Bob Baxley: Why design must live in a startup's founding DNA

1. 0:00 – 3:52

   Introduction to Bob Baxley

   1. BBBob Baxley0:00

      Almost everyone living in a modern economy now is going to have hundreds of interactions with a phone or with a computer. And unfortunately, a lot of those interactions are not gonna be great. We have an obligation as product people to put that emotional energy back into people's lives.

   2. LRLenny Rachitsky0:14

      You actually have a really unique perspective on just what is design.

   3. BBBob Baxley0:17

      Design is trying to imagine the future you wanna live in, and then take the steps to make it real. Saying a company is design-led does not mean it's designer-led. I've never seen somebody grafted on after the fact. It's there at the beginning, in the root DNA, or it doesn't exist.

   4. LRLenny Rachitsky0:31

      It wasn't a successful stint at Pinterest?

   5. BBBob Baxley0:33

      I just sort of bounced off the culture. I came in thinking I was supposed to behave the way I behaved at Apple, which is very direct, fighting hard.

   6. LRLenny Rachitsky0:40

      Why did you decide to join Apple?

   7. BBBob Baxley0:42

      I just seek out opportunities to witness history. The whole company is constantly asking, "How can the thing that I'm working on be a little bit better?"

   8. LRLenny Rachitsky0:49

      Why do you think that people that have left Apple, like a lot of amazing things haven't emerged? Today, my guest is Bob Baxley. Bob is a designer, executive, and advisor, who's built and led design teams at Apple, Pinterest, Yahoo, and most recently, ThoughtSpot. Over the course of his career that spanned over three decades, Bob has played a pivotal role in the design of the Apple online store, the Apple App Store, Pinterest, and early in his career, Yahoo Answers, products that have been used by hundreds of millions of people around the world. Bob also mentors individuals and advises organizations that are working to improve the practice, craft, and culture of digital product design. There is something in this conversation for everyone, from why you should consider having design report to engineering, why it's your moral obligation to build great products, why you should wait as long as possible to draw a picture or create a prototype of your idea, to what the Moon landing can teach us about building better teams and products. I could listen to Bob all day. I learned a ton from this conversation, including a bunch of really unique insights that I've never heard before. A big thank you to Annie Warner, Andrew Hogan, Irene Aw, and Joff Redfern for suggesting questions for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, to become an annual subscriber of my newsletter, you get a year free of a bunch of incredible products, including Linear, Superhuman, Notion, Perplexity, Granola, and more. Check it out at lennysnewsletter.com and click "bundle." With that, I bring you Bob Baxley. This entire episode is brought to you by Stripe. There's a reason that I've had more guests on this podcast from Stripe than any other company. It's because they hire the best people and they build incredible products. You probably know them for their payments platform, which powers my newsletter, and also companies like NVIDIA and Salesforce and Zoom and DoorDash. What you may not know is that they have several other products that can help accelerate your revenue, such as Stripe Billing, which powers billing for companies that you may have heard of: OpenAI, Anthropic, Figma, Atlassian, and over 300,000 other companies. Stripe Billing lets you bill and manage customers however you want, from simple recurring billing to usage-based billing to sales negotiated contracts. There's also Stripe's optimized checkout suite, which is a plug-and-play, super optimized payments flow that natively supports over 100 global dynamic payment methods. There's also a product called Link, which is an accelerated checkout experience built specifically to increase your checkout conversion. Every single one of the Forbes top 50 AI companies that have a product in the market today use Stripe to monetize it. Half of Fortune 100 companies use Stripe. $1.4 trillion flows through Stripe annually, which is equivalent to over 1% of global GDP. Use Stripe to handle all of your payment-related needs, billing, manage revenue operations, and launch or invent new business models. Learn more at stripe.com.

2. 3:52 – 6:15

   Apple's lasting culture

   1. LRLenny Rachitsky3:54

      Bob, thank you so much for being here, and welcome to the podcast.

   2. BBBob Baxley4:00

      Lenny, thank you so much. Thanks for having me, but also just thank you for what you do.

   3. LRLenny Rachitsky4:04

      Hmm.

   4. BBBob Baxley4:05

      You know, I, we are still in early days of trying to figure out how to make software together. I think of it sort of like where the film industry was in the 1920s. We've had our talkie moment. We're kind of on the cusp of having our shift to color movement, but we're still trying to figure out how to make movies, and a podcast like yours, specifically yours, I think is one of the greatest resources we have for learning from one another. So I appreciate all you're doing for the community and for helping us as a community make better software.

   5. LRLenny Rachitsky4:31

      Wow. Well, I really appreciate that. That means a lot coming from you. There's so much I want to talk about in our conversation. There's a story that I hear that you often tell, which is when somebody asked Steve Jobs once, "What is your favorite product that you've built, that you've worked on?" Ooh, and, and his answer. Uh, what's that story?

   6. BBBob Baxley4:49

      So I actually can't remember where I heard this, so, but I, I believe the story's true. Steve at one point was recounting the products that he had created, uh, that he was most proud of, and if I recall the whole list, it was the Apple II, the Mac, the iPod, the iPhone. I think Apple Retail was in the list. And then he said Apple itself, and when I heard that and when I've reflected on it, you know, that is the longest lasting thing. And I, I remember there was also a story that Steve was talking to, I think it was, it was either Ed Catmull or John Lasseter at Pixar, and he said, "You know, everything we make is gonna be a doorstop in three years, but the stuff you guys make, they're still gonna be watching in 100 years." And so, I think Steve had some concept of the longevity of these things. They knew the products themselves were very ephemeral, but there's something about the culture of Apple that's lasted a very long time, and I personally believe will last for, for, uh, some time yet to come. And it's a way of making decisions. It's a way of behaving. It's a way of seeing, uh, the value of technology in the world, uh, and it infuses everything in that company. I mean, everything from the checkout system when you go to the receptionist to what it's like in the cafeteria, you know? They, the, uh, at least when I was there, they had patented the pizza box 'cause they had reinvented the pizza box that you would get at Cafe Max (laughs) 'cause they're just, the whole company is constantly asking...... how can the thing that I'm working on be a little bit better? And I think that was something Steve brought to them and had them constantly asking

3. 6:15 – 13:19

   Navigating unique company cultures

   1. BBBob Baxley6:15

      that question.

   2. LRLenny Rachitsky6:16

      One more Apple question, then I want to move on to other stuff.

   3. BBBob Baxley6:18

      (laughs)

   4. LRLenny Rachitsky6:19

      Why do you think that people that have left Apple, a lot of them j- like a lot of amazing things haven't emerged a- as a, uh, from people that have left? Like Humane was a recent example. You know, this, we're recording this the day after Johnny Ive and OpenAI emerged, so we'll see what happens there. It just feels like there hasn't been a ton of alumni that have built incredible things.

   5. BBBob Baxley6:37

      Yeah, I'm hard pr- so obviously, Tony Fadel would be one with Nest, um, and he would, he'd be an outlier. I think the people that... You know, I went to Pinterest and, and did not have a, a successful time in my year and a half at Pinterest. Um, you know, I think my own particular mistake, and I've seen this with some other Apple executives as well, is we went directly from Apple... Like I went, I left Apple on a Friday and I started Pinterest on a Monday, and I didn't give myself time to, to recalibrate to the, to the Pinterest culture. So I think, I think at some level, a lot of the challenge is that when you... A- Apple, and it's not just Apple, I think every major tech company, like they have really powerful cultures, you know? You get kind of indoctrinated to those, all those standards, and it's, it's really deep. It infuses all of your behavior and how you conduct yourself in the company, away from the company. And so I think it's, it's pretty hard to emigrate successfully from one of those environments to another. And Apple is one of the strongest cultures, and there's not many other cultures that sort of natively operate like that. Uh, Airbnb is one exception, and so you have guys like Hiroki Azai who's, leads all of marketing and all of product, and Hiroki is crushing it at Airbnb. He was incredibly successful a- at Apple. It also should be noted that he had... It was a multi-year gap between the time he left Apple and the time he started Airbnb, so he gave himself a little bit of time to get through the... You know, we (laughs) at Apple, I think it was Tim or Steve used to talk about the Apple car wash, and that when you started at Apple, they kind of had to take you through the car wash and get off all that stuff that you'd accumulated at other places. Turns out, there's a car wash you need to go through when you leave Apple as well. (laughs) And so I think Hiroki gave himself time to do that, and I think that's probably a lot of why he's been so successful at Airbnb. The thing I took away from Apple, and I think this is true for anybody changing from one major culture to another, is most likely the new place hires you because of the values of the organization you left, but not the behaviors. And so I think it's important to kind of recalibrate and say, "Well, I want to hold on to these values," so at Apple, attention to detail, product excellence, you know, uh, doing everything you can for the customer and the user. So try to hold on to those values, but then think, "Okay, how are those values best expressed in this culture?" And I was more successful at expressing those values in the culture of ThoughtSpot, which was my last job, than I was in the culture of Pinterest. Um, if I had to do it again, I could probably do better at Pinterest. (laughs) So I think that's, I think that's useful for anybody leaving one very specific culture and going someplace else, is like try to hold on to the values but not the behaviors.

   6. LRLenny Rachitsky8:59

      This is so interesting, (clears throat) and I appreciate you sharing that. You... The way you described it, that it wasn't a successful stint at Pinterest. A lot of people don't share that sort of story and don't put it that way. You know, they see on their LinkedIn, "Oh, I had a design at Pinterest." "Oh, amazing. So cool." And then, you know, if you're like, "Oh, okay, but it w- didn't work out that well," I think that's really interesting. Is there anything more you can share there about what you learned for other people to maybe avoid that sort of situation? Anything you take away from that experience?

   7. BBBob Baxley9:25

      One of my friends that was at Pinterest I'm still friends with, he said, you know, "I just sort of thought, thought of it as you bounced off the culture." And I think that's kind of the way to think of it. I, I came in thinking I was supposed to behave the way I behaved at Apple, which is, you know, very direct, fighting hard. You know, it's very, it's, it's, um, everybody cares about each other. It's never insulting, but it's intense. And that's not really where Pinterest was at the time. And again, all this is like a decade ago, so I don't know what any of these companies are like today. But at least when I was there, uh, Pinterest had posters in every conference room that said, a big poster that said, "Say the hard thing." Well, that's where Pinterest was at the time, and I can assure you, nobody at Apple was having to remind you to say the hard thing, (laughs) you know? And so I probably could have picked up on that better, um, than I did. You know, I'll say like, these careers are really hard, you know? And the higher up you go, I sort of... People think of it like you're climbing a pyramid. I think of it more like you're going out on a branch on a tree, and the branch gets a lot more flimsy, and can break, and you can fall, and you get buffeted about by the wind, and it's often at a time in your life when there's a lot going on with your family, um, there could be things going on with your parents' health. I lost my mother when I was at Pinterest, you know, my kids were starting high school so we're struggling with the teenage years. I had a long, long commute. I mean, there's just a... There's a lot going on, and these jobs are super demanding. Everything around you is changing really rapidly, and you're under tremendous pressure because the financial and success, uh, you know, stakes are super high. So I think the... People like falling off of these jobs is, is the common use case. That is the common story. We have a bias towards survivors, and we all talk about how it looks like they made it to the top, but for everybody that makes it to the top, there's hundreds of people that don't. I've- I... One of the things I took away when I was at Pinterest was I came to think that the job of a startup was to grow the founder so they could continue to lead the startup. And I think what's true for founders is also true for a lot of other folks on the executive staff. It's very hard to grow emotionally and developmentally at the rate that the company grows. A lot of times, I think people get outgrown by their role, and I saw that across Apple. I've experienced that myself at different times in my career. I see that happening with my friends, and it, it feels like a failure. It's... I mean, it's, that is the human experience. That's what happens. It's very hard to grow as fast as some of these companies are growing, and I... You know, we could debate the, we could debate the merits of Mark Zuckerberg, for example, but when you think about the trajectory from being, you know, a kid in a dorm room to a... You know, within like five years, he's... Like, Facebook's a big thing. I mean, think of your own life. Can you like... Can you process that level of evolution and change? And, you know, that's just...I don't know, man. (laughs) I think that's like really super hard to do that and stay balanced.

   8. LRLenny Rachitsky12:15

      And also, keep doing that for, for so long. Like, Airbnb founders, I think was Brian's maybe first job or second job, and he's doing it now-

   9. BBBob Baxley12:22

      Oh, yeah.

   10. LRLenny Rachitsky12:22

       ... for, you know, 15 years in a row.

   11. BBBob Baxley12:24

       Well, founders, it's their life. It's very unusual to see founders move out. I, I had this other theory that a startup is still a startup until the founder moves aside. So by my definition of... Uh, even Meta is still a startup in a way that Amazon's not. And you know, an Airbnb is still a startup in a way that Pinterest is not, 'cause Ben's moved on. It's, it's really... You don't find out if the culture can sustain itself until the founders are gone, and then you really see what's gonna happen.

   12. LRLenny Rachitsky12:49

       Just to close the loop here, uh, one takeaway here that I think is really interesting is that you can fail in a job and things will be okay. Clearly, you're doing A-okay. And having a place that doesn't work out doesn't destroy your career, which I think a lot of people feel like if they're not doing well in their current job, it's over. Things are all gonna go downhill.

   13. BBBob Baxley13:08

       Yeah. Your career's not your life, you know? There's a lot more to it than that.

   14. LRLenny Rachitsky13:11

       And then just to, uh, give someone something tactical here. So you've realized the culture at Pinterest, w- you bounced off of it. I love that

4. 13:19 – 15:46

   Finding a company that truly values your role

   1. LRLenny Rachitsky13:19

      metaphor. If you were to... When you're looking at new companies, is, what's like one thing you look at or a question you ask or something you now look at to make sure you avoid that in the future, that culture clash?

   2. BBBob Baxley13:29

      Yeah. So I'm fortunate at this stage of my career that I usually get to interview with the CEO or the founders or something like that. So what I'm usually looking for is, do they have a story as to why they believe in design? Like, really in their heart and soul, do they care about design? 'Cause if I go into a company that doesn't really value the thing that I do, I'm just not gonna have a great time, uh, and I'm gonna be constantly buffeting up against all sorts of people. So I wanna make sure I've got air cover from the highest people in the company setting the culture. In the case of my... Again, my most recent job was with a company called ThoughtSpot, and ThoughtSpot was founded by a gentleman named Ajit Singh. And Ajit grew up in rural India, but he tells this really great story about, uh, early in his career, he, he studied chemical engineering, he moves to the United States. Early in his career, he's working for Honeywell, and they did a couple of engagements with IDEO. And as a very young person, he got to see what IDEO did and he realized the power of design, and he's taken that to all of his companies. He, uh, started Nutanix before he came to ThoughtSpot, before he started ThoughtSpot. And so when I heard that, I'm like, "Oh, this is a guy that gets design right from the very beginning." And I've also come to believe that I've... I, I actually have never seen a company that grafted design on after the founding. So I've seen lots... I could name lots of companies that I think are kind of design led, not always designer led, but design led or design centric, but I've never seen somebody graft it on after the fact. It's there at the beginning in the root DNA or it doesn't exist. And so the thing that I'm looking for when I interview is, is it there at the beginning? Uh, could I get a, a credible story that tracks it back to that? And if that's the case, then I think I can find a way to navigate in that culture. Like, we sort of have a shared value system in a, in a way that like, you know, as an American I could, I could immigrate to Australia and the culture would be slightly different, but we'd have a shared value system that I could relate to. If I moved to, I don't know, Burma or China or something, it would be wildly more challenging 'cause the, the base, uh, view of the world, the base understanding of the world's just different. And it'd be very... It'd be much harder for me to adapt to that.

   3. LRLenny Rachitsky15:29

      Mm-hmm. So I think a way to extrapolate that insight is just whatever function you're in, get a sense of how important that function is to that business. Do the founders value engineering? Do they value product? Do they value design? If... Depen- depending on who you are.

   4. BBBob Baxley15:41

      Yeah. Why would you want to work in a place that doesn't value the thing that you do? That would just... God, that would

5. 15:46 – 17:17

   What is design?

   1. BBBob Baxley15:46

      suck, (laughs) you know?

   2. LRLenny Rachitsky15:46

      Yeah. You actually have a really unique perspective on just what is design that I haven't heard before. Let me... So let me ask you that question, just what is design?

   3. BBBob Baxley15:55

      Well, I'm gonna go back to the Edward Tufte quote that I use all the time, which is, "Design is clear thinking made visible." And so, you know, I think most people when they talk about design, they think of it as the visual expression of an idea, they think of it as a team or a function or a group. I think of it as a holistic mindset. It's... You know, like when design thinking became big, I was always really confused 'cause I didn't know how else you could think. That was just sort of how I naturally thought, which is... You know, design is, is trying to imagine the future you want to live in and then take the steps to make it real. You know, it's, it's living with a certain type of intentionality in almost sort of a Buddhist-type way, which is different from science, which is sort of observational, trying to understand. It's a little bit different from engineering, which is, you know, we kind of know where we want to go at the end, but we're trying to go- kind of go one step at a time versus design's trying to like see some, you know, further out future state and account for a, a larger or sort- a different set of constraints and issues than engineering or some of the other problem-solving methodologies. So I look at... Again, I look at it as, as a company. Does the company think in a design mindset? And Apple does, Airbnb does. I don't get the sense that Google does. Um, and I don't get the sense that Amazon does. And that's, that's not a critique on them. I don't think that those organizations are competing on design in the same way. But again, I, like, I want to go work in a place that, that as an organization thinks in a design-type

6. 17:17 – 23:08

   How to help founders understand the value of design

   1. BBBob Baxley17:17

      method.

   2. LRLenny Rachitsky17:19

      So along those lines, a lot of people... I imagine every founder, every product builder would... Is just like, "Yes, I love amazing design. I'd love our products to be incredibly beautiful, intuitive, so easy for everyone to use and understand," but they don't actually invest in these areas and they don't put a lot of resources into the designing process. Uh, what's the way... What's the best pitch you can make and that you do make to companies to help them see the value, the strategic value of design and the, you know, the, the bottom line of the value of design?

   3. BBBob Baxley17:50

      Let me back up and just dissect a little bit the way you described design 'cause you described it in really tactical terms.

   4. LRLenny Rachitsky17:55

      Mm-hmm.

   5. BBBob Baxley17:55

      You said beautiful, intuitive, uh, products that make sense. I think it was something like that.

   6. LRLenny Rachitsky18:00

      Yeah.

   7. BBBob Baxley18:00

      So what you were describing was... You were describing the part of the iceberg that sits above the waterline, (laughs) you know, which is the result, that's one of the outcomes of design, but that's not the real heavy lifting of design. Design's more like liberal arts or philosophy or something. It's, it's like, what are we trying to achieve at a much lower level?And so when I talk to founders and people about the value of design, what I'm pushing them on is when we can get organizational alignment around what we want to do philosophically. Why do we exist? What's the vision for the company? How do all these things ladder up through vision, through mission, through specific, uh, uh, tenets, design strategies? And then into actual execution, how do we ladder that whole thing up so it makes sense as a whole? That's the magic of design, right? So the, the difference is when you design things, you end up with a bunch of bricks that are piled into a beautiful impenetrable wall. And if you don't do that, you end up with a bunch of bricks scattered across the backyard, and they don't really add up to anything. And I think that's one of the things if you look, you know, again, to go back to Apple, but we could also talk about Lego, Leica, Porsche, um, Airbnb. I mean, there's other companies, uh, Patagonia. There's other companies that, that make sense as a design-centered organization. And if you think about, like, everything they do, it all ladders together into, like, one cohesive sensical thing. It's integrated, makes sense as a unit. Um, and I think that's a huge difference and an incredible strategic advantage, 'cause the company can operate with much greater efficiency. They can onboard new people and get them in line. Like, you know, at Apple, for example, on my, uh, the store that des- or the team that designed the online store, you know, we, we had six designers. For a store that ran in 30 some odd countries, 12,500 instances of the store doing billions of dollars of revenue, we had six designers. Like, any other company would have had 60 or more. So Apple's able to operate with much l- smaller staff because they have real clarity of vision of what they're doing. And the benefit of operating with a smaller staff is not just that it saves money on payroll. It's that you have, uh, uh, y- you know, the way the minds come together to create something that feels like a single whole is a much higher chance when you have fewer people involved. You know, you don't... I sort of joke about the Beatles. You get the Beatles with four people. You don't get the Beatles with eight people, and you certainly don't get it with 24 people, right? (laughs) There's no, like, the teams get too big and you just, you can't get that, that what Brian Eno calls, uh, scenius. So, so Brian Eno has this great word that he uses. Scenius is, uh, the genius that comes when you have a group together. So scenius is sort of the collective idea of genius. And I think that's something that's really magical and that I've experienced in my career. But, but usually in s- in smaller groups. It's hard to do with a giant group, so.

   8. LRLenny Rachitsky20:40

      I love this, I love this metaphor of the Beatles as, uh, you know, the way most people describe this is, uh, design by committee never works. And I love that your exam- you're, the way you describe it is the Beatles is, is kind of like the ideal size in, you know, of a, uh, like a small group versus a committee.

   9. BBBob Baxley20:54

      I just always have to point out to people that there are 20 people that worked on the original Mac. I mean, there's 20 of them. That, that's it, 20. Susan Kare was one of them. You know, you get Andy Hertzfelder. You go through the list. 20 of them were on the patent. There's 24 that were, that are on the iPhone patent. Now, there's other people involved, but generally there's 24 people on the iPhone patent, and that's, that was kind of the team. That was like Project Purple that was doing that stuff. These are not massive, massive groups doing these things. And if you had put a massive group, I, I don't know, man, you know? Like, maybe you'd end up with a Zune or something completely different. Who knows? Um... (laughs)

   10. LRLenny Rachitsky21:24

       They probably did have a massive group on a Zune, yeah.

   11. BBBob Baxley21:27

       Yeah. So there's something that... You know, it's, uh, like, the four is too few for what we're trying to achieve at scale. But even if you, if you look at Pixar or any good movie, like, on the s- on the scripting and story side, it's usually a fairly small team. Even when you move into, um, like character development, stuff like that, it's fairly small. And then it really scales when you move into production. It's just hard to figure out something new to do together when there's too many people involved.

   12. LRLenny Rachitsky21:49

       I think that word new is really key here. I think when people hear this sort of advice, you know, they're thinking at their existing company, "Should we just keep our company small? Should we not scale this thing that we have?" And I think what you're describing, which I completely agree with, is new stuff, for sure, you want to keep the team small and, and tight. But I, you know, as things grow in scale, uh, your se- what's your take on just like, okay, actually, it's okay to have a lot of people on this?

   13. BBBob Baxley22:13

       Well, you have to bring a lot of people in once you've got, once you kind of figure out what you're doing, right? And so to your point, like, once you realize you're building Disneyland and you've kind of got the whole thing set and people know what it's about, then they can come in and understand, "Oh, I'm playing my piece over here. I'm supposed to, you know, I'm supposed to design the, design the ride for the new, or design the line experience for the new ride sitting in Tomorrowland. But I know where that fits into this larger thing." So I think you can scale once you have clarity of vision. But it's very difficult to get vision with a lot of people.

   14. LRLenny Rachitsky22:42

       Great.

   15. BBBob Baxley22:42

       You know?

   16. LRLenny Rachitsky22:42

       I think that's really powerful advice. It's just, when you're starting something new... I actually had a, uh, CP of N26 who was at, uh, who was basically leading Google Hangouts, the initial launch of Google Hangouts. And he told a story of, they put so many resources on it. Like, "We gotta win. We gotta do this." Uh, Larry Page or Sergey was sitting next to him just like, "We gotta make this work," and putting everything they could into it. And it didn't work out. And I think this explains partly why.

   17. BBBob Baxley23:05

       No, no, the more, the more people you put in it, the slower everything becomes.

7. 23:08 – 26:31

   How to align product managers and designers

   1. BBBob Baxley23:08

      Um, yeah.

   2. LRLenny Rachitsky23:09

      Yeah. I want to go back to something you said about what design is. I think this is really interesting. And so the way you describe design, to a lot of people it sounds like that's also, that's like product management also, and product leadership, setting strategy, vision, figuring out how everything fits together. I think your experience here, uh, I think Apple is a very different kind of company where design actually leads a lot of this.

   3. BBBob Baxley23:28

      Yup.

   4. LRLenny Rachitsky23:28

      At a lot of other companies, it doesn't work that way. Any thoughts on just, like, how you advise companies think about the split between design and product management that aren't Apple?

   5. BBBob Baxley23:37

      One of the best lines I ever heard was from my friend Joseph O'Sullivan at a dinner one night. He said, uh, you know, "Saying a company is des- is design-led does not mean it's designer-led." And so, what I try to hammer home with people is that when I talk about design as a mindset, I'm talking about it as a mindset. Like, anybody could have that mindset functioning in any role. Any designer could have a product mindset. In fact, I think that's a lot of what the design community is trying to get at now when they say designers should be speaking the language of business. I think what they're saying is designers need to inhabit the product mindset as well. And, and maybe to some degree even the sales mindset. So look, both functions matter. I look at, uh, I look at my counterparts in product, and I assume that they are much better connected to the customer, that they understand much better the, the business realities. And I expect them to drive the roadmap.I may have some points of view on the roadmap, I may offer some critique, I may have my own suggestions and agenda in there, but once they say, "This is the roadmap," I have to believe that they're right and I don't try to bleed into their space. I- I very much believe that once you get into a company, your job is to figure out your role and ret- and respect the boundaries between the different groups. So I'm like, "You, you guys, you know, tell us what you need us to do, what the features need to be, when they need to be delivered, what the issues are, and then give us the time and space to come up with a solution to those problems, and then we can work together to decide whether or not our solutions actually solve the problem as you understand it." But I'll stay out of your roadmap and you stay out of my design stuff, (laughs) you know? And, and, and let's try to get to the, the promised land together. So I- I assume that the product managers, particularly in enterprise SaaS companies, like my team, Th- ThoughtSpot did data analytics. My team didn't know anything about data analytics. We didn't have any of that insight. We didn't have the bandwidth, the mental horsepower to go out and do that stuff. Like, we had our hands full just trying to figure out the UI. And it's, and it's one of the points I try to make too when people are starting to theorize that gen AI can remove teammates, you know, and, "Oh, the designers don't need engineers and the PMs don't need the designers," and, like, everybody thinks they can throw engineering overboard. And I'm like, like, "S- stop it." Like, we all need each other, and we need each other because we need those different mindsets. And any one of those mindsets is just too mu- it, like, it... One of those mindsets inhabits somebody's head completely. I just don't think you can simultaneously hold multiple mindsets in your head. So it's not that one of my PM counterparts couldn't bring a lot to the design table, it's just I need you to play that position. It's like in baseball, like, you know, you don't p- y- like the second baseman doesn't cover first. That's not how it works. (laughs) Like, you know? Everybody's, everybody's gotta spread the field and play their position so we can take care of the whole thing and respect that together we're gonna come up with something better than any one of us would have come up with alone and embrace the creative tension, welcome it. You know? We still have to all go out to lunch and love each other and have fun together and keep in mind that we're having fun together. But, you know, I like, I like the rub. That's where all the magic happens.

   6. LRLenny Rachitsky26:28

      That was a, a very illuminating, uh, clarification.

8. 26:31 – 30:54

   Design reporting to engineering

   1. LRLenny Rachitsky26:32

      Something else that, uh, I heard you believe that I haven't heard before is that design should report to engineering.

   2. BBBob Baxley26:38

      So I'll say that every company culture is different and different organizations work in different ways. In my experience, I think that design is most successful at impacting what ships at the end if design is considered phase zero of the engineering process, rather than a byproduct or a part of the product process. So I just think what I've seen happen over and over in my experience at Yahoo, at ThoughtSpot, Pinterest, other places, you know, when you're working directly with product, it's easy to kind of leave engineering out of the loop and product and design can go cook up stuff that doesn't quite make sense technically or is really hard to implement or is just a bridge too far. And I think that engineering doesn't feel like they're a part of it, so you bring them in at the end and they haven't really been brought along so they don't quite understand how to extrapolate from the specs you make into what should really ship. They're may- maybe they don't bring their same level of enthusiasm to it 'cause they haven't been brought along. So I think there's something about having the design and engineering team very tightly connected, um, and kind of living together. And I, and it's not that you have to do that structurally from an organization point of view. But I... It's hard-pressed if you don't. I also think you can just account for timelines and costs and things better when design is part of engineering. And many of my design friends will push back on this and they'll say design should be its own thing and it should be an independent group and we should have, you know, three co-equal branches of government. Um, and that's a, you know, that's a solid argument as well. And there are some places where that works beautifully. My experience is that design rarely has a budget or an army. And so it's very hard for them to really hold their own in that, that sort of a setting. Also, although, you know, you'll see people argue with me on LinkedIn about how design needs to be measured and we need to have metrics and be held accountable for a number, I don't really believe that in my heart. I think it's very... I- I've just never seen a number that you could apply to design that we could reliably affect. So I think it's very hard to hold design as an organization accountable for a particular outcome the way that most of the other C-level, uh, roles are held accountable. Sales has a number. Engineering has very specific expectations. Product has very specific expectations. And although I know this will frustrate some of my friends, (laughs) I just haven't been able to figure out how that works for design. And again, it can vary from culture to culture. Certainly, there's very successful chief design officers and we could go through the list. I just think in many companies, that's, um, it's a stretch. It's just hard.

   3. LRLenny Rachitsky28:56

      What I see work, and I'm curious to get your take, is just, uh, product engineering and design have exactly the same goal. And the more everyone i- and, and their performance as an employee is tied to the same thing essentially, because then everyone is pushing in the same direction versus like, "Oh, I have my engineering goal, I have my design goal, I have my PM goal," which just creates all kinds of weird incentives.

   4. BBBob Baxley29:17

      Yeah. Look, I- I would kind of defer to you on that, honestly.

   5. LRLenny Rachitsky29:19

      Hmm.

   6. BBBob Baxley29:19

      Like, you've talked to a lot more people across a lot more companies so you have a much broader set of information you're working with. You know, if you add my whole career together, I've worked at maybe half a dozen places, (laughs) you know? So I... A fairly limited sample set. And every design team, uh, that I've ever been a part of, I've been a part of. So I also kind of have a, a biased view as to what did and w- didn't work for me in those particular organizations. So I'll go back to what I said. Every company is different. Every culture is slightly different. It's not one size fits all. I, I, I point out the idea of design reporting to engineering just 'cause I don't think people consider the possibility often enough. Um, so there's, you know, there's three options. Design is its own thing, design is part of product, design is part of engineering. And I think there's a moment when you can back up and make an intelligent choice about the pros and cons for each of those options inside your org. And so I would encourage people to just take a design mentality, you know, (laughs) and put on that designer mindset just for a moment and say, "Well, what's the thing that we're trying to produce? What's the incentives that we're trying to create? What's the, what's the future state that we're trying to get to? And which of these three options, permutations is going to help us get there the best?"

   7. LRLenny Rachitsky30:24

      I, I love how radical this idea is. I've not heard it, I think,... uh, designers'll be like, "Oh, you sh- you sh- stop it. Just stop it."

   8. BBBob Baxley30:32

      (laughs)

   9. LRLenny Rachitsky30:33

      Uh, so have you operated this way? Have you had design report to engineering at companies you've worked at?

   10. BBBob Baxley30:37

       Yeah. That was, you know... Sorry, but like that's how it worked at Apple the whole time under Steve.

   11. LRLenny Rachitsky30:41

       Hmm.

   12. BBBob Baxley30:41

       Design always reported to engineering. You know, they're, they're... Now, I think it's structured a little bit differently, but design has always been part of engineering at Apple. So I saw it work quite effectively there, obviously.

   13. LRLenny Rachitsky30:53

       It's so interesting.

9. 30:54 – 33:43

   Integrating engineers early in the design process

   1. LRLenny Rachitsky30:54

      Okay, so say... Just to give someone something very tactical to do on their team, say they don't wanna go to this extreme and move the design org under engineering. What's something you've seen work that helps achieve similar outcomes with having engineers design, uh, integrated early in the design process?

   2. BBBob Baxley31:09

      Yeah. Look, I think you have to find some way that you, that you are able to identify a few people in engineering that I refer to as, uh, creative technologists. So these are people that can come into a... What's ultimately kind of a fairly airy-fairy, philosophical discussion about what we could do and like what's right from a conceptual model perspective, and it's... Ultimately, it's sort of a philosophy issue. And, uh, there's not that many PMs or engineers that can sit in that space and be comfortable with the ambiguity of it all. Like a- a PM is likely gonna come in and they're gonna say, "Okay, well, that was a great one hour. What's the next step?" And, you know, as a designer, I'm always like, "Well, the next step is we're gonna have another meeting and we're gonna talk again." (laughs) You know, and, and the engineers oftentimes when they're starting to hear different ideas, they're already cutting into the code and they're trying to figure out what's hard and what's easy. And so I think the trick is at the beginning, can you find a small group of people from the different functions that can sit with the ambiguity of the space and talk through a broad range of ideas to identify the direction we want to go into? And then once everybody kind of falls in love with the direction, then you can go into the more tactical mindset of, okay, well, when we can ship it and who can we show it to and, you know, how are we gonna code it and when's it gonna go live and all those sorts of things. But the, the trick is to try to find a group that can sit in the, again, in the ambiguous maybe space. I do think it's critical to have everybody together at the beginning so they all feel like they're part of it. And the, the, the worst thing is when you bring something fully baked. Well, the worst thing is when you bring something fully baked to anybody for their approval, you know. We could talk about this with... When you take a, a final design to an exec and an exec sees it for the first time in a high resolution state. We... I'll get to that in a second. But when you go to an engineering team that says, "Hey, you know, we've been working in the lab for six months and we have this thing that we love it, and we just can't wait for you guys to build it, and here it is," I don't know. Like that's not something engineers are gonna be, be excited about. They're not order takers, you know. How do you make them part of the process? And you know, most every product of Consequence that I worked on, there was some moment when we were showing it to some critical person and you could see that they fell in love with it. You know, sometimes they're like literally pointing at the comps on the board. Sometime you're in a meeting and they're just like, "God, I just love this." And for me that was always, that was always the critical moment, because I knew that d- you know, design can't bring any of this stuff into the world on its own. Like we, we can't raise this baby. We need the village, and we need the village to fall in love with the baby. And so until that happens, you're not really quite sure if this thing's gonna l- take off or not. And so it was always extremely important to me that you had a few key engineers and some product people fall in love with it so they could defend it and embrace it and enhance it and c-

10. 33:43 – 35:14

    The maker mindset

    1. BBBob Baxley33:43

       add to it. And you gotta bring them along at the very beginning.

    2. LRLenny Rachitsky33:46

       What I'm hearing there is there's a big part of just buy-in, and then there's also just obviously more good ideas early are great.

    3. BBBob Baxley33:52

       Yeah. Sorry. Uh, uh, uh, buy-in doesn't feel quite right to me-

    4. LRLenny Rachitsky33:55

       Mm.

    5. BBBob Baxley33:55

       ... 'cause buy-in feels like, "Oh, I've come to agree with you." And that's different from, "It's a part of me." You know, I, I... When I'm talking to, to teams, the thing I try to tell them is I walk into the office every day with the idea that everyone that I work with is a... Fundamentally a maker. Like everybody in product, design, engineering, we've all chosen these careers. Everybody's super smart. Everybody's super ambitious. Everybody coulda done a thousand other things, but they're choosing to spend their precious lifetime and creative energy creating software. And so I believe in my heart that they're all fundamentally makers. And the thing that I know about makers is that they all want to make something they're proud of so they can take it home at the end of the day and show it to their parents and say, "Look at what I made at school with my friends today." Like that's the fundamental thing. And they're all doing it from their own different points of view and their own different incentives and mindsets, but they all, at the end of the day, want to make something they're proud of. And so it's not a matter of getting their buy-in. It's a matter of them being a part of it, you know. That it's like... It's... I don't know. It's a part of their soul in a really deep, meaningful way, and I don't... I'm not sure you can graft that onto somebody after the fact. They kinda need to be there at the moment of, uh, inception, if you will.

    6. LRLenny Rachitsky35:11

       Hmm. Wow, that's a really beautiful answer.

11. 35:14 – 38:04

    Challenging the assumption that design is time-intensive

    1. LRLenny Rachitsky35:14

       I imagine for a lot of people hearing this, making every feature and product they build a part of their soul feels like a very high bar if they're building, you know, some kind of B2B SaaS software. So just... I guess, just thoughts on just how much you should spend... How much time, how many resources, how deep you go in design for all these things you're building. Say you're building some kind of, I don't know, expense management system or HR, HRs thing. Uh, just like where do you, where do you... What do you recommend people do with... In terms of just how far to go in design as a lever, as a, as a op- as a differentiator maybe?

    2. BBBob Baxley35:49

       Well, you know, inherent in your question is this assumption that design takes more time-

    3. LRLenny Rachitsky35:53

       Mm-hmm.

    4. BBBob Baxley35:53

       ... and so I'm gonna kind of reject that premise, 'cause I don't think design takes more time. (laughs) I think design exists, you know. There is going to be a design. It's whether it's gonna be a good one or not. And I think there's things that you can do so that you're able to operate at a, at a quicker pace as design. If you... Again, if you kind of get the te- We haven't talked about tenants yet, but we'll get to that in a moment. You know, if you kind of create a f- a shared philosophical understanding of the product and what you're trying to do, you can go really fast because you're not asking the question of what should you do. You're asking the question of what would this company, with what we stand for, do for this thing? And that's a much easier question that's much smaller. So if you look at the companies that have the largest design teams, they're often the companies that have the most ambiguous cultures and the most unclear design vision-Right? When you, when you go to companies that really know what they're doing, you know, and they- and they're- they're clear that this is who we are, this is what we stand for, the design teams are super small. Because they're not sitting there trying to do all these permutations with color and typography and i- ideas. Like, they're- they're operating in a really narrow vein because they know who they are. It's very much like individuals, you know? When you're a teenager or young adult, you can spend a lot of time trying to figure out what to wear 'cause you haven't really sorted it out yet. But by the time you get to be a little bit older, you've kinda got your personal style. And so like, dressing in the morning gets to be a lot easier. And it's the same thing at... Like at Pinterest, I was at Pinterest at a point when Pinterest wasn't quite sure what it, who it was. And so when we were gonna do like an onboarding flow, we had to look at a really broad sweep of things 'cause we were trying to sort it out. But if you guys you had other places that knew what they were about, you know, Apple's the key example there, like, we weren't trying to figure out what it was about. We were trying to figure out what was the Apple way to do this particular thing. And so that moves a lot faster. And I agree, like, look, having your soul in every little checkbox is, sounds like a high bar. And in some ways it is. But you also need to, I think you need to be able to back up and look at the product, maybe not at every state but, you know, generally, every six months or a year, you need to back up and ask yourself, "Am I, am I proud of this? Is this something I am happy to be a part of? Do I believe in this?" You know? "Is it representative of my best work given the circumstances I was in, which has limitations around time and resources and everything else? Is this the best I could do? Or am I just sort of trying to get

12. 38:04 – 45:25

    Design tenets vs. design principles

    1. BBBob Baxley38:04

       through the day 'cause I have other goals?"

    2. LRLenny Rachitsky38:06

       So let's actually follow the thread of design tenets and, uh, and principles. So this is something I've heard about you, that, uh, you're a big fan of design tenets versus design principles. What is the difference? Why is this so important?

    3. BBBob Baxley38:20

       Yeah, so look, there's whole websites dedicated to design principles. And if you go and you read it, you'll see a lot of principles like simple, clear, beautiful, uh, uh, fast, secure. You know, you'll, you'll hear these words. And all these words are great. I mean, obviously I have nothing against any of these words. But they're not useful as decision making tools because nobody would ever argue the opposite. You know, nobody ever sat in a meeting and said, "Oh, let's, ah, forget clear. Let's try to make it as confusing as possible." So the idea of clear, it's nice to have out there as a, I don't know, sort of a platitude to move towards, but I just don't help but think it helps you make decisions. And so tenets are really decision making tools. And it's sort of, you know, like the classic one is paper versus plastic. Like, it's just too complicated to reconsider that every time you're at the grocery store. So you sort of make a rule for yourself and you're just a paper person or a plastic person and you move on from there. And so it's sort of that at scale. And the story comes from when they were starting to work on Keynote, apparently the guy who was responsible for originating Keynote went to Steve and said, you know, "How should we think about Keynote?" And, uh, and Steve said, "I want you to keep three things in mind. One is it should be difficult to make ugly presentations. Two, you should focus on cinematic quality transitions. And three, you should optimize for innovation over PowerPoint compatibility." And if you take that last one in particular, if he hadn't kind of said, "We're gonna go this way instead of that way," that team would have spent the next 10 years gouging each other's eyes out over whether they should try to go for PowerPoint compatibility or innovation. And so when I was at ThoughtSpot, I realized pretty early on that I wasn't gonna be able to have any sort of command and control over everything that was gonna happen in the product. There was too many people involved, too many engineering teams, most of them were in India. Like, I needed to move from a mindset of, uh, of control to one of choreography. I needed to try to set the culture and set certain design tenets that everyone could internalize and follow and hopefully then make the right decisions in that, in that groove, if you will. And so we had three. I think you can't have more than three or four 'cause you need everybody to memorize them. You can't, you know, you, they can't be consulting a handbook. And so, uh, one of them was, documentation is a failure state, right? Like, in enterprise companies, a lot of times people think, "Oh, we'll just put it in the manual, it'll be part of the training." And I would constantly be coming back and go, "Stop it. Nobody wants to learn our software. Nobody cares. We are just one more browser tab in a world of browser tabs. We are not this user's complete world. They do not wanna learn this stuff. Documentation is a failure state. Maybe we can't always avoid it, but we should do everything we can to simplify things so you can figure it out in the context of the product." That was number one. Number two is, every interaction should start simple and the user should have to opt into complexity. So our main competitor at the time was Tableau. Tableau started with complexity. That was their whole value prop is like, "We are a super powerful tool. We can do all sorts of stuff." So when you sit down at Tableau, you know, it feels like you're flying the space shuttle. And if you're a, a professional data analyst, like, that's great, that's the kind of tool you wanted. That wasn't what ThoughtSpot was about. We were trying to take data analytics into the hands of what I call mere mortals, also known as business users, uh, people who didn't live and breathe this stuff every day. So our goal with them was that they could sit down and it was an approachable piece of software, and they could turn on all the bells and whistles and power if they wanted it. So that was the second one. Start simple, let the users opt into complexity. And the third one was, the entire product should look and feel like it came from a single mind. And this was a tenet to try to combat the natural tendency of enterprise companies to really fragment, because you have all these different teams working on... They're incented to work just on their little piece. And so they think about what's right for them and they don't back up to look at the whole thing. And so we had this tenet, you know, the whole thing should look and feel like it came from a single mind to just try to remind people, how does this fit into the whole system? And sometimes we need to go along and do things that work for the product that don't necessarily work quite the way we might want them to for our feature. And so th- those tenets were all, again, they were all decision making tools. And when we would have design debates, we could just come back to those, "Wait, are we actually starting simple and forcing them to opt into complexity or are we doing something else here?"

    4. LRLenny Rachitsky42:21

       So there's kind of this implication in this discussion about tenets is- i- is- is that you need to be very opinionated.

    5. BBBob Baxley42:27

       Yeah.

    6. LRLenny Rachitsky42:27

       There's like a clear, here's what's in and here's what's out.

    7. BBBob Baxley42:30

       Yeah.

    8. LRLenny Rachitsky42:31

       Is there anything more along those lines? And are there other tenet examples you could share to give people some inspiration as they think about their potential tenets?

    9. BBBob Baxley42:39

       You know, it's very context specific so it's (laughs) a little bit like, you know, what are your tenets for parenting? It's a very specific, personal type thing that's germane to your particular context. So I'm not sure if I have a lot of other examples and I haven't heard this used by a lot of other companies. So I have a-... you know, been able to- to add a bunch of stuff. We tried to come up with tenets for individual features, and we kind of had trouble with that. It felt like they kind of operated at, uh, at sort of the design strategy level. And I just think that varies dramatically from company to company. What, what I would look for is, uh, you know, if you're a design leader or product leader, uh, try to pay attention to what are the debates that we keep having over and over, where people kind of seem to be digging in and- and things sort of seem to be, you know, uh, bifurcating into two camps. And then is there something we can do where we just settle that r- you know, we just have that debate once and for all, we decide as an organization we're going left instead of right. And you're- and you're absolutely correct, you have to be opinionated, but that's how you're gonna win. You know, there's- there's no un-opinion s- un-o- un-opinionated software that's been successful. You have to have a point of view. The question is, what's it gonna be? So I'd say practically, like, just try to look for places where it seems the team's having the same debate over and over, and then have it once, get it done, and put it behind you.

    10. LRLenny Rachitsky43:51

        Hmm. And make it a tenet. And what's- why is the word tenet versus principle so important?

    11. BBBob Baxley43:57

        I don't know. I settled on (laughs) I settled on tenet. I'm not even g- I'd have to go look up the- the definition. I was trying to differentiate it from principles.

    12. LRLenny Rachitsky44:05

        Hmm. Yeah.

    13. BBBob Baxley44:05

        'Cause I think principles are just, you know, it's, uh... I describe principles as sort of Apple Hood and mother pie. Um, again, they're just not something people are gonna argue over, and so I d- I didn't think it was wise to try to co-opt that word and change how people think about it so much as I might be more successful just coming up with a different word altogether.

    14. LRLenny Rachitsky44:24

        (laughs) Makes sense. (instrumental music) This entire episode is brought to you by Stripe. Every single one of the Forbes top 50 AI companies that has a product in the market today uses Stripe to monetize it. $1.4 trillion flows through Stripe annually, which is equivalent to over 1% of the entire global GDP. And Stripe isn't just a payments platform. They also have a product called Stripe Billing, which powers billing for companies that you may have heard of, OpenAI, Anthropic, Figma, Atlassian, and over 300,000 other companies. Stripe Billing lets you bill and manage customers no matter your pricing model, from simple recurring billing to usage-based billing to sales negotiated contracts. Collect and retain more revenue, automate revenue management workflows, and accept payments globally. Use Stripe to handle all of your payment-related needs, including billing, revenue operations, checkout flows, or simply launching or inventing new business models. Learn all the ways that Stripe can grow revenue for your business at stripe.com.

13. 45:25 – 51:48

    The moral obligation of great design

    1. LRLenny Rachitsky45:26

       Okay. I wanna zoom out a little bit. And another theme that came up a bunch when I asked people about you and how you think is that you have a really, uh, strong feeling that building great product and building successful product is an, uh, a moral obligation of people that are in, in tech. Talk about why you feel that way and what that even means.

    2. BBBob Baxley45:45

       Well, look, the example I use mostly is if you go to an airport and you wa- and you look around. You'll see a lot of people using their phone to navigate that system. You know, they're trying to figure out where their gate is, what time their flight's on, whether or not they, can they pull up their boarding pass, et cetera. And just, just watch people. Watch their faces. Watch the level of confusion and frustration. You know, some of 'em, some of 'em are tech superheroes like you and me and most of your listeners, but a lot of 'em are just mere mortals, and they're not living and breathing this stuff all the time. And a lot of times, they're super frustrated, you know? And then take that and scale it out to their entire day. And almost everyone living in a modern economy now is going to have hundreds of interactions with the phone or with a computer, and a lot of those interactions are gonna be consequential. And unfortunately, a lot of those interactions are not gonna be great. They're gonna be confusing and frustrating. And when I'm speaking to live audiences, I often kind of ask people, you know, "Okay, please raise your hand if you've had a frustrating or, uh, you know, confusing experience with software in the last month." And obviously, yeah, every hand goes up. "Okay, how about so far this week?" Most of, all the hands stay up. I'm like, "Okay, how about so far today?" You know? And most of the hands stay up. And it's often that I speak in the morning, I'm like, "Okay, everybody's had a frustrating experience with software and it's 10 o'clock in the morning." Like, that's a problem, people. Because each one of those interactions, it takes a little bit of energy away from you, and it ups- it ramps your frustration just a little bit. And the- the bummer about software, both for the audience and for the creators, is that it's an anonymous, uh, medium. Like, nobody gets to see who's making these things. You and I together, we might be able to name six designers that have worked on products we care about, and the only reason we could do that is 'cause I'm a designer and I know a bunch of 'em. (laughs) By yourself, I'd be surprised if you could name more than a handful. So, you know, and the- and again, we work in tech, so if you think about the billions of people out there that don't work in tech, to them these products are just these crazy faceless things created by a bunch of people, you know, who knows where, and these products are causing them untold amounts of frustration and confusion, and it- it just takes away from their life quality. And they... I think we have an obligation as product people to put that emotional energy back into peoples' lives. You know, they don't- they don't want to try to figure out how to navigate our login screens or go through our onboarding process, they just wanna get home and spend time with their families and pet their dogs and have a nice dinner. (laughs) Like, I- I just think every time we make a demand on the audience, that's a failure on our part. And so I- I do think it kind of comes... I- I- I cast it in a moral way, and I talk about it that way because I don't think many people working in the industry understand the scale of what they're doing. Again, 'cause it's an anonymous field. Like, we don't- we never see anybody on the other side of the glass. But I think with- you know, with this podcast, it'll go out to, I don't know, hundreds of thousands of people. Like, if you and I saw all the people that will potentially listen to this in one place, we would think to ourselves, "Oh my goodness, that's, like, a lot of people." (laughs) We- And we might think of it differently, we might behave differently. You know, I s- my team at- at Apple, but also, you know, my friends that are working at Facebook or Google or wherever, it's very hard to really understand that they're creating something in Figma on their computer that's going to be interacted with by billions of people, thousands and thousands of times. And I... If you lose sight of that, I think you just-... I don't know, you, you get sloppy and disrespectful is the wrong word, but I think you just lose sight of h- how much impact you're having on other people.

    3. LRLenny Rachitsky49:06

       Wow. That's really inspiring. That makes me wanna (laughs) build products and make them awesome. Uh, there's so much power to that. Uh, I think a little bit... What this makes me think about a little bit is, it's kinda random, but when I see someone click and watch one of my y- my podcast videos on YouTube, I'm like, "Wow, that's like one person that's gonna spend their time watching this thing. Wow, I really wanna make..." It gives me more, uh, motivation to make these even better and better.

    4. BBBob Baxley49:31

       Yeah. Look, I think you have to find ways to go, uh... You have to, you have to find mechanisms where you go out of your way to see people using software in real time. I've worked on products that have been used by billions of people. I have friends that have touched billions of people. None of us ever get to see anybody use this stuff in the wild, in their natural state. Maybe we see them in a lab or something like that, but yeah, I've never seen anybody just randomly using even Pinterest, you know? But there's ways that you can go, and as a creator, as a maker, you can go and watch people using software in the wild. So I go watch, just go observe people going through self-checkout at Target, which is the best self-checkout, self-checkout I've ever seen. Go wa- go watch that, then go watch it at some other grocery store where it's not as great, you know, and, and like really notice what happens with people. Much to my kids' frustration when they, when their friends are over, I often grab their friend's phone and just sort of flip through it to try to understand how people are organizing their home screens and which apps they use and maybe there's something in there that I'll, that I haven't seen. I'll ask them what that is and ask them to kind of give me a tour of it. Like, I think we're living in a time where people don't do so many usability studies, so a lot of folks get pretty far into their careers without ever, ever having watched mere mortals actually use software. Instead, we're lo- relying on metrics and stuff, which is... I sort of joke that, like, relying on metrics to understand what's happening at the user level is like, uh, looking at raw data from a radio telescope instead of just going outside and looking at the night sky. Like, you know? (laughs) So like, you gotta find a way to watch the audience. Uh, movie f- you know, filmmakers can go to a theater, they can watch people understand stuff. Comedians can go to a comedy club, they can help start to develop an intuition about why people laugh. None of us have an obvious way to go watch people use software, so we don't really understand how humans process what's happening on the screen. And you have to just find ways to do that. And fortunately, software is everywhere. It's not just desktop or, or mobile software. I mean, there's ATM machines, there are ticketing kiosks, uh, kiosks. There's point of sale systems everywhere. Just, I mean, go watch somebody over 70 fumble with a, with a chip card insert, you know? Or s- watch somebody try to figure out Apple Pay. Like, and these are pretty seamless experiences, and still there's cognitive friction and all this time. Just go rent a car and then look, notice how long it takes you to figure out what the heck is going on with the dashboard, you know? Like, there's, there's lots of opportunities to try to develop that intuition of how people navigate the human-computer interaction,

14. 51:48 – 1:01:20

    Understanding software as a medium

    1. BBBob Baxley51:48

       and we d- we need to find ways to go do that.

    2. LRLenny Rachitsky51:50

       An important, uh, element of what you're describing here, which I think, uh, uh, maybe people miss is that you're talking about just any software in order... not your own product, in order to start building your sense of taste and gut feeling for what works and doesn't work. And, uh, I had a guest on recently, Guillermo Rauch from Vercel, founder of Vercel, and he had a really great phrase, uh, something, something they do at their company. They, uh, they have this, uh, kind of mission of exposure hours.

    3. BBBob Baxley52:19

       Mm-hmm.

    4. LRLenny Rachitsky52:19

       Increase your exposure hours to people using our product and it... And then you can extrapolate that to any product.

    5. BBBob Baxley52:26

       Yeah. Well, there's using your product, but I always think when you're watching somebody use your product, you come into it with a psychological bias that makes it hard for you to really see what's going on. So there's something about just understanding the audience and how they process information on a screen, uh, not your product. Like at one point when I was, uh, redesigning a checkout system, uh, we did what I called a reality check, which was we held a traditional usability style exercise in a lab and all that sort of stuff, but we had the subjects come through and go through checkout in other products. So we watched them go through, like, eBay and Williams-Sonoma and Amazon or something like that. And we learned a ton about checkout, about what was important to them, how, like, it turns out, like, ship quote is almost as important as price. Like, things that if we had been watching them use our own product, I'm not sure we would have picked up on because we would've been sitting there, you know, yelling at them to click on the button or, you know, we, we would've had a bias in wanting to see the positive things. Whereas if you just watch people that are using adjacent products, it can be super useful. And again, you know, we, we work in a medium. Software is a medium, and we need to understand our medium in the same way, again, musicians go to concerts, filmmakers go to movies, you know, comedians go to comic clubs. Like, when do people like you and I go watch people just use software? Where do we develop that intuition? And, and unfortunately, I think you have to go out of your way to, to do it.

    6. LRLenny Rachitsky53:42

       Talk about more about this idea that software is a medium. This is, uh, something that came up a bunch also in, in conversations with folks that have worked with you, that this is something that you believe.

    7. BBBob Baxley53:51

       Yeah. Yeah, you're so good with the research, Lenny. Um, so, um, yeah, look, so, so I left Pinterest in 2014... f- uh, 2016, sorry, 2016. And I didn't have anything lined up, so I had some time to myself and I was driving all, up and down the peninsula here in Silicon Valley, meeting with other design leaders and just sort of, you know, I don't know, commiserating with people. And you may remember, there was a very consequential presidential election in United States in 2016, and there was some impression that social media had had a, uh, a, a significant impact on that election. So I was kind of driving around Silicon Valley and I was just sort of wondering like, "What the heck happened?" You know, I mean, I moved here in 1990 when the hippie ethos that was really at the core of Silicon Valley... And the hippie o- ethos was still very visible and you could... I mean, it was very much a part of what was interesting to me about the Valley when I moved here, but, you know, 2016 is a long time later and that hippie ethos had gotten pretty quiet. And so I was listening to a podcast about the history of Silicon Valley by a Stanford group, uh, the podcast was called Raw Data and it was, uh, season two. And it starts off with an episode called, um, dead u- m- A Monument to a Dead Child, which is about Stanford University, and it ends with Zuckerberg's testimony in front of Congress. And in the middle of that, they start talking about the counterculture revolution in the late 1960s in San Francisco and elsewhere, and they quote this book by a guy named, uh, Fred, uh, uh, is it Fred Turner, I think it is? The book's called From Counterculture to Cyberculture.And he has this quote that is, "You have to ask why it is personal computing got started in northern California in the late 1960s, when at the time, every major tech company in the country was on the East Coast. And the answer is because there was a very small group of people in and around Stanford University that cau- that saw software as a new form of media on par with movies, music, and books." And when I heard that, all of a sudden I went, "Wait a second," like, boom. Like, that- that is why I do this. I am fundamentally a maker. In high school I was a photographer. In college, I was gonna be a filmmaker. After college, I went to music school. After music school, I started a graphic design studio. I am a maker, and I realize looking back, I was just hunting for my medium, and it took me until I was 27 to find software as my medium. That's like, "Oh, I'm a maker that designs software." And then- then when I heard that, software as a medium, th- that whole, you know, c- concept of what I've been doing with my life and who I was about, it just sort of, like, all came together really quickly. And I realized, "Oh, I am into software because software makes me feel a certain way, um, when it- when it's working well." And what I find so troubling now is that a lot of time it's not working that way. And I remember the first time I saw a computer. I mean, probably a lot of people on- on listening to the show can remember maybe the first time they saw a desktop computer, probably the first time they saw a pinch-and-zoom on a phone. You remember all that stuff? Like, it was just freaking magic, man. I mean, it was the future. It was so cool, and it just felt like the most amazing aurora borealis or sunrise or whatever. There was, like, a sense of awe and wonder that filled me and probably a lot of, uh, listeners. You know, that's probably the thing that motivated you to be in the field. And so, I- I realized, like, software is a medium because there's an emotional component to it, you know? Like a- like a hammer and saw, I don't... They're not really pulling out an emotion for me. Like, maybe there's some if you're a carpenter, but I don't naturally have an emotion with kitchen tools or, you know, things that think even more sophisticated tools like calculators and pullies, I still don't have an emotional response to them. But every piece of software I have an emotional response to. I either feel confused or empowered, you know? I feel like my world's gotten bigger or my world's gotten smaller. Like, they all have an emotional component. And I think once you realize and accept that, then you can say, "Oh, there- there is an emotional component to what we're doing with this product. I could just leave that to chance," which is what most people do, "or I could try to be conscious of it and we could try to bring that into our conception of what the product's about and try to be purposeful in the emotion we're trying to, uh, to- to elicit from the user." And I think that's where design, and particularly visual design, can have a huge impact. So again, in- in many conversations that I'd have in design reviews, some- some executive would go, "I don't know. Ultimately, this just kind of comes down to a matter of opinion, right?" And I was always like, "No, it does not." Like, whether we choose blue or red is going to elicit a certain diff- a certain emotional response from the user. What is it we want them to feel? And then let's make sure that we design something visually that evokes that emotion. So, um, again, I- I think once you really get your head around the fact that there are people on the other side of the glass, real live human beings having emotional moments, you know, with the thing that you're putting in their hand and that they're focusing their attention on. Like, you are in those moments, and are you gonna own it and show up and be the person you want to be in those moments or not? You know, a few- few months ago I was... Or I guess a little longer ago, I was talking to the team at Toast who makes the handheld point-of-sale stuff that they use in restaurants. And the thing I was trying to tell them is, "Whether or not you see it this very... You know, tonight you're gonna be at dinner with a few hundred thousand people all across the country. And if we take just one example, you know, you're gonna be at a very nice diner with a grandmother and her two teenage sons in Ohio. And the check's gonna come, and the waiter- the waiter or the waitress is gonna hand over the device to that grandmother and... 'cause she wants to pick up the bill. And you have the opportunity to either make her look like a superhero 'cause she knows what she's doing, or to make her look like a fool and one of her teenage grandsons is gonna grab the device and do it for her. You're at the dinner table. What are you gonna do for grandma? Are you gonna show up as well as you can, or are you gonna just, like, let this whole thing fall apart 'cause you didn't think hard enough about grandma?" And that's true for Toast. That's true for every product any of us are working on all the time.

    8. LRLenny Rachitsky59:38

       Mm-hmm. This is so interesting and fascinating and inspiring. I was gonna ask how you use this insight that software is kind of the most powerful medium- media, more even than TV and movies, and, uh, you shared it, which I think is really important. So, just to kind of double down on this is, the advice here is think about the emotion you want the user of your software to have as you're starting the design process, not just what do you want them to do, how do you want... how fast do you want them to get through this flow. It's what's the emotion you want them to have.

    9. BBBob Baxley1:00:09

       Yeah, I often don't think about what I want them to do. I just think that's sort of a selfish way to think about it, you know? Like, I... L- like, they- they have something they want to do. Like, I'm trying to help them. Like, I'm not... (laughs) If... I- I just don't ever approach these things of the user is something for me to exploit and take advantage of and manipulate. I know there's people that do approach it that way, which I think is a little unfortunate. But I just... as a designer, I guess I have my own set of values, my own kind of compass on these things that push me in a certain way of thinking about it. And so I'm kind of constantly asking, "What's the right thing for the user?" And I believe in my heart that if we prioritize that, wonderful things will happen for all the metrics, including the money metrics that matter. I've never seen a product be successful that used metrics as a driver for what they were doing. I've seen a lot of companies be really successful seeing metrics as a consequence and a way to evaluate the quality of their decisions, and then using those to, you know, triangulate and make better decisions moving forward. So, they're kind of an- a- a very useful feedback mechanism. But I think, you know, there's definitely a risk to- to confusing doing something because it's a driver versus something as a consequence.

    10. LRLenny Rachitsky1:01:19

        There,

15. 1:01:20 – 1:07:04

    Reducing ambiguity for product teams

    1. LRLenny Rachitsky1:01:20

       there's a few more questions I want to ask, but I wanna come back to something that I asked earlier that I think is on the minds of a lot of, say, founders and product managers listening to this, of just like, "Okay, this all is, sounds really great. I would love to make these experiences so great. I just, it's gonna take us a lot of time to do this really, really well." You said that it doesn't have to. What's like a tactical tip or two that you can suggest to a founder or product manager to help them con- kind of contain the design process while also achieving these outcomes that you're describing?

    2. BBBob Baxley1:01:53

       Well, I think if you can give... Y- you know, I mean, (laughs) maybe one way to think about it is like a big giant AI prompt. You know, the more context you can give it, the more specificity you can give it, the more, "This is what I'm about and what we're trying to get to," the more the designer's gonna be able to figure out which s- swim lane they're supposed to be in to produce something. So if you, I, I think if you're going into it feeling like the design process is gonna take a lot of time, it's because you haven't been cl- you haven't been clear in your creative brief, so to speak, which often means you're not really clear in your own head. And I think a l- I have worked with a lot of founders, and we could identify a bunch of big companies who I think got started that weren't clear in their o- own head. I mean, I don't want to... You know, Yahoo was an amazing company, but, but if we just look at Yahoo for a second, it... I worked there. It was never clear to me what the founding vision of Yahoo was. And I talk a lot about vision statements, and we could say, like, the vision statement of Google is organizing all the world's information. That's a great vision. They'll never achieve that. That's a, that's something that's always over the horizon, and it's been a very useful organizing principle for their acquisitions and how the company grows. Amazon, to be the earth's most customer-centric company. Okay, great. That gives, that's, that's a vision. They will never get there. It tells you how they're gonna expand. Apple doesn't have an explicit vision, but I might describe it as personal computing can have a transformative effect on the lives of individuals, right? And that, and I think that kind of focuses a lot of what they're trying to do. Disneyland, still the best vision statement of all time, which is, the happiest place on Earth. So once you tell an employee, "This is supposed to be the happiest place on Earth," then you're signaling all sorts of things about how they need to pick up the trash, and how they need to show up on time, and how they need to wear their, their, uh, their uniform. Like, you're just signaling a whole bunch of stuff. So when I talk to founders, a lot of times they just don't have that clarity of what's the vision of the company. To go back to Yahoo for a second, I never heard a vision, and so I'm not really sure what they were ever about. They kind of stumbled into the directory and then they added a bunch of stuff around the edges, but it never seemed to make a lot of sense. And so I think people operating inside Yahoo, you know, they, they... It ended up t- it ended up being inefficient because they were having to deal with all that ambiguity. So I think that- that can also be a pretty big risk for founders. They end up kind of with a product idea, um, and they think that the company is the product. The company is not the product. The product is the product, and the company is bigger than the product. And so you need to have some vision that speaks beyond just this particular thing. Um, I think Slack, Slack and fr- o- honestly, both, uh, Slack and Pinterest I think are examples of companies, uh, uh, products that became companies, but neither one of those places really knew what to do next 'cause they didn't have a bigger vision of the change they were trying to see in the world. So, I, I mean, back to your... You were asking a very pragmatic question. Like, I think you need to work on your prompt (laughs) before you go to your designers and try to give them as much clarity about what you want to produce as possible. And I think if you leave it open as to the emotional response you want users to have, you're inviting a lot of ambiguity, which is gonna invite a lot of inefficiency. Yeah.

    3. LRLenny Rachitsky1:04:49

       I love that answer. And it's so interesting that, uh, AI can help us work better together as humans, because when you find that it, the AI is not achieving the outcome you want as effectively as you want, that's a lesson. This y- this also translates to working with humans. Like, make the prompt more specific, add more context in life, not just, uh, when you're talking to AI.

    4. BBBob Baxley1:05:12

       Yeah. Yeah.

    5. LRLenny Rachitsky1:05:13

       I love that.

    6. BBBob Baxley1:05:13

       Yeah.

    7. LRLenny Rachitsky1:05:14

       That's so interesting. So the, so the advice here is just if you're finding design is taking too long or you want to just level up your, uh, success with your design team, give more context, spend more time on the brief, on what you're actually trying to achieve, and make sure there's a clear vision or mission that everyone can row towards.

    8. BBBob Baxley1:05:32

       Yeah. Look, design is a problem-solving methodology, so the more variables you can remove before they go into the process, the more efficient it's gonna be. And if you give designers a lot of ambiguity, they're gonna l- spend a lot of time spinning around. And honestly, that's your fault as the client, you know? I mean, as a design leader, I think one of my main challenges is frankly trying to make the PMs better clients, you know, helping them get more specific. It's very common that for a design team to get extremely ambiguous asks from a product team, and then they ha- And the problem for design is they have to take all that ambiguity and they've gotta wring it all out, so when they give it to engineering, engineering knows exactly what to code, because computers don't tolerate ambiguity. Like, engineers need to know what the thing is gonna be. And so, design gets stuck with a really ambiguous input, but they have to have a highly specific output, and then they're often time boxed to do that. And it's just not a recipe for success. So you're much better off either kind of compressing the PRD experience, you know, and bringing the designers into that, kind of co-creating with product and design really rapidly. But you, you need to... I mean, you could think of it in some ways as designers are gonna draw the storyboards, and if you don't give them a great script, they're gonna have a very hard time. Yeah. And then you give... You know, you can't give the shooting crew ambiguous storyboards, or you're just gonna waste untold amounts of money on set. So if you think about those three steps, from script, to storyboard, to production, like, it's all about getting rid of ambiguity. And so the more ambiguity that can be removed upstream, the faster design is gonna go.

Episode duration: 1:41:58