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Katie Dill

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98
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2023-10-15
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2023-10-15
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  1. Well, first off, please do find me online because as I talked about, we're 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 Lil underscore Dill on Twitter. And then I think that name was taken on threads. So I'm Lil underscore Dillee with a Y on threads. And then I'm on LinkedIn. And find me there. We're hiring. So definitely reach out at our job board to stripe.com slash jobs. Definitely check us out. We definitely would love to hear from you.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. He moved his seat back and like a lot. And so he was now like kind of out of touch with the controls. Like he could jump there if he needed to, but he really pulled back. And it was such an incredible visceral experience. I was like, he trust me. Right now, he is like, he is showing his faith in me to take this and like take this challenge on. And I think about that all the time. It's just like, you know, how can I show my team people I work with, like my support and trust in them, you know, to take that challenge on. And so like, you know, I can't always move my seat back, but like, what might be the way? And so that's been a, you know, pretty, pretty great example of like something I want to pull forward.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. Yeah. First of all, Lorene Fly has been such an amazing experience because there haven't been many things in my adult life where you feel like you'reself 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 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 have 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 usually he's right there at the controls with me. So if like something goes wrong when I'm flying, he's right there. And I remember one of the first times when I was learning how to land where

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. Thought about that the other day because I was riding in a lift to the airport. This was also at like 4 a.m. So it was like a really hard time to be in a lift and got into the airport. And the driver was telling me about his kids. 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. My girl, she's my princess. And, 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 going to let her take out the garbage. 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 she's not, you know, able to do the jobs, even the hard ones and even the bad ones, like taking off the trash. And, you know, 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. Yeah, I think about this a lot. I am a mom of twin girls. And I feel so lucky that my parents raise me to see that accomplishment is based on merit and hard work. And they never made me feel like, you know, because I was small and that I was not as strong as, you know, 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 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 don't look like me and, you know, wanting to or just not letting that hold me back.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. I don't say this out loud, but I do, I've had it as a post it 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 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 now today, tomorrow is now.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. So who can't? The Tony Backs. I should have brought it over too. So 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 the 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. 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 what they like to do and where they're kind of like gravity pulls them.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

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

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. It's a beautiful story. It's like it'll make you laugh. It teaches you a thing or two. And one of the best quotes in it is one of our greatest freedoms is how we react to things.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. Brothers by David McCaul, I think. I've been learning how to fly. And so 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 kind of talks about the impossible challenge of like nobody thought it could be done. Even, you know, the American Institute of Science didn't think it could be done. And these individuals that had the like resolve and the commitment to make it happen. I think also the power of this like beautiful partnership, of course, the brothers. That doesn't always mean you get along. But there are brothers and they, you know, 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 ask me 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. One, how to win friends and influence people. It's an oldie but a goody. 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 cover is funny. You know, 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 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 still a couple years old. It's about the right.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  13. Okay, great. And I also love the way that you set these things up. You had said to me in the thing that you set me, she's just like, if it's not good, we're not going to ship it. And you said it in very nice ways, by the way. But 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 going to, you know, embarrass me to the rest of the world, hopefully. And 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 leading to a belief of the level of quality of what somebody 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, we'll end up leading to better, you know, quality overall. So kudos to you.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. These creative skills and this great taste is an incredible, important thing to bring into the organization. But I think 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 like I love how you don't have your guests tell about their background, right? Because like when someone tells about their background, like that is interesting, but like it's not really like usable information of like, oh, I can take this information and run with it and bring it to my own team and make my work better.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. Bringing intentionality to the decisions that you make and thinking about who is this thing for? So 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, any old function can put that intentionality. If you think about who is impacted by this, who is using this? And 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 like design expertise of people that have

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. We talked a little bit about the importance of different disciplines and the importance of quality being a group effort. And I hope this doesn't insult my function, as I say, but at the core design is simply intention.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. Part it's like in some ways, like how they get to know us and they get to see the care that we put into any number of things.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. Yeah, well, Stripe's mission is to increase the GDP of the internet. We strive to build global economic prosperity because that's greater access across 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 enables them to accomplish more. 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 feel we are or we strive to be and you know we're excited to share that with people so you know

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. It is press.stripe.com will be where you can see all the books that we have at StripePress. And I believe the first one in the line. 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 what would be a great experience for understanding different books. And when you go into a bookstore, like you see the spines of the books and you 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 should stop describing it. Just go and check it out. And you'll see as we saw it too, deliver this work in a way that would be aligned with what a reader would want to pursue.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. It's pretty awesome. And that's our website team is just like, you know, we talked about the importance of design and engineering, working super closely together, and it's just like that. Wild. That art and science coming together into something that hopefully is fun and engaging and people want to, you 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  21. It's a fascinating book and it's 20 years old. It's actually Charlie Munger's words, but Peter Kaufman, a friend and a colleague of his, assembled all of these documents over the years of things that 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  22. And we take great care to 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 actually pre-

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  23. Oh, yeah, we got a good one that I'm so excited about. Well, first off, I don't know if everybody knows this, but Stripe prints books

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  24. Contingent on like what is the thing? What is the user need? So something that is really great. Like we do a lot of tools that 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 easily accessible. But we'll definitely feel different than perhaps a consumer product that is meant to be extremely light and sparse and directive to one individual thing at a time. So it really kind of depends on the context of the product sometimes. So that's why it's hard to kind of quote an individual book. But yeah, I mean, I can think on it and we can put it in the show notes. There are definitely books that talk about like the principles of great design. And we can look at that.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  25. You know, it's like if you had all the different 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 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 a strategy that will help to be user focus from the start. So maybe a great way of doing that is kind of having like a more senior leader design advisor and then a kind of executor or doer full-time on the team.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  26. And that hustle to like try to execute on that rapidly is, of course, essential as you're hiring really any stage company. And I guess lastly, I think you were asking in particular, like especially with younger companies or startups. I think one thing that can be hard is like, do you hire a more junior doer or a more senior kind of like thinker operator?

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  27. That they have that respect and empathy and understanding and enthusiasm for the folks around them, but also the users. So 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 strive to navigate these things to make it better. And then I guess the last piece would just be hustle or hutzpah. I'm not sure exactly what's the right way to put it, but the design and the creative functions is the act of creation. And it's scary. It's like to take a blank piece of paper and propose something that you think is better is scary to have the courage to say this is not good enough. And we should do it again is scary. And so having somebody that has that kind of like courage inside them to, you know, fight for great is pretty important.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  28. 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, you know, kind of like their hit rate for great judgment and great taste and how they've honed that even if they're not very experienced just to like see do they have that natural inclination for great things. The other piece of it is that certainly you want to find somebody with great talent for sure and high craft, but you also want to find somebody that's humble, you know, that like, you know, folks that aren't 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 in a team, you need to work together. And it is important.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  29. Like, you know, kind of North Star lays out the process in a way that I think allows for big risk taking in a way that is measured and thoughtful and actually also feels like progress as you step towards that versus like, you know, trying to like get there day one and likely end up giving up.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  30. Yes, exactly. 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. Show what that ideal version is. If you don't know what that is, like what are the chances that you're going to increment yourself to the right outcome in the end? And as I talked about before, like building the house, like 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 in 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. I'm not suggesting you have to ship the whole thing at once.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  31. 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 for the stars and land on the moon. And what I mean by that is that vision work is really important. And I think 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 seated on a shelf and nobody ever builds it. 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 entirety of the experience, a comprehensive approach, a journey approach, and thinks about how these things, you know, various things may come together to be better and sketch out the ideal version. And I think Brian Chesky talks about it. I think it was like the 11th star experience, I think you once said.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  32. 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 like, you know, 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 like actually like, you know, if we just like make an incremental approach, it's very measured and we can, we know what the outcome is 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 like what quality means, you know, and you think about it as like, well, like quality is really, you know, your users are the judge of that and the way that they experience things oftentimes are like across products, across surface, across time. If you just think about 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 make the whole thing better.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  33. Not in a locked room, and I joined Stripe. It was a Zoom universe, so it's a little bit different. But we do even today, we have a studio space where we have all the great tools of craft. And when you do go into the offices, we do have places where 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 folks that work kind of across all of the things that we do. And so 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 I love that so much. I go into the office about halftime now. And, you know, I think over time we'll probably build 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  34. Yes, yes. Like literally and figuratively, we broke down the wall and brought the teams physically together so that they would work together. And then, you know, we had an org jar 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 aligning on shared goals about the overall experience, but also making sure that we could work well with our partners.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  35. The folks that don't work in an embedded fashion will sit. But we had 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 that room for creative space, like literally the room and literally the room in terms of figuratively speaking for allowing for creative exploration, but more aligned.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  36. 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 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, had done it with an approach about listening and came into that with a kind of better understanding of getting to know the team and getting to know engineering and product and 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 on the day that we opened the doors and brought design and engineered product together and had spaces for folks to work together and like they actually sat with each other, we still kept the creative space for this is where we'll do crits. This is where we'll do working sessions.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  37. Yeah, yeah, yeah. And, you know, absolutely, there are a lot of tie-ins to what I had seen. And the interesting part about how actually teams were working is that you would see that there was like a lot of wasted work and there was a lot of like misalignment in what we were trying to do because there was 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 like, you know, they meet up and it's like, well, that's not aligned. Like, no, that doesn't fit the goal. And like, you know, you went that way. We were supposed to go over this way. And so, you know, interference in the sense that it was like, it was wasted work. It wasn't actually aligned to the goals. It was slower. And, you know, there were definitely benefits. Like there was real reasons for doing this. And I know there are companies, including Apple, that have, you know, kind of like separation of these things. But I think if you're going into that kind of way of

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  38. 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 very safe space for creative discovery and exploration and communication. There was work all over the walls. It was like wall-to-wall whiteboards. And it was just like absolutely a place where creativity could thrive.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  39. Actually, goes back to org design that we talked about earlier and where people sit. 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 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  40. Curtain and showing the work in progress. It can feel hard at first, but I think people have started to see the benefits in doing that. And then usually that will lead to better outcomes in the long run in the culture too.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  41. You know, and actually another part of it that is another benefit of opening up the curtain a little bit of like we, you know, we do, you know, certainly we have to take things seriously in terms of like, you know, confidential work, it's work in progress. You know, it's not ready to go live. You know, we're not ready to critique all the details about this. We do need to make it very clear to folks that this is like work in progress, but also that 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 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  42. Yeah, yeah. And we experiment with how often we ask folks to share and also the granularity of what they're doing. Like it is not meant to be a status check. We're not asking you 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, show us like the medium and large projects, you know, if there's just 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, but it adds up, you know, if it's, feels like it's arduous task.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  43. 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 critically, I want all functions to be able to look at it. And if not everybody is on FigMond, if they were, that'd 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 send it off. It's behaviors that people are really used to commenting. But yeah, maybe one day.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  44. A slide and 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 whether or not they're a team of 10 or 170 or whatever it might be, what is happening. And they can say like, oh my gosh, like you're working on that surface. Like, so am I. And let's talk about it. Or, oh, that's an interesting pattern, like, you know, maybe we could use this in more places. And we send it to the product managers and the engineer leaders and the leaders in the company because it is also a really great way for them to understand what's happening and what are we building together because going earlier, as I talked about, the importance of thinking about things as a journey. So what's happening in the marketing side? What's happening in this aspect of the product and seeing how all these pieces really fit together? That has been 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  45. More informed in terms of as you improve the processes. One of the things that I've been working on since I work 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 is people lose touch with what's happening in different parts of the organization. And, you know, everybody's got like a doc that, you know, their PRD where they've written down what they've done and it's got like tons of 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 strong believer that a picture tells a thousand words and a prototype tells, you know, 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  46. 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 how can I increase potential? How can I decrease interferences? And over time, especially as your company grows, you know, you're going to have to keep doing that. Like, you know, the design work has never done in designing a team because the more people you bring in, the more it puts your processes in a faulty state. We intentionally, or I have intentionally runs where you get to a point where it's kind of like running hot, right? It's just like, okay, like with 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, you know, making those changes as needed helps to make them more sought after.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  47. 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 your customers and you're having more business effect, 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 compared 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  48. One of the things that has stuck with me, and through all the trials and tribulations of leading, 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 like 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.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  49. Within, or that you're creating the API, or that you're building the interface, or that you're talking to people on support calls, like the meticulous craft is something that, you know,

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source

  50. Great work happening even when it's not necessarily materially moving that number. The other part of it is we have a levelless 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 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 and that what we pursue is building these 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 designing the space that we work.

    2023-10-15 · Lenny's Podcast · Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft) · IDENTIFIED FROM THE TRANSCRIPT · source