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

Katie Dill (00:00:00):
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, "Well, functionality is king. Functionality is what matters." As if people think about functionality and beauty as like two opposite things. 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.

(00:00:32):
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.

Lenny (00:00:55):
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 hypergrowth companies, seen 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.

(00:01:25):
In our conversation Katie shares stories of trials and tribulations of leading large design teams, processes she's put in place for operationalizing quality, how she thinks about quality and beauty very practically, how design can directly lead to growth, and examples of this that led to a big lift in conversion at Stripe, plus a math formula she uses to increase team performance, how she suggests organizing your design and product teams, what to look for in design hires, and so much more. I was really lucky to get to work with Katie while at Airbnb, and I am so excited to have her on this podcast. With that, I bring you Katie Dill after a short word from our sponsors.

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Say goodbye to your spreadsheets and the never-ending alignment efforts. The old way of doing product management is over. Rediscover what's possible with Jira Product Discovery. Try it for free at atlassian.com/lenny. That's atlassian.com/lenny. Katie, thank you so much for being here. Welcome to the podcast.

Katie Dill (00:04:52):
Thanks for having me. Good to be here.

Lenny (00:04:54):
It's absolutely my pleasure. So as we were preparing for this podcast, you hinted at a story that you had from your time at Airbnb where the design team staged an intervention with you which I had no idea about. Because I was there during this time and I did not know this was happening. I am so curious to hear the story. Can you share what happened?

Katie Dill (00:05:15):
Ah, starting with the easy questions I see. All right.

Lenny (00:05:18):
Right into it.

Katie Dill (00:05:20):
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. It happened in my early days at Airbnb. 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.

(00:05:47):
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. So 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.

(00:06:08):
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. 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 AM, it was an hour and a half with half of the Design team, so that was five people, and our HR partner.

Lenny (00:06:38):
Oh, no.

Katie Dill (00:06:38):
Usually not a good sign.

Lenny (00:06:38):
That's never a good sign.

Katie Dill (00:06:40):
Yeah. And I remember this so vividly. I remember walking into the office, and all the rooms in Airbnb's office are very unique spaces that look like Airbnb's. But of course this was the one room with all white walls and just a gray flat rectangle table. I walked into the room and there were five of them seated around the table. 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.

(00:07:22):
It was a really hard moment there. I went through all the usual kind of like stages of grief when one hears feedback, which is just like an immediate want to respond to be like, "Yeah." Like, "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, thank goodness I had the sense to just listen and not respond in that way. I mean, clearly what they were telling me is that that was one of the things that was missing.

(00:07:49):
So I heard them out and took it all in. And regardless of each individual saying, what was very clear was that the missing piece, the theme that was across all of that, is that I hadn't earned their trust. So whether how right or how wrong what I was doing was, is the key piece is that I wasn't bringing the team along with me. They had no idea that they could trust in what I was trying to build, and what I was trying to shape, and that I cared about them, and that I had their best interests and shared goals at heart. And that was absolutely my fault.

(00:08:24):
In retrospect, as hard as that was, I'm very grateful and very amazed that they could come together and share that with me. It can be hard to bring feedback forward like that. So it was an extremely valuable learning experience. 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.

(00:08:57):
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 trust is the key element there. And then a couple months later, we had the best engagement scores in the company.

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So it did objectively improve the situation, and since then taken that on into next steps in other companies that I've joined. And just think about instead of coming in 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 that you bring along with you.

Lenny (00:09:42):
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?

Katie Dill (00:09:52):
Before I got there I think there was a little of like, "Design is just going to sit with Design and not necessarily work in close proximity with engineers and product managers, et cetera." And one of the things that I believe as a necessary part of building a high-functioning organization is that, one, building together is important. So having engineers, and product managers, and designers be together, have shared goals, and align on that and be able to just look over each other's shoulder and talk about things, is important. So sitting together is important.

(00:10:21):
However, that Thayer thing that you're talking about actually was like 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. Like Joebot at Airbnb once said, "It's like, well, what T-shirt do you wear? What team are you on?" And I was like, "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, Thayer was a good spot for that.

Lenny (00:10:56):
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, partly because the ROI is just really unclear.

(00:11:16):
If we spend another month making this more awesome and making this even more amazing design-wise, experience-wise, 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.

Katie Dill (00:11:39):
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 probably because the quality bar keeps evolving, keeps rising. But I think first to kind of level set before we dive into that I would say that there are levels of quality. There is the, does the thing work? Does it provide some sort of value proposition? It like executes on its job. That's baseline quality.

(00:12:06):
Next is that, 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. Then beyond that, like level three, level four, level five, does it exceed expectations and it does something that you weren't even 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.

(00:12:36):
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, what about just like another feature and being seduced by the chase of another feature versus actually taking your features to a level of being great? That is hard. And I get it when you look at your user base and they're all shouting from the rooftops for this additional feature.

(00:13:05):
Of course you're going to want to prioritize that over something they never asked for. 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.

(00:13:21):
Of course that's going to be enchanting to want to go after the things that you can actually measure, you know that they're going to have that impact. But the companies that know that quality is non-negotiable, it is a long-term necessary aspect of what they build, don't play that numbers game. Or what they do is they recognize that it is absolutely functionality, but the quality of those features that is actually going to get to great usability, desirability in their product.

(00:13:53):
Actually, I think it's kind of like an analogy for going to the gym or working out. I don't know about you, but literally every time I think to do this, there's a fight in my head of like, "Ah, do I really need to work out today? Is this one day going to give me six-pack abs?" Like, "Of course not." So like, "Why go? Why not just skip it today?" But of course then at some point, hopefully, I realize that it's like, "Well, if I skip it today, what's to stop me from skipping it another day?"

(00:14:21):
And really in the belief of that these things, it really does add up to a better outcome in the end, and so a longer, healthier life. So hopefully I can get myself together and go to the gym. I do think some of the best companies on the planet think that way. I recognize that 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 they might be asking for in more improved features.

(00:14:53):
But some of the levels of quality, the level two, and three, and four, you might not get direct asked for. But I guess I'll give you another analogy. If you don't have competition, that's fine. Right? If you think about the first car, I am sure that wheel was really hard to turn, and I'm sure that seat was not comfortable, and you 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 cars today it's like the stitching, the choice of the leather, the sound of the door.

(00:15:28):
These distinguish a, hmm, okay car to a high-end special car with higher value. This is very much by understanding how the details matter and how execution of quality will take it to the next level. Lastly, I'll just say that I know there's this saying of it's growth versus quality, but quality is growth. And if you think about how you can make your product easier to use and more understandable, that will of course drive people to use it, and use more of it, and have a better experience with it that they'll want to talk about with others.

(00:16:08):
In fact, at Stripe our Growth team I would say is 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 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.

(00:16:38):
One of the biggest examples that I've seen of business impact through quality is actually in the checkout experience. We've done research on the checkout experience in some of the top e-commerce sites. 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. These small things, really they're quality issues.

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They're just that if you really understand what a consumer is trying to get out of the experience, then you can make it better. 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 business' revenue from 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.

Lenny (00:17:51):
You mentioned this before we started recording, but you guys power the checkout flow for some very big sites. Can you mention a few of these because they'll give people a sense of like holy moly.

Katie Dill (00:18:00):
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. The work that we do, it ranges.

(00:18:20):
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 to sweat the details of how these things work.

Lenny (00:18:46):
I just want to follow this thread a little bit. You talked about these opportunities to improve the checkout flow through a design lens. You could also think of it from like 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, let's just move this metric and here's all the things that are stopping people." What would you say is the designer's lens on that, if there's anything there?

Katie Dill (00:19:13):
Honestly, a pet peeve of mine is this way of talking about things as there's business goals and there's design goals. Because I think maybe the first conversation one should have is that, "What are we trying to build towards?" And I would think that folks that want to create really impactful products, they want to create quality products, and that they want to create things that actually serve their customers in a positive and beneficial way because they know that will build a stronger business in the long run.

(00:19:47):
So yes, there may be slight prioritization details different through the process where a designer might be thinking more about the emotional experience and how somebody feels, because that's oftentimes how they're wired, and that is an important lens to bring on it. Whereas somebody else might just be like, "Well, just make the button bigger and they'll click it more often, and that's the outcome that we seek."

(00:20:10):
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 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 we can recognize the fact that it isn't just that utility is an incredible important part of that, but so is usability and so is desirability because these things together make something truly great.

(00:20:38):
So 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 build towards something better. I think that beauty on its own or just craft on its own without utility, I mean that's like, I don't know, that's like Blu-ray or PATH. Right? That does not lead to a high-quality product. So it is the combination of these things, and so it's like stepping towards that.

(00:21:10):
But if you really want your product, those features, to be utilized for all that they're worth and to actually gain such 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 my mental model," that craft and that quality of the execution of those details is going to be paramount.

Lenny (00:21:40):
You mentioned this word beauty, and I wanted to follow on this a little bit of just ... This is a big question, but just what is great design? What is beauty? Is there like a objective definition where if a designer is like, "This is great design," is there just like, "Yes, that is true." Or is it just an opinion? How do you think about what is great design? What is beauty, Katie Dill?

Katie Dill (00:21:59):
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, "Beauty? We're talking about business here." Which is great. Actually, there's a fun fact. Stefan Sagmeister and Jessica Walsh have a book called Beauty. 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 pretty dramatically.

(00:22:34):
It's aligned with this idea of like, "Well, functionality is king. Functionality is what matters," as if people think about functionality and beauty as like two opposite things. But what the whole book talks about is that like, "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. And there is actually some objectivity to whether or not beauty enhances things.

(00:23:05):
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. 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. 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.

(00:23:43):
If you've been to those places I'm sure 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. So the things that you create have this impact. And if you're thinking about like, "I want people to enjoy using my-

Katie Dill (00:24:00):
... have this impact. If you're thinking about, "I want people to enjoy using my product, I want them to feel 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 care about other details that you can't see too.

(00:24:37):
Then, secondly, it is easier to use, as I've mentioned, it gives better user outcomes. 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. By bringing a interface or 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. When our business users or the consumers see the beauty and the care and the creativity that we put into things we deliver, then that again reassures them of just the care that we put into them. Actually, a perfect example of this, have you seen the show The Bear?

Lenny (00:25:23):
I have, yes. Great example. Yeah.

Katie Dill (00:25:25):
All right. Okay. All right. No spoilers, but all I have to say is peeling mushrooms. Do you know what I mean?

Lenny (00:25:30):
Yeah.

Katie Dill (00:25:30):
Yeah. Such a good example. Such a good example.

Lenny (00:25:33):
Someone just mentioned that same episode on a recent podcast episode.

Katie Dill (00:25:36):
Okay. All right. Well, it's that good. It's that good. I wish I could remember which episode that was, but it was seven? I forget. But anyway.

Lenny (00:25:44):
Yeah, that's exactly right. That's exactly right.

Katie Dill (00:25:45):
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 care into our work, more people will want to work with us, because they want to see their time spent and the care for their craft recognized and utilized and see that that can be put together into something really impactful. We really put that on the pedestal, because we know how much it matters to our users and then how much it matters to the people that work with us. Beauty is an important part of it all.

Lenny (00:26:20):
Amazing. Speaking of beauty, 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, "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?

Katie Dill (00:26:45):
Yeah, there's definitely a couple of things we could talk about in terms of operationalizing quality. Because the gravitational pull is to mediocrity. 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 certainly a lot of effort, and it's a concerted effort. I will definitely say we are a work in progress and we have not nailed all the things and it is an ongoing pursuit of excellence.

(00:27:21):
The way that we build the website is that we certainly do put a lot of care into what we're putting out into the world, and we view it as a articulation of how we care about our users in all that we provide for them. So, we take that very seriously. We try to meld art and science. So, it's the creativity of the work, but it's also just the technical power of the way that we show it.

(00:27:49):
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. 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. Together, quite literally, as we were talking about earlier, if we were physically together, they would be sitting side by side and they're batting ideas back and forth, because the engineer on the team has a great idea for how we could go about executing on it. And the designer on the team has another idea how to push that a little further. So, that rapid cycle of iteration is really, really powerful, especially when we're trying to move quickly, but at an extremely high standard.

Lenny (00:28:44):
That's super interesting. Is there anything else that you've found to be really helpful in just operationalizing great design, craft, beauty, any processes, systems, frameworks?

Katie Dill (00:28:54):
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.

Lenny (00:29:02):
Awesome.

Katie Dill (00:29:02):
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. There are a couple of themes that are clearly coming through.

(00:29:28):
Number one is that quality is definitely a group effort. You're sunk if you think that you can just hire some incredibly talented person and they'll do it, that'll be fine. The rest of us will do what we're doing and they'll do it, or that it's just one organization that's going to look out for quality or QA is going to solve it all for you. It really does need to be an organizational and a group effort. If you think about the way that you run 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.

(00:30:20):
Number two is that there needs to be some amount of vision and alignment. So, if you hire all the best people in the world and you just 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? Even if they all have incredible taste and they're very good at what they do, there is subjectivity to every decision in some part. So, that they might end up with some things that are really great but don't fit together as a really nice whole.

(00:30:49):
The perfect example would be building a house. You have the person that works on the roof and the person that works on the deck and the person that does the siding, et cetera, et cetera, et cetera. A house is arguably far less complex than most of the technical products that we all know. Yet, there is painstaking effort put into having the plans and having 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.

(00:31:19):
I think a big pair on that is then the next piece, which is editing. And you might call that your GC or your architect or somebody that sees how all these things fit together, and then has an ability to help narrow and reduce and remove the things that don't fit. At Airbnb, Brian Chesky is the editor of all the things that come together. At the Economist, there's a chief editor. But other organizations, they might decentralize that approach, which is certainly possible, but challenging, because you do need somebody to help see these things come together.

(00:31:53):
That pairs with the next piece, which is about courage, the ability to actually say, "No, this isn't good enough." 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 a team puts all this care and effort into something and then you're going to say, "Actually, unfortunately we're just not there yet. Let's try again." That is, I think, incredibly important part of getting there and building the fitness of what you do.

(00:32:28):
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 gets me into my fixation with journeys, because that is how a user sees it. The user very, very, very rarely just 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 something just changed and now they need to use that product in some other way. You have to understand it from that point of view to really understand whether or not the quality is there. I think that's a critical piece of building teams that have empathy for their users.

(00:33:16):
So, we have been operationalizing that. All the things that I just mentioned, but one of the key pieces is to bring that approach to understanding the quality of the product. So, our goal was to set out to try to solve the fact that products can be shipped and they could be at their highest game when you ship them, they go through all the processes internally to be a high quality thing, and then it gets out into the world and then, over time, the quality regresses. Some of the reasons for that is that other things are being shipped. 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 paint the little aspects and you've put new plates on the lights, now all of a sudden that room is great, but it makes everything else look worse and the whole composite is worse.

(00:34:10):
That is something that can happen to products is actually they get worse over time. Then you organize a company oftentimes and parts to be able to focus on their key business areas. That's a very good thing because they get focused and they know what they're building towards and they get expertise and they're laser focused on that. So, 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 part of their product experience is intimately tied to another.

(00:34:44):
So, what we did was we set out to, number one, increase the kind of awareness and accountability of leaders to own their journeys. What we have established are 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 is 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, and we must get right at the highest level of quality possible.

(00:35:20):
Those 15 things then each have engineering, product and design leaders that are responsible for the quality of those products. 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. They will write what they have seen, what's working, what's not working. They're viewing this from, they're trying to put themselves in the shoes of their user. This of course doesn't replace user research, but it substitutes it and it adds to that.

(00:35:58):
So, they go through the experience and noting what's working and what's not working. And very critically, it's a journey, so a lot of times it starts from internet search, it starts on Google trying to understand something, goes to the website, they end up on Docs, they end up in the dashboard, and they're seeing it as a user might. With that, they're able to find the entailments of the experience that may or may not be working. 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. Then on, again, a regular cadence, we come together in almost like a calibration, where we meet and we talk about the score of their work.

(00:36:40):
It relates to performance reviews. Performance reviews, managers are assessing an individual's performance, which is hard. 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, "Okay, how well is our interpretation of our ladders document? And how well does that performance align? And are we doing it consistently across the rest of the organization?" 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 uplevel and bring more shared understanding of our quality bar across the company. These moments of calibration start that. Then having leaders do this creates this, number one, it cascades this idea of the importance of owning your journey and then also has upstream impact.

(00:37:43):
Because when people see the state of products in the wild as a user would, they learn a lot about 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 even better things coming into the wild? One of the best parts of this is, since then we've learned that folks have seen that like, "Oh my goodness, our SEO for this particular product or 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." They're seeing that and they're now able to make that happen even faster to make some of the changes there.

(00:38:27):
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 just like, "Oh, I was so very focused on executing the technical ability of what I do on this thing, but I hadn't seen it from this lens before." Now there're actually converts of like, "Yes, this is a really important part of it." That goes back to the point of it's a group effort. 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 walking the store, seeing the experience, feeling it firsthand, I think will lead to better care in all of the details that will aligned to better craft in the end.

Lenny (00:39:12):
Oh man, what an awesome process. I have a million questions I want to ask to better understand how you operationalize this. I'll try to ask just a few. But one thing that stood out about this process is I think people kind of don't trust their own judgment when they're looking at their own product. They kind of, especially product managers, almost have to feel like they have to rely on user research or data to know a thing versus like, "I just see this and it feels bad to me." 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, I love that this actually relies on your personal judgment trying to use a thing, which I think people undervalue.

Katie Dill (00:39:53):
Yeah.

Lenny (00:39:54):
A couple of just very tactical questions, how often roughly does this happen? Is it once a quarter?

Katie Dill (00:40:00):
To your first point, 100%, they're all just forms of input. I'm definitely not saying do this instead of user research, do this instead of data. It's like these things in additional sense. I do think what's so powerful about doing it firsthand is that, although I am the biggest supporter of user research, even hearing somebody talk about an experience, while that is really, really powerful, feeling the pain firsthand is just this next level of visceral understanding of like, "Oh, this could be better." Your users, they might not always say what's missing or what's wrong, or maybe they don't know that certain aspects of it could be better. 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.

(00:40:49):
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. The quarterly aspect of walking the stores by no means meant to be like that's the only time people do it. But that is the time where we're looking for update your scorecard and share the information in a dashboard where everybody can see. That is feeling right now to be the right cadence because that's enough time that there can be material differences made. You can see the scores evolve over time. But also frequently enough that you're not missing that perhaps there's been a setback since. But, of course, my real hope is that they're happening weekly, just perhaps in different parts of the organization.

Lenny (00:41:46):
I want to ask a couple more questions so that folks can try this at home. I was just thinking this podcast is the opposite of don't try this at home. It's like, "Here, try this at home?"

Katie Dill (00:41:54):
Try it at home.

Lenny (00:41:55):
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. Who's in these meetings? Do you join these walkthroughs? Does David join? What do you suggest there?

Katie Dill (00:42:07):
Yeah. For what we're doing for each team is they do them themselves together. At bare minimum, it should be the engineer, product manager and designer doing it together. 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. Let's say somebody in the room might be like, "Oh my goodness, the load time didn't feel really good there." And like, "Oh, whoa, the way we're stating this is not consistent per page. And that's not on our design system."

(00:42:41):
So, it is really powerful to have folks come together and do it. In fact, David Singleton, who you mentioned, he and I do these things very regularly, too. This is outside the essential journeys program, but he and I walk the store and we'll just pick random flows and go through it together. I can't code, but he can. So, he'll do the code part and I'll be sitting there being, "What? Do they really do that? How can we make that better for them?"

(00:43:08):
I really love the multidisciplinary approach, but then when we do the calibration after the team has done these walkthroughs and they've gotten their own perspective and they fill out the scorecard based on our rubric for quality, we will come together in what we call PQR, product quality review. And they will take us through what they have experienced, and then they'll talk about, "So, this is why we've scored this, a yellow or a yellow green." Then we might have a conversation about that.

(00:43:39):
It's like, "Well, actually, that felt a little worse than you've described it. 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."

(00:43:59):
We will debate that there. In those meetings you'll have, yes, myself, David Singleton, Will Gaybrick, 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. 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, the expected product in the room as we discuss what our quality bar is.

Lenny (00:44:36):
Awesome. Okay. That makes a lot of sense. In terms of scoring, are you scoring individual steps of these journeys or is it yellow for segments? What are you scoring?

Katie Dill (00:44:44):
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 screenshots and then what they experienced. Then there is a tool to tag for each moment. It's like, "Oh, that was a nice touch." Or, "Ooh, that is not great. We should consider a fix." Or different levels 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.

(00:45:11):
Then there is a summary score at the end, which is based on a rubric that we have that talks about the importance of quality from the point of view of usability, utility, desirability, and actually going to that next level of surprisingly great. Then we'll ask them to score on a whole what they felt of these things. 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 A-minus and B?

Lenny (00:45:42):
[inaudible 00:45:42].

Katie Dill (00:45:42):
Yeah. 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 to your point, especially in subjective things, and it's just like, "Oh, it's like, well, is it really a six or is it a seven?" We didn't want people to get a little too worried about how does... It's not meant to be an objective quantitative score. It is qualitative, it is judgment. We hire people for judgment, so we want them to bring that to the conversation. That's how we chose the score, because we felt that would actually lead to quicker but straightforward opinions and decisions.

Lenny (00:46:25):
At a lot of companies, you have these reviews and the founders share all this like, "Oh, this is broken, this is busted." And as a product team, you're like, "Goddammit, we have these goals we got to hit. We have this roadmap. And now we're going to get a hundred things that the founder's like, 'Got to fix this.'" I'm curious just how you tell teams to take this stuff and prioritize it amongst all the other things they're going to do. Is it just up to them, is they're like, "Need to fix this"? Anything you can share there, but just how to actually operationalize taking this feedback and doing something with it?

Katie Dill (00:46:54):
Yes. Yeah. I've seen some organizations talk about when they're doing planning, you do your OKRs quarterly or half year or year, whatever, recommendations of like, 10% of your time should be spent on fixing things, and 20% on growing things, and the rest on keeping the lights on, whatever it might be. Yes, I've seen different companies build a recommendation based on certain percentages of how they think teams should be spending their time.

(00:47:28):
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 number one. Then, you can give a lot of trust to people based on that commitment to building great things that they will use that in their decision-making. Then, of course, it needs to be very clearly advocated for at the highest levels of the...

Katie Dill (00:48:01):
... Advocated for at the highest levels of the company. And with that, I think that fuels people's thinking as they're building their plans, but there is iteration in the plans and we do have multidisciplinary 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 together get to it, but there's no formula that we ask people to.

Lenny (00:48:30):
So basically what I'm hearing is it's the cultural just people are hired with this expectation we are going to focus on quality and we'll prioritize things even though they may not move metrics because we know that this will generally improve and grow the business.

Katie Dill (00:48:43):
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 talked about earlier, but that actual quality improvements do increase growth, they do improve the bottom line. For example, we saw that folks were reaching out to support because they didn't know the state of how one of their invoices was performing. And when we dig in, we realized it's, well, we had a button that 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 want to have to call somebody to find the answer to their problem. And so with that, we've made an improvement and we, of course, improve the bottom line because of that.

(00:49:38):
So I actually think that maybe one of the steps that somebody should consider in their organization is just you have those examples, every company does, where 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 it's 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." Some of them are longer term and so you have to look out for a while to see that change and the beliefs of your customers or how often they're sharing your product or how often they're succeeding in what they're trying to do, but some of them are short-term impacts and that is an important thing for people to be aware of because it will give them ideas of, oh, we could do this in our team too, we could have a higher quality product and actually move the business metrics.

Lenny (00:50:28):
Is there anything you do in how you evaluate performance of teams that helps prioritize this sort of thing? So generally it's just, cool, this team moved this metric by a ton, they're doing great. 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?

Katie Dill (00:50:54):
Well, I think one part is being clear on what impact means, because I do think that in some companies impact is just, okay, what business metric did I move and how much? And there are certainly really important impact projects that folks can have that maybe they're multi-quarter, multi-year, and so maybe you didn't move this incredibly important business metric in one quarter, but actually 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're 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, it's just really honing in on what does impact mean, and then a lot comes from that and being able to and celebrate and recognize great work happening even when it's not necessarily materially moving that number.

(00:51:59):
The other part of it is we have a ladder system. So it's a document that's not meant to lay out here's the checklist of all the things you need to do, but it's 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 what we pursue is building these things that are great. And another part of that is also the operating principles, which is the thing that we align on underneath all of these 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 having that meticulous care for all that you do, whether it's you're 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 talking to people on support calls, the meticulous craft is something that is actually expected of everybody.

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(00:54:09):
I'm going to shift to a different topic and this is just the last area I want to spend some time on, which is team building leadership, that sort of thing. So you've led design at three hypergrowth companies, two of them, Airbnb and Stripe, are two of the biggest companies in the world, and also just known for great design. And I'm just going to ask a broad question, what have you learned about building, leading, managing, scaling large teams, are there lessons that stick with you? Anything come to mind when I ask that broad question?

Katie Dill (00:54:40):
One of the things that has stuck with me 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 as 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.

Lenny (00:55:10):
I love that.

Katie Dill (00:55:10):
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 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, and, 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 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.

(00:56:14):
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're going to have to keep doing that. The design work is never done in designing a team, because the more people you bring in, the more it puts your processes in a faulty state. I have intentionally run teams where you get to a point where it's like running hot, it's just like, "Okay, we've outgrown our processes." And that's okay because then you can learn as to, 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.

(00:57:05):
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, is people lose touch with what's happening in different parts of the organization, and everybody's got a doc, their PRD, where they've written down what they've done and 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 decade or more, is having people within the design team share as a screenshot or a prototype of what they're working on in a shared deck.

(00:57:54):
And so they add this to a slide, in Google Slides 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, "Oh my gosh, you're working on that surface, so am I. And let's talk about it. Or Oh, that's an interesting pattern, 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 one of the things I will take wherever I go, whatever I do, because it has just been a very, very useful tool.

Lenny (00:58:51):
I remember that at Airbnb, and 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, just flip through what's going on around the company, I'm like, "Oh wow, look at this thing. That's amazing." And it's interesting that ends up in a deck, it feels like Figma would be really good for that too, but somehow decks are still really handy for simple things like that.

Katie Dill (00:59:11):
One of the key pieces is just 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 Figma, if they were, that would be great too, but if they're not, it's just flipping through really easy, touch of a button, you can just send it off, it's behaviors that people are really used to and commenting. But maybe one day Figma.

Lenny (00:59:42):
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?

Katie Dill (00:59:48):
Yeah, and we experiment with how often we ask folks to share and also the granularity of what they're doing. It is not meant to be a status check. We're not asking everyone, "Show us what you're doing." It's more of what are the projects that are happening? And we might ask, "Show us the medium and large projects," if there's such, it's too much going on and all of a sudden it's 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 biweekly, which I loved because I really love looking through, but if it's feels like it's a arduous task then it's not succeeding.

Lenny (01:00:31):
And especially knowing designers, they'd want to make sure it's the best version of what they've done, and it takes all this extra time to, okay, we got to make this beautiful mock to show [inaudible 01:00:39] working on.

Katie Dill (01:00:39):
And actually another part of it that is another benefit of opening up the curtain a little bit of 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 critique all the details about this. We do need to make it very clear to folks that this is 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, oh my gosh, this is the same project that we're doing over here and this can be completely redundant, or these two things are on a path to collide.

(01:01:25):
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 opening up that 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.

Lenny (01:01:46):
Going back to this formula you shared, which I love, performance equals potential minus interference, is there an example that comes to mind of helping with the interference where you found that, oh, wow, this is really slowing things down and you change something?

Katie Dill (01:01:59):
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 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 beautifully designed, separated from engineering and product and all the other functions by a locked door. And that was really interesting to see because of course there were a lot of benefits to it, which is that design had this very safe space for creative discovery and exploration and communication, there was work all over the walls, it was wall to wall whiteboards, and it was just absolutely a place where creativity could thrive.

Lenny (01:02:58):
It sounds exactly like the Airbnb situation, by the way.

Katie Dill (01:03:02):
The current Airbnb situation or the past?

Lenny (01:03:05):
The original, the [inaudible 01:03:05] times.

Katie Dill (01:03:07):
Yeah. And 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 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 it's like, "That's not aligned. No, that doesn't fit the goal. And you went that way, we were supposed to go over this way." And so interference in the sense that 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 separation of these things.

(01:03:58):
But I think if you're going into that 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 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.

(01:04:22):
And, again, had done it with an approach about listening and came into that with a 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 product together and had spaces for folks to work together and they actually sat with each other, we still kept the creative space for this is where we'll do grits, this is where we'll do working sessions, this is where the folks that don't work in an embedded fashion we'll 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 faster iteration cycles, better clarity on how the work was working, and we still kept and protected that room for creative space, literally the room in terms of figuratively speaking for allowing for creative exploration, but more aligned.

Lenny (01:05:23):
And just so I understand, essentially you reorged the teams and not just physically moved people, but you changed the way the product and design and eng team was even organized?

Katie Dill (01:05:35):
Yes, literally and figuratively we broke down the wall and brought the teams physically together so that they would work together, and then 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 the safety team, and then they would sit with their respective engineers and product managers. And then as I talked about earlier, we would come together at key moments to make sure that we as a design function, we're still aligning on shared goals about the overall experience, but also making sure that we could work well with our partners.

Lenny (01:06:11):
So interesting that that was a recurring pattern at the places you went. I imagine Stripe was not like that, there was not all designers sitting in that locked room.

Katie Dill (01:06:18):
Not in a locked room. When I joined Stripe, it was a Zoom universe, so it's a little bit different, but 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. For example, we have brand and marketing creative, we have the website team, and we have folks that work across all of the things that we do. And so for sure there usually is some sort of creative space, which I actually think having a physical space for creative discovery and exploration and having that up on the wall, I love that so much. And I go into the office about halftime now, and I think over time we'll probably build that out more and more, because it is really powerful in addition to having teams sit by the disciplines that they work with every day.

Lenny (01:07:17):
It reminds me of a quote I have on my wall that I think I found in the Rick Rubin book, but it's by someone else, so I don't know exactly where I found it, but it's the object isn't to make art, it's to be in that wonderful state which makes art inevitable.

Katie Dill (01:07:32):
Ooh, that's good. I like that very much.

Lenny (01:07:34):
By Robert Henry. That's what I try to do in this little podcast studio that we got here.

Katie Dill (01:07:39):
That's awesome.

Lenny (01:07:41):
Is there anything else that you think would be useful to share either from scaling design teams or broadly?

Katie Dill (01:07:50):
I think one of the other tendencies I see of companies in 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 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, and you think about it as, well, quality is really your users are the judge of that, and the way that they experience things oftentimes across products, across surface, across time, if you just think about these incremental approaches to the scope of whatever that is that you own, you are very likely not to make the whole thing better.

(01:08:57):
So I think we have to fight against that. And the way I look at it is, the way I talk about it is 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 you 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 vision work that absolutely does look at the entirety of the experience, a comprehensive approach, a journey approach, and thinks about how these 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 the 11-star experience I think he once said.

Lenny (01:09:45):
[inaudible 01:09:45] stuff. That's what we talked about a couple of times in this podcast.

Katie Dill (01:09:47):
Exactly. Looking at it as a journey. It's not the five-star approach, it's not the six-star approach, but the 11-star approach, but show what 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 and 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.

(01:10:17):
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 maybe we ship this piece first so that we can study it and learn and 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, but that 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 trying to get their day one and likely end up giving up.

Lenny (01:11:02):
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, just a founder of product team, what should you look for that may be a red flag or something that you want to look for to feel good that they're going to be a good fit?

Katie Dill (01:11:23):
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. Their hit rate for great judgment and great taste, and how they've honed that, even if they're not very experienced, just to 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...

Katie Dill (01:12:00):
Talent, for sure, and high craft, but you also want to find somebody that's humble. Folks that are really good at what they do aren't always, but humility is a really important part. I think it's a really important part for anybody on a team because if you're working on a team, you need to work together. And it is important that they have that respect and empathy and understanding and enthusiasm for the folks around them, but also the users. 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. The last piece would just be hustle or chutzpah. 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.

(01:12:53):
And it's scary. 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. Having somebody that has that courage inside them to fight for great is pretty important. And that hustle to try to execute on that rapidly is, of course, essential as you're hiring at any stage company.

(01:13:23):
Lastly, I think you were asking in particular, especially with younger companies or with startups, I think one thing that can be hard, it's like do you hire a more junior doer or a more senior thinker/operator? It's like if you had all the money in the world, 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 lens of how do you build an organization that's user-focused and the way that they operate and the way that they work together, and bringing a strategy that will help to be user-focused from the start. Maybe a great way of doing that is having a more senior leader, design advisor, and then a kind of executor or doer full-time on the team.

Lenny (01:14:10):
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 a book you'd recommend or trick? Or is it just trust your judgment and does this feel great to you?

Katie Dill (01:14:28):
It's contingent on what is the thing, what is the user need? Something that is really great, we do a lot of tools that we strive to make them power tools for our users. And a lot of times that means dense information that is still easily accessible, but will 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 depends on the context of the product sometimes. That's why it's hard to kind of 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.

Lenny (01:15:12):
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 y'all have worked on at Stripe?

Katie Dill (01:15:21):
Oh yeah, we got a good one that I'm so excited about. First off, I don't know if everybody knows this, but Stripe prints books. Stripe Press, we print books that are, we consider, ideas of progress. It's our intention of bringing great ideas out there. 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.

Lenny (01:15:50):
I have many of them in my background here. I'm a huge fan of Stripe Press.

Katie Dill (01:15:55):
Nice. And we take great care to deliver these ideas of progress and books that hopefully feel beautiful. We have a new book coming up that you can pre-order now, and it is Poor Charlie's Almanac. It's actually-

Lenny (01:15:55):
Already pre-ordered.

Katie Dill (01:15:55):
You did? I actually excited to hear that.

Lenny (01:15:55):
I'm really excited for it.

Katie Dill (01:16:12):
It's a fascinating book. 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 anthology. And so this book is really fascinating and it's not really a linear story so much. We have reprinted this book. We created a teaser site that I strongly recommend you all check out. It's really, really fun.

Lenny (01:16:41):
Oh, man, 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.

Katie Dill (01:16:49):
It's pretty awesome. Our website team is... We talked about the importance of design and engineering working super closely together. It's just like that. That art and science coming together into something that hopefully is fun and engaging and people want to pursue it. So 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 read the book online in a special way. So yeah, very big fan of this.

Lenny (01:17:17):
What's the website for folks? Do you happen to have the URL? Otherwise, we'll link to it in the show notes for

Katie Dill (01:17:21):
The book. Yeah, 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 actually what you'll see in the website is that we originally had a typical buying model of the squares outlined. One of the things that we sought to do with the website is to consider what would be a great experience for understanding different books. And when you go into a bookstore and you see the spines of the books and you pick them up and you turn them around and you look at them. And so that's actually what you will... I should stop describing it. Just go and check it out and you'll see we sought to deliver this work in a way that would be aligned with what a reader would want to pursue.

Lenny (01:18:07):
I can't help but ask, but how did that even come together? Was it just like this passion project of like, "This book's coming out, I just want to invest a bunch of time resources into this?" Or how does that happen at Stripe?

Katie Dill (01:18:19):
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. It is like the lifeblood of businesses, and it enables them to accomplish more. But this notion of ideas of progress is another angle into that. 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 the pursuit of creativity and excellence. It is a part of our identity. It is a part of who we feel we are or we strive to be, and we're excited to share that with people. It's in some ways how they get to know us and they get to see the care that we put into any number of things.

Lenny (01:19:19):
Katie, is there anything else you want to share or touch on before we get to our very exciting lightning round?

Katie Dill (01:19:24):
We talked a little bit about the importance of different disciplines and the importance of quality being a group effort. I hope this doesn't insult my function, as I say, but at the core, design is simply intention. You're bringing intentionality to the decisions that you make in thinking about who is this thing for. If you're designing a doorknob, let's say, and it's like, "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?" 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.

(01:20:17):
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. Obviously, great design is also creative, and it also is demonstrated with great taste for what is beauty. Of course, that's where I would say that design expertise with people that have these creative skills and this great taste is an incredible important thing to bring into the organization. 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.

(01:20:56):
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. It's just like, your podcasts... There's more usable learning per minute than most. I don't know if that's a metric that you're measuring, but I love how you don't have your guests tell about their background. Because when someone tells about their background, that is interesting, but it's not really usable information. It's like, "I can take this information and run with it and then bring it to my own team and make my work better." You have clearly thought about that. Well, I don't know if that's why you made that decision.

Lenny (01:21:38):
Absolutely. That is exactly [inaudible 01:21:40]

Katie Dill (01:21:41):
Okay, great. I also love the way that you set these things up. You had said to me, in the thing that you set me, it's just like, "If it's not good, we're not going to ship it." And you set it in very nice ways, by the way. But at first I had this like, "Oh gosh, what if it's not good?" But I also had this moment of like, "Well, that's pretty great because if it's not good, he's not going to 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 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. Again, one workout isn't going to be a six-pack, but every one of those things will end up leading to better quality overall. I don't know, kudos to you. You're nailing it. So great.

Lenny (01:22:36):
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 of make it as useful as possible per minute without removing the humanity. And I realized that's what I do, is I could cut all the stories of everyone's backgrounds, but that sucks. It's optimize for value and concrete, tactical advice, but also make it fun and human and interesting.

(01:23:15):
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?

Katie Dill (01:23:24):
I'm ready.

Lenny (01:23:25):
Okay, let's do it. What are two or three books that you've recommended most to other people?

Katie Dill (01:23:30):
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. I think it was in the 1930s? The cover 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 can always do for another because it is a great reminder of just how important the way you articulate things are. And not in a negative or gross kind of way, but people care first and foremost about themselves. That's the body that they're within, that is the context that they're within. Recognizing that 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, whatever it might be. I'm a big fan of that one.

(01:24:19):
The other one is a newer book, I think actually still a couple of years old. It's about the Wright Brothers by David McCullough, I think. I've been learning how to fly, and so I'm very obsessed with this, but I think it's a book that's relevant to everybody. Especially even entrepreneurs, because it just talks about the impossible challenge of 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, they're brothers. That doesn't always mean you get along, but they're brothers and they did, and it's a beautiful story. Big, big, big fan of that.

(01:25:05):
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 could read that, but The Boy, the Mole, the Fox, and the Horse. This book was given to me by Jenny Yarden, which I think you may know. It's wonderful. It's a beautiful story. It makes 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."

Lenny (01:25:32):
Very Buddhist.

Katie Dill (01:25:33):
Yes.

Lenny (01:25:35):
What is a recent favorite movie or TV show that you really enjoyed?

Katie Dill (01:25:39):
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.

Lenny (01:25:55):
I've not seen that. What is a favorite interview question that you like to ask candidates?

Katie Dill (01:26:01):
Tell me what work you are most proud of. And the reason I ask that is because 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 their gravity pulls them.

Lenny (01:26:28):
Is there a favorite product you recently discovered, be it an app or physical thing? Anything?

Katie Dill (01:26:32):
Yeah. As a parent, you should definitely know the Toniebox.

Lenny (01:26:37):
Ooh, I don't don't know this. The Toniebox?

Katie Dill (01:26:40):
It's so good. The Toniebox. 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. This is also a brilliant product because you want to buy all these figurines. But the little figurines, it could be like Belle from Beauty and the Beast or Elsa from Frozen, and they place the figurine on top and that activates the stories that 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 Toniebox, pretty awesome.

Lenny (01:27:20):
I just texted my wife to check this out so I don't forget. Amazing. Great. Very handy and timely. Do you have a favorite life motto that you'd like to share, come back to, find meaningful?

Katie Dill (01:27:31):
I don't say this out loud, but 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 I will in my head be like, "I'll do that tomorrow. I'll eat better tomorrow. I'll think about that vision tomorrow. I'll communicate better expectations tomorrow." And it's like those joke signs that "Free beer tomorrow." Because very easily, tomorrow just always moves on. And I needed to remind myself that it's actually, it is now today. Tomorrow is now today.

Lenny (01:28:14):
I love that one. I feel like I need to take all these mottoes, which are amazing. I love this question that I just invented. And just put them all on my wall here in this office.

Katie Dill (01:28:22):
Yes, that's a great idea. You should make a book. Book of Lenny Mottoes.

Lenny (01:28:26):
Oh, man. The Tribe of Mentors version of Lenny's podcast.

Katie Dill (01:28:29):
That's awesome.

Lenny (01:28:30):
Is there a lesson that your mom or dad taught you that has really stuck with you, especially as a newish parent?

Katie Dill (01:28:39):
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. 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. My dad had me chopping wood and mixing cement as a young kid, and that certainly led me in one part to be a designer, but also to be able to pursue leadership. Even though sometimes I'm comfortable willing to be in the room where I am vastly outnumbered by people that don't look like me or just not letting that hold me back.

(01:29:31):
And actually, I thought about that the other day because I was riding in a Lyft to the airport. This was also at 4:00 AM, so it was a really hard time to be in a Lyft to gone to the airport. 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. He's like, "Yeah, yeah, yeah, my girl, she's my princess. My son doesn't understand why I don't let her take out the garbage and why her job is to sweep and that's his job." He's like, "I'm not going to let her take out the garbage." I was sitting in the back of the car wondering, "Should I tell him, you're screwing it up?"

(01:30:07):
Just because she's a female doesn't mean that she's not able to do the jobs, even the hard ones and even the bad ones taking off the trash. I really do think that I'm so fortunate that that was never the way that my parents were looking at it. Now, today, I feel like that is very much a part of a little bit of my chutzpah and willingness to step out there because I hadn't been held back from those hard jobs earlier.

Lenny (01:30:39):
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've brought into product, leadership, design? Anything come to mind?

Katie Dill (01:30:57):
First of all, learning to 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 knowing nothing about something and being able to do something, and what an incredible journey that is. Whether it's learning a language or whatever, that is awesome and highly recommended. But 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 getting to the stage of being able to do things myself... My instructor is sitting there next to me and usually is right there at the controls with me, so if something goes wrong when I'm flying, he's right there.

(01:31:46):
I remember one of the first times when I was learning how to land where he moved his seat back. A lot. And so he was now out of touch with the controls. 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 trusts me. Right now, 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?" 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.

Lenny (01:32:35):
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 online if they want to reach out and maybe ask some questions? And how can listeners be useful to you?

Katie Dill (01:32:50):
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 Lil_Dill on Twitter, and then I think that name was taken on Threads, so I'm Lil_Dilly, 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, too. Stripe.com/jobs. Definitely check us out. We definitely would love to hear from you.

Lenny (01:33:30):
Katie. Again, thank you so much for being here.

Katie Dill (01:33:33):
Thank you, Lenny.

Lenny (01:33:34):
Bye, everyone.

(01:33:37):
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.