35 years of product design wisdom from Apple, Disney, Pinterest and beyond | Bob Baxley
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Almost everyone living in a modern economy now is going to have hundreds of interactions with the phone or with a computer. And unfortunately, a lot of those interactions are not going to 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 grafted on after the fact.

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? I just seek out opportunities to witness history. The whole company is constantly asking, how can the thing that I'm working on be a little bit better? Why do you think that people that have left Apple, like a lot of amazing things haven't emerged?

Today my guest is Bob Baxley. Bob is a designer, executive, and advisor who's built and led design teams at Apple, Pinterest, Yahoo, and most recently ThoughtSpot. Over the course of his career that spanned over three decades, Bob has played a pivotal role in the design of the Apple online store, the Apple app store,

Pinterest, and early in his career, Yahoo Answers, products that have been used by hundreds of millions of people around the world. Bob also mentors individuals and advises organizations that are working to improve the practice, craft, and culture of digital product design.

There is something in this conversation for everyone, from why you should consider having designed report to engineering, why it's your moral obligation to build great products, why you should wait as long as possible to draw a picture or create a prototype of your idea, to what the moon landing can teach us about building better teams and products.

I could listen to Bob all day. I learned a ton from this conversation, including a bunch of really unique insights that I've never heard before. A big thank you to Annie Warner, Andrew Hogan, Irene Ah, and Joff Redfern for suggesting questions for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, 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 Lenny's Newsletter.com and click bundle. With that, I bring you Bob Baxley. This entire episode is brought to you by Stripe. There's a reason that I've had more guests on this podcast from Stripe than any other company. It's because they hire the best people and they build incredible products. You probably know them for their payments platform, which powers my newsletter, and also companies like NVIDIA and Salesforce and Zoom and DoorDash.

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$1.4 trillion flows through Stripe annually, which is equivalent to over 1% of global GDP. Use Stripe to handle all of your payment-related needs, billing, manage revenue operations, and launch or invent new business models. Learn more at stripe.biz. Bob, thank you so much for being here and welcome to the podcast.

Lenny, 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. I think of it sort of like where the film industry was in the 1920s. We've had our talkie moment. We're kind of on the cusp of having our shift to color movement, but we're still trying to figure out how to make movies. And a podcast like yours, specifically yours, I think is one of the greatest resources we have for learning from one another.

So I appreciate all you're doing for the community and for helping us as a community make better software. Wow. Well, I really appreciate that. That means a lot coming from you.

There's so much I want to talk about in our conversation. There's a story that I hear that you often tell, which is when somebody asked Steve Jobs once, what is your favorite product that you've built that you work on? And his answer, what's that story? So I actually can't remember where I heard this, but I believe the story is true. Steve at one point was recounting the products that he had created that he was most proud of. And if I recall the whole list, it was the Apple II, the Mac, the iPod,

the iPhone, I think Apple retail was in the list. And then he said Apple itself. And when I heard that and when I've reflected on it, you know, that is the longest lasting thing. And I remember there was also a story that Steve was talking to, I think it was either Ed Catmull or John Lasseter at Pixar. And he said, you know, everything we make is going to be a doorstop in three years. But the stuff you guys make is still going to be watching in 100 years. And so I think Steve had some

concept of the longevity of these things. They knew the products themselves were very ephemeral, but there's something about the culture of Apple that's lasted a very long time. And I personally believe it'll last 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 the value of technology in the world. And it infuses everything in that company. I mean, everything from the checkout system, when you go to the receptionist, to what it's like in the cafeteria, you know, the

At least when I was there, they had patented the pizza box because they had reinvented the pizza box that you would get at Cafe Max because they're just the whole company is constantly asking, how can the thing that I'm working on be a little bit better? And I think that was something Steve brought to them and had them constantly asking that question.

One more Apple question, then I'll move on to other stuff. Why do you think that people that have left Apple, a lot of them, like a lot of amazing things haven't emerged from people that have left? Like Humane was a recent example. You know, we're recording this the day after Johnny Ive and OpenAI emerged, so we'll see what happens there. But it just feels like there hasn't been a ton of

alumni that have built incredible things. Yeah, I'm hard. So obviously, Tony Fidel would be one with Nest and he would he'd be an outlier. I think the people that, you know, I went to Pinterest and did not have a successful time in my year and a half at Pinterest. You know, I think my own particular mistake and I've seen this with some other Apple executives as well as we went directly from Apple. Like I went I left Apple on a Friday and I started Pinterest on a Monday and I didn't give myself time to to recalibrate to the to the Pinterest culture. So I think

I think at some level, a lot of the challenge is that when you, 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 into those, all those standards. And it's really deep. It infuses all of your behavior and how you conduct yourself in the company, away from the company. And so I think it's 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 companies

that sort of natively operate like that. Airbnb is one exception. And so you have guys like Hiroki Izai, who leads all of marketing and all of product, and Hiroki is crushing it at Airbnb. He was incredibly successful at Apple. It also should be noted that he had, he was

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, at Apple, I think it was Tim or Steve used to talk about the Apple car wash. And then when you started Apple, they kind of had to take you through the car wash and get off all that stuff that you'd accumulated at other places. Turns out there's a car wash you need to go through when you leave Apple as well. And so I think Hiroki gave himself time to do that. And I think that's probably a lot of why he's been so successful at Airbnb. The thing I took away from Apple, and I think

this is true for anybody changing from one major culture to another, is most likely the new place hires you because of the values of the organization you left, but not the behaviors. And so I think it's important to kind of recalibrate and say, well, I want to hold onto these values. So at Apple, attention to detail, product excellence, doing everything you can for the customer and the user. So try to hold onto those values, but then think,

okay, how are those values best expressed in this culture? And I was more successful at expressing those values in the culture of ThoughtSpot, which was my last job, than I was in the culture of Pinterest. If I had to do it again, I could probably do better at Pinterest. So I think that's useful for anybody leaving one

very specific culture and going someplace else and like try to hold on to the values, but not the behaviors. This is so interesting. And I appreciate you sharing that you, the way you described it, that it wasn't a successful stint at Pinterest. A lot of people don't share that sort of story and don't put it that way. You know, they see on their LinkedIn, Oh, head of design at Pinterest. Oh, amazing. So cool.

And then, you know, if you're like, OK, but it didn't work out that well. I think that's really interesting. Is there anything more you can share there about what you learned for other people to maybe avoid that sort of situation? Anything you 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 came in.

thinking I was supposed to behave the way I behaved at Apple, which is very direct, fighting hard. Everybody cares about each other. It's never insulting, but it's intense. And that's not really where Pinterest was at the time. 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, Pinterest had posters in every conference room that said, a big poster that said, say the hard thing.

Well, that's where Pinterest was at the time. And I can assure you, nobody at Apple was having to remind you to say the hard thing. And so I probably could have picked up on that better than I did. I'll say like,

these careers are really hard, you know, and the higher up you go, I sort of people think of it like you're climbing a pyramid. I think of it more like you're going out on a branch on a tree and the branch gets a lot more flimsy and can break and you can fall and you get buffeted about by the wind. And it's often at a time in your life when there's a lot going on with your family. There could be things going on with your parents' health. I lost my mother when I was at Pinterest. You know, my kids were starting high school. So we're struggling with the teenage years. I had a long, long commute. I mean, there's just a

There's a lot going on. And these jobs are super demanding. Everything around you is changing really rapidly. And you're under tremendous pressure because the financial and success stakes are super high.

So I think the people like falling off of these jobs 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. One of the things I took away when I was at Pinterest was I came to think that the job of a startup was to grow the founder so they could continue to lead the startup.

And I think what's true for founders is also true for a lot of other folks 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. And it feels like a failure. I mean, 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 we could debate the...

We could debate the merits of Mark Zuckerberg, for example. But when you think about the trajectory from being a kid in a dorm room to within five years, Facebook's a big thing. I mean, think of your own life. Can you process that level of evolution and change? And that's just, I don't know. I think that's really super hard to do that and stay balanced. Yeah.

And also keep doing that for so long. Like the Airbnb founders, I think it was Brian's maybe first job or second job, and he's doing it now for 15 years in a row. Oh, founders, it's their life. It's very unusual to see founders move out. I had this other theory that a startup is still a startup until the founder moves aside. So by my definition, even Meta is still a startup in a way that Amazon's not. And Airbnb is still a startup in a way that Pinterest is not because 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 going to happen. Just to close the loop here. One takeaway here that I think is really interesting is that you can fail in a job and things will be OK. Clearly, you're doing a OK and having a place that doesn't work out doesn't destroy your career, which I think a lot of people feel like if they're not doing well in their current job, it's over. Things are all going to go downhill.

Yeah, your career is not your life. There's a lot more to it than that. And then just to give someone something tactical here. So you've realized the culture of Pinterest. You bounced off of it. I love that metaphor. When you're looking at new companies, what's 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...

Do they have a story as to why they believe in design? Like really in their heart and soul, do they care about design? Because if I go into a company that doesn't really value the thing that I do, I'm just not going to have a great time. And I'm going to 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 in the case of my again my most recent job was with a company called thoughtspot and thoughtspot was founded by a gentleman named ajit singh and ajit grew up in rural india but he tells this really great story about uh early in his career he studied chemical engineering he moves to the united states early in his career he's working for honeywell and they did a couple of engagements with ideo and as a very young person he got to see what ideo did and he realized the power of design and he's taken that to all of his companies he

started Nutanix before he came to ThoughtSpot, before he started ThoughtSpot. And so when I heard that, I'm like, oh, this is a guy that gets design right from the very beginning. And I've also come to believe that I actually have never seen a company that grafted design on after the founding. So I've seen lots, I could name lots of companies that I think are kind of design-led, not always designer-led, but design-led or design-centric, but I've never seen somebody grafted on after the fact. It's there at the beginning in the root DNA or it doesn't exist.

And so the thing that I'm looking for when I interview is, is it there at the beginning? Can I get 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 culture.

value system in a way that like, you know, as an American, I could, I could immigrate to Australia and the culture would be slightly different, but we'd have a shared value system that I could relate to. If I moved to, I don't know, Burma or China or something, it would be wildly more challenging because the, the base culture,

few 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. 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, to the founder's value engineering, do they value product? Do they value design? Depending on who you are. Yeah. Why would you want to work in a place that doesn't value the thing that you do? That would just, God, that would suck. Yeah. You actually have a really unique perspective on just what is design that I haven't heard before.

Let me ask you that question. What is design? Well, I'm going to go back to the Edward Tufte quote that I use all the time, which is design is clear thinking made visible. And so 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. When design thinking became big, I was always really confused because I didn't know how else you could think. That was just sort of how I naturally thought, which is

you know, design is trying to imagine the future you want to live in and then take the steps to make it real. You know, it's living with a certain type of intentionality and almost sort of a Buddhist type way, which is different from science, which is sort of observational, trying to understand. It's a little bit different from engineering, which is

We kind of know where we want to go at the end, but we're trying to kind of go one step at a time versus designs, trying to see some further out future state and account for a larger or sort of a different set of constraints and issues than engineering or some of the other problem solving methodologies. So I look at, again, I look at it as a company. Does the company think in a design mindset? Yeah.

And Apple does. Airbnb does. I don't get the sense that Google does. And I don't get the sense that Amazon does. And 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 want to go work in a place that as an organization thinks in a design type method. So along those lines, a lot of people, imagine every founder, every product builder would

It's just like, yes, I love amazing design. I'd love our products to be incredibly beautiful, intuitive, so easy for everyone to use and understand. But they don't actually invest in these areas and they don't put a lot of resources into the design process.

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 bottom line of the value of design? Let me back up and just dissect a little bit the way you described design because you described it in really tactical terms. You said beautiful, intuitive products that make sense. I think it was something like that. So what you were describing was

You were describing the part of the iceberg that sits above the waterline, which is the result. That's one of the outcomes of design, but that's not the real heavy lifting of design. Design's more like liberal arts or philosophy or something. It's like, what do we try to achieve at a much lower level? And so when I talk to founders and people about the value of design, what I'm pushing them on is when we can get organizational alignment around what we want to do philosophically, why do we exist? What's the vision for the company? How do all these things ladder up?

through vision, through mission, through specific 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 difference is when you design things, you end up with a bunch of bricks that are piled into a beautiful, impenetrable wall. And if you don't do that, you end up with a bunch of bricks scattered across the backyard and they don't really add up to anything. And I think that's

One of the things, if you look, you know, again, to go back to Apple, but we could also talk about Lego, Leica, Porsche, Airbnb. I mean, there's other companies, Patagonia. There's other companies that make sense as a design centered organization. And if you think about like everything they do, it all ladders together into like one cohesive, sensical organization.

thing. It's integrated, makes sense as a unit. And I think that's a huge difference and 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, at Apple, for example, on my, the store that, or the team that designed the online store, you know, we had six designers. For a store that ran in 30 some odd countries, 12 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 60 or more. So Apple's able to operate with much smaller staff because they have real clarity of vision of what they're doing. And the benefit of operating with a smaller staff is not

Just that it saves money on payroll. It's that you have, you know, the way the minds come together to create something that feels like a single whole is a much higher chance when you have fewer people involved. You know, you don't, I sort of joke about the Beatles, you get the Beatles with four people, you don't get the Beatles with eight people. And you certainly don't get it with 24 people, right? Like the teams get too big and you just, you can't get that.

that what Brian Eno calls a seniors. So, so Brian Eno has this great word that he uses. Seniors is the genius that comes when you have a group together. So seniors 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 usually it's in smaller groups. It's hard to do with a giant group. I love that. I love this metaphor of the Beatles as, as,

you know, the way most people describe this is designed by committee never works. And I love that your example, the way you describe it is the Beatles is kind of like the ideal size in, you know, like a small group versus a committee. I just always have to point out to people that there are 20 people that worked on the original Mac.

I mean, it's 20 of them. That's it. 20. Susan care was one of them. You know, Andy Hertzfeld, you go through the list, 20 of them are on the patent. There's 24 that were that are on the iPhone patent. Now there's other people involved, but generally there's 24 people on the iPhone patent. And that's, that was kind of the team that was like project purple that was doing that stuff. These are not massive, massive groups doing these things. And if you had put a massive group, I don't know, man, like maybe it'd end up with the Zune or something completely different. Who knows? They probably did have a massive group on the Zune. Yeah.

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 this 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. It's just hard to figure out something new to do together when there's too many people involved.

I think that word new is really key here. I think when people hear this sort of advice, you know, they're thinking if they're existing company, should we just keep our company small? Should we not scale this thing that we have? And I think what you're describing, which I completely agree with is new stuff. For sure. You want to keep the team small and, and tight, but I, you know, as things grow and scale, uh,

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

clarity of vision, 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 CP of N26 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 got to win. We got to do this. Larry Page or Sergey was sitting next to him, just like we got to make this work and putting everything they could into it.

And it didn't work out. And I think that's the more people you put in it, the slower everything becomes. 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 your experience here, I think Apple is a very different kind of company where design actually leads a lot of this. Yeah. 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 at a dinner one night. He said, you know, saying a company is design-led does not mean it's designer-led. And so what I try to hammer home with people is that...

When I talk about design as a mindset, I'm talking about it as a mindset. Like anybody could have that mindset functioning in any role. Any designer could have a product mindset. In fact, I think that's a lot of what the design community is trying to get at now. And they say designers should be speaking the language of business. I think what they're saying is designers need to inhabit the product mindset as well. And maybe to some degree, even the sales mindset. So look, both functions matter. I look at my counterparts in product and I assume that they are much better connected to the customer

that they understand much better the business realities, and I expect them to drive the roadmap. I may have some points of view on the roadmap. I may offer some critique. I may have my own suggestions and agenda in there. But once they say this is the roadmap, I have to believe that they're right, and I don't try to bleed into their space. I very much believe that once you get into a company, your job is to figure out your role and respect the boundaries between the different groups.

So I'm like, you guys, tell us what you need us to do, what the features need to be, when they need to be delivered, what the issues are, and then give us the time and space to come up with a solution to those problems. And then we can work together to decide whether or not our solutions actually solve the problem as you understand it. But I'll stay out of your roadmap and you stay out of my design stuff. And let's try to get to the promised land together. So I...

assume that the product managers, particularly in enterprise SaaS companies, like my team, ThoughtSpot did data analytics. My team didn't know anything about data analytics. We didn't have any of that insight. We didn't have the bandwidth, the mental horsepower to go out and do that stuff. Like we had our hands full just trying to figure out the UI. And it's,

It's one of the points I try to make, too, when people are starting to theorize that Gen AI can remove teammates, you know, and oh, the designers don't need engineers and the PMs don't need the designers and like everybody thinks they can throw engineering overboard. And I'm like, stop it. Like, we all need each other and we need each other because we need those different mindsets. And any one of those mindsets is just too much. It's like it.

One of those mindsets inhabits somebody's head completely. I just don't think you can simultaneously hold multiple mindsets in your head. So it's not that one of my PM counterparts couldn't bring a lot to the design table. It's just, I need you to play that position.

Like in baseball, like, you know, you don't like the second baseman doesn't cover first. That's not how it works. Like, you know, everybody's got to spread the field and play their position so we can take care of the whole thing and respect that together we're going to come up with something better than any one of us would have come up with alone and embrace the creative tension, welcome it. You know, we still have to all go out to lunch and love each other and have fun together and keep in mind that we're having fun together. But, you know, I like I like the rub. That's where all the magic happens.

That was a very illuminating clarification. Something else that 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 is different and different organizations work in different ways. In my experience, I think that design is most successful at impacting what ships at the end if design is considered phase zero of the engineering process.

rather than a byproduct or a part of the product process. So I just think what I've seen happen over and over in my experience at Yahoo, ThoughtSpot, Pinterest, other places, you know, when you're working directly with product

It's easy to kind of leave engineering out of the loop and product and design can go cook up stuff that doesn't quite make sense technically or is really hard to implement or is just a bridge too far. And I think that engineering doesn't feel like they're a part of it. So you bring them 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. Maybe they don't bring their same level of enthusiasm to it because they haven't been brought along. So I think there's something about having the design and engineering team very tightly connected and kind of living together. And it's not that you have to do that structurally from an organization point of view, but it's hard pressed if you don't. I 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 three co-equal branches of government. And that's a solid argument as well. And there's some places where that works beautifully. My experience is that design rarely has a budget or an army. And so it's very hard for them to really hold their own in that sort of a setting.

Also, although 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've just never seen a number that you could apply to design that we could reliably affect. So I think it's very hard to hold design as an organization accountable for a particular outcome the way that most of the other C-level roles are held accountable. Right.

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 chief design officers and we could go through the list. I just think in many companies, that's a stretch. It's just hard. What I see work, and I'm curious to get your take, is just product engineering design have exactly the same goal.

And the more everyone and their performance as an employee is tied to the same thing, essentially, because then everyone is pushing in the same direction versus like, oh, I have my engineering goal. I have my design goal. I have my PM goal. It just creates all kinds of weird incentives.

Yeah, look, 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 add my whole career together, I've worked at maybe half a dozen places, a fairly limited sample set. And every design team that I've ever been a part of, I've been a part of. So I also kind of have a biased view as to what didn't work for me and those particular organizations.

I'll go back to what I said. Every company is different. Every culture is slightly different. It's not one size fits all. I point out the idea of design reporting to engineering just because I don't think people consider the possibility often enough. So there's three options. Design is its own thing. Design is part of product. Design is part of engineering. And I think there's a moment when you can back up and make an intelligent choice about the pros and cons for each of those options inside your org. And so I would encourage people to just take a design perspective

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, 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 love how radical this idea is. I've not heard it. I think designers will be like, you should just stop it. Just stop it. Yeah.

So have you operated this way? Have you had design report to engineering companies you've 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, now I think it's structured a little bit differently, but design has always been part of engineering at Apple. So I saw it work quite effectively there, obviously. Yeah.

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. What's something you've seen work that helps achieve similar outcomes with having engineers integrated early in the design process?

Yeah, look, I think you have to find some way that you are able to identify a few people in engineering that I refer to as creative technologists. So these are people that can come into what's ultimately kind of a fairly airy-fairy philosophical discussion about what we could do and what's right from a conceptual model perspective. And ultimately, it's sort of a philosophy issue. And there's not that many PMs or...

that can sit in that space and be comfortable with the ambiguity of it all. Like a PM's likely going to come in and they're going to 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 going to have another meeting and we're going to talk again. And the engineers oftentimes when they're starting to hear different ideas, they're already cutting into the code and they're trying to figure out what's hard and what's easy. And so I think the trick is at the beginning, can you find a small group of people from the different functions that can sit with the ambiguity of

of the space and talk through a broad range of ideas to identify the direction we want to go into. And then once everybody kind of falls in love with the direction, then you can go into the more tactical mindset of, okay, well, when we can ship it and who can we show it to? And, you know, how are we going to code it? And when's it going to 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 worst thing is when you bring something fully baked. Well, the worst thing is when you bring something fully baked to anybody for their approval. You know, we could talk about this with when you take a final design to an exec and an exec sees it for the first time in a high resolution state. We'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.

I don't know. Like that's, that's not mentioned here. So going to be, be excited about, they're not order takers, you know, how do you make them part of the process? And,

Most every product of consequence that I worked on, there was some moment when we were showing it to some critical person and you could see that they fell in love with it. Sometimes they're 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 the critical moment because I knew that design can't bring any of this stuff into the world on its own. We can't raise this baby. We need the village. And we need the village to fall in love with the baby.

And so until that happens, you're not really quite sure if this thing's going to 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 add to it. And you got to bring them along at the very beginning. What I'm hearing there is there's a big part of just buy-in and then there's also just obviously more good ideas early are great. Yeah. Sorry. Buy-in doesn't feel quite right to me because buy-in feels like, oh, I've come to agree with you. And that's different from it's a part of me. You know, I, I,

When I'm talking to 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 fundamentally a maker. 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 lifetime and creative energy creating software.

And so I believe in my heart that they're all fundamentally makers. And the thing that I know about makers is that they all want to make something they're proud of so they can take it home at the end of the day and show it to their parents and say, look at what I made at school with my friends today. Like that's the fundamental thing. And they're all doing it from their own different points of view and their own different incentives and mindsets. But they all at the end of the day want to make something they're proud of. And so it's not a matter of getting their buy-in. It's a matter of

Them being a part of it, you know, that it's like, it's, I don't know, it's a part of their soul in a really deep, meaningful way. And I don't, I'm not sure you can graph that on to somebody after the fact, they kind of need to be there at the moment of inception, if you will. Wow, 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 B2B software.

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 you're building. Say you're building some kind of, I don't know, expense management system or HRS thing. Just like, where do you, what do you recommend people do in terms of just how far to go in design as a lever, as a differentiator maybe? Yeah.

Well, you know, inherent in your question is this assumption that design takes more time. And so I'm going to kind of reject that premise because 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 going to be a good one or not.

And I think there's things that you can do so that you're able to operate it at a quicker paces design. If you, again, if you kind of get the, we haven't talked about tenants yet, but we'll get to that in a moment. You know, if you kind of create a shared philosophical understanding of the product and what you're trying to do, you can go really fast because you're not asking the question of what should you do? You're asking the question of what would this company with what we stand for do for this thing? And that's a much easier question. That's much smaller. So if you look at the company,

companies that have the largest design teams, they're often the companies that have the most ambiguous cultures and the most unclear design vision. When you go to companies that really know what they're doing and they're clear that this is who we are, this is what we stand for, the design teams are super small because they're not sitting there trying to do all these permutations with color and typography and ideas. They're operating in a really narrow vein because they know who they are. It's

It's very much like individuals, you know, when you're a teenager or young adult, you can spend a lot of time trying to figure out what to wear because you haven't really sorted it out yet. But by the time you get to be a little bit older, you've kind of got your personal style. And so like dressing in the morning gets to be a lot easier. And it's the same thing. Like at Pinterest, I was at Pinterest at a point when Pinterest wasn't quite sure what it, who it was. And so, yeah.

when we were going to do like an onboarding flow, we had to look at a really broad sweep of things because 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 I agree, like, look, having your soul in every little checkbox sounds like a high bar. And in some ways it is, but you also need to, I think you need to be able to back up and look at the product

Maybe not at every state, but generally every six months or a year, you need to back up and ask yourself, am I proud of this? Is this something I am happy to be a part of? Do I believe in this? 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 because I have other goals?

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

Yeah. So like 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, 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 forget clear. Let's try to make it as confusing as possible. So the idea of clear, it's nice to have out there as a,

I don't know, sort of a platitude to move towards, but I just don't 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. And so it's sort of that at scale. And the story comes from when they were starting to work on Keynote. Apparently, the guy who was responsible for originating Keynote went to Steve and said, you know, how should we think about Keynote?

And Steve said, "I want you to keep three things in mind. One is it should be difficult to make ugly presentations. Two, you should focus on cinematic quality transitions. And three, you should optimize for innovation over PowerPoint compatibility." And if you take that last one in particular, if he hadn't kind of said, "We're going to go this way instead of that way," that team would have spent the next 10 years gouging each other's eyes out over whether they should try to go for PowerPoint compatibility or innovation.

And so when I was at ThoughtSpot, I realized pretty early on that I wasn't going to be able to have any sort of command and control over everything that was going to 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 through a mindset of control to one of choreography.

I needed to try to set the culture and set certain design tenants that everyone could internalize and follow and hopefully then make the right decisions in that groove, if you will. And so we had three. I think you can't have more than three or four because you need everybody to memorize them. They can't be consulting a handbook. And so one of them was documentation is a failure state, right? Like in enterprise companies, a lot of times people think, oh, we'll just put it in the manual, be part of the training. And I would constantly be coming back and go, stop it. No.

Nobody wants to learn our software. Nobody cares. We are just one more browser tab in a world of browser tabs. We are not this user's complete world. They do not want to learn this stuff. Documentation is 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. 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 is like, we're a super powerful tool. We can do all sorts of stuff. So when you sit down at Tableau, you know, it feels like you're flying the space shuttle. And if you're a 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, people who didn't live and breathe this stuff every day. So our goal with them was that they could sit down and it was an approachable piece of software

and they could turn on all the bells and whistles and power if they wanted it. So that was the second one. Start simple, let the users opt into complexity. And the third one was the entire product should look and feel like it came from a single mind.

And this was a tenant to try to combat 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 quite the way we might want them to for our future.

And so 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? Are we doing something else here?

So there's kind of this implication in this discussion about tenants 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,

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 haven't been able to add a bunch of stuff. We tried to come up with tenants for individual features and we kind of had trouble with that. It

It felt like they kind of operated at the, 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, 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 kind of seem to be digging in and things sort of seem to be bifurcating into two camps. And then is there something we can do where we just settle that? We just have that debate once and for all. We decide as an organization, we're going left instead of right. And you're absolutely correct. You have to be opinionated, but that's how you're going to win. There's no unopinionated software that's been successful. You have to have a point of view.

The question is, what's it going to be? So I'd say practically, like just try to look for places where it seems the team's having the same debate over and over and have it once, get it done and put it behind you. And make it a tenant. And why is the word tenant versus principal so important?

I don't know. I settled on tenant. I'd have to go look up the definition. I was trying to differentiate it from principles because I think principles are just, you know, I describe principles as sort of apple hood and mother pie. Again, they're just not something people are going to argue over. And so I didn't think it was wise to try to co-opt that word and change how people think about it so much as I might be more successful just coming up with a different word altogether. Makes sense.

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Okay, I want to zoom out a little bit. And another theme that came up a bunch when I asked people about you and how you think is that you have a really strong feeling that building great product and building successful product is a moral obligation of people that are in tech. Talk about why you feel that way and what that even means. Well, look, the example I use mostly is if you go to an airport and you look around and

You'll see a lot of people using their phone to navigate that system. You know, they're trying to figure out where their gate is, what time their flight's on, whether or not they can pull up their boarding pass, et cetera. And just watch people. Watch their faces. Watch the level of confusion and frustration. You know, some of them are tech superheroes like you and me and most of your listeners, but a lot of them 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 experience.

and scale it out to their entire day. And almost everyone living in a modern economy now is going to have hundreds of interactions with the phone or with a computer. And a lot of those interactions are going to be consequential. And unfortunately, a lot of those interactions are not going to be great. They're going to be confusing and frustrating. And

And when I'm speaking to live audiences, I often kind of ask people, you know, okay, please raise your hand if you've had a frustrating or, you know, confusing experience with software in the last month. And obviously, yeah, every hand goes up. Okay. How about so far this week? Most of all 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. It's 10 o'clock in the morning. Like,

That's a problem, people, because each one of those interactions, it takes a little bit of energy away from you and it ramps your frustration just a little bit. And the bummer about software, both for the audience and for the creators, is that it's an anonymous medium. Like nobody gets to see who's making these things. You and I together, we might be able to name six designers that have worked on products we care about. And the only reason we could do that is because I'm a designer and I know a bunch of them. By yourself, I'd be surprised if you could name more than a handful. So-

And again, we work in tech. So if you think about the billions of people out there that don't work in tech, to them, these products are just these crazy faceless things created by a bunch of people who knows where. And these products are causing them untold amounts of frustration and confusion. And it just takes away from their life quality. And I think we have an obligation as entrepreneurs

product people to put that emotional energy back into people's lives. You know, they don't, they don't want to try to figure out how to navigate our login screens or go through our onboarding process. They just want to get home and spend time with their families and pet their dogs and have a nice dinner. Like I just think every time we make a demand on the audience, that's a failure on our part. And so I do think it kind of comes, I,

I cast it in a moral way and I talk about it that way because I don't think many people working in the industry understand the scale of what they're doing. Again, because it's an anonymous field. Like we don't, we never see anybody on the other side of the glass.

But I think with this podcast, it'll go out to hundreds of thousands of people. 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. And we might think of it differently. We might behave differently. My team at Apple, but also my friends that are working at Facebook or Google or wherever, it's very hard to really understand that they're creating something in Figma on their computer that's going to be interacted with by billions of people

Thousands and thousands of times. And I, if you lose sight of that I think you just, I don't know you 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.

Wow, that's really inspiring. That makes me want to build products and make them awesome. There's so much power to that. I think a little bit what this makes me think about a little bit is kind of random. But when I see someone click and watch one of my my podcast videos on YouTube, I'm like, wow, that's like one person that's going to spend their time watching this thing. Wow, I really want to make it gives me more motivation.

motivation to make these even better and better. Yeah, look, I think you have to find ways to go. You have to find mechanisms where you go out of your way to see people using software in real time. I've worked on products that have been used by billions of people. I have friends who have touched billions of people. None of them

None of us ever get to see anybody use this stuff in the wild, in their natural state. Maybe we see them in a lab or something like that. I've never seen anybody just randomly using even Pinterest, you know, but there's ways that you can go. And as a creator, it's 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 I've ever seen. Go, 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 mere mortals actually use software. Instead, we're 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 looking at raw data from a radio telescope instead of just going out inside and looking at the night sky. Like you got to find a way to watch the audience.

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. And fortunately, software is everywhere. It's not just desktop or mobile software. I mean, there's ATM machines, they're ticketing chaos, the kiosks, there's

point of sale systems everywhere. I mean, go watch somebody over 70 fumble with a chip card insert, you know, or watch somebody try to figure out Apple Pay. And these are pretty seamless experiences. And still there's cognitive friction and all this stuff. Just go rent a car. And notice how long it takes you to figure out what the heck is going on with the dashboard. You know, like there's lots of opportunities to try to

develop that intuition of how people navigate the human computer interaction. And we need to find ways to do that. An important element of what you're describing here, which I think maybe people miss, is that you're talking about just any software in order, not your own product, in order to start building your sense of taste and gut feeling for what works and doesn't work.

And I had a guest on recently, Guillermo Rauch from Vercel, founder of Vercel. And he had a really great phrase of something they do at their company. They have this kind of mission of exposure hours. Increase your exposure hours to people using our product. 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 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, not your product. Like at one point when I was redesigning a checkout system, we did what I called a reality check, which was we held a traditional usability style exercise in a lab and all that sort of stuff. But we had the subjects come through and go through checkout in other products.

So we watched them go through like eBay and Williams Sonoma and Amazon or something like that. And we learned a ton about checkout, about what was important to them, how 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 him to click on the button or, you know, we would have had a bias in wanting to see the positive things.

Whereas if you just watch people that are using adjacent products could be super useful. And again, you know, we work in a medium. Software is a medium and we need to understand our medium in the same way. Again, musicians go to concerts, filmmakers go to movies, you know, comedians go to comic clubs. Like when do people like you and I go watch people just use software? Where do we develop that intuition? And unfortunately, I think you have to go out of your way to do it.

Talk about more about this idea that software is a medium. This is something that came up a bunch also 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. So, yeah.

Yeah, look, so I left Pinterest in 2016 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, you know, commiserating with people. And you may remember there was a very consequential presidential election in the United States in 2016. And there was some impression that social media had had a significant impact on that election.

So I was kind of driving around Silicon Valley and I was just sort of wondering, like, what the heck happened? You know, I mean, I moved here in 1990 when the hippie ethos that was really at the core of Silicon Valley and the hippie ethos was still very visible. And you could I mean, it was very much a part of what was interesting to me about the valley when I moved here. But, you know, 2016 is a long time later in that hippie ethos had gotten pretty quiet.

And so I was listening to a podcast about the history of Silicon Valley by a Stanford group. The podcast was called Raw Data, and it was season two. And it starts off with an episode called A Monument to a Dead Child, which is about Stanford University. And it ends with Zuckerberg's testimony in front of Congress. And in the middle of that, they start talking about the counterculture revolution in the late 1960s in San Francisco and elsewhere. And they quote this book by a guy named Fred Kuhn.

Fred Turner, I think it is. The book's called From Counterculture to Cyberculture. And he has this quote that is, you have to ask why it is personal computing got started in Northern California in the late 1960s when at the time every major tech company in the country was on the East Coast. And the answer is because there was a very small group of people in and around Stanford University that saw software as a new form of media on par with movies, music, and books.

And when I heard that, all of a sudden I went, wait a second, like, boom, like that, that is why I do this. I am fundamentally a maker. In high school, I was a photographer. In college, I was going to be a filmmaker. After college, I went to music school. After music school, I started a graphic design studio. I am a maker. And I realized looking back, I was just hunting for my medium. And it took me until I was 27 to find software as my medium. It's like, oh, I'm a maker that designs software. And then when I heard that software is a medium, that whole thing,

you know, concept of what I've been doing with my life and who I was about, it just sort of like all came together really quickly. And I realized, oh, I'm into software because software makes me feel a certain way when it's working well. And what I find so troubling now is 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 listening to the show can remember maybe the first time they saw a desktop computer, probably the first time they saw a pension Zoom on a phone.

You remember all that stuff? It was just freaking magic, man. I mean, it was the future. It was so...

cool and it just felt like the most amazing roar borealis or sunrise or whatever there was like a sense of awe and wonder that filled me and probably a lot of listeners you know that's probably the thing that motivated you to be in the field and so i i realized like software is a medium because there's an emotional component to it you know like a like a hammer and saw i don't

they're not really pulling out an emotion for me. Like maybe there's some, if you're a carpenter, but I don't naturally have an emotion with kitchen tools or, you know, things that I think even 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 realize and accept that,

Then you can say, oh, there is an emotional component to what we're doing with this product. I could just leave that to chance, which is what most people do. Or I could try to be conscious of it and we could try to bring that into our conception of what the product's about and try to be purposeful in the emotion we're trying to elicit from the user. And I think that's where design, and particularly visual design, can have a huge impact. So

Again, in many conversations that I'd have in design reviews, some executive would go, I don't know. Ultimately, this just kind of comes down to a matter of opinion, right? And I was always like, no, it does not. Like whether we choose blue or red is going to elicit a certain 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, again, 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 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 going to own it and show up and be the person you want to be in those moments or not?

A few months ago, 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, you know, tonight, you're going to be at dinner with a few hundred thousand people all across the country. And if we take just one example, you know, you're going to be at a very nice diner with a grandmother and her two teenage sons in Ohio. And the check's going to come and the waiter, the waiter, the waitress is going to hand over the device to that grandmother because she wants to pick up the bill.

And you have the opportunity to either make her look like a superhero because she knows what she's doing or to make her look like a fool and one of her teenage grandsons is going to grab the device and do it for her. You're at the dinner table. What are you going to do for grandma? Are you going to show up as well as you can or are you going to just like let this whole thing fall apart because 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 going to ask how you use this insight that software is kind of the most powerful medium media more than even than TV and movies. And you shared it, which I think is really important. So just to kind of double down on this is the advice here is think about the emotion you want the user of your software to have as you're starting the design process, not just what do you want them to do? How do you want how fast you want them to get to this flow? It's 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 have something they want to do. Like I'm trying to help them. Like I'm not, I just don't ever approach these things of the user something for me to exploit and take advantage of and manipulate. I know there's people that do approach it that way, which I think is a little unfortunate, but I just, as a designer, I guess I have my own set of values, my own kind of compass on these things that push me in a certain way of thinking about it. And so I'm kind of constantly asking what's the right thing for the user. And I believe in my heart,

that if we prioritize that, wonderful things will happen for all the metrics, including the money metrics that matter. I've never seen a product be successful that used metrics as a driver for what they were doing. I've seen a lot of companies be really successful seeing metrics as a consequence and a way to evaluate the quality of their decisions and then using those to triangulate and make better decisions moving forward. So they're kind of a very useful feedback mechanism. But I think

There's definitely a risk to confusing doing something because it's a driver versus something as a consequence. There's a few more questions I want to ask, but I want to come back to something that I asked earlier that I think is on the minds of a lot of, say, founders and product managers listening to this. I'm just like, okay, this all sounds really great. I would love to make these experiences so great. I just...

It's going to take us a lot of time to do this really, really well. You said that it doesn't have to. What's like a tactical tip or two that you can suggest to a founder or product manager to help them kind of contain the design process while also achieving these outcomes that you're describing?

Well, I think if you can give, you know, I mean, 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 is going to be able to figure out which swim lane they're supposed to be in to produce something. So if you, I think if you're going into it feeling like the design process is going to take a lot of time, it's because you haven't been, 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 I have worked with a lot of founders and we could identify a bunch of big companies who I think got started that weren't clear in their own head. I mean, I don't want to, you know, Yahoo was an amazing company, but if we just look at Yahoo for a second, I worked there, it was never clear to me what the founding vision of Yahoo was. And I talk a lot about vision statements and we could say like the vision statement of Google is

organizing all the world's information. That's a great vision. They'll never achieve that. That's something that's always over the horizon. And it's been a very useful organizing principle for their acquisitions and how the company grows. Amazon, to be the Earth's most customer-centric company. Okay, great. That's a vision. They will never get there. It tells you how they're going to expand. Apple doesn't have an explicit vision, but I might describe it as personal computing can have a transformative effect on the lives of individuals. And I think that kind of

focuses a lot of what they're trying to do. Disneyland, still the best vision statement of all time, which is the happiest place on earth. So once you tell an employee this is supposed to be the happiest place on earth, then you're signaling all sorts of things about how they need to pick up the trash and how they need to show up on time and how they need to wear their uniform. You're just signaling a whole bunch of stuff

So when I talk to founders, a lot of times they just don't have that clarity of what's the vision of the company. 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, it ended up being inefficient because they were having to deal with all that ambiguity. So I think that that can also be a pretty big risk for founders. They end up

kind of with a product idea. Um, and they think that the company is the product. The company is not the product. The product is the product and the company's bigger than the product. And you need to have some vision that speaks beyond just this particular thing. Um,

I think Slack and honestly both Slack and Pinterest, I think are examples of companies, products that became companies, but neither one of those places really knew what to do next because they didn't have a bigger vision of the change they were trying to see in the world. So 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. Yeah.

and try to give them as much clarity about what you want to produce as possible. And I think if you leave it open as to the emotional response you want users to have, you're inviting a lot of ambiguity, which is going to invite a lot of inefficiency. I love that answer. And it's so interesting that

But AI can help us work better together as humans because when you find that the AI is not achieving the outcome you want as effectively as you want, that's a lesson. This also translates to working with humans. Like make the prompt more specific, add more context in life, not just when you're talking to AI. Yeah, yeah. I love that. That's so interesting. So the advice here is just if you're finding design is taking too long or you want to just level up,

your success with your design team. Give more context, spend more time on the brief on what you're actually trying to achieve and make sure there's a clear vision or mission that everyone can row towards. 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 going to be. And if you give designers a lot of ambiguity, they're going to 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?

you know, helping them get more specific. It's very common for a design team to get extremely ambiguous asks from a product team. And then they have, and the problem for design is they have to take all that ambiguity and they've got to wring it all out. So when they give it to engineering, engineering knows exactly what to code because computers don't tolerate ambiguity. Like engineers need to know what the thing's going to be. And so design gets stuck with a really ambiguous input, but they have to have a highly specific output. And then they're often time boxed to do that.

And it's just not a recipe for success. So you're much better off either kind of compressing the PRD experience, you know, and bringing the designers into that kind of co-creating with product and design really rapidly. But you need to,

I mean, you could think of it in some ways as designers are going to 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 going to waste untold amounts of money on set. So if you think about those three steps from script to storyboard to production, like it's all about getting rid of ambiguity. And so the more ambiguity that can be removed upstream, the faster design is going to go.

This begs the question then, 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, just...

how to navigate that? Well, if you go back to my example of the script and storyboard scripts, don't, 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, 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. The thing that I will say about, uh, to keep in mind for PMs is

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, 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 it's a point of pride. There's no way I'm going to go execute that exact thing.

So you're right. PMs have to give you the space to operate. And I think a lot of what they're trying to achieve can be done in more informal ways, conversationally and whiteboards, things like that. But you need to narrow the problem for the designers. They need constraints. They don't need...

They don't need a tiny little box, but they need constraints. Think in terms of, you don't give them an airport tarmac, and you don't even give them a football field. You give them something more like a basketball court. There's sort of a scale at which they can do their design thing. 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 another 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. I think that pushes against...

all the gen ai tools that help you create prototypes there's obviously a lot of excitement around that i can just give a prompt and the the ai is going to they're going to crank out a ui for me so i don't think i'm using the term right but i had this idea from art that i call the primal mark and that's the first mark that you make on the canvas and once you make that mark on the canvas 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. And people are 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 of,

that looks even slightly realistic, much less something that comes out of one of these Gen IA tools. Everybody kind of goes, oh, that's the thing. You just keep doubling down on that thing. And what's happened is you've taken 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 of thinking. And so 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 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 do we got? You know, there's one story that's kind of related that's useful. In one of my previous jobs,

I was responsible for the public website. I remember 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's like, yeah, yeah, but we just have to make it blue. It's like, well, we're not making it blue. And a couple of days go by and I saw the homepage and the link had been made blue because she had got around me and she got engineering and just made it blue. 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 the thing that came to you first because you're not a designer. And like, it's naturally, 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 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, I do the same thing on the roadmap. Like,

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 going to trust that you are trained and you know what you're doing and you're going to 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 making that primal mark, which I love that term.

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, pre-ems 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 I...

I mean, I haven't played with it a lot myself because I'm not in an operational role right now, but presumably it's really useful at cranking out that actionable prototype, which you can click and 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 going to happen. So when the idea is ready to be expressed, I think those tools are probably fantastic. But ideas start off pretty fragile and the best ideas start off really fragile. 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 going to squash them. I often think about him like the little plant in the Pixar movie WALL-E. You've got to 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 going to make it. And so I think a lot of

There's a lot of very fragile, interesting, quiet ideas that I think you need to give some space. And when you jump to the expression of them, I think you're putting them at risk. I'll also say that everybody, 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 going to get is going to be about colors and shapes and these presentation layer things, which are very...

loosely related to usability and value, right? It's like...

It's like focusing on the special effects of a movie that has a really bad story. And so at ThoughtSpot, we used to use what we called block frame 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. And because it was so low fidelity, people couldn't get into commenting on what it looked like. 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 wireframes

like to kind of the final expression. And I think it helped us 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, initially it made the product team really nervous because we would be sitting in these block frames and wire frames for sometimes weeks. And they'd be like, when are we finally going to see the comps? And then what would happen is because we had such a robust design system, once we locked down on the block frames, we could send it to an agency and they could do the full high-res comps like

like in a day, you know, because they knew exactly what they were doing. And so the PMs were always like, what the hell happened overnight? You're like, well, it turns out that the high res 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. And I think you end up spending a lot more time churning if you didn't. Again, I'm going to go back to the movie metaphor because I studied film. You know, if

If you're trying to fix script issues when you're in production or storyboarding, you're going to churn. You're going to waste a lot of effort. So you kind of, you got to figure out what you're trying to do before you go draw the high res stuff. And I think a lot of the Gen AI tools, it's this seductive thing of, hey, let's just go

let's go make the comp and see what we think. I just, I don't, I don't really know if you're going to get anything great out of that process. Maybe. 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 realized there's many CPOs. Uh,

She has this concept of demos before memos and just like prompt sets or new PRDs, you should just be prototyping all your ideas. And so it's interesting to hear the perspective of maybe it's actually hurting your ability to come up with a really clever solution versus 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 frankly, that you're proud of and that your users find value in. And if you're just throwing so much spaghetti at the wall, I don't know if having a spaghetti throwing machine that goes faster is, you know, I mean,

I mean, look, there's a counter argument that's, you know, you can say, oh, it's like Darwinian evolution and we're just going to spin through a bunch of random mutations and see what, you know, what happens. And I used to joke that, you know, it's true that, you know, if you take a bunch of hydrogen atoms and give them 14 billion years, you could end up with a tiger. But you don't know you're going to get a tiger and you could get a six headed shrimp instead. And you don't really know when it's going to 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 want to take us to a recurring segment on the podcast called AI Corner. 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. And so the thing I've been using AI for is I've very explicitly been using it as a life coach. And so I had seen a couple of prompts about asking it what the blind spot was or what my strengths and weaknesses were. I'd seen some prompts about that stuff. And one of them was really fantastic. One of them was, what's an outdated mindset that I'm holding onto that's not still serving me? And he came back with this very polite prompt or very polite response.

about, well, given your age and your profession, 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 going to suit the thing you're trying to do next, which is writing and publishing and speaking and stuff. And 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 really useful. I asked it 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 I realized that it was inferring these things about me from the things that I had asked it to help me with in the past. So instead, I just switched. I just went to ChatGPT, started 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 it's been really useful for me. It's no substitute for a therapist or a real coach or anything like that. It's 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 helping.

reflecting back to me things that I think have been floating around in my undermined. And so I, there's, there's a wonderful book called hair brain tortoise mind by a gentleman named Guy Claxton. And in that he talks about the undermined and sometimes you might've heard this as your unconscious or something like that. But, but I think of your undermine as the part of your brain that's processing information before it gets to language. And then 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 multilingual speakers, they'll tell you that they can think things in other languages than what they can think in English. So if you only speak English, you're only in one vein of what you can think. But your undermined is operating through all this other stuff.

And, you know, for the computer nerds out there, you could think about it as a 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 kind of has different orientations. And we call that consciousness. So I was feeding chat GPT all this stuff over the last year or so. And there are all these patterns in my undermine that had been going into that, that I wasn't able to express with conscience conscious language. Right.

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 undermined. But because it was putting them into language, my conscious mind can now recognize them and respond to them. And so, again, I found it as a sort of a life coach. I found it very useful as a mirror back to things that I was probably already thinking. And it helped me clarify my thoughts.

It's not pushing me in new directions that like a human might do, but it's still been super useful. That is extremely cool. That is a really cool use case. I don't know if you heard the Jerry Colonna episode that I did recently. He has, okay, we'll link to it. He's got four questions that he suggests people ask themselves. 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 helping achieve a thing. It's a powerful word. Yeah. And then also, and it's an important element of say you don't want, like you say you don't want to be busy, but something you just 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, one final question before we get to our very exciting lightning round. This is one that I don't think you have any idea I'm going to ask you about. And so I'm curious where this goes. This is a story that Joff Redfern suggested I ask you. He told me that you're obsessed with space. You love talking, researching space, telling stories about space. There's a story that you share about this guy named John Hobolt.

Does that ring a bell? Oh, yeah, totally. Okay. Share that story because I think there's something really powerful here for people building products. So I should clarify, I am a fan of astronomy and 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. And I think it's an incredible, 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. Let's do it. Here we go. The particular question you're asking is John Holwell. So John was, I can't remember exactly where he was in the NASA hierarchy, but 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 19th September, May 1962. And he gives the famous moon speech. We choose to go to the moon, not because 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 is the perfect TED talk. It clocks in right at 18 minutes. 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 going to happen, how much money it's going to cost, the way he puts the passion, why we're going to go to the moon, the whole thing. It is an incredible talk.

is the only moonshot talk ever ever because a moonshot has to actually go to the moon and so it is it is an incredible talk so go watch the talk but he steps off the stage and people at nasa are like you know we've we've only recently put alan shepard into space and he just went up and went down i mean that was like almost like a it was a blue origins types thing that was just up and down we didn't even do a lap around the earth like the russians did with yuri gagarin and now we're talking about going to the moon like

Nobody knows how to go to the moon. And there was 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 Wernher von Braun, who was the main rocket guy in the world. A little bit of a complicated past, but nevertheless, Wernher 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.

People are like, yeah, the problem is when you get to the moon, the rocket's still super big. So these guys are going to have to descend a big ladder. That's kind of a problem. So that was one idea. There was another...

called Earth Orbit Rendezvous, where you send two spacecraft into Earth and then you link them up in Earth orbit and then one of them goes off to the moon, but you still got to land that thing on the moon. And then there's a third idea called Lunar Orbit Rendezvous, which is where you build a spacecraft that includes a smaller spacecraft. So you send up two spacecraft together, one of them smaller, much lighter, and you use that just as the ship that goes down to the moon's surface and back up. And that spacecraft is truly a spacecraft. It only flies in space. Right?

which means the engineering requirements around it are profoundly different.

Because it doesn't have to survive 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 got to lift all the stuff off the Earth, which is incredibly expensive for fuel. They got to land it on. I mean, there's just a lot goes on. And so Hubalt had come across this paper from a gentleman named Yuri Kondratyuk, who was living in Ukraine in like the 1916, 1918 when he wrote this paper. And he was the first guy to theorize lunar orbit rendezvous.

And I try to take people back to that. Like you and I can think about going to the moon, but Yuri Kondratyuk in 1918 is on the plains of Ukraine looking at the moon. And he's actually thinking about how to really go to the moon. Like he's figuring it out. And so he writes this paper. John discovers it years later. And John's trying to sell Lunar Orbit Rendezvous. It's not going over at NASA. And

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. The memo starts somewhat as a voice in the wilderness and then it goes on. 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. And this was the only way to do it. And there was no other options 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 I think it was another year or so after that famous memo, which you could read online. It's like nine pages long or something after the after the memo. It was still some time before they adopted lunar orbit rendezvous. But eventually they do. And even with Don Braun himself was very complimentary to Hubolt for kind of pushing that perspective. So I tell the story one.

Because it's just an amazing story. And it does kind of force you to go back to the moment of like, wait, they didn't actually know how to do it. Like, we only know how to do it now because they've done it, you know, but there's that moment of uncertainty. I think you kind of have to embrace and be amazed at that. And it also shows you the power of these ideas, like a really great idea 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 to the world and it just sat around and then somebody discovered it and dusted it off and was able to push for it and it came through. And then maybe the third lesson is like ideas need champions. 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. Such a great story.

I love that you summarize the takeaways, too, by the way. So 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 to is be patient. You know, it may take a little bit of time for an idea to like a radical idea, especially to resonate and stick and get adoption. So if you're pitching a big new product idea, like don't assume 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 just add to that one thing. Like, 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 because like, well, I don't want to be, you know, I don't be self promoting. And I try to counsel them like, look, it's not about self promotion, like it's like there are ideas that you care about that you want to see succeed in the world. And so get out there as an advocate of the idea. It's not about you, it's about the idea. And like, don't be afraid 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? Yeah, let's go. We added a ding to this. I like that drum roll you added. It's a whole thing now. Okay, first question. What are two or three books that you find yourself recommending most to other people? So the three books I'm going to recommend, the first one's...

A beautiful poetic book about typography called The Elements of Typographic Style by Robert Bringhurst. Robert was the Poet Laureate of Canada. And the first 80 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. 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. 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. So it talks about quality and the importance of how things integrate into a cohesive whole, which I believe is the main

facing most software teams. 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 Robert Gruden. It's just a very interesting collection of things

sort of impressionistic views of time and how time passes and what time means. So that's very different from the others. And it's not something probably gets recommended on your show too often, but I think it will, I think it'll help people in their lives in a powerful way. I think these are all brand new entries in this question.

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. I was intrigued with the story and the characters. And I think as someone who's worked in corporate America, when you understand that it's basically critique and commentary about the modern workplace, there were times that I just thought were unbelievably funny and insightful. It was definitely interesting watching it with my wife, 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 that we're using was all around the language you would hear around a layoff. And so like I was laughing myself to death, but she was like, what, like what's going on? So I thought Severance is 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.

Lawrence of Arabia is, I think, one of the two or three best expressions of the medium of film. 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 Lawrence of Arabia is probably one of the two or three most complete expressions of what the medium is capable of.

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 in a really coherent, powerful, full on way? I love that movie. Next question. Do you have a favorite product that you have recently discovered that you really love?

You're focused on recent and I'm just going to push back. No, there's nothing terribly recent. The stuff that I go back to, I'll give you a couple of nerdy ones. I have a Leica M6 camera, which is a film camera. And I recently started shooting with film again, which I absolutely love because it forces me to slow down. I always talk about Leica cameras. They're obscenely expensive. But the thing about Leica cameras is you show up different when you shoot with a Leica. So when people think about cameras, they think about the quality of the image. They don't think about how the tool is going to change them.

And when you show up with an iPhone, you're thinking about sharing. When you show up with a film camera, you're thinking about saving film and you're spending more time composing and thinking exactly about the shot. When you show up with a digital SLR, you just take a whole bunch of pictures and hope something's going to turn out. And so I think these cameras are a very useful metaphor for being conscious about how the tools you pick are going to impact the thing that you produce.

So once you go into Figma, you've made a decision about the thing you're going to produce. If you stay in a sketchbook, you've made a different decision. If you go into something else, you've made a different kind of decision. So I say the Leica M6 with film because of that. And then the software product I would point out, which is not terribly new, but I think it's worth noting, is a tool called Habitica.

And Abitica is 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 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,

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. 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 Habedica is really interesting because it mixes genres. It mixes role-playing game with to-do manager. And so I think it's a really powerful example of how you can

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 two genre mashups are really interesting. When you come to a rom-com, you have a certain expectation of what's going to happen to a rom-com. If somebody suddenly got shot in 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 Habitica is just the most interesting example I've ever found is somebody really doing a fascinating mashup

of conceptual models, which is, sorry, I'll stop. It's just, it's an unexplored and unexploited possibility of software ideas. I love how profound this lightning round already is. The point about Leica changing the way you even think about the photo is so interesting. I've never thought of it that way.

You mentioned Star Wars. Have you seen Andor, by the way? I know, but everybody's raving about it. I've been watching basketball, so I just haven't had spare time yet. Okay, 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 and work during life? 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 Tufte.

Second one is from the American landscape photographer Ansel Adams. And I've also alluded to this. And the quote is, there's nothing worse than a brilliant image of a fuzzy concept. And then the last one is an African proverb. And it goes like this. If you want to go fast, go alone. If you want to 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 kind of collide in an interesting way. You know, people 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 tingle 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. And so they're just like fancy potato chips. There's no, there's no nourishment there, man. Like, yeah.

I love that this connects back to the vibe coding apps and prototypes that people build that, you know, you can do it really quickly, but it won't go too far. Potentially. Yeah. Not to hate on those tools. They're amazing. Okay. They are. They are like all this AI stuff is profoundly amazing. And 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 theorized for well over 50 years. So there is a vast, a vast warehouse of,

of interesting, amazing thoughts from philosophers and engineers and social scientists and people thinking about what is this moment going to mean when we have this sort of artificial intelligence that challenges our conception of what it means to be human. So like there's so much stuff you could be reading to help you process this moment and the, and the very intense and profound psychological challenges it's bringing forth. It definitely feels like we're finally living in the future. Like the future is,

actually happening is gonna be robots walking around soon we got self-driving cars all over San Francisco it's yeah really really stark it's a future yeah it's a future well that's that's my concern with a lot of the fiction of the future is most of it is dystopian and like here's all the problems that we're gonna run into which and you know is gonna be useful like here's the robot laws that we gotta be thinking about yeah I just I

Just to go back to this idea of how once you create an expression of something, people baseline off of it. I recently got to hear Henry Modisette, who's head of design at Perplexity, give a talk. And one of the things he said that just really struck me was that people's conception of AI was put out there by Hollywood years ago. So this idea that AI is going to take stuff over and is ultimately really dystopian and malevolent towards humans and stuff like that, it's actually something that's created by Hollywood.

And now we're trying to outlive Hal and stuff like that. And so it's 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 really good point. Yeah. It's much more entertaining to watch AI try to kill us all, not just, oh, everything's amazing. Great job, AI. 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. What would you change? What would you change to help them win? You know, a team, like a real team, can't be dependent on a single player. And I think there's such a dramatic difference.

in the Warriors when Steph is on the court and off the court. If you listen to the local announcers, they're always like, these non-Steph minutes really matter. 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 like Steph and the band of Merrymen. And the Warriors are bigger than that, right? And most of these basketball teams are bigger than that. 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 success. And that just seems dangerous and not a team. So-

I mean, I kind of don't know what to say. I don't know how you replace Steph Curry. He is a singular, I don't even know if you can call him a generational player. It's bigger than that. He is unequivocally the greatest shooter in the history of the game. And he's one of only two or three players that's actually fundamentally changed how the game's played. But I just know for winning, the Warriors are at risk because Steph is meaningfully old for an NBA player. And you can't have the whole franchise built around just him.

I love this hot take a great way to end it. Bob, I could listen to you all day. This is so fun and interesting in so many ways on so many levels.

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? So bobbaxley.com is the easiest place. Right now, it's just a Bento site, but I'll get some more stuff up there in the coming days. Hopefully before this episode goes out, we'll see. But there's plenty of links there that'll help you connect to me on LinkedIn and some of my talks and a few links to some other things that I find useful. Just find me on LinkedIn. You know, I publish pretty much every day on LinkedIn. That's an easy way to find me. Yeah.

Yeah, I'm happy to be connected to whoever is interested in being connected. And then in terms of how you can help me, you know, I'll go back to what I said earlier. It's not really about me, Lenny. 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, it's not about me. It's about us together trying 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. You know, you and 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, I just, I hope people take that responsibility more seriously and try to

to help clean things up a little bit. I think we've made a dent in that. Bob, thank you so much for being here. Thank you so much, Lenny. It's been a real honor, privilege, and just a ton of fun. So thank you so much. Same for me. 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 lennyspodcast.com. See you in the next episode.