and where people sit. So when I joined Lyft, 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 and needing to transform the organization and was hopefully much better at it because I had learned so much. 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, separated from engineering and product and all the other functions by a locked door. Oh, my God. 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 creativity could thrive.

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

The current Airbnb situation.

Yeah, the Thayer, Thayer times.

Yeah, yeah, yeah. And, you know, absolutely there are a lot of like tie ins to, you know, what I had And the interesting part about how actually teams were working is that you would see that there was a lot of wasted work and there was a lot of misalignment in what we were trying to do because there was 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'd meet up and they're like, well, that's not aligned. That doesn't fit the goal. You went that way, we were supposed to go over this way. And so interference in the sense that it was like, it was wasted work. It wasn't actually aligned to the goals. It was slower. And there were definitely benefits. There was real reasons for doing this. And I know there are companies, including Apple, that have kind of like separation of these things. But I think if you're going into that kind of way of working, 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, it's kind of like the composite of all these aspects coming together that was not leading to, you know, more efficient 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 to see what our goals were together so that when we were making changes, we were making the changes together. And we actually were aligned so that like on the day that we opened the doors and, you know, brought, you know, design and engine 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 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 for allowing for, you know, creative exploration, but more aligned.

And just to 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.

Yes, yes. Like literally and figuratively, we broke down the wall 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 safety team. And then they would sit with their respective engineers and product managers. 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 well with our partners.

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.

Not in a locked room. And when I joined Stripe, it was a Zoom universe. So it's a little bit different. But, you know, we do, even today, we have, you know, a studio space where, you know, we have all 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. We have the website team. 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 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 love that so much. And, you know, I go into the office about half time 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 disciplines that they work with every day.

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, the object isn't to make art, it's to be in that wonderful state which makes art inevitable.

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

By Robert Henry.

Okay.

I recommend that. That's what I try to do in this little podcast studio that we got here. That's awesome. Is there anything else that you think would be useful to share either from scaling design teams or broadly?

I think one of the other tendencies I see of companies at different stages of their growth is a fear of bold ideas. What happens is that it can happen at small sizes and then it can happen at large sizes actually. It's just that a fear of kind of like, shaking things up too much or big ideas with lots of things changing at once are really hard to measure. And so actually if we just make an incremental approach, it's very measured and we know what the outcome is going to be. It feels safer. 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 dangerous tendency because I think if we go back to 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, you know, to the scope of whatever that is that you own, you are very likely not to, like, make 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, 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 the 11 star experience. I think you once said, plus, so.

It'S like listen to white stuff. Yes, exactly.

Times on this podcast. Looking at it as a journey. Yeah. Like it's not the five star approach. It's not the six star approach, but like the 11 star approach, but like a show with that ideal version. is, because if you don't know what that is, what are the chances that you're going to increment yourself to the right outcome in the end? And as I talked about before, building the house, you want to see what that picture looks like in how all these pieces come together. And I strongly recommend you want to see what it looks like in an ideal form, because you can always work back from that. And so it's like, okay, if this is what we want to get to, this is what our product is going to look like in two years. how do we get there? And what very likely is, it's a team effort and various parts of your organization are going to have to own various parts. And, you know, maybe we ship this piece first so that we can study it and learn 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 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.

I love that. Reach for the Stars, land on the moon. That could be a metaphor for so many things. 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 a founder or product team, just like, what should you look for that may be a red flag or something that you want to look for to kind of feel good that they're going to be a good fit?

The key, I think, to keep in mind is it's easier to teach tools and process than it is taste and character. So I would certainly pay a lot of attention to that, kind of like their hit rate for great judgment in in 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 for great things? The other piece of it is that, you know, certainly you want to find somebody with great talent for sure in high craft, but you also want to find somebody that's humble, you know, that, like, you know, folks that are really good at what they do aren't always, 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, 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 navigate these things to make it better. And then I guess the last piece would just be, you know, hustle or chutzpah. 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, take a blank piece of paper and propose something that you think is better 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 hiring, you know, really any stage company. And I guess lastly, I think you were asking in particular, like, you know, especially with younger companies or with startups, you know, I think one thing that can be hard is like, do you hire a, you know, more junior doer or a more senior, you know, kind of like thinker operator? You know, it's like if you had all the development in the world, like all of it. But I do think in your early stages, you probably do need a doer. But it is important to also have that kind of lens of, you know, how do you build an organization that's user focused in the way that they operate and the way that they work together and bringing, you know, a strategy that will help to be user focused from the start. So, you know, maybe a great way of doing that is kind of having like a more, you know, senior leader design advisor and then a, you know, kind of executor or doer, you know, full time on the team.

That's a really cool tip. On the craft and taste piece, a lot of times people don't have that themselves necessarily. Any tip for how to measure that? Is there, I don't know, a book you'd recommend? trick, or is it just trust your trust your judgment and like, does this feel great to you?

It's contingent on like, what is the thing? What is the user need? You know, so something that, you know, is, is really great. Like, you know, we do a lot of tools that, like, we strive to make them power tools for our users. And a lot of times that means like dense information that of course is like still, you know, easily accessible, but, you know, we'll definitely feel different than perhaps, you know, a consumer product that is meant to be extremely light and sparse and directive to one individual thing at a time. So it really depends on the context of the product sometimes. So that's why it's hard to quote an individual book. But yeah, I can think on it and we can put it in the show notes. There are definitely books that talk about the principles of great design and we can look at that.

Amazing. We'll link to extra books that come to mind after. One other question I wanted to ask is what's a favorite project that you all have worked on at Stripe?

Oh, yeah, we got a good one that I'm so excited about. We, well, first off, I don't know if everybody knows this, but Stripe prints books. So Stripe Press, we print books that are, you know, we consider ideas of progress. It's, you know, our intention of bringing great ideas out there. They don't all have it, you know, most of them don't have anything to do with financial infrastructure. It might be any number of interesting problems and opportunities of things and ideas that people have talked about.

I have many of them in my background here. I'm a huge fan of Stray Press.

Nice. And we take great care to, you know, kind of like deliver these ideas of progress in books that hopefully feel beautiful. And we have a new book coming out that you can pre-order now, and it is Poor Charlie's Almanac.

And so it's already pre-ordered.

You did? I'm so excited to hear that.

I'm really excited for it.

It's a fascinating book, and it's 20 years old. It's actually Charlie Munger's words, but Peter Kaufman, a friend and colleague of his, assembled all of these documents over the years of things that, you know, Charlie had written and said and put it into this kind of like anthology. And so this book is really fascinating, and it's not, you know, it's not really a linear story so much. And so we have reprinted this book. We also have we created a teaser site that I strongly recommend you all check out.

It's unreal. I remember when you launched that, I was like, it just keeps going and gets crazier and wilder and amazing.

I don't even know how that's possible on a website. It's pretty awesome. And that's our website team is just like, you know, we talked about the importance of like design and engineering working super closely together. And it's just like that. And wild. You know, that art and science coming together into something that, you know, hopefully is fun and engaging and people want to, know, pursue it. And so we're working on that the book will be coming out soon and we're working on an update to the site that we're really, really thrilled about. So you can kind of read the book online in a really in a.

Special kind of way.

So yeah, very big fan of this.

What's the website for folks? Do you happen to have the URL?

Otherwise we'll link to it in the show notes. Yeah, it is press.stripe.com will be where you can see all the books that we have at Stripe Press. And I believe the first one in the line and And actually, what you'll see in the website is that we originally had a kind of like, you know, typical buying model of like the squares outlined. And one of the things that we sought to do with the website is to kind of consider like what would be, you know, a great experience for understanding different books. And like when you go into a bookstore, like you see like, you know, the spines of the books and you, you know, kind of pick them up and you turn them around and you look at them. And so that's actually what you will experience. I mean, I should stop describing it. Just go and check it out and you'll see, as we sought to deliver this work in a way that would be aligned with what a reader would want to pursue.

I can't help but ask, but how did that even come together? Was it just like this passion project of like, oh, this book's coming out. I just want to invest a bunch of time and resources into this. How does that happen at a Stripe?

Yeah, well, I mean, Stripe's mission is to increase the GDP of the internet. We strive to build global economic prosperity because that's greater access Cross the globe, but there's more ways to do that than financial infrastructure. Financial infrastructure is absolutely a major part of that, right? And it is like kind of like the lifeblood of businesses and it enables them to accomplish more. But this notion of like ideas of progress is another angle into that. So while it might not be our core business, it is very much aligned with our mission. And so, yes, it takes time, but we feel that it's important for what we're setting out to do. and it also relates to, you know, the pursuit of, you know, creativity and excellence. It is a part of, you know, our identity. It is a part of, you know, who we, we feel we are or we strive to be. And, you know, we're excited to share that with people. So, you know, in part, it's like, in some ways, like how they get to know us and they get to see, you know, the care that we put into, you know, any number of things.

Katie, is there anything else you want share or touch on before we get to our very exciting lightning round.

We talked a little bit about, you know, the importance of different disciplines and the, you know, kind of importance of quality being a group effort. And, you know, I hope this doesn't insult my function, as I say, but like at the core design is simply intention. Bringing intentionality to the decisions that you make and thinking about, you know, who is this thing for? So like, if you're designing a doorknob, let's say, and it's like, okay, does the doorknob speak to whether or not I'm going to push or pull or turn? Is it comfortable in the hand? Is it easy to manufacture? Is it easy to put on and remove? You'll see these are some of the intentional decisions one could make, whether or not they're a designer, an engineer, the product person, you know, any old function. can put that intentionality if you think about who is impacted by this, who is using this. That literally could be anything from designing a doorknob to designing your org structure to designing your strategy. Now obviously great design is also creative and it also is demonstrated with great taste for what is beauty. And so of course that's where I would say that design expertise with people that have these creative skills and these great taste is an incredible, important thing to bring into the organization. But I think, you know, day one, everybody can bring more care and intentionality. And I think that will result in better outcomes internally and externally in the long run. I think your podcast is a great example of great craft and great quality. I was just saying this to my husband the other day as I was talking about doing this, and it's just like, your podcasts, there's like more usable learning per minute than most, I don't know if that's like a metric that you're measuring, but I love how you don't have your guests tell about their background, right? Because when someone tells about their background, that is interesting, but it's not really usable information of like, oh, I can take this information and run with it and then bring it to my own team and make my work work better. And so, like, you have clearly thought about that. Well, I don't know if that's why you made that decision. Absolutely. That is. Okay. It's great. And I, and I also love, you know, the way that you, you set these things up. You know, you had said to me, you know, in the thing that you sent me, it's just like, if it's not good, we're not gonna ship it. And you said it in very nice ways, by the way. But like, at first I had this like, oh gosh, like, if it's not good, what if it's not good? But I also had this moment of like, oh, well, that's pretty great. Because if it's not good, he's not gonna, you know, embarrass me to the rest of the world. I love that because that was that courage that I was talking about earlier too, of that like, you're not going to let bad go out because you know that each one of these little things will end up, you know, leading to a belief of the level of quality of what somebody, you know, can rely on getting when they listen to your podcast. And, you know, again, like one workout isn't going to be a six pack, but like every one of those things You know, will end up leading to better, you know, quality overall. So kudos to you. You're nailing it.

It's so great. Katie, what a nice way to end it. I really appreciate that. That's exactly how I think about it. Actually, you cracked my whole strategy of just making it as concretely useful as possible. I was actually on David Perell's podcast recently and he had this really good way of describing this, which is exactly what I've tried to do, but I haven't put my words into it. make it as useful as possible per minute without removing the humanity. And I realize that's kind of what I do is like, you know, I could cut all the stories of everyone's backgrounds, but that sucks. So it's just optimized for value and concrete tactical advice, but also make it fun and human and interesting.

Yeah.

So thank you for the kind words. And with that, we've reached our very exciting lightning round. I've got a number of questions for you. Are you ready?

I'm ready. Let's do it.

What are two or three books that you've recommended most to other people?

One, How to Win Friends and Influence People. It's an oldie but a goodie. I forget how many years old it is, but many, many decades. Yeah, I think it was like in the 1930s. But yes, I mean, the COVID is funny. You might be embarrassed to read it on a bus. I don't know. But the learnings from it are timeless. And I've actually read it four times. and I'm gonna always do for another because it is a great reminder of just like how important the way you articulate things are. And, you know, not in a, you know, negative or gross kind of way, but like people care first and foremost about themselves. Like that's the body that they are within. That is the context that they are within. And recognizing that, you know, I think can be really powerful as you think about leading teams, as you think about working with other people, as you think about being a good spouse, like whatever it might be. So I'm a big, big fan of that one. The other one is a newer book, I think actually, well, it's still a couple years old. It's about the Wright Brothers by David McCullough. I think I've been learning how to fly. And so like I'm very obsessed with this, but like I think it's a book that's relevant to everybody, especially even entrepreneurs because it just like kind of talks about the, you know, impossible challenge of like Nobody thought it could be done. Even the American Institute of Science didn't think it could be done. And these individuals that had the resolve and the commitment to make it happen. I think also the power of this beautiful partnership, of course, the brothers. That doesn't always mean you get along, but they're brothers and they did so. And it's a beautiful story. So big, big, big thing, a fan of that. And then third book, I would just say is actually I brought it over because I knew you were going to this question. I don't know if you can read that, but the Boy, the Mule, the Fox, and the Horse, this book was given to me by Jenny Arden, which I think you may know. It's wonderful. It's a beautiful story. It's like, you know, it makes you laugh. It's, you know, it teaches you a thing or two. And, you know, one of the best quotes in it is, One of our greatest freedoms is how we react to things.

Very booted.

Yes.

Yes. awesome. What is a recent favorite movie or TV show that you really enjoyed?

Oppenheimer was amazing. And TV show shrinking. And that one was really good. And it actually really surprised me how, like, funny and, like, positive it was because the trailer for it does not give that impression, but it was really good.

Sweet. I've not seen that. What is a favorite interview question that you like to ask candidates?

Tell me what work you are most proud of. And the reason I ask that is because, well, it helps me understand their taste and their judgment, what motivates them, what work they view as good and as a good outcome. It also helps me understand a little bit about, you know, what they like to do and where, you know, they're kind of like, Gravity pulls them.

Is there a favorite product you recently discovered? Be an app or physical thing, anything?

Yeah. Well, as a parent, you should definitely know the Tony Box.

Oh, I don't know this. The Tony Box.

So good. Okay. The Tony Box, I should have brought it over too. So it's a, it's like a squishy box, but it's a speaker and your kids can control it. And the way they control it is these little figurines. I mean, this is also like a brilliant product. because you want to buy all these figurines. But the little figurines, so it could be like, you know, Belle from Beauty and the Beast or like Elsa from Frozen. And, you know, they place the figurine on top and that activates the stories that this book, the thing reads to you or the songs that it plays for you. You can record your own voice so that you're telling stories to your child and they control it all by themselves and they can drop it on the floor and it's all good. But the Tony Box. Pretty awesome.

I just texted my wife to check this out. Amazing. Great. Very handy and timely. Do you have a favorite life motto that you'd like to share, come back to, find meaningful?

I don't say this out loud, but I do, I've had it as a Post-it, like in my jewelry box and that I see regularly. Tomorrow is today. And what I mean by that is that so often, you know, I will, like, in my head, be like, oh, I'll do that tomorrow. Like, oh, I'll eat better tomorrow. Oh, I'll, I'll, I'll think about that vision tomorrow. Oh, I'll, you know, communicate better expectations tomorrow. And, you know, it's kind of like those, like, joke signs that, like, free beer tomorrow, because, you know, very easily tomorrow just always moves on. And I needed to remind myself that, like, You know, it's actually, it is now today. Tomorrow is Monday.

I love that one. I feel like I need to take all these mottos, which are amazing. I love this question that I just invented and just put them all on my wall here in this office.

Yes, that's a great idea.

You should make a book, a book of Lenny Mottos. Oh man, the tribe of mentors version of Lenny's podcast. That's awesome. Is there a lesson that your mom or dad taught you that has really.

Stuck with you, especially as a newish parent? Yeah, I think about this a lot. I am a mom of twin girls and I feel so lucky that my parents raised me to see that accomplishment is based on merit and hard work. And they never made me feel like because I was small and that I was not as strong as somebody whatever it might be that I wasn't able. And so, like, my dad had me, you know, chopping wood and mixing cement as a young kid. And, you know, that certainly led me, you know, in one part, to be a designer, but also, you know, to be able to pursue leadership and be, you know, even though sometimes I'm comfortable, like, willing to be in the room where I am vastly outnumbered by people that, you know, don't look like me and, you know, wanting to or just, like, not letting that hold me back. And I actually, I thought about that the other day because I was riding in a, a lift to the airport. This was also at like 4:00 AM. So it was like a really hard time to be in a, in a lift and got into the airport. And the driver was telling me about his kids. Um, and actually he had twins. It was one boy and one girl. And so we were talking about twins. And he's like, yeah, yeah, yeah. You know, like my girl, she's my princess. And, you know, I, you know, my son doesn't understand why I don't let her take out the garbage and like, why her job is to sweep. And, you know, that's his job. He's like, I'm not gonna let her take out the garbage. Like, and I was just, I was sitting in the back of the car wondering, like, should I tell him, like, you're screwing it up. Like, no, like, just because, you know, she's a female doesn't mean that, like, she's not, you know, able to do the jobs, even the hard ones and even the bad ones, like, taking out the trash. And, you know, I, I really do think that I'm so fortunate that, you know, that was never the way that my parents were looking at it and that, you know, now today I feel like that is very much a part of a little bit of my chutzpah and willingness to, you know, kind of like step out there because I hadn't been held back from those hard jobs earlier.

Beautiful. Final question. You mentioned that you fly planes, and this is actually related to my last question. I guess one that I was going to ask if that's true, you mentioned it is true, is there a lesson that you've taken from learning to fly and flying? that you can, that you've brought into product, leadership, design. Anything come to mind?

Yeah. First of all, learning fly has been such an amazing experience because there haven't been many things in my adult life where you feel like yourself going from, like, knowing nothing about something and, like, being able to do something. And it's just like, what an incredible kind of Journey that is. And so, you know, whether it's, like, you know, learning a language or whatever, like that, that is awesome and highly. recommended. But no, one of the key things that has definitely sat with me from the experience of learning how to fly that I definitely thought about how to bring it into my work is that when I was kind of getting to the stage of being able to do things myself, so my instructor is sitting there next to me and, you know, usually he's right there at the controls with me. So if, like, something goes wrong when I'm, you know, flying, he's right there and. I remember the, you know, one of the first times when I was, like, learning how to land where he moved his seat back and, like, like a lot. And so, like, he was now, like, kind of out of touch with the controls. Like, he could jump there if he needed to, but, like, he really pulled back, and it was such an incredible, like, visceral experience. I was like, he trusts me. Like, in, like, right now, he is, like, he is showing his faith. in me to take this and take this challenge on. And I think about that all the time. It's just like, how can I show my team, people I work with, my support and trust in them to take that challenge on. And so I can't always move my seat back, but what might be the way? And so that's been a pretty great example of something I want to pull forward.

That is an awesome metaphor. I feel like this whole episode is just full of beautiful metaphors, also just full of beauty. Katie, thank you so much for being here. Two final questions. Where can folks find you online if they want to reach out and maybe ask some questions? And how can listeners be useful to you?

Yeah. Well, first off, please do find me online because as I talked about, we are in the pursuit of trying to build excellent things and it's always a work in progress. And so I'm always interested to learn how others do it and see how we can improve our own methods. I am a Lil dill on Twitter. And then I think that name was taken on threads. So I'm lildely with a y on threads. And then I'm on LinkedIn. Find me there. We're hiring, so definitely reach out at our job board too. Stripe.com/jobs. Definitely check us out. We definitely would love to hear from you.

Katie, again, thank you so much for being here.

Thank you, Lenny.

Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com See you in the next episode.