35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley

0:00 Almost everyone living in a modern economy now is going to have hundreds of interactions with the phone or with the 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. You actually have a really unique perspective on just what is design. Design is trying to imagine the future you want to 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 grab It's there at the beginning in the root DNA or it doesn't exist. It wasn't a successful stint at Pinterest. 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. Why did you decide to join Apple? 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? 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 in led design teams at Apple.

1:02 Pinterest. Yahoo and most recently ThoughtSpot. Over the course of his career that spanned over three decades, Bobbis 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.

1:21 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.

1:54 A big thank you to Annie Warner, Andrew Hogan, Irene A, and Joff Redford for suggesting questions for this conversation. If you enjoyed this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you 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 Ladies Newsletter.com and click bundle. With that

2:20 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.

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3:51 Dot Come on. Bob Thank you so much for being here and welcome to the podcast. Letty, thank you so much. Thanks for having me. But also just thank you for what you do. You know, I we are still in early days of trying to figure out how to make software together.

4:09 I think of it sort of like where the film industry was in the nineteen twenties. 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.

4:24 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. 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.

4:37 There's a story that I here that you often tell which is when somebody asked Steve Jobs once What is your favorite product? That you've built. That you work on w and and his answer. Uh what's that story?

4:49 So I actually can't remember where I heard this, so but I don't I believe the story's true. Steve at one point was recounting the products that he had created. uh that it was most proud of and if I recall the whole list it was the Apple two. The Mac. The iPod.

5:03 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.

5:12 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 Catmill or John Lasseter at Pixar. And he said, You know, everything we make is gonna be a door stop in three years. But the stuff you guys make, they're still gonna be watching in a hundred years.

5:28 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 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

5:47 uh the value of technology in the world. Uh and it infuses everything in that company. I mean everything from the check out system when you go to the receptionists to What it's like in the cafeteria, you know, they the uh it 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. 'Cause they're just the whole company is constantly asking

6:08 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 that question. Why do you think that people that have left Apple, a lot of them just 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. But Just feels like

6:34 There hasn't been a ton of alumni that have built incredible things. Yeah, I'm hard press so obviously Tony Fidel 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 uh 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 l I left Apple on a Friday and I started Pinterest on a Monday. And I didn't give myself time to

7:00 to recalibrate to the So I think I think at some level a lot of the challenge is that when you 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 to those all those standards and it's it's really deep. It infuses all of your behavior and

7:19 how you conduct yourself in the company, away from the company. And so I think it's It's pretty hard to immigrate successfully. From one of those environments to another. And Apple is one of the strongest cultures, and there's not many other

7:30 cultures that sort of natively operate like that. Uh Airbnb is one exception. And so you have guys like Heroki as I who's leads all of marketing and all of product, and Heroki is crushing it at Airbnb, who's incredibly successful at at Apple. 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 at Apple, I think it was Tim or Steve used to talk about the Apple car wash.

7:55 And then when you started Apple, they kinda had to take you to the car wash and get off all that stuff. that you'd accumulate it at other places. Turns out there's a car wash you need to go through when you leave Apple as well. And so I think A Roki gave himself time to do that. And I think that's probably a lot of why he's been so successful at Airbnb.

8:11 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 hired 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

8:26 I want to hold on to these values. So at Apple attention to detail, product excellence. You know 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 Thought Spot, which was my last job.

8:45 Than I was in the culture of Pinterest. Um, if I had to do it again, I could probably do better at Pinterest. So I think that's I think that's useful for anybody leaving One

8:54 very specific culture and going someplace else is like trying to hold on to the values but not the behaviors. This is so interesting. And I appreciate you sh 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 head of design of interest. Oh, amazing. So cool. And then you know, if you're like okay, but it wouldn't work out that well.

9:16 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 took away from that experience? 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

9:34 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.

9:46 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 uh big poster that said say the hard thing. Well, that's where Pinterest was at the time.

10:02 And I can assure you, nobody at Apple was having to remind you to say the hard thing. You know, and so I probably could have Picked up on that better. Um that I did. Yeah, I'll say like

10:14 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.

10:29 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 a 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's changing really rapidly.

10:49 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

11:01 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 Everybody that makes it to the top, there's hundreds of people that don't. I I one of the things I took away when I was at Pinterest was I came to think that the job of a startup

11:18 was to grow the founder so they could continue to lead the startup. And I I think what's true for founders is also true for a lot of the other folks in 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 the 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.

11:40 And it it feels like a failure. It's I mean if 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 I you know, within like five years, he's like p Facebook's a big thing. I mean

12:02 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. I think that's like really super hard.

12:13 To do that and stay balanced. And also keep doing that for for so long. Like their BB founders I think was Brian's maybe first job or second job, and he's doing it now for Now, fifteen years in a row. Founders it's their life. It's very unusual to see founders move out. I I had this other theory that A start up 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.

12:38 And you know, and 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. Just to close the loop here, uh one takeaway here that I think is really interesting is that You can

12:53 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

13:01 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. Yeah, your career's not your life. You know, there's a lot more to it than that. And then just to uh give someone something tactical here, so you Realize the culture Pinterest w you bounced off of it. I love that metaphor.

13:19 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. 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 uh Do they have a story as to why they believe in design? Like really in their heart and soul do they care about design?

13:43 '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 want to make sure I've got air cover. From the highest people in the company setting the culture.

13:57 In the case of my again, my most recent job was with uh company called ThoughtSpot, and ThoughtSpot was founded by a gentleman named Acheet Singh. And a Jeep grew up in rural India. But he tells us 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 IDO.

14:16 And as a very young person, he got to see what IDO 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 Thought Spot. 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

14:36 design on after the founding. So I've seen Lots of 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

14:55 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 in a way that like You know, as an American I could I could Immigrate to Australia.

15:11 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. 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. Mm-hmm.

15:29 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 depending on who you are. Yeah, why why would you want to work in a place that doesn't value the thing that you do? That would just God, that would suck. Yeah. You actually have a really unique perspective on just what is design. That I haven't heard before.

15:52 Let me so let me ask you that question, just what is design? Well, I'm gonna go back to the Edward Tufti 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 because I didn't know how else she could think. That was just sort of how I naturally thought.

16:19 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. Yeah, it's it's living with a certain type of intentionality in almost sort of a Buddhist type way. Which is different from

16:33 science, which is sort of observational, trying to understand. It's a little bit different from engineering, which is You know, we kinda know where we want to go at the end, but we're trying to g kinda go one step at a time versus designs trying to like see Some You know, further out future state. And account for a a larger or sort a different set of

16:50 constraints and issues than engineering or some of the other problem solving methodologies. So I look at again, I look at it as a a 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.

17:03 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 wanna go work at a place that But as an organization thinks in a design type.

17:17 Method. 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

17:34 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.

17:50 Let me back up and just dissect a little bit the way you describe design,'cause you described it in really tactical terms. You said beautiful, intuitive uh products that make sense. I think it was something like that. Yeah so what you were describing was You're describing the part of the iceberg that sits above the water line. You know. Which is the result that's one of the outcomes of design, but that's not the real heavy lifting of design.

18:12 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.

18:33 Through specific uh tenants, 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 back yard. And they don't really add up to anything.

18:56 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, Lica, 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 latters together. into like one cohesive cynical

19:16 It's integrated, makes sense as a unit. Um and I think that's a huge difference and at an incredible strategic advantage because the company can operate with much greater efficiency. They can onboard new people and get them in line, like You know, Apple, for example, on my the store that does or the team that designed the online store.

19:34 You know, we we had six designers for a store that ran in thirty some odd countries, twelve and a half thousand instances of the store, doing billions of dollars of revenue. We had six designers like any other company. Would have had sixty or more. So Apple's able to operate with much l smaller staff. Because they have

19:52 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 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.

20:09 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 twenty four people, right? Like the teams get too big and you just you can't get that. that what Brian Eno calls uh senius. So so Brian Eno has this great

20:24 Word that he uses senius is uh the genius that comes when you have a group together. So senius is sort of the collective idea of genius. And I think that's something that's Really. magical that I've experienced in my career, but but usually in s in smaller groups. It's hard to do with a giant group. I love that I love this metaphor of the Beatles as

20:42 You know, the way most people describe this is uh design by committee never works. And I love that your example you're the way you describe it is The Beatles is is kinda like the ideal. size in you know of a like a small group versus a committee. I just always have to point out to people that there are twenty people that worked on the original Mac. Minutes. Twenty of'em. That's it. Twenty. Susan Care was one of them, you know, you g Andy Hartzfell, you go through the list. Twenty of them are on the patent.

21:05 There's twenty four that were that are on the iPhone patent. And there's other people involved, but generally there's twenty four 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'd put a massive group, I I don't know, man. Like

21:21 Maybe it ended up with the Zune or something completely different. Who knows? They probably did have a massive group on the Zune. Yeah. So there's something that you know it's like the Four is too few for what we're trying to achieve at scale. But even if you if you look at Pixar, 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 like character development, stuff like that, it's fairly small. And then it really scales when you move into production.

21:44 It's just hard to figure out something new to do together. When there's too many people involved. I think that word news 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

22:04 And tight. You know, as things grow and scale. Uh Your sense what's your take on just like, okay, actually it's okay to have a lot of people on this. Well, you have to bring a lot of people in once you've got once you kinda figure out what you're doing, right? And so to your point, like once you

22:19 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 decide the design the ride for the new or design the line experience for the new ride sitting in tomorrow land, but I know where that fits into this larger thing. So I think you can scale once you have Clarity of vision.

22:39 But it's very difficult to get vision with a lot of people. Great. I think that's really powerful advice. It's just when you're starting something new, I actually had a Uh CP of N twenty six who was at who was basically leading Google Hangouts, the initial launch of Google Hangouts, and he told the story of They put so many resources on it. Like we gotta win. We gotta do this, uh

22:57 Larry. Paige 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. Yeah, I think that's exactly. No, no, the more the more people you put in it, the slower everything becomes. Um Yeah. 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

23:23 your experience here. I'll I think Apple is a very different kind of company where design actually leads a lot of this. Yeah. 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. One of the best lines I ever heard was from my friend Joseph O'Sullivan that at a dinner one night he said, Uh you know.

23:43 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 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.

24:05 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 I look at my counterparts and 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.

24:29 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'm I very much believe that Once you get into a company, your job is to figure out your role and pret 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.

24:49 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 stop, you know, and And and let's try to get to the

25:04 The promised land together. So I I assume that the product managers, particularly in enterprise SaaS companies like my team Thoughts about 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.

25:22 And it's Yeah, 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. I'm like like s stop it.

25:37 Like we all need each other. And we need each other because we need those different mindsets. And any one of those mindset It's just too mo it like it. One of those mindsets inhabits somebody's head completely.

25:48 I just don't think you can simultaneously hold multiple mindset 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. Like in baseball, like

26:01 Yeah, you don't Like the second basement doesn't cover first. That's not how it works. Like you know, every 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.

26:18 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. That was a a very illuminating uh clarification. Something else that uh I heard you believe that I haven't heard before is that design should report to engineering. So I'll say that every company culture's different and different organizations work in different ways.

26:43 In my experience, I think the 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. Yeah, yeah, ThoughtSpot, Pinterest, other places, you know, when you're working directly with product

27:05 It's easy to kinda 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 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. There may maybe they don't bring their same level of enthusiasm to it'cause they haven't been brought along.

27:29 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

27:41 I it's hard pressed if you don't. Also think you can just account for timelines and costs and things better. When design's 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

27:56 co equal branches of government. Um, and that's a you know, that's a solid argument as well. And there's some places where that works beautifully. My experiences at 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

28:10 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 sea level

28:32 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. 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

28:49 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. What I see work and I'm curious to get your take is just uh product engineering design have exactly the same goal. And the more everyone in and their performance

29:05 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 and just create all kinds of weird incentives. Yeah, look, I I would kind of defer to you on that, honestly. 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 had my whole career together, I've worked at maybe half a dozen places. You know, so I

29:28 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 kinda have a a biased view as to what didn't what didn't work for me and those particular organizations. I'll go back to what I said. Every company's different. Every culture's slightly different. It's not one size fits all. I

29:45 I I point out the idea of design reporting to engineering just because I don't think people consider the possibility often enough. Um, so there's you know, there's three options. Design's its own thing, design's 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.

30:02 options inside your org. And so I would encourage people to just take a design mentality, you know, 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

30:16 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. I I love how radical this idea is. I've not heard it. I think

30:28 Uh Designers will be like, you sh you should stop it. Just stop it. Yeah. Uh so have you operated this way? Have you had design reports engineering companies you worked at? Yeah, that was you know, sorry, but like that's how it worked at Apple the whole time under Steve. Design always reported to engineering. You know, they're there now I think it's uh structure a little bit differently, but

30:47 Design has always been part of engineering at Apple. So I saw it work quite effectively there, obviously. It's so interesting. Okay, so say just to give someone something very tactical to do on their team, say they don't want to go to this extreme and move The design org under engineering.

31:02 What's something you've seen work that helps achieve similar outcomes with having engineers design uh integrated early in the design process? 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 A creative technologist. 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

31:26 Ultimately it's sort of a philosophy issue. And Uh it there's not that many PMs or Engineers that can sit in that space. And be comfortable

31:36 With the ambiguity of it all. Like a uh a PM's 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 in open 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.

31:54 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

32:15 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

32:30 The worst thing is when you bring something fully baked. Well, the worst thing's when you bring something fully baked to anybody. 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 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.

32:52 I don't know. Like that's that's not mentioned here's 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 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. Sometimes you're in a meeting and they're just like, God, I just love this. And for me that was always

33:15 That was always the critical moment. Because I knew that d you know, design can't bring you 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. І сонтил да.

33:29 You're not really quite sure if this thing's gonna 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 add to it. And you gotta bring them along at the very beginning.

33:46 What I'm hearing there's there's a big part of just buy in. And then there's also just obviously more good ideas early are great. Yeah, sorry, uh uh uh buy in doesn't feel quite right to me,'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

34:03 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 could have done a thousand other things. But they're choosing to spend their precious

34:24 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

34:38 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

34:55 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

35:04 Graft that on to somebody after the fact. They kinda need to be there at the moment of uh inception, if you will. Mm. Wow.

35:12 That's a really beautiful answer. 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 B to B Saf software.

35:26 So Just I guess just thoughts and just how Much You should spend how much time, how many resources, how deep you go on design for all these things in your building, say you're building some kind of I don't know, expense management system or HRS thing.

35:40 Uh, just like where do you where do you What do you recommend people do with in terms of just how far to go design as a lever as a as a oper as a differentiator, maybe? Well, you know, inherent in your question is this assumption that design takes more time. And so I'm gonna kinda reject that premise. 'cause I don't think design takes more time. 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.

36:02 And I think there's things that you can do. So that you're able to operate it up at a quicker pace is design. If you again, if you kinda get the ten we haven't talked about tenants yet, but we'll get to that in a moment. You know, if you kind of create a s 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?

36:26 And that's a much easier question. It'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're and they're they're clear that this is who we are, this is what we stand for. The design teams are super small.

36:45 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 a young adult, you can spend a lot of time trying to figure out what to wear because 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

37:06 Dressing in the morning gets to be a lot easier. And it's the same thing it Like at Pinterest. I was at Pinterest at a point when Pinterest wasn't quite sure what it Who it was. And so

37:14 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 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 and I agree, like look, having your soul at every little checkbox isn't sounds like a high bar.

37:35 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 in every state, but you know, generally every six months or a year, you need to back up and ask yourself, Mike. Am I proud of this? Is this Something I am

37:50 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 through the day'cause I have other goals.

38:06 So let's actually follow the thread of design tenants and uh In principle. So is this something I've heard about you? That uh you're a big fan of design tenants. versus design principles. What is the difference? Why is this so important?

38:20 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 let forget clear. Let's try to make it as confusing as possible.

38:44 So the idea of clear, it's nice to have out there is 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 tenants are really decision making tools. And it's sort of You know, like a 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, you move on from there.

39:07 And so it's sort of that at scale. And the story comes from when they were starting to work on keynotes, 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.

39:26 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

39:39 That team would have spent the next ten 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

39:53 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

40:14 Then that. Group, 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

40:25 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, be part of the training. And I would constantly be coming back and go, Stop it. Nobody wants to learn our software.

40:37 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 want to learn this stuff. Documentation's a failure state. Maybe we can't always abort it, but we should do everything we can to simplify things so you can figure it out in the context of the product.

40:55 That's 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. It's like We are super powerful tool. We can do all sorts of stuff.

41:10 So when you sit down a 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 breed this stuff every day. So our goal with them was they could sit down and it was an approachable piece of software.

41:30 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.

41:44 the natural tendency of enterprise companies to really fragment because you have all these different teams working on their incentive 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 tenant, 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.

42:06 quite the way we might want them to for our feature. And so that those tenants 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? So there's kind of this implication in this discussion about tenants is is

42:25 Is that you need to be very opinionated. There's like a clear here's what's in and here's what's out. Yeah. Is there anything more along those lines? And are there other tenant examples you could share to give people some inspiration as they think about their potential tenants? You know, it's very context specific, so it's a little bit like

42:42 You know, what are your tenants 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 out with tenants for individual features and we kinda had trouble with that. It felt like they kinda operated at the

43:03 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. Try to pay attention to what are the debates that we keep having over and over. where people kinda seem to be digging in and things sort of seem to be

43:20 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

43:35 Unepin, saw unopinionated 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.

43:48 Then have it once, get it done, and put it behind you. Mm-hmm. And make it a tenant. And what's why is the word tenant versus principle so important? I don't know. I decided. I'd settle on Tenet. I'm not even I'd have to go look up the The definition. I was trying to differentiate it from principles. Because I think principles are just, you know, it's I describe principles as sort of apple hood and mother pie.

44:10 Um, again, they're just not something people are gonna argue over. And so I I didn't think it was Wise to try to Co-op 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. Makes sense. This entire episode is brought to you by Stripe.

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45:14 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 Dot com. Okay, I wanna zoom out a little bit. And then 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.

45:36 And building successful product is an a moral obligation. Of people that are in in tech. Talk about why you feel that way and what that even means. Well look the example I

45:46 use mostly is if you go to an airport and you walk 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 flights on, whether or not they Can they pull out 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

46:05 Some of them 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. In almost everyone living in a modern economy now. Is going to have hundreds of interactions with the phone or with the computer.

46:25 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 kinda 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?

46:44 Most all hands stay up. I'm like okay, how about so far today? You know, in 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 ten o'clock in the morning. Like That's a problem, people.

46:57 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.

47:17 And the only reason we could do that is'cause I'm a designer and I know a bunch of'em. I'd by yourself, I'd be surprised if you could name more than a handful. So You know, and th and again, we work in tech. So if you think about the

47:28 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? These products are causing them

47:39 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 people's lives. You know, they don't

47:53 They don't want to try to figure out how to navigate our login screens or go through our onboarding process. They just want to get home and spend time with their families and pet their dogs and have a nice dinner. Like I I think every time we make a demand on the audience, that's a failure on our part. And so I I do think it kinda comes I I I cast it in a moral way and I

48:12 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. We

48:33 And we might Think of it differently, we might behave differently. You know, I My team at at Apple, but also yet my friends that are working at Facebook or Google or wherever, it's very hard to really understand.

48:44 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

48:54 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 how much impact you're having on other people. Oh, that's really inspiring. That makes me want to build products and make them awesome. Uh there's so much power to that. Uh

49:14 I think a little bit. What this makes me think about a little bit is kinda random, but when I see someone click and watch one of my you 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 want to make it gives me more uh motivation to make these even better and better. Yeah, look, I think you have to find ways to go, uh you have to you have to find mechanisms when 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 of

49:40 touch billions of people. None of us ever get to see anybody use this stuff in the wild in their natural state. Maybe we see'em 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 like go watch just go observe people going through self checkout at Target, which is the best self checkout self checkout I've ever seen.

50:05 go wa go watch that and 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 having watched

50:33 Mere mortals actually use software. Instead we're l 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 out inside And looking at the night sky. So

50:50 Like you gotta find a way to watch the audience. Uh, movie, 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. Unfortunately, software's everywhere. It's not just

51:12 desktop or or mobile software. I mean there's ATM machines, they're ticketing kiosk, the kiosk. There's Point of sale systems everywhere. Just I mean, go watch somebody over seventy 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 of them. Just go rent a car. And then well notice how long it takes you to figure out

51:35 What the heck is going on with the dashboard, you know? There's there's lots of opportunities to try to Develop that intuition. Of how people navigate the human computer interaction. And we we need to find ways to go do that.

51:50 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

52:01 Taste and gut feeling for what works and doesn't work. And Uh I had a guest on recently, Gamma Rausch from Vercell, founder of Vercelle. And he had a really great phrase. Uh something.

52:13 of something they do at their company. They uh they have this uh Kind of mission of exposure hours. Increase your exposure hours to people using our product. And it and then you can extrapolate that to any product. 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.

52:31 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 those subjects come through and go through checkout in other products.

52:54 So we watch them go through like ebay and William 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 have been sitting there, you know, yelling at'em to click on the button or you know, we we would have had a bias. And wanting to see the positive things.

53:17 Whereas if you just watch people They're using adjacent products could 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.

53:30 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. 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. Yeah, you're so good with the research, Lenny. Um so

53:54 Um Yeah, look, so so I left Pinterest in two thousand four. Oh, two thousand sixteen, sorry, two thousand six. And I didn't have anything lined up, so I had some time to myself and I was driving up and down the peninsula. Here in Silicon Valley, meeting with other design leaders and just sort of

54:09 You know. I don't know, commiserating with people. And you may remember there was a very consequential presidential election in the United States in two thousand sixteen, and there were some impression that social media had had a uh a significant impact on that election. So I was kinda driving around Silicon Valley and I was

54:24 Just sort of wondering like what the heck happened. You know, I mean, I moved here in nineteen ninety when the hippie ethos. that was really at the core of Silicon Valley. The hippie 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, two thousand sixteen's a long time later, and that hippie ethos had gotten pretty quiet. And so I was listening to a podcast

54:46 About the history of Silicon Valley by a Stanford group. The the podcast was called Raw Data and it was uh season two. And it starts off with an episode called Um Dead 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 nineteen sixties in San Francisco and elsewhere. And they quote this book by a guy named uh Fred uh uh Fred Turner, I think it is. The book's called From Counterculture to Cyberculture.

55:16 And he has this quote that is you have to ask why it is personal computing got started In Norden California in the late NT sixтіs. When at the time Every major tech company in the country was on the east coast. And the answer is

55:30 Because there was a very small group of people in and around Stanford University that call that saw software as a new form of media. on par with movies, music, and books. І 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 as a photographer. In college I was gonna be a filmmaker. After college I went to music school.

55:52 After music school I started a graphic design studio. I am a maker. And I realized looking back, I was just hunting for my medium. And it took me until I was twenty-seven to find software as my medium. It's like, oh, I'm a maker that designed software. And then and then when I heard that software as a medium, that that whole s you know, the 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. I realized oh I'm into software.

56:17 Because software makes me feel a certain way. When it when it's working well. And what I find so troubling now. Is it 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 Pension Zoom on a phone.

56:37 You remember all that stuff? Like it was just Freaking magic, man. I mean it was The future it was so Cool.

56:45 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 Listeners. Yeah, that's probably the thing that motivated you to be in the field. And so I I realized like

57:00 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 I think even

57:16 More sophisticated tools like calculators and pulleys, 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, my world's gotten smaller. Like they all have an emotional component. And I think once you

57:32 Realize and accept that. Then you can say, Oh, I 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

57:46 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

58:02 Some executive would go, I don't know. Ultimately this just kinda 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

58:22 Yeah, I I think what you really get your head around the fact that there are people on the other side of the glass, real life human beings having emotional The 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.

58:44 You know, if you Few months ago I was 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. The thing I was trying to tell them is Whether or not you see it. This very t you know, tonight you're gonna be at dinner.

58:57 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 uh Waiter the waiter, the waitress is gonna hand over the device to that grandmother and'cause she wants to pick up the bill.

59:15 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? You to show up as well as you can.

59:29 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. 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.

59:49 More than even than TV and movies and Uh you shared it, which I think is really important. So just to kinda 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 you want them to get to this flow. It's

1:00:07 What's the emotion you want them to have? 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 Like they they have something they want to do. Like I'm trying to help them. Like I'm not.

1:00:21 If I i I d I just don't ever approach these things of the user's 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

1:00:37 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

1:00:54 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 it a very useful feedback mechanism. But I think

1:01:12 You know, there's definitely a risk to to confusing Doing something because it's a driver versus something as a consequence. There's there's a few more questions I would ask, but I wanna come back to something that asked earlier that I think is on the minds of a lot of say founders and product managers listening to this have just like Okay, this all is sounds Really great. I would love to make these experiences.

1:01:33 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?

1:01:46 to help them can can it contain the design process while also achieving these outcomes that you're describing. Well, I think if you can give w yeah, maybe 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

1:02:07 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 clean.

1:02:18 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 can identify a bunch of big companies. who I think got started that weren't clear in their own 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.

1:02:39 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.

1:02:55 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 a 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

1:03:13 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 They're their uniform, like you're just signaling a whole bunch of stuff.

1:03:33 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. And 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 it ended up to 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

1:03:57 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's bigger than the product. And s you need to have some vision that speaks beyond just this particular thing.

1:04:10 Um Next slack. Slack and for 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

1:04:24 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 before you go to your designers. And try to give them as much clarity about what you want.

1:04:37 to produce was 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. I love that answer. And it's so interesting that

1:04:51 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.

1:05:03 That's a lesson. This you 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. Yeah, yeah, I love that.

1:05:14 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.

1:05:28 And Make sure there's a clear vision or mission that everyone can row towards. 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.

1:05:42 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.

1:05:57 that for a design team to get extremely ambiguous asks from a product team. And then they have and the problem for designers, they have to take all that ambiguity and they've got to ring 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's gonna be. And so design gets stuck with a really ambiguous input.

1:06:18 But they have to have a highly specific output. And then are often time boxed to do that. And It's just not a recipe for success. So you're much better off

1:06:28 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 y 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 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.

1:06:51 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's gonna go.

1:07:03 This begs the question then. Uh a lot of you know, you don't want to give designers here exactly, here's the thing we're designing, make it really great. And pretty. You know, there's always this balance of just give designers space to think and be creative and explore. Advice there of just How to navigate that.

1:07:20 Well if you go back to my example of the script and storyboard, scripts don't cum don't contain pictures, right? There's still a lot of opportunity to think differently and you know, and to come up with with original things and to im and have a lot of creative input in the storyboarding process. So the script is living mostly in words, which is largely how PMs uh how PMs function. Uh to keep in mind for PM.

1:07:42 It's there's always a tendency on PMs to want to draw something. And then try to give a sketch to a designer, and I would caution them against that. Sometimes they have to draw themselves so they can think it out. But Like

1:07:54 Yeah, if the if a PM came to me with something That was drawn and kind of fully baked. My response was like Thanks for giving me that. Now I know exactly what we're not going to do. Because you know, as a point of pride, there's no way I'm gonna go execute that exact thing. So the so you're right, like PMs have to give you the space to operate.

1:08:12 And I think a lot of what they're trying to achieve could be done in more informal ways, conversationally and whiteboards, uh thing things like that. But yet You need You need to narrow the problem for the designers. Um

1:08:25 You know, get y they need constraints. They don't they don't need They don't need a tiny little box. But they they need Constraints. You know, if they can

1:08:33 Think in terms of like you don't you don't give'em an airport tarmac. You and you don't even give'em a football field, they give them something more like a basketball court. Yeah. scale at which they can do their design. Thing.

1:08:45 Mm. I want to talk about basketball later, but not yet. You've shared a lot of counterintuitive Lessons on building product, designing, building teams, leadership. Is there is there another

1:08:56 very counterintuitive. lesson you've learned about building products, hiring leading teams that goes against common startup wisdom. The thing I would say is that you should wait as long as possible to draw a picture. Like

1:09:10 Uh and s and that I think that pushes against All the Gen AI tools that help you create prototypes. And there's obviously a lot of excitement around that. I can just give a prompt and the uh the AI's gonna they're gonna crank out a UI for me. So I don't think I'm using the term right, but uh I had this idea from art that I call the primal mark.

1:09:27 And that's the first mark that you make on the canvas. And once you make that mark on the cannabis, everything you do after that is in response to that mark. It sort of sets your baseline. And so For me, I always felt that as soon as we drew a picture that looked even remotely real. Like everybody gravitated towards that and said, Oh, that's the thing.

1:09:46 And people were so uncomfortable with ambiguity. That they can't really deal with the tension of Well, that might not be the thing. And so As soon as you draw a picture That looks even slightly realistic, much less something that comes out of uh one of these Gen IA tools.

1:10:02 You know, everybody kinda goes, Oh, that's the thing you just keep doubling down on that thing. And what's happened is you've taken the the possibilities from this big broad thing down to this tiny little thing. from an AI system that's trained on existing solutions and existing ideas and maybe not even thinking about it the right way because all you've really given it is your first order thinking.

1:10:21 And so I I think there's a way you can stay in these things. Conceptually and conversationally. Where you can get to your second, third, fourth idea. And that's where stuff gets really interesting. And again, I don't think that has to take a lot of time. That can be

1:10:35 Over the course of a single meeting you could get to a second, third, fourth idea. You just have to be willing to not jump at the first thing that looks like a possibility. Like you get that possibility, you go. Okay, well that's interesting. Let's table that. What else have we got? Yeah, there's one story that's kinda related that's useful. Uh in one of my previous jobs Uh I was responsible for the public website. I remember

1:10:54 coming across one of the product managers one day and she's like, Hey, this link on the homepage, you know, we have to make it blue. I was like, Well, we don't use blue links anywhere. She says Yeah, yeah, but we just have to make it blue. It's like, Well, we're not making it blue. A couple of days go by and I saw the homepage and the link had been made blue'cause she had got around Me and she gone to engineering and just made it blue.

1:11:11 And I saw her in the hallway again, I was like, you know, what the hell's up with that? And she goes, Well, people couldn't see it. And I'm like, Oh, they couldn't see it. So it wasn't prominent enough, right? She's like, Yeah, it wasn't prominent enough. I'm like, Well great. You know, there's like a hundred different things we could do to make it more prominent. One of which is making it blue, you know, which is

1:11:26 The thing that came to you first because you're not a designer and like it that's naturally what because it's the most obvious thing, but it actually doesn't fit in with these larger things we're trying to do. So I've often I try to encourage the product managers to like what's the

1:11:40 What's the problem with the thing? And then let us solve it. Don't Don't jump to it and tell us this is what we're supposed you know, don't tell us this is just exactly what we're supposed to do. And again, it I do the same thing on the roadmap. Like

1:11:51 You decide the roadmap, tell us what we're supposed to do. I will ask you about it and I may push back and We may have some back and forth, but that's your responsibility. I'm gonna trust that you are trained and you know what you're doing and you're gonna make the right call. And I just want you to give me the same level of respect. This advice about not drawing quickly and not

1:12:10 Making that primal mark, which I love that term. is I imagine I'm curious your take on AI prototyping tools these days, because that's like the extreme version of that. Not only are you just creating a sketch, it's like oh it's working. Here it is. Here's what it looks like. Thoughts on that. Do you discourage people from doing that? VMs especially. Well, I think it's a production tool, right? So like once you know what you want and you can give it a really robust prompt, then uh I I mean I haven't played with it a lot myself'cause I'm not in operational role right now, but

1:12:37 You know, presumably it's really useful at cranking out that uh actuable prototype which you can click and you know, experience. And I've said for a long time that an interactive idea needs to be expressed interactively. So we're not talking with our hands and we can really understand what's gonna happen. So when the idea is ready to be expressed, I think those tools are probably fantastic. Um But you know, ideas start off pretty fragile and the best ideas start off really fragile.

1:13:00 And I think when you push them to develop too quickly and you put them out in the world and expect them to be able to stand up to critique too early, you're just gonna squash them. I often think about him like the little plant in in the Pixar movie Wally, you know, you've kinda You gotta give that little guy a little space, a little time, some water and some nourishment and You can't really just suddenly put him out in the wind and think he's gonna make it.

1:13:22 And so I think a lot of A lot of very fragile, interesting, quiet ideas. that I I think you need to give some space. And when you when you jump to the expression of them, I think you're putting them at risk. I'm also saying that

1:13:34 You know, everybody when they when they look at a prototype, what they're focusing on is the visual and textual expression. And so as soon as you produce something in high resolution, the feedback you're gonna get It's gonna be about colors and shapes and like these these presentation layer things, which are very loosely related to uh usability and value.

1:13:54 Right. It's it's like It's like focusing on the special effects of a movie that has a really bad story. And so at at ThoughtSpot we used to use what we called block brain diagrams, which were Even simplified versions of wireframes. It was just big chunky blocks of here's how the screen could be and where things might be located.

1:14:10 And because it was so low fidelity. People couldn't get into commenting on what it looked like, you know, we had to talk about conceptually what it was. And so we were trying to build up this firm foundation where we could go from the block frames to wire frames. Like to kind of the final expression. And I think it helped us.

1:14:26 clarify what we were trying to do conceptually. So that by the time we got to the final visual presentation. That stuff was actually really simple. I mean it initially it made the product team really nervous because we would be sitting in these block frames and wireframes for Sometimes weeks. And they'd be like, When are we finally gonna see the comps? And then what would happen is because we had such a robust design system.

1:14:45 Once we lock down on the on the uh block frames, we could send it to an agency and they could do the full high res comps. Like in a day. You know,'cause they knew exactly what they were doing. And so the PMs were always like What the hell happened overnight?

1:14:57 Like Well it turns out that the high rest stuff that's not the hard thing. The hard thing is like The heavy lifting of thinking. What are we really trying to do? That's the hard part. And if you do the high res stuff, you just You really muddy the waters.

1:15:10 Um and I think you end up spending a lot more time churning. If you didn't Again, I'm gonna go back to the movie metaphor'cause I study film. You know. If you're trying to fix script issues

1:15:20 when you're in production or storyboarding. You're gonna churn and you're gonna waste a lot of effort. So you kinda you gotta figure out what you're trying to do before you go Draw the h high red stuff. And I think a lot of the Jet AI tools. It's this seductive Hey, let's just go

1:15:34 Let's go make the comp and see what we think. I don't I don't really know if you're gonna get anything great out of that process. Maybe. Mm.

1:15:41 That's that's a really interesting counter. narrative because it feels like every product team now is just like straight to prototypes. I just had the C Uh, she's one of the CPOs at Microsoft. I realize there's many CPOs. Yeah. She has this concept of uh

1:15:55 demos before memos and just like prompt sets written EPRDs. You should just be prototyping all your ideas. And so it's interesting to hear the the perspective of maybe it's actually hurting your uh ability to come up with a really clever solution versus the the obvious solution. Yeah, look, I think at some point hopefully people just back up and ask themselves, Are we actually producing better product because of this process? You know, I mean and we're going faster, but faster can't be the ultimate goal. Like you need to be creating something great as well, right? Something that's sustainable and that and frankly that you're proud of and that your users find value in.

1:16:26 And if you're just throwing so much spaghetti at the wall, I don't I don't know if having a Spaghetti throwing machine that goes faster. You know. I mean I look there's a there's a counter argument that's You know, you can say, Oh, it's like Darwinian evolution and we're just gonna spin through a bunch of random mutations and see what you know, what happens. And I used to joke that, you know, it's it's true that, you know, if you take a bunch of hydrogen atoms and give them fourteen billion years, you could end up with a tiger.

1:16:49 But you don't know you're gonna get a tiger and you could get a six headed shrimp instead, and you don't really know when it's gonna ship. So I'm Not exactly sure Darwinian evolution is the way we create great product. But a lot of companies are Making a run at it. I wanna take us to a recurring segment on the podcast called AI Corner.

1:17:06 And in AI corner, I ask guests to share what's one way that you've learned or figured out to use AI in your job to help you do better work, to help you do Faster work. Well, my job right now is trying to figure out what my job is. Um and so the thing I've been using AI for is I've very explicitly been using it as a life coach.

1:17:25 And so I had seen a couple of prompts about asking it if You know, what the blind spot was or what my strengths and weaknesses were. I'd I'd seen some props about that stuff. And one of them was really fantastic. One of one of them was uh what's a What's an outdated mindset that I'm holding on to that's not still serving me? And he came back with this a very polite prompt or very polite response. About well, given your age and your profession.

1:17:47 It's not surprising that you're very wedded to the idea of control. But that's not really the world we're living in anymore. And that's not probably gonna suit the thing you're trying to do next, which is writing and publishing and speaking and stuff. And uh, although it's statistically derived, it did come back with a really nice phrase, which I've used in your show. Which was try to focus on choreography over control. And so I thought that was

1:18:10 That was really useful. I asked some of my blind spots, that was also useful. I use it for a lot of exercise input, that's useful. And the exercise that I've gone through most recently was Uh I I I realized that it was inferring these things about me.

1:18:23 From the things that I had asked it to help me with in the past. So instead I just switched, I just went to Chat GPT, start a new project. And said, I want you to be my life coach. I want you to ask me five questions a day for the next five days. Let's go through those so you can explicitly become better at helping me with this task. And so we've just gone through that process. And and it's been it's been really useful for me. It's no substitute for

1:18:46 A therapist or a real coach or anything like that is not a human being. It doesn't care about me. I'm not saying that you should use it instead of these other options you need A human being as well. But it's been very good at Reflecting back to me.

1:19:00 Things that I think have been floating around in my undermind. And so I There's there's a a wonderful book called um hair brain uh tortoise mind. by a gentleman named Guy Claxton. And in that he talks about the undermined. And sometimes you might have heard this as you're unconscious or something like that, but

1:19:15 But I think of your undermine as The part of your brain that's processing information before it gets to language. And then uh when you go to consciousness, you've turned it into language. And language isn't the full universe of things you can think. Language is what you can think in English. And if you talk to multi lingual speakers, they'll tell you that they can think things in other languages than what they can think in in English. So if you only speak English, you're only in one vein of what you can think. But your undermind is operating through all this other stuff.

1:19:41 And you know, for the computer nerds out there, you could think about it as an uh compiled code versus interpreted code. Right. So you undermine how to work in a compiled code. And it can do a lot of stuff. that you can't really do in the interpreted code, which moves slower and is kinda has different orientations and we call that consciousness. So I've feeding Chat GPT all this stuff over the last year or so.

1:20:00 And Th there are all these patterns in my undermine that had been going into that that I wasn't able to express with conscious conscious language. And so when I started asking it questions, I think what it was doing was it was statistically reflecting patterns back to me that already existed in my undermind. But because it was putting them into language, my conscious mind could now recognize them. And respond to them.

1:20:20 Um And so I again I found Yeah. as a as a sort of a life coach, I found it very useful. As a mirror back to things that I was probably already thinking.

1:20:29 And it helped me clarify my thoughts. It's not pushing me in new directions that like a a human might do. But it's still been super useful. That is extremely cool. That is a really cool use case. Uh, I don't know if you heard the Jerry Colonna episode that I did recently. He has okay, uh we'll link to it. He's got four questions that he suggests people ask themselves.

1:20:50 The first is the title of the actual episode. How are you complicit in creating the conditions you say you don't want? And this often leads to a lot of interesting insights about yourself. And there's an important part of it, like complicit being like you're not responsible, but you're actually achieved. Helping achieve a thing. Powerful word. Yeah. Yeah. And then also uh and it's an important element of uh say you don't want, like

1:21:12 You say you don't want to be busy. But something you just create keep creating busyness for yourself. Maybe you do want this. So anyway, we'll link that episode. There's a lot of good stuff there. Yeah, that's great. Okay.

1:21:23 One final question before we get to our very exciting lightning round. This is one that we uh that I don't think uh you have any idea I'm gonna ask you about. And so I'm curious where this goes. This is a story that Joff Redford suggested I ask you. He told me that you're obsessed with space. You love talking looking researching space, telling stories about space. There's a story that you share about

1:21:45 This guy named John Hobolt. Does that ring a bell? Oh yeah, totally. Okay. Share that story and'cause I think there's something really powerful here for people building products. So I should clarify, I I'm also I am a fan of astronomy in space, but I'm a particular fan of the Apollo program. Because I view the Apollo program and the moon landings as the greatest peacetime accomplishment of mankind ever.

1:22:06 And I think it's Uh An incredible There's there's a profound number of leadership lessons and individual lessons to be learned from that program. And I've done multiple talks about this. I could go on for hours.

1:22:19 Let's do it. The particular question you're asking is John Holwalt. So John was uh I can't remember exactly where he was in the NASA hierarchy. But uh he was one of the people that was tasked with figuring out the question of how do you go to the moon. So just to take yourself back in history a little bit, John Kennedy, President Kennedy goes to Rice University, I believe it's nineteenth September or May nineteen sixty two.

1:22:41 They gives the famous moon speech. We choose to go to the moon not because of it's easy, but because it is hard. That whole thing, which I also have to say and maybe a link to this in the show notes as well. Everyone should go watch that talk. That That is the perfect TED talk. It clocks in right at eighteen minutes.

1:22:56 It shows you how to sell a big, giant, bold vision. the specifics that Kennedy gets into, the way he sets context at the beginning, the technical problems are gonna happen, how much money it's gonna cost, the way he puts the passion, why we're gonna go to the moon, the whole thing. It is an incredible talk. Is the only moonshot talk ever. Because a moonshot has to actually go to the moon. And so it is

1:23:17 It is an incredible talk, so go watch the talk. But he steps off the stage. And people are Nasser like You know, we've we've only recently put Alan Shepherd into space, and he just went up and went down. I mean, that was like almost like a was a blue origins type thing. That was just up and down. We didn't even do a lap around the earth like the Russians did with Uri Guerin.

1:23:36 And now we're talking about going to the moon, like Nobody knows how to go to the moon. And there were three different options for going to the moon. One at the time, one was to build a big giant rocket. And just go straight to the moon. It's called direct descent. And the main advocate for that was Warner Von Braun, who was the main rocket guy in the world. Little bit of a complicated past, but nevertheless, Warner Von Braun's a big guy. He's got the president's ear. Yeah, he's like, Let's build a big giant rocket, go to the moon.

1:23:59 People are like, Yeah, problem is when you get to the moon, the rocket's still super big. So like these guys are gonna have to descend a big ladder. That's kind of a problem. So that was one idea. There was another called uh Earth Orbit Rendezvous where you spend two send two spacecraft to the earth and then you Yep, link them up in earth orbit and then one of them goes off to the moon, but you still gotta land that thing on the moon.

1:24:17 And then there's a third idea called lunar orbit rendezvous. Which is where you build a spacecraft that includes a smaller spacecraft. So so you send up two spacecraft together. One of them smaller, much lighter, and you use that just as a s the ship that goes down to the earth the moon's surface and back up. And that spacecraft is truly a spacecraft, it only flies in space. Which means the engineering requirements around it are profoundly different.

1:24:40 'Cause it doesn't have to survive uh re entry into the earth, right? And so as a result, it can be much lighter. And it turns out that the whole problem of landing on the moon is it's a weight problem. Like you gotta lift all the stuff off the earth, which is incredibly expensive for fuel. They gotta land it on them. I mean, there's just a lot goes on. And so Hubalt had uh come across this paper from a gentleman named Yuri Kondrachak. who was uh living in ukraine in like the nineteen sixteen nineteen eighteen when he wrote this paper

1:25:05 And he was the first guy to theorize lunar orbit rendezvous. And I try to take people back to that, like You and I could think about going to the moon. But Uri K and Drachak in nineteen eighteen. Is on the planes of Ukraine looking at the moon, and he's actually thinking about how to really go to the moon.

1:25:22 Like he's figuring it out. And so he writes his paper. John discovers it years later. And John's try to sell lunar orbit rendezvous. It's not going over at NASA. And so eventually he decides to go around all the hierarchy and he sends a very famous memo to one of the top guys at NASA.

1:25:38 The memo starts. Somewhat as a voice in the wilderness. And then it goes on. And then there's points in there where he's really emphatic, do we want to go to the moon or not? And then he goes through all the math of how going to the moon is all about weight.

1:25:51 And this was the only way to do it and there there was no other option and stuff like that. He just made the case. And you know, it was I mean, he risked his whole career. The whole thing could have blown up. He could have been fired for going around the hierarchy and all that sort of stuff. But of course He's able to champion the idea and and I think it was another year or so after that that famous memo, which you could read online. It's like nine pages long or something. um after the after the memo. Um it was still some time before they adopted Lorner Lunar Orbit Rendezvous, but eventually they do, and even with Valent himself was very

1:26:18 uh complimentary to that to Hubalt for kind of pushing that perspective. So I I tell the story one 'Cause it's just an amazing story. And it does kinda force you to go back to the moment of like, Wait, they didn't actually know how to do it. Like

1:26:31 We only know how to do it now because they've done it. You know, but there's that moment of uncertainty. I I think you kinda have to embrace And be amazed at that. And it also shows you the the power of these ideas, like a really great idea.

1:26:44 Somehow finds a way to live on. Somehow it just sits out there and it just waits for its time. You know, and Yuri had brought this idea into the world and it just sat around And then somebody discovered it and dusted it off and was able to pushed for it and it came through. And then

1:26:58 Maybe the third lesson is like ideas need champions, and they need champions willing to put themselves on the line for them. So if you believe in something. And you've made your case and you can really make your case. You know, have the courage to have the courage of your convictions and get behind it and fight as hard as you can for it. Mm.

1:27:15 Such a great story. Yeah, I love that you summarized the takeaways too, by the way. So the Like to me the takeaways and the lessons here is One is coming back to your Pinterest board in the office, say the hard thing. Two is

1:27:29 Be patient. You know, it may take a little bit of time for an idea to like a radical idea specially to resonate and stick and get adoption. So if you're you know you're pitching a big new product idea, like give don't assume that they'll immediately agree. Also just this idea of like if you really believe in it, do go ahead and go and champion it. There needs to be someone passionately arguing for this. Yeah, I'll do I'll just add to that one thing, like

1:27:51 I think people need to understand that they're advocating for ideas and not for themselves. And when I talk to a lot of designers, it may be true for PMs, I hear a lot of people Say that they're reluctant to post on social media or on LinkedIn or something'cause like, Well, I don't want to be you know, I don't be self promoting.

1:28:06 And I try to counsel them like look it's not about self promotion. Like it's a like there are ideas that you care about. Та й вона сіди ін на вород. Інсо гетар из на адре. It's a it's not about you.

1:28:19 But the idea. And and like don't be a Fray to stand behind the idea. We've spread a lot of good ideas in this conversation. Bob, with that we reached our very exciting lightning round. Are you ready?

1:28:32 Yeah, let's go. We added a ding to this. There's the whole thing now. Uh okay, first question. What are two or three books that you find yourself recommending most to other people? So the three books I'm gonna recommend. The first one's a uh a a beautiful poetic book about typography called The Elements of Typographic Style. By uh Robert Bringhurst. Robert uh was the poet laureate of Canada.

1:28:55 And the first eighty pages will change how you think about typography. It will open you up to the wonderful world of typography that we all live in. You will think differently about every sign you look at, about every movie credit you see. Like and it will give you an insight. I think into the designer mindset that is like when you understand typography, I think you understand where designers come from.

1:29:16 And the best designers I know are just total type nerds. So highly recommend elements of typographic style. Second book, Zen and the Art of Motorcycle Maintenance. Many people may know. Ultimately a philosophy book, but it's about the concept of quality. Which I think is a very important topic.

1:29:32 So it talks about quality and the importance of how things integrate into cohesive whole. Which I believe is the main challenge facing most software teams. They uh they create something that's highly fragmented. Instead of a single hole. So Zen and the Art of Motorcycle Maintenance. And then the last one is a book called Time and the Art of Living by uh Robert Uh Gruden.

1:29:51 It's just a very interesting collection of sort of impressionistic views of time and how time passes and what time means. So it's very different from the others. And it's Not something probably gets recommended on your show too often.

1:30:05 But I think it will I think it'll help people in their lives in a powerful way. Mm-hmm. Yeah, you think these are all brand new. Uh entries in the in this question.

1:30:16 Next question. Do you have a favorite recent movie or TV show you really enjoyed? So I really enjoyed Severance. I enjoyed it as a filmmaker, I really I was just blown away at the filmmaking. Uh I was intrigued with the story and the characters. Um And I think as someone who's worked in corporate America, when you understand that it's um

1:30:32 uh basically critique and commentary about the modern workplace. There were times that I just thought were unbelievably funny and insightful. It was it was definitely interesting watching it with my wife, who ha who was an attorney and hasn't worked in those kinds of environments. So it's like an episode where some people kind of got disappeared, and the language they were using was all around the language you would hear around a layoff. And so like I was laughing myself. But she was like what, like what's going on?

1:30:55 So I thought severance was super fascinating. And then I'll throw one other in there, which is not Something I've recently seen, but something I highly recommend for everybody, which is Lords of Arabia. Lords of Arabia. is is I think one of the two or three best expressions of the medium of film.

1:31:11 And so when you think about The ability to hold moving pictures, characters, story, music, photography, set design, costume, like the whole constellation of variables that come to play into a movie. I think Lords of Arabia is probably One of the two or three most complete expressions of what the medium is capable of.

1:31:30 And I think it's useful to think about in technology. all the different elements of a product and all the different elements of a user interface and how you can break those down the way You can break down all these elements of a movie and how many pieces of software do we use Where somebody is actually conducting that symphony.

1:31:47 In a really coherent Power full on way. I love that movie. Next question. Do you have favorite product that you have recently discovered that you really love?

1:31:58 You're focused on recent and I'm I'm just gonna push back. No, there's not the terribly recent The stuff that I go back to. I'll give you a couple of nerdy ones. I have a Leica M six camp, which is a film camera, and I recently started shooting with film again. Which I absolutely love'cause it forces me to slow down. I always talk about like a cameras, they're obscenely expensive, but the thing about Leica cameras is you show up different when you shoot with a Leica.

1:32:20 So when people think about cameras, they think about the quality of the image, they don't think about how the tool is gonna change them. And when you show up with an iPhone, you're thinking about sharing. When you throw up when you show up with a film camera, you're thinking about saving film and you're you're spending more time composing and thinking exactly about the shot. When you show up with the digital SLR

1:32:40 You just take a whole bunch of pictures and hope something's gonna turn out. And so I I think it's a I think these cameras are very useful metaphor. For being conscious. about how the tools you pick are gonna impact the thing that you produce.

1:32:53 So once you go into Figma, you've You've made a decision about the thing you're gonna produce. If you stay in a sketchbook, you've made a different decision. You know, if you go into Something else, you've made a different kind of decision. So I I I'm Say the like a M six with film because of that. And then the the the software product I would

1:33:08 point out, which is not terribly new, but I think it's worth noting. Is a tool called Habitica. And Abitica's really fascinating. It's a It's ultimately it's a habit tracker and task management app. But it's fundamentally a game. It's a role playing game where you create a character

1:33:23 And your character evolves and can buy armor and go on quests and things. As you check off your habits and stuff. And it is The most interesting expression of shifting conceptual models that I've ever seen. So if you Think about a conceptual model, it's sort of the software equivalent of a genre in a movie.

1:33:39 And so like once you say it's a project management software, you're kind of in a certain genre. If you say it's a A productivity tool, you're kind of in a certain genre. So if it's you know social media, you're kind of in a certain genre. So these are different genres, and Habitica is really interesting because it it mixes genres. It mixes role playing game. With pro with uh with the do manager. And so I think it's a really powerful example of how you can

1:34:00 really shift the user's thinking in the same way like movies, for example, like Star Wars is ultimately A cowboy movie set in space. And when you come to that those those two genre mashups are really interesting. When you come to a rom com you have a certain expectation of what's gonna happen to a rom com sudden if somebody suddenly got shot a rom com, you would like That would not make sense to you in the same way that if somebody made a really funny joke in a John Wick movie, it wouldn't make sense. So I think

1:34:24 Habitic is just the most interesting example I've ever found is somebody really doing it. Fascinating mashup. of uh conceptual models. Which is Sorry, this and then I'll stop. It's just it's an unexplored and unexploited possibility of software ideas.

1:34:38 I love how profound this lightning around already is. The the point about Leica changing the way you even think about the photo is so interesting. I've never thought of it that way. Um, you mentioned Star Wars. Have you seen Andor, by the way? Uh no, but my wife everybody's raving about it. It just I've been watching basketball, so I just haven't had the spare time yet. But I have a basketball question, but first of all Before we get to that. Do you have a favorite life motto that you often come back to find useful in work or in life?

1:35:04 Yeah. So there's three quotes that I come back to all the time that I repeat in most of my talks. First one I've already used, which is design is clear thinking made visible by Edward Tufty. Second one is from the American landscape photographer Ansel Adams, and I've also alluded to this. There's nothing worse than a brilliant image of a fuzzy concept.

1:35:23 And then the last one is an African proverb and it goes like this. If you wanna go fast, go alone. If you wanna go far, go together. And I think we've kind of touched on all three of those things today. When we've talked about the resolution of comps, we've talked about using Gen AI to try to go faster, things like that. And you know, those two ideas uh kinda collide in an interesting way. You know, people

1:35:44 think if they cut their colleagues out of the pie they can go faster. And it's true, they can go faster. You just can't go very far. Like you need a group if you want to go far. And just because you can create a brilliant image doesn't mean you got a good concept. Go look on Instagram. You'll find plenty of photographs that like

1:36:01 Tangle your senses from a visual perspective. And you will forget them by the time you close the app. Because they don't mean anything. And so we live in a time when it's very easy to produce things at incredibly high production values. But they don't mean anything.

1:36:14 And so they're just like Fancy potato chips. There's no there's no nourishment there, man. Like I love that this connects back to the vibe coding apps and prototypes that people build. But you you know you can do it really quickly.

1:36:27 But It won't go too far. Potentially. Yeah. Not to hate on those tools, they're amazing. They are. They are at like all this AI stuff is per

1:36:36 Profoundly amazing. Um and I I I I will encourage people, like one of the most amazing things for me about this moment in AI Is that this the kind of AI we're experiencing has been theorised for well over fifty years. So there is a vast No a vast Warehouse of

1:36:50 of interesting, amazing thoughts from philosophers and engineers and social scientists and people thinking about what is this moment gonna mean when we have this sort of Artificial intelligence that challenges our conception of what it means to be human. So Like

1:37:04 There's so much stuff you could be reading to help you process this moment in the in the very intense and profound psychological challenges it's bringing forth. Mm. It definitely feels like we're finally living in the future. Like the future's Actually happening. Self driving cars all over San Francisco. It's yeah really really stark.

1:37:22 It's a future, yeah. I say future. Well that's that's my concern with a lot of the the fiction of of the future is most of it is dystopian and like here's all the problems that we're gonna run into. Which in you know is gonna be useful. Like here's the robot laws that we gotta be thinking about. Yeah, I s you're just Just to go back to this idea of how once you ex once you create an expression of something, people baseline off of it. I recently got to hear Henry Motiset, who's uh head of design at uh Perplexity. give a talk. And one of the things he said that just really struck me was that people's conception of AI

1:37:53 was founded by was was uh put out there by Hollywood. Years ago. So this idea that h that AI is gonna take stuff over and is ultimately like really uh dystopian and malevolent towards humans and stuff like that. It's actually something that's created by Hollywood. And we're all like and now we're like trying to outlive how, you know, and stuff like that.

1:38:11 And so it's just Just such a great example of somebody put the concept out there and planted that seed in people's heads. And now we're struggling to get people off that baseline and to look at it with fresh eyes. That's a that's a really good point.

1:38:26 Yeah. It's it's much more entertaining to watch, uh Yeah, I try to kill us all, not just oh, everything's amazing. Great job, uh yeah. Okay, final question. I know you're a huge sports fan, in particular you're a big Warriors fan. So let me just ask you this. Say you were running the warriors. Say you were the owner of the Golden State Warriors.

1:38:44 What would you what would you change? What would you change to help them win? You know, a a team, like a real team. Can't be dependent on a single player. And I think There's such a dramatic difference.

1:38:57 In the Warriors when stuff is on the court and off the court, you know, if you listen to the to the local announcers, they're always like these non stuff minutes really matter, you know? Like I look at that and I'm like that's not That's not really a team then, right? That's like Steph and you know, it's it's like Steph and the in the in the band of Merryman. And and the Warriors are bigger than that, right? And Most of these basketball teams are bigger than that. It's it

1:39:17 currently I think across a lot of places in the NBA there's a single player that can go down that makes a difference in the organization's uh success. And that just seems Dangerous and not a team. So I mean, I kinda don't know what to say. I don't know how you replace Steph Curry.

1:39:33 He is a s you know, singular I don't even if you know, even call him a generational player, it's a bit bigger than that. You know, he is Unequivocally the greatest shooter in the history of the game, and he's one of Only two or three players has actually fundamentally changed how the game's played. But I just know for winning.

1:39:47 The warriors are at risk. Because Steph is meaningfully old for an NBA player and You know, you can't have the whole franchise built around just him. I love this hot take. A great way to end it.

1:40:00 Bob, I can listen to you all day. This is so fun and interesting. In so many ways, on so many levels. Uh, two final questions. Where can folks find you online if they want to reach out and maybe learn more about what you're up to? And how can listeners be useful to you? Uh, so BobBaxley dot com is the easiest place. Right now it's just a Bento site, but I'll Get some more stuff up there uh in the coming

1:40:19 coming days, hopefully before this episode goes out. We'll see. But there's plenty of links there. That'll h help you connect to me on LinkedIn and and some of my talks and a few Links to some other things that I find useful. Uh just find me on LinkedIn. You know, I publish pretty much every day on LinkedIn. That's an easy way to find me. Yeah, I'm happy to

1:40:35 Happy to be connected to whoever uh is interested in being connected. And then it turns out you can help me, you know? I'll go back to what I said earlier. It's not really about me, Lenny. It's it's about these ideas. It's about the idea that software matters. You know, that we're making something for people on the other side of the glass and that it's a way that we show that we care and that we should care. So I wouldn't

1:40:54 It's it's not about me. It's about Us Together try to create a digital world that we want to live in. You know, the digital world right now. It's not something we really want to live in. It's not a place any of us would turn our kids loose in.

1:41:06 You know, you know, I talked about this earlier, like The digital world's not safe for our kids, like Haven't we kind of done something wrong? So I just uh

1:41:15 Yeah, I just I I hope people take that responsibility more seriously and try to But help clean things up a little bit. I think we've we've made a dent in that. Bob, thank you so much for being here. Yeah, thank you so much, Lynn. It's been it's been a real honor, privilege, and a just a ton of fun. So thank you so much. Same for me.

1:41:32 Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show. At Lenny's podcast dot com.

1:41:54 See you in the next episode.

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