Full Transcript for Katie Dill: Quality Control

When I was at Art Center, I had a teacher named Norm Sherman, and he used to say to me multiple times that it's all about mileage. And what he meant was that I had to essentially do the time, get in there with the work and, you know, and spend some time in the pixels and, you know, with your hand skills and like really, you know, get close to the craft.

First of Kind is a new series about design and tech told by its pioneers. Sponsored by Framer, Cursor, Purcell, and Profound. Katie Dill has led design at Stripe, Lyft, and Airbnb. She's built world-class teams at three iconic companies, proving that thoughtful design can shape quality at scale. Katie, thank you so much for doing this. It is such an honor to be here in your beautiful headquarters at Oyster Point in San Francisco.

Stripe is the home to an incredible design team and an incredible design legacy. But the thing I'm most excited about talking about today is your career path to this role. This whole series is about first-of-kind designers. It's about telling the story of modern design through conversations with its pioneers. And when I think about your career thus far, you've been at the helm of not one, not two, but three story design organizations.

Design organizations that have been the stage for incredible work and incredible designers to produce that work. And, you know, to use an NFL analogy, it's like helming a championship team across three franchises. And so when I sat down and started making a short list of people to talk to for the second season of First of Kind, your name was super high on that list because I feel as though you are a singular person in the tech ecosystem.

And I just think it's such a privilege to get to chat with you about your biography, your story, and learn more about what brought you here. Well, thank you. Geez, wow. It's not often that people align me in the NFL. So thanks for that. But no, that is extremely flattering. And I wouldn't say I necessarily deserve that, but I appreciate it very much.

And I'm glad you're here. It's this real treat. I'm such a big fan of First of Kind. So to be a part of it is an honor. Awesome. So I wanted to start off with a little anecdote. I've learned recently that you are now piloting planes. And once I got past it, like, why would you do that? I started wondering to myself, it's like, well, anytime you take on a new hobby, a new capability, it folds itself back into the rest of the work that you do.

And I'm really curious to know, out of the gate, what is flying teaching you about design? How is it shaping the way that you lead and the way you operate in the world? Why did you decide to learn how to fly? I love this topic. And so much to your questions there. Well, I grew up back in New York. My father was a pilot. He went to the Air Force, and later in his life, he was a private pilot.

And so on the weekends, we would fly from Westchester, New York, just outside the city, up to the Adirondacks. So basically, it's kind of like in the San Francisco ratio, it's like the Marin to the Tahoe. And spending time in Little Plains was an incredible privilege and joy, and it was just a wonderful way to grow up and got me excited about that.

I think also in my family, we just had a penchant for vehicles and driving and, you know, I My mom used to say when I'd leave the house, drive fast, take chances, a joke. But it was, you know, kind of a part of our family. It's just like driving and being a part of, you know, kind of exploring the world in different ways. I love that because when I first met you, you were in like a biker outfit, holding your biker helmet.

And you came visited the Dropbox office. Yes. And I'm like, who is this woman? Motorcycles are a great way to get around. Yeah. As it turns out. Yes. Yes. But yeah, actually, so I rode motorcycles for quite a while. I used to ride with my dad. And actually, the last time I saw him was on a motorcycle trip through the Rockies. We did 2000 miles, me and his biker gang.

It was amazing. But the story ends in a sad note where that was the last time I saw him. And he passed away on a motorcycle. And I rode for a little bit longer after that. It still, you know, somehow kind of like drew me to him. And, you know, it felt like, you know, it was something I loved to do. But then as I had kids, I realized it was just like, it kind of felt hypocritical to keep riding.

Like, I don't think my father would have kept riding if, you know, I had gone. And, you know, I thought about the, like, just being there for my family and the risks involved. And so I, you know, sold my bike and then made the decision to learn to fly. Yeah. So you traded structural risks. I did this less frequently. Exactly. I did a little bit of data, like, you know, what is the risks involved? But yeah, I guess I still needed the adrenaline rush.

And it was one became a new addiction about learning. And what an incredible feeling going from not really knowing how to do something to To being able to speak this new language and being able to understand it. I mean, that was just like it was an incredible feeling. And, you know, it was also just like a wonderful thought of like, I can do this.

I can learn things wholly new. So I think your other question of just like, well, what does that do for you and work and where do you take that? I think that's one. It's just like I feel less intimidation about things that I don't understand because now I've proved to myself that I can go from knowing nothing to to being, you know, capable of flying a plane over San Francisco.

I think secondly, you know, kind of maybe related to your point about it was like your own time is that, you know, people always tell me I got to meditate. You know, apparently that's a thing people do and it's a good idea. Every time I try, I am just like going through the to-do list. Eyeball sleep. Really? That's all I know. That's a moment of Zen.

So that's, you know, maybe working for you. But yes, I couldn't, you know, relax and just not be busy in my brain. But with flying, I have no choice. I have to be in the moment. I have to really just like lean into that and not be distracted with the pressures and the concerns that I have about work or whatever it might be. And so it actually is my moment of Zen.

I was definitely nervous when I was driving to the airport, thinking about it, thinking about all the things that could go wrong. But kind of related to the moment of Zen, like when you actually get in the plane, you can't really focus on what you're nervous about. And instead, you just kind of have to focus on what you're doing. And that, I think, is a correlation for Zen.

things that I need to be doing and work as well, where, you know, you could stick like nervous, like I'm going to sit there and talk to Saleo and oh my goodness, we're going to have this interview. Is it going to go terribly wrong? It's just like, well, right now we're just here, you know, and we're just having a conversation. And I've talked about this with my team as well.

It's just like, you could do this. And like, once you're, you know, in that conversation, the nerves can fall away. And so you're usually the most nervous before you even get there. So the thing I've always loved about the field of design is that unlike being a lawyer or even being like a software engineer, when you look at people's backgrounds, it's such a wide gamut.

The minority people even go to design school. And I'm always particularly drawn to people who are coming from areas of study that are way a field of design. I'm a music major. That's what I studied in undergrad. I was just really proficient with web browsers and Photoshop on the side. And that sort of spiraled into a full-time job for me.

And in the process of kind of preparing for this conversation, I learned that you studied history. I really want to know what that transition was like to go from studying history to finding your way into the world of design and ultimately in in-house roles as a tech executive. That's not the most obvious pathway, right? That's not a playbook that you would typically hand over to somebody who's starting off their career path.

So I'd love to hear a little bit about how you arrived at that field of study and where design kind of emerged for you as a path in life. I totally agree. I think it is so interesting about design and, you know, because perhaps it's defined as a bit of a newer discipline, but yes, we all have such securitist paths to it. The reason why I chose to study history in my undergrad was because I just wanted to know why things are the way they are.

I just infatuated with the stories of, you know, where, you know, lines were divided between countries and the stories of how different cultures came to be and You know, why the architectural direction went that way versus this and how it's ended up impacting the way we live and how we are. And, you know, of course, if I speed up to the future, it's like, well, of course, the next juxtaposition was then like, well, why can't it be a different way? Why can't it be better? And that is, of course, design.

But the real story about how I ended up transitioning to that was that I was studying in Florence, studied abroad while I was in college in my junior year. And of course, I mean, in Florence, you can't help but be just taken by the art and the architecture. You're surrounded by beauty. Exactly. And it's just like there's something here. And it's like it is, of course, you know, history and beauty interwoven.

But I remember a vivid example of where we were on a class trip to Santa Maria Novella, the church in Florence. And we were there. We were talking about the history of the space in the area. But I was just just taken by the beauty of this building, you know, from the 1400s. And the facade is done by Alberti. And it just really is a perfection of harmony and balance and proportion.

And, you know, when you just spend some time with that, you just like think about what people are capable of, you know, in the 1400s and, you know, what the impact of these things can have on people's lives and actually even, you know, shape history made me just want to I want to spend time on that. That's all that's all I want to do. I want to be closer to that.

And so I thought I wanted to be an architect. And I decided to finish my degree at Colgate in upstate New York, a liberal arts school. And then I thought, OK, after this, I'm going to go into architecture. Moved to Boston with that as my aim. Started talking to architects like, how do I get into this? This is amazing. And it was interesting to hear about their profession and what they did and You know, I could definitely hear some stories about like, well, and you're doing outlets in a hotel room and they're all the same.

You know, I was like, that doesn't sound very exciting. But there was definitely something to it. But at the same time, my roommate, who I lived with back at school and then again in Boston, her name was Tiffany. She saw the 60 Minutes special on IDEO about making the shopping cart. And so she learned about product design. And this was not something people talked a lot about on the East Coast.

You know, I think we were a little bit behind. We knew about interior design and architecture and fashion, but not about product design. And so she told me about it because she knew about the little things that they'd call Dillisms, which were my little inventions that I would make at the house or back in college. But she's like, Dillisms is product design.

You should check this out. And so I started talking to product designers. And it's just like, wow, you get paid to do this? You get paid to solve problems, try to understand, you know, why things are the way they are and why can't they be better and, you know, come up with little things that are just going to make people's lives better? Like, that is what I need to do.

And so I just, you know, went on the hunt for how do I get into that? And they're like, well, you got to go back to school because you know nothing about design. Turned right back around. Exactly. Exactly. Yeah. So I mean, honestly, one of the hastiest decisions of my life, I essentially, you know, fell in love with design and moved to California.

And so I went to Art Center and studied industrial design and kind of took me to this path now. It's amazing. And I love that sometimes the most consequential decisions in life can be that impulsive. It's kind of instinctive. So when you look at your relationship to architecture, to industrial design, even these fields are very far removed from software.

What have those disciplines taught you about product making quality in a software and digital context? Because again, it's like I can... theorize how music has shaped the way that I approach design, right? This idea of spontaneity around structure, inventiveness. There's a songwriting quality that I can never really escape with design. And that sometimes it is an act of courage of just do the thing that feels best.

Like do the thing that's right. Don't overthink it. But with fields as story and as established a set of patterns as architecture, Or even with industrial design, when you are taking into serious regard the constraints, the materials, the legality, the regulations, all the things that are essential to making something that's both like really useful and desirable.

How have those fields informed the way you think about software? How has that sort of been a conduit to your foray into digital design? Yeah. For sure, architecture, there's so much that we can learn from just because it's an older profession. One thing that's a fantastic concept is the idea of parti. Have you ever heard of that? No. It's spelled with an I, P-R-T-I.

And basically what it means is like the core design, the core concept. And so you can imagine like drawing with a really thick Sharpie. What's the concept of the building? It's like, oh, well, it's like it's an L shape or spokes on a wheel all around a center. And so a great architect is going to think about like, well, what's the core design of what I'm doing here? And then like holding that true as you build out the details kind of helps to create the integrity of that design and like keep that concept whole.

That, I think, is something that we should think about from the design side as well. It's so easy to think about, like, well, I do this part of this thing, or when you get down into the details, you know, you can lose sight of, like, well, what's the big idea here? What are we really trying to achieve? What's the core concept? So I love that, like, party.

Secondly, I think on the architecture front, You know, architects, you know, it is like exactly what you just said, like the legality, the safety, the like really taking ourselves seriously, like stamping our documents that like I put my pride and my integrity behind this work. I think sometimes, you know, with product design, you know, we whip something up and, you know, cool.

But, like, it impacts people's lives. Like, people's work, their business, their day is impacted by the decisions we make. We should take them as seriously as an architect takes their work, too. Yeah. I want to make sure we go back to this gap still where I think when I met you, you were working in venture or in some venture capacity. Yeah.

And when we powwowed, you were really interested in navigating, well, what are the design leadership opportunities within software companies? And I never really got filled in on how you went from point A to point B. So I'd love to kind of go through that because I see it as central to the golden thread of your career. Yeah. You have a great memory.

I cannot believe you remember that from when we first met. But yes, I went to Art Center studying industrial design. And what I thought I wanted to do going into that was that I wanted to come out and I wanted to work on products like OXO, right? It's just like they figured out how to make the best hand peeler or the best measuring cup or whatever it was.

And I was like, I want to make products that are just going to make people's lives better. But while I was at ArtCenter, there were two major shifts in my thinking, one of which was I went to INSEAD, a business school, while I was at ArtCenter. really an incredible opportunity to better understand the business side of building products. But I took away something in addition to that, that I think changed the course of my life, which was the power of working with people that thought a very different way than I did.

So like, for example, in one of the classes that I was in, which was creating new products, I was on a team of five people and I was one designer and they were four MBA students. And we somehow got on the thought that we were going to build a water bottle. We wanted to create a water bottle and solve the plastic problem. So good luck with that.

But we set out to do this. Four of them had just awesome data on what is the water bottle industry today? You know, who's buying? What's the TAM? You know, all that stuff. What did I come back with? I had user interviews. I had user journeys about like, well, when are people drinking and what is the role the bottle plays in their life? And so you like lay this all out and like that is a full set of insights that will help to drive the next idea.

And so that has definitely contributed greatly to the way I think about teams and the way I think about design, working with engineering and product management, data science, and just the value that different mindsets bring to the work and how it's great that we all have a different way of looking at it. But even better when we bring those things together in how we work.

With that, I was looking for my next job. And so that's where I ended up at that VC you mentioned. It was called Green Start. And one, we were focused on early stage organizations that were basically in the green space and trying to, you know, build better products and services that, you know, had a positive impact on the earth. And that's where, yes, you met me.

And I mean, it was awesome. It was a great, you know, kind of model and a great organization to be a part of. But it didn't scratch that itch of getting closer and being there to like see things through. Like actually owning the product development. Yeah. Yeah. Yeah. And so that's where I was like, OK, I want to go in-house. What are those roles like? And, you know, I heard I heard about you and heard about all the cool things that you've done and was such a huge fan of the Dropbox team and what you built there.

Yeah. The way I ended up at Airbnb is actually kind of interesting as well. I was asked to speak at an event. Finn Barnes reached out to me and he's like, I'm doing this event. And I forget what it was called, but he's like, we're, you know, I'd love for you to talk about, you know, do a presentation on design critique or something like this.

And I was like, OK, about ready. And then he told me, you know, like, well, El Luna's speaking like, oh, man, I've seen El Luna speak. She speaks really well. I don't know if I should go. And I was really ready to say no. And then there was this like voice inside me. It's just like, you don't want to do this. You're nervous to do this. That's why you got to do it.

You know, like, don't don't wimp out on this. Like this is like, you know, maybe the reason why you're nervous is because this matters. And that's that's that's a great thing. And so I, you know, talked myself into it, said yes. And like, I look back at that so often. It's like, thank gosh I did. And, you know, what other examples of things I'm afraid of today that I should be saying yes to? Isn't it wild? Like those little pivot points where like you, it could have been a coin toss, right? Yeah.

Yeah, because if I didn't, or actually, well, I'll tell you what happened. So I spoke, Joe Gabio was in the audience. And then afterwards, he's like, I want you to interview for this role. And so I interviewed for the role and they hired me as their head of experience design. And then I was at Airbnb for, you know, the next very meaningful part of my life.

But I want to stop for a second because you said something that I think is really important. There was that voice in your head that told you, you need to go on that stage and confront your fear. And so I wanna get your perspective or your advice on like, how do we help designers and creatives hear and honor that voice? It is a great question.

And I do wish I knew exactly how that is done so that I can, you know, help people on my team or like the kids I'm raising. In terms of showing support so that somebody can increase their courage, there's just one example of when I was flying with my instructor, I was getting ready to be able to land the plane by myself. And my instructor, you know, for many of like our, you know, coming around, coming around, He would be there, you know, he's like, I'm on the controls if you need help, right? He's right there.

He's got his feet on the rudder just in case like anything goes wrong. And so like that makes me feel like good and safe, like he's right there. And then one time we're coming around and he reaches down and he adjusts his chair. He pushed his chair so far back that he like barely grabbed the yoke or touched the rudder pedals if he needed to.

And that has stuck out with me as just like this really visceral moment of just like he just showed me he trusted that I got it. And it felt so cool because it was just like, oh, my. Like, he's still in the plane. Like, if something really goes bad, he's going to just, like, lean in and be able to grab it. But it was just like he didn't have to say any words.

He just, like, you know, pulled the thing and moved it back. That was, like, very clearly saying, like, you got this. Without saying it. Right? I think that's the thing that's really artful about it. He's not sort of declaring, now you're in control, right? Yeah, yeah. It's much more like let you perceive what's happening. Yeah. And recognize what it means.

And that's so different, right? Yeah. It was a really clarifying way. And I always think about, like, how can I do that for people, you know, in my team, right? It's just like, you know, that person's taken over that project. Like, you know, I'm out of it. And like, you know, you go ship something great and I can't wait to see it. But what does that look like? What is my pull back my chair moment? So I think that's a beautiful segue for talking a little bit about these three distinct design cultures that you came to helm.

And the thing that I probably admire most about you, having worked in a similar role, is that exercise of both adapting to the native tongue, to the native way of doing things, but also advancing your way, your philosophy, your approach to design that both sits naturally within that environment, but is also true to you. It's the reason why you got hired, the reason why they called you up and asked you to lead the team.

Yeah, good question. Because the truth is, at first, I really screwed it up.

When I first joined Airbnb, they were, you know, during the interview process, actually, I was talking to the leaders of the team and the individuals in the team and the PMs and the engineers, etc. And I got a sense of what was working and what wasn't. And so Airbnb is known for, it has a really strong culture. It's a great energy and it's very much driven to do great design.

But I also learned about some of the tensions. There wasn't really great dynamics between product management and design coming together, engineering and design. And there were a couple of things that I just understood as opportunities for growth in the team. And so when I got in there, I'm like, I'm ready. I'm going to like, well, let's change this.

Let's make this better. Cool. And so, you know, just set to work right away to try to like start to impart these changes. Well, you probably know where this story is going to go. About a month into my time there, I got a meeting invite on my calendar for an hour and a half with five people from the design team. And keep in mind, the design team was 10 people at that time.

I had taken over from they were reporting directly to one of the founders. And then so they had been reporting to me. So five of those 10 people and somebody from HR on my calendar. What? Yeah. So Wednesday morning, I go into the office and go into this room. And it was like, first of all, Airbnb, every room is awesome. They're so beautiful.

They're all like different scenes from Airbnbs around the world. This is the one room that's gray and has no windows. Oh, no. So it's like a totally gray room. The scene is set. Oh, yes. Oh, yes. And it's just like this oval table. And then the five people are sitting there. There's like a stack of paper in front of them. And then they just take turns reading from the stack of paper telling me all the things they do not like about my leadership and like about me.

Wow. Well, I mean, it was it was it was not my favorite moment. That's trauma. Oh, my gosh. But like, all right. The only way I get through life about like anything I mess up is like the silver lining is what do we what do we learn from that? Yeah. But like I, you know, sitting there listening to this and I mean, there were definitely moments where I wanted to be like, but that's not, you know, how it was or whatever.

But like. I had the sense to not push back and just like, you know, take it all in. And as I was hearing this and thinking about, you know, my thoughts on the subject and I realized like, oh, yeah, there's truth here. And the truth is I did not earn their trust at all. They had no reason to trust in what I was doing. They had no reason to trust that I knew who they were or what they were trying to do or what they were great at or what struggles they had.

They had no reason to believe that I was there trying to help the situation or help them. It was a month into my time there and I was already making changes without, you know, transparency and context to them and that they hadn't seen me or felt me really try to understand them. And so that was an incredible learning. I mean, and, you know, whether or not the changes were the right ones, it was more about the how I was going about it.

And so, yeah, from there I just had to correct the way I was working. And the good news is that it definitely taught me quite a bit that I could implement right away and I could spend time with the individuals on the team and really understand them and be more transparent about what I was understanding about the situation and why I was making changes that I was making and make them with them, not to them.

Right. And, you know, interestingly enough, we had the worst engagement scores in the company before this happened. And then we had the best after like just a few months after this. And yeah, we started to reshape the team. My time there, you know, I grew the team from 10 to 100. I can tell you the room that I interviewed every single one of those designers in.

And you hired exceptional people. I mean, folks that have gone on to do extraordinary things, you know, kind of in some respects got their start in that franchise. I love that you took this extremely difficult, bloodletting experience and folded it into something better and maybe a different approach to thinking about trust. Has that translated over to how you think about building trust within users or just building more trustworthy products? How is like your experience at Airbnb then sort of like folded into your time at Lyft and your time here at Stripe? Help me understand like what are some of the cascading lessons that have come from entering a role in design

leadership? Well, to your point of like what that lesson has taught me, where it's taken me, like I do want to answer that in two ways. One of which is like after Airbnb, I went to Lyft to lead the design organization there. And it was an awesome chance to like, you know, come into a new org or come into an org that already exists. And, you know, knowing what I now know about like, OK, how do I come in here and demonstrate my learning, you know, before I start, you know, kind of trying to implement change.

But one of the really interesting things about the Lyft team is when I came there, the design organization sat in a room, a beautiful room, all white and perfect. It looked like an Apple store with locked doors separated from the rest of the organization. This is an actual ivory tower. Yeah. I've always used that metaphor. Literally, it was a white ivory tower.

It was a beautiful room. But yeah, you had to badge in and only the designers could go into this room. Wow. Yeah. Yeah. And so like, you know, when we talk about like collaboration between Eng and design and the importance there, like clearly that was not, you know, the epitome of collaboration. Yeah. You know, there's like you had to like schedule time with someone to get them out of the room or like, you know, get permission to get in there.

And so it was very clear once again, like during the interview process, what some of these gaps were and some of the problems that things to fix. But thank goodness, you know, with the now learning of, OK, let's let me spend time with folks to truly, you know, understand where they're coming from and help them understand the situation themselves so that we can like you know design the solution together eventually when we kind of like broke down the walls and opened the doors it was like a group effort but i wouldn't say what they wanted that at first right like the designers liked their beautiful spot like it was hard to say like okay we're gonna open this up but i think

it was a process of which we you know kind of all saw like well what are the the benefits of doing that like are we gonna have more say in the work because we're actually, you know, there during those conversations and we're working hand in hand and we share goals with our teammates and product and engine. So now we are on the same page when we're trying to, you know, kind of go after change there.

A great piece of advice I once got is that, you know, speak into their listening. So what it really means is like think about what that individual cares about. Really try to understand that. And so for the folks in the design organization, you know, they liked where they were because it was their creative space. You know, we talked about courage before and new ideas are fragile, right? And it's just like creative concepting and putting yourself under the page and it's like an empty page and like what is this idea that takes place? a lot of courage and it's scary.

And so to be surrounded by other designers that are like, you know, kind of contributing to that versus what they were afraid of was like, well, if the PM's an engine around, they're going to like tear down my ideas right away. And it just doesn't feel safe to like creatively concept. And then the other piece was that, you know, they kind of worried about whether or not they could have a say in the work that they did and, you know, that they could really, you know, shape the direction that the company was going, the strategy, the product direction.

And so it's like if you piece these things together, the things that they wanted, and then think about like, okay, well, this is what you want. You know, how do we get that for you? And if we think about like, well, where are the PMs and the engineers? When are they making the decisions? Why aren't you able to make that decision with them? And then, you know, it kind of like all comes together.

And so it's not so much me saying like, this is what we're going to do. And it's like, they're saying, you know what we should do? We should open up the door. And, you know, like, sure enough, like, People can, you know, get more of what they wanted from that. But like we had to like see that first. But I do think like your point there as well as like vision of like, well, what are we trying to get to? Like where are we today? But like really where do we want to be? And then what are the steps to get there I think is an important thing to have as an open dialogue with people.

I look back on my career as an investor and you look at the whole trajectory of mistakes and it's like, oh my gosh, I was so naive. Or like, ah, like I would have crushed that situation knowing what I know now. And it's not like I'm that fundamentally different, but it's mostly knowledge, hard earned knowledge. When you look on your own career path and you look at people who are early in their design executive path, What are the things that you find yourself gravitating back to as like tried and true lessons that you feel like, okay, this is the thing that I wish I can just sort of like punt back into my, you know, 2015 version of myself or 2018 version of myself.

This is the thing I wish somebody had said to me when I was in that situation and that you find yourself saying to your reports today. Yeah. When I was at Art Center, I had a teacher named Norm Sherman. And he used to say to me multiple times that it's all about mileage. And what he meant was that I had to essentially do the time to put in the effort to learn and get better and better by doing.

And I didn't want to hear that because I wanted to just like rush ahead. I was, you know, a student in design school thinking, like, I wanted to get into strategy and I want to be a leader. And his point was, you know, you have to build the hard skills to be somebody that, one, people are going to listen to and to know, you know, kind of the— the materiality of what you're talking about.

Because actually knowing what it takes to make great things, knowing what that process is like, knowing how important it is to get a sense of flow and a time of focus, knowing how important it is to try a lot of bad ideas to find a good one, knowing what it's like to develop that taste and know how hard the tools can be a part of the process.

Definitely made me a better leader. And so I had heard that voice of Norm in my head of just like, yeah, it is all about the mileage. I wish, you know, I had put that time in then. And so a lot of times, you know, folks will reach out, you know, they're like, I'm about to graduate and I, you know, I really want to get into strategy. I'm like, what?

Like, you know, take the time to, you know, just like get in there with the work and, you know, and spend some time in the pixels and, you know, with your hand skills and like really, you know, get close to the craft before you start to try to like have opinions about other people's craft. That resonates. And in particular, I think one of the things that you had said earlier was recognizing that sometimes the troubleshooting, the problem solving doesn't just lie within your team.

It lies along the seams between your team and the rest of the organization. If I were to go back in time and just like direct energy to my prior self working at Dropbox, I would have said like spend half of your time on things outside of design. That like so much of it was like, you know, this is my team. This is what I'm responsible for.

So this is the scope of my influence. And that ended up just becoming a set of blinders to like how design sort of like interface with the broader organization as it scaled. Because early on, it was easy. You sort of it was tractable. Yeah. You had engineering over here. You had, you know, marketing over there. You have product. But as the team grows and scales, like the number of relationships, the number of edges also scales non-linearly.

And all of a sudden, it's a lot of mouths to feed. And I don't think I had fully kind of prepared for how much our reputation really rode on our ability to interface well with the broader organization. It's not just how we operated internally, how people felt on the team itself. Yeah. Yeah. I mean, as we all know, you know, nobody wants when you move the cheese, right? Like you change the product out from underneath them and, you know, it can be jilting, right? And, you know, at Stripe, we're building products for millions of businesses around the globe.

It could be like a single entrepreneur. It could be a large enterprise. And what we do in the product matters a lot, right? Like they're running their business on this product. Like if we change something or we screw something up, like that could mean that they're not going to be able to make payroll that week, right? Right. So we have to take these things very, very seriously.

And I do think trust is a big part of it. So I think there's one is just like as you're imparting change or you're trying to drive a behavior in the product, like how do you build that trust? And I think that learning that you're bringing up is like, well, how about transparency? Like what can we show? Why are we recommending this? But I think the other piece about trust is like actually the risk of like not having it.

And, you know, what the role of quality and beauty plays in it. So, you know, we do care a lot about the utility of a product. Like, how is it? Is it powerful? Is it going to solve real problems and make a difference for our user? Huge paramount matters first and foremost. But secondly, is like, is it well crafted? Can I access that power? Is it easy to use? Is it intuitive? Otherwise, the power is kind of no use, right? If I can't actually access it.

But then third, is it beautiful? And that matters. That's a part of what defines quality. Because the beauty part, one, it certainly helps the thing be more usable. It actually means like I want to use it. So I want to give it my time and engage with it. But it's also that trust piece. By showing the love and care at the surface, you're actually showing the love and care underneath the surface as well.

And I mean, I'll give like the opposite fact, right? It's just like if there is a bug in the system, like a typo or, you know, the design system is like erratic and it doesn't actually like, you know, it's not consistent. And I'm like, why is this like new typeface over here? Why is this like, you know, not lined up neatly? You start to lose faith that the rest is actually thought about.

You know, and we're, you know, kind of playing a big role in an organization's money movement and, you know, their personal information and what they're doing for their users. Like that matters most to them. And so if like it looks buggy on the surface, like that has a huge impact. So I do think about like the way we build trust in all levels of how we're building a product and all levels of quality and all of those different dimensions.

Yeah. And I appreciate in particular this idea that like it's if it's an object that can cause you harm or cause you doubt, the trust that kind of evaporates immediately. It's like it changes your relationship to the object. Even if it carries on and does everything else perfectly going forward, you still sort of like reset the relationship with the product immediately.

And when it comes to financial matters, that's where, like, that's your bread and butter. You want to make sure that anything affiliated with that screen, that surface, that product carries its own weight in gold. It is as reliable as any other entity on the planet. Because in so many respects for so many people, it's their lifeblood. It's like how they feed themselves and their families and the families of their employees.

Yeah. Yeah. Maybe we should go back to the airplane example for a minute. What has flying taught you about trust in a life or death kind of context, right? Yeah. Well, you know what's really interesting about what I didn't know about flying for sure beforehand was just the history and the systems and the simplicity and the beauty of some of these things.

So for example, I fly a Cessna 172. That's probably from the 70s. The number of things that are analog in this thing would surprise you. So one, when I pull back on the yoke, it is pulling a cable that is then adjusting the elevator on the tail. it's a cable um i was like really surprised when i saw that it just and i don't know why i had you know like less trust in a cable than you know in maybe a digital experience but like actually you know that that is simple true you know when it's not working yeah and and in fact like i've come to feel you know a great amount of confidence in these like very analog systems like The gauges that I use, they're literally nicknamed like

steam gauges, and they have worked for many, many decades. And so I think the takeaway that I've had from like just seeing, you know, these really thoughtful systems, it's like when you understand something so well and you can kind of like boil it down to these simple parts is really powerful and long withstanding. And just to know that, like, how long that has been the case and that I can, you know, trust in these systems that have worked for many years.

And I have my POH or the pilot's operating handbook that will tell me, you know, how many feet of the runway I will need. based on the weather at the time and based on how much fuel I have and all these things, that is awesome, like that history there. So it gives me just like a hell of a lot of esteem for one, just like the thought that goes behind it.

It makes me think about how can we know our work better when we set out to do something? Like if we're going to, let's say, create a checkout product, right? And so Stripe builds checkouts that can help any business be able to take funds online or in person. what is the best checkout in the world? Thinking about like the user, the customer at the end of the day or the business, like what is the best in the world? And actually start with that as the question, because if you're just like, all right, let's make a checkout.

Yeah, just finish the thing, move on to the next thing. It's a different thing. Yeah. But you're like, no, let's make the best one in the world. It begs you to ask and understand the use case and the people that are using it and the circumstances of the use, the 360 degrees of context.

So deeply that you can come up with what could be, you know, the best long withstanding and simple right answer for the question. And I think another kind of key piece of that, though, is also just like always progressing. Like, how do you keep making it better? And so, like, for example, like, we, like, the checkout products that we have, you know, we've had for many years, we've never stopped working on it.

It's not like, oh, we got the form and now it's the best one ever. It's like, well, it was the best one at the time. Right. But we know more now. Users' needs have changed. Circumstances have changed. GenTech commerce. People have new payment methods. Exactly. It's like we continue to iterate on it and, like, think about it, you know, from soups to nuts.

Like, both, like, you know, how do the pixels, like, how do we perfect the pixels? But also, you know, how is it working? How is it, like, how fast is it? How reliable is it? How can we enhance those things? And, like, today our checkout experience actually can create 11.9% more revenue for our users based on it being a better version than it was in the past.

Just by, like, keep dedicated to that mission of improving it. I don't know. It feels like gratifying, I would say, from like design's job is never done, but also like being aware that things are changing around us. And so like take that into the work and continue to make it better. Well, Katie, I always learn something new when I talk to you.

Thank you so much for hosting me here. And thank you for leading the way. I really do mean it. I admire like what you've been able to accomplish and the impact you've had on so many careers and companies that I just profoundly, profoundly respect. Thanks, Leo. So nice to be here with you. Appreciate you. Thank you. This is First of Kind, a new series about design and tech told by its pioneers.

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