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

Podcast: Lenny's Podcast: Product | Growth | Career
Source: whisper-tiny
URL: https://api.substack.com/feed/podcast/165214874/f570e1cb862763cdb7276ccb6ee954e4.mp3
Fetched: 2026-03-05 01:07:13

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 designed. 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 designed led does not mean it's designed or led. Have never seen somebody grafted on after the fact. It's there at the beginning in the route DNA or doesn't exist. It wasn't a successful standard interest. 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 in led design teams at Apple, Pinterest, Yahoo and most recently thought spot. Over the course of his career that's spanned over three decades, Bob has played a pivotal role in the design of the Apple online store, the Apple App Store, Pinterest, and early in his career Yahoo answers. Products that have been used by hundreds of millions of people around the world. Bob also mentors individuals and advises organizations that are working to improve the practice, craft, and culture of digital product design. There is something in this conversation for everyone, from why you should consider having design, report, 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 and Drew Hogan, Irene Aught, and Joff Red for enforce adjusting questions for this conversation. If you enjoyed this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you've 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. What you may not know is that they have several other products that can help accelerate your revenue, such as Stripe billing, which powers billing for companies that you may have heard of, OpenAI, and Thoropic, Figma at Lassian, and over 300,000 other companies. Stripe billing lets you bill and manage customers however you want, from simple recurring billing to usage-based billing to sales negotiated contracts. There's also Stripe's optimized checkouts suite, which is a plug-in play, super optimized payments flow that natively supports over 100 global dynamic payment methods. There's also a protocol link, which is an accelerated checkout experience built specifically to increase your checkout conversion. Every single one of the Forbes top 50 AI companies that have a product in the market today use Stripe to monetize it. Half a Fortune 100 companies use Stripe. $1.4 trillion flows through Stripe annually, which is equivalent over 1% of global GDP. You Stripe to handle all of your payment-related needs, billing, manage revenue operations, and launch or invent new business models. Learn more at Stripe.com. Bob, thank you so much for being here and welcome to the podcast. Letty, thank you so much. Thanks for having me, but also just thank you for what you do. You know, 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 talky moment, we're kind of on the cusp of having our shift to color development, but we're still trying to figure out how to make movies. And the podcast, like you're 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 asks 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's true. Steve at one point was recounting the products that he had created that it 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 Catmill or John lastider at Pixar. And he said, you know, everything we make is going to be a door stop in three years. But the stuff you guys make is still going to be watching in a hundred years. And so I think Steve had some concept of the longevity of these things. They knew the products themselves. We're very ephemeral. But there's something about the culture of Apple that's lasted a very long time. And I personally believe it 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 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. And I want to 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 as from people that have left. Like, he main was a recent example. You know, this, we're recording this today after Johnny I, then I open a, I merge. So we'll see what happens there. But 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 had been 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 of 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 get myself time to, to recalibrate to the, to the Pinterest culture. So I think I think it's 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, it's really deep that infuses all of your behavior and how you can doctor yourself in the company away from the company. And so I think it's, it's pretty hard to immigrate successfully from one of those environments to another. And Apple is one of the strongest cultures. And there's not many other cultures that sort of natively operate like that. Airbnb is one exception. And so you have guys like Haroki as I who's leads all of marketing and all of product and Haroki is crushing it, Airbnb is incredibly successful at Apple. And also should be noted that he had, he was a multi or 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, it Apple, I think it was 10 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 washing you to go through when you lead Apple as well. And so I think Haroki gave himself time to do that. And I think that's probably a lot of wise, 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 hired you because of the values of the organization you left, but not the behaviors. And so I think it's important to kind of recalibrate and say, well, I want to hold onto these values. So it Apple, attention to detail, product excellence, you know, doing everything you can for the customer and the user. So try to hold onto those values, but then think, okay, how do those values best expressed in this culture? And I was more successful at expressing those values in the culture of Thought Spot, which is my last job that 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, I think that's useful for anybody leaving one very specific culture and going someplace else. Like try to hold onto the values, but not the behaviors. This is so interesting. And I appreciate you sharing that. The way you describe it, that it wasn't a successful standard Pinterest. A lot of people don't share that sort of story and don't put it that way. You know, they see on their LinkedIn, oh, I had a design at Pinterest. Oh, amazing. So cool. And then, you know, if you're like, okay, 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 take 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 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, you know, very direct, fighting hard. You know, it's very, it's, 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 what 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. It happens. So I probably could have picked up on that better than I did. You know, I'll say like, these careers are really hard, you know? And the higher up you go, I sort of people think of it like your climate impairment. 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 the 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 a Pinterest. You know, my kids were starting high schools who were struggling with the teenage years. I had a long, long commute. I mean, there's just a lot going on. And these jobs are super demanding. Everything around she's changing really rapidly. And you're under tremendous pressure because the financial and success, you know, stakes are super high. So I think the people like following 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. I, one of the things I took away when I was at Pinterest was I came to think that the job of a startup was to grow the founder so they could continue to lead the startup. And I think what's true for founders 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 out grown 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, if that is the human experience, that's what happens. It's very hard to grow as fast as some of these companies are growing. And 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, you know, within like five years, he's like Facebook's a big thing. I mean, think of your own life. Can you, like, can you process that level of evolution and change? And, you know, that's just, I don't know, I think that's really super hard to do that and stay balanced. And also keep doing that firm for a so long. Like 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 of even meta is still a startup in a way that Amazon's not. And, you know, an Airbnb still a startup in a way that Pinterest is not because Ben's moved on. 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 okay. Clearly, you're doing a okay and having a place that doesn't work out, doesn't destroy your career, which I think a lot of people feel like. If they're not doing one, they're current job, it's over. Things are all going to go downhill. Yeah, your career's not your life. You know, 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 bound stuff of it. I love that metaphor. If you're to, when you're looking in new companies, what's like one thing you look at or question you ask or something you now look at to make sure you avoid that in the future in the culture class? 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 Thought Spot and Thought Spot was founded by a gentleman named Jeet Singh and a jeet grew up in rural India, but he tells us really great story about 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 IDO. And as a very young person, he got to see what IDO did and he realized the power of design and he's taken that to all of his companies. Started new tannics before he came to Thought Spot before he started Thought Spot. And so what I heard that, I'm like, oh, this is a guy that gets design right from the very beginning. And I've also come to believe that I've actually have never seen a company that grafted design on after the founding. So I've seen lots of, I could name lots of companies that I think are kind of design lead, not always design her lead, but design lead 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 doesn't exist. And 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 that culture, like we sort of have a shared value system. In a way that like, you know, as an American, 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 face, 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, to the value product, to the value design, depending on who you are. Yeah, well, I would you want to work it a place that doesn't value the thing that you do. That would just guide it with 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 is what is design? Well, I'm going to go back to the Edward TuptiQuote that I use all the time, which is design is clear thinking made visible. And so, you know, I think most people when they talk about design, they think of it as the visual expression of an idea. They think of it as a team or a function or a group. I think of it as a holistic mindset. It's, you know, like when design thinking became big, I was always really confused, because I didn't know how else 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, it's living with a certain type of intentionality in almost sort of a Buddhist type way, which is different from science, which is sort of observational trying to understand. It's a little bit different from engineering, which is, you know, we kind of know where we want to go at the end, but we're trying to kind of go one step at a time versus designs trying to, like, see some, you know, 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 as a, as a company, as the company think in a design mindset 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, that's not a critique on them. I don't think that those organizations are competing on design in the same way, but again, I, like, I want to go work in a place that, that is an organization thinks in a design-type method. So along those lines, a lot of people, imagine every founder, every product builder, would, is just, like, yes, I'd love amazing design, I'd love our products to be incredibly beautiful and intuitive, so easy for everyone to use that 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 way, what's the best pitch you can make, and that you do make two companies to help them see the value, the strategic value of design, and the, you know, the bottom line of the value of design? Well, let me back up and just dissect a little bit the way you described design, because you described it in really tactical terms, and said beautiful, intuitive products that make sense, I think it was something like that. Yeah. So what you were describing was, you were describing the part of the iceberg that sits above the water line, you know, which is the result, that's one of the outcomes of design, but that's not the real heavy lifting of design. Designs more like liberal arts or philosophy or something, it's, it's like, what do we try to achieve at a much lower level? And so, what I talked to founders and people about the vibe 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, like a 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 thing, it's integrated, makes sense as a unit. And I think that's a huge difference. And it an incredible strategic advantage, because the company can operate with much greater efficiency. They can onboard new people and get them in line. Like even Apple, for example, on my, the store that are the team that design the online store, you know, we had six designers for a store that ran in 30 somewhat countries, 12 and a half thousand instances of the store joined billions of dollars a 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 hole is 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? That's like the teams get too big and you just, you can't get that, that what Brian, you know, calls seniors. So, so Brian, you know, 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 in smaller groups, it's hard to do with a giant group. So, I love that, I love this metaphor of the Beatles as, you know, the way most people describe this is designed by committee, never works. And I love that you're, you're the way you describe it as the Beatles, is kind of like the ideal size, 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, you know, Andy Hart's value. You go through the list. 20 of them were on the patent. There's 24 that worked 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 ended up with the Zoom or something completely different. Who knows? They probably did have a massive group on the Zoom. Yeah. So, there's something, you know, it's like the force too few for what we're trying to achieve at scale. But even if you look at Pixar or any good movie, like on the 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 we're news really key here. I think when people hear the 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, there's new stuff for sure. You want to keep it team small and tight. But, you know, as things grow in scale, you're set, 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 Disney land and you've kind of got the whole thing set and people know what it's about, then they can come in and understand, oh, I'm playing my piece over here. I'm supposed to, you know, I'm supposed to decide the design, the ride for the new or design, the line experience for the new ride sitting in tomorrow land. But I know where that fits into this larger thing. So I think you can scale once you have clarity of vision, but it's very difficult to get vision with a lot of people. Great. I think that's a really powerful advice. If 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, Paige or Sergei 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 like, no, no, the more part of the more people you put in it, the slower everything becomes. 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 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 out of a lot of other companies. It doesn't work that way. And he thoughts and 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 for my friend Joe was supposed to solve under the dinner one night. He said, you know, saying a company is design lead does not mean it's designer lead. And so what I try to hammer home with people is that when I talk about design is a mindset, I'm talking about as a mindset. Like anybody could have that mindset functioning in any role. Any designer could have a product mindset. In fact, I think that's a lot of what the design communities trying to get at now and they say designers should be speaking the language of business. 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 road map. I may have some points of view on the road map. I may offer some critique. I may have my own suggestions and agenda in there. But once they say, this is the road map, 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, you know, tell us what you need us to do, what the features need to be, when they need to be delivered, what the issues are. And then give us the time and space to come up with a solution to those problems. And then we can work together to decide whether or not our solutions actually solve the problem as you understand it. But I'll stay out of your road map and you stay out of my designs to help. And let's try to get to the promised land together. So I assume that the product management is just particularly an enterprise SaaS company. It's like my team thought about did data analytics. My team didn't know anything about data analytics. We didn't have any of that insight. We didn't have the bandwidth, the mental horsepower to go out and do that stuff. Like we had our hands full just trying to figure out the UI. And it's, you know, 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 the designers don't need engineers, and the PMs don't need the designers. And like everything's they can throw engineering overboard. And I'm like, 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 two, one of those mindsets inhabit 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 know, like the second basement 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 anyone 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, yeah, thoughts about 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. They're 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. 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 cost and things better when designs are part of engineering. And many of my design friends will push back on this and they'll say design should be a their 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 experiences at design rarely has a budget or an army and so it's very hard for them to really hold their own and that's sort of a setting. Also, although, you know, you'll see people argue with me on LinkedIn about how design needs to be measured and we need to have metrics and be held accountable for a number. I don't really believe that in my heart. I think it's very, I just never seen a number that you could apply to design that we could reliably affect. So I think it's very hard to hold design as an organization, accountable for a particular outcome, the way that most of the other sea level roles are held accountable. Sales has a number, engineering has very specific expectations, product has very specific expectations and although I know this will frustrate some of my friends, I just have it 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 a hard. What I see work and I'm curious to get your take is just a product engineering design have exactly the same goal and the more everyone in 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 P.M. goal and 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 company. 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. It's by 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's different, every culture, 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, you know, there's three options designed to own thing, designs part of product, designs part of engineering. And I think there's a moment when you can back up and make an intelligent choice about the pros and cons for each of those options inside your org. And so I would encourage people to just take a design mentality, you know, 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 what are 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 stop it to stop it. So have you operated this way? Have you had design report engineering companies you've worked at? Yeah, that was, you know, sorry, but like that's how it worked at Apple. The whole time understood design always reported engineering. You know, they're, now I think it's a structure a little bit differently, but design has always been part of engineering in Apple. So I saw it work quite effectively there, obviously. It's so interesting. Okay. So say, just to give someone something very tactical to do on their team, say they don't want to go to this extreme and move the design org under engineering. What's something you've seen work that helps achieve similar outcomes with having engineers design 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, very philosophical discussion about what we could do and like what's right from a conceptual model perspective. And it's ultimately sort of a philosophy issue. And there's not that many pms or engineers that can sit in that space and be comfortable with the ambiguity of it all. Like a pms 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 design of an hour, I'm always like, well, the next step is we're going to have another meeting and we're going to talk again and open. And the engineers oftentimes when they're starting to hear different ideas, they're already cutting into the code and they're trying to figure out what's hard and what's easy. And so I think the trick is at the beginning, can you find a small group of people from the different functions that can sit with the ambiguity of the space and talk through a broad range of ideas to identify the direction we want to go into? And then, once everybody kind of falls in love with the direction, then you can go into the more tactical mindset of, okay, well, when you can ship it and who can we show it to and, you know, how are we going to code it and when it's going to go live and all the sorts of things. But 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 exact and an exact season for the first time in a high resolution state. We could get to that 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 how mentioned here. So it be excited about. They're not order takers. You know, how do you make them part of the process? And, you know, most every product of consequence that I worked on, there was some moment when we were showing it to some critical person. And you could see that they fell in love with it. You know, sometimes they're like literally pointing at the cops on the board. Sometimes you're in a meeting and they're just like, kind of just love this. And for me, that was always, that was always the critical moment. Because I knew that, you know, design can't bring you the stuff in the world on its own. Like we, we can't raise this baby. We need the village. And we need the village to fall in love with the baby. And so until that happens, you're not really quite sure if this thing kind of 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. When I'm hearing there's a big part of just buy-in. And then there's also just obviously more good ideas early are great. Yeah, sorry. A 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, when I'm talking to teams, the thing I try to tell them is I walk in the office every day with the idea that everyone that I work with is a fundamentally a maker. Like everybody in product design engineering, we've all chosen these careers. Everybody's super smart. Everybody's super ambitious. Everybody could have done a thousand other things. But they're choosing to spend their precious 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 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, 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. Well, 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 be-to-be-saf 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, either building, say you're building some kind of, I don't know, expense management system or HRS thing. Just like, where do you recommend people to do with, in terms of just how far to go design as a lever, as a, as a differentiator, maybe? Well, you know, inherent in your question is a 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 pace as design. If you, again, if you kind of get the tech, we haven't talked about tenancy yet, but we'll get to that 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 companies that have the largest design teams, they're often the companies that have the most ambiguous cultures and the most unclear design vision, right? When you go to companies that really know what they're doing, you know, and they're clear that this is who we are, that's 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 like they're operating in a really narrow vein, because they know who they are. It's very much like individuals, you know, when you're a teenager or a young adult, you can spend a lot of time trying to figure out what to wear, because you haven't really sorted it out yet. But by the time you get to be a little bit older, you've 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 a Pinterest, I was at Pinterest at a point when Pinterest doesn't quite sure what it, who it was. And so 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 guys, you know, other places that knew what they were about, you know, apples, the key example there, like we were trying to figure out what it was about. We were trying to figure out what was the apple way to do this particular thing. And so that moves a lot faster. And I agree, like, look, having your soul in every little checkbox is it 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 it every state. But, you know, generally every six months or a year, you need to back up and ask yourself, am I, am I proud of this? Is this something I am happy to be a part of? Do I believe in this, 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 threat of design tenants and principles. Is this 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 look, there's whole websites dedicated to design principles. And if you go on your read it, you'll see a lot of principles like simple, clear, beautiful, fast, secure. 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, it's sort of a platitude to move towards, but I just don't help 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 keynotes. Apparently, the guy who was responsible for originating keynotes went to Steve and said, you know, how should we think about keynotes? 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 thoughts about it, I realized pretty early on that I wasn't going to be able to have any sort of commanded 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. You can't, you know, they can't be consulting a handbook. And so one of them was documentation is a failure state, right? Like an enterprise company is a lot of times people think, oh, we'll just put it in the manual to be part of the trading. And I would constantly be coming back and go stop it. Nobody wants to learn our software. Nobody cares. We are just one more browser tab in a world of browser tabs. We are not this user complete quarrel. They do not want to learn this stuff. Documentations of 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 users should have to opt into complexity. So our main competitor at the time was tablo, tablo started with complexity. That was their whole value product. It's like we are super powerful tool. We can do all sorts of stuff. So when you sit down to tablo, it feels like you're flying the space shuttle. And if you're a professional data analyst, that's great. That's the kind of tool you wanted. That wasn't what Thought Spot was about. We were trying to take data analytics into the hands of what I call mirror mortals, also known as business users. People who didn't live and read 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. But 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 feature. And so those tenants were all, again, they were all decision-making tools. And when we would have designed debates, we could just come back to this. Wait, are we actually starting simple? And forcing them to opt into a complexity? Or are we doing something else here? So there's kind of this implication in this discussion by 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? They 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 don't want 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, you know, 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 felt like they kind of operated at the design strategy level. And I just think that varies dramatically from company to company. What I would look for is, you know, if you're a design leader or a 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, you know, bifurcating into two camps. And then as there's something we can do where we just settled that, you know, we just have that debate once and for all, we decide as an organization. We're going left instead of right and you're absolutely correct. You have to be opinionated. But that's how you're going to win. You know, there's no unopinian saw, unopinianated saw for this been successful. You have to have a point of view. The question is what's it going to be? So it's a practically like just try to look for places where it seems that the teams have in the same debate over and over and it haven't once get it done and put it behind you and make it attend it. And what's, why is that we're tenant versus principal some important? I don't know. I said, well, I'd said a lot of tenant. I'm not even, 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, it's, I just wrote principles to sort of Applehood and Mother Pi. 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-op that word and change how people think about it so much as I might be more successful just coming up with a different word altogether. This entire episode is brought to you by Stripe. 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Okay, I want to zoom out a little bit and another theme that came up a bunch when 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 want and you look around, you'll see a lot of people using their phone to navigate that system. You know, they're trying to figure out where their gate is, what time their flights are, and whether or not they can pull it through boarding pass, et cetera. And just just watch people, watch their faces, watch the level of confusion and frustration. You know, some of them, some of them tech superheroes like you and me and most your listeners, but a lot of them are just mere mortals and they're not living in breathe in this stuff all the time. And a lot of times they're super frustrated, you know, and then take that and scale it out to their entire day. And almost everyone living in a modern economy now is going to have hundreds of interactions with the phone or with the 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 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 a hand stay up. I'm like, okay, how about so far today, you know, in most of the hand 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 wraps 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, you know, 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 untolds amounts of frustration and confusion. And it just takes away from their life quality. And they, I think we have an obligation as product people to put that emotional energy back into people's lives. You know, they don't, 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 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 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, you know, with this podcast, it'll go out to hundreds of thousands of people. Like, if you and I saw all the people that will potentially listen to this in one place, we would think to ourselves, oh my goodness, that's like a lot of people. And we might think of it differently. We might behave differently. You know, I's 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 and I, if you lose sight of that, I think you just, I don't know, you get sloppy and disrespectful is a wrong word, but I think you just lose sight of how much impact you're having on other people. Well, 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 podcast videos on YouTube, I'm like, wow, that's like one person that's going to spend their time watching this thing while I really want to make, it gives me more motivation to make these even better and better. Yeah, look, I think you have to find ways to go, you have to, you have to find mechanisms where you go out of your way to see people using software in real time. I've worked on products have been used by billions of people at friends and touch billions of people. None of us ever get to see anybody use this stuff in the wild in their natural state. Maybe we see them in a lab or something like that, but I've never seen anybody just randomly using even Pinterest, you know, but there's ways that you can go and as a creator to make or you can go and watch people using software in the wild. So I go watch, just go observe people going through self-check out it target, which is the best self-check out I've ever seen. Go watch that and go watch it. It's some other grocery store where it's not as great. You know, and like really notice what happens with people, much to my kids frustration when they, when their friends are over, I often grab their friends phone and just sort of flip through it to try to understand how people are organizing their home screen and which apps they use and maybe there's something in there that I haven't seen. I'll ask them what that is and ask them to kind of give me a tour of it. Like I think we're living in a time where people don't do so many usability studies, so a lot of folks get pretty far into their careers without ever ever having watched mere mortals actually use software. Instead we're 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 filmmakers can go to a theater, they can watch people understand stuff, comedians can go to a comedy club, they can start to develop an intuition about why people laugh. None of us have an obvious way to go watch people use software, so 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 that are taking chaos to the kiosk. 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 trying to figure out Apple Pay. And these are pretty seamless experiences and still there's kind of friction in all of the stuff. Just go rent a car and then look, notice how long it takes you to figure out what the heck is going on with the dashboard. 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 get to do that. An important element of which you're describing here, which I think maybe people misses 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, Giamar Rausch from Versel, Founder Versel, and he had a really great phrase of something, 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 use in 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 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 check out in other products. So we watched them go through like eBay and William Sonoma and Amazon or something like that. And we learned a ton about checkout about what was important to them, how like it turns out like shipcode 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 yelling at them 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 they're using adjacent products could be super useful. And again you know we we work in a medium software is a medium and we need to understand our medium in the same way again musicians go to concerts, filmmakers go to movies you know comedians go to comic clubs like wind 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 something like came up a bunch also and conversations with folks that have worked with you that this is something that you believe. Yeah you're so good with the research, Lening. So yeah look so so I love Pinterest in 2014 or 2016 sorry 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 and a 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 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's a long time later and that hippie ethos had gotten pretty quiet and so I was listening to a podcast about the history of Silicon Valley by a Stanford group that the podcast was called Rod data and it was season two and it starts off with an episode called Monument to a Dead Child which is about Stanford University and it end with Zuckerberg's testimony in front of Congress and in the middle of that they start talking about the counter culture revolution in the late 1960s in San Francisco elsewhere and they quote this book by a guy named Fred Turner it is the book's called from counter culture to cyber culture 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 called that saw software as a new form of media on par with movies and music and books and when I heard that all of a sudden it weighed 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 I'm a maker that designed software and then when I heard that software is a medium that that whole 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 away when it's working well and what I find so troubling now is it a lot of time it's not working that way and I remember the first time I saw a computer I mean probably a lot of people on 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 like it was just freaking magic man I mean it was the future it was so cool and it just felt like the most amazing roborialis 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 car vendor but I don't naturally have an emotion with kitchen tools or you know things that think even more sophisticated tools like calculators and pullies I still don't have an emotional response to them but every piece of software I have an emotional response to I either feel confused or empowered you know I feel like my world's gotten bigger my world's gotten smaller like they all have an emotional component and I think once you realize and accept that then you can say oh there there is an emotional component to what we're doing with this product I could just leave that to chance which is what most people do or I could try to be conscious of it and we could try to bring that into our conception of what the products about and try to be purposeful in the emotion we're trying to to to elicit from the user and I think that's where design a particularly visual design can have a huge impact so again in many conversations that I'd have in design reviews some some executive would go I don't know ultimately this just kind of come 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 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 gonna own it and show up and be the person you want to be in those moments or not you know a few you want to go I guess a little longer ago I was talking to the team at toast who makes the handheld point of sale stuff that they use in restaurants and the thing I was trying to tell them is whether or not you see it this very you know tonight you're 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 checks going come in the waiter the waiter the waitress is going to hand over the device to that grandmother and 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 whatever teenage grandson is going to grab the device and do it for you're at the dinner table what are you going to do for grandma get a show up as well as you can 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 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 motion 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 fast you want them to get to this for low it's what's the motion you want them to have yeah I often don't think about what I want them to do I just think that's sort of a selfish way to think about it you know like I like they they have something they want to do like I'm trying to help them like I'm not if 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 to do a project 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's pushed 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 do I've seen a lot of companies be really successfully seeing metrics as a consequence in a way to evaluate the quality of their decisions and then using those to you know trying you like make better decisions moving forward so they're kind of a very useful feedback mechanism but I think you know there's definitely a risk to confusing doing something because it's a driver versus something as a consequence there's there's a few more questions I'll ask but I want to come back to something that asked earlier that I think is on the minds of a lot of safe founders and product managers listening to this I've just like okay this all is 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 a product manager to help them can 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 what do I 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 designers going to be able to figure out which swimway and they're supposed to be and 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 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 at Google is organizing all the world's information that's a great vision they'll never achieve that that's that's something that's always over the horizon and it's been a very useful organizing principle for their acquisitions and how the company grows Amazon to be the Earth's most customer centric company okay great that gives that's that's a vision they will never get there it tells you how they're going to expand Apple doesn't have an explicit vision but I might describe it as personal computing can have a transformed effect on the lives of individuals right and I think that kind of focuses a lot of what they're trying to do Disneyland still the best vision statement of all time which is the happiest place on earth so once you tell an employee this is supposed to be the happiest place on earth then you're signaling all sorts of things about how they need to pick up the trash and how they need to show up on time and how they need to wear their their uniform like you're just signaling a whole bunch of stuff so what I talked of 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 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 and they think that the company is the product the company is not the product the product is the product and the company is bigger than the product and you need to have some vision that speaks beyond just this particular thing and it's lack and obviously 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 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 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 you this also translates to work with humans like make the prompt more specific add more context in life not just when you talk to AI yeah I love that that's so interesting so the so the advice here is just if you're finding design is taking too long or you want to just level up your 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 vision that everyone can wrote 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 spending around and honestly that's your fault as the client you know I mean as a design leader I think one of my main challenges is frankly trying to make the pms better clients you know helping them get more specific it's very common for a design team to get extremely ambiguous asks from a product team and then they have in the problem for designers they have to take all that ambiguity and they've got to ring it all out so when they give it to engineering engineering knows exactly what to code because computers don't tolerate ambiguity like engineers need to know what the thing is going to be in design gets stuck with a really ambiguous input but they have to have a highly specific output and then they're often time box 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 a storyboard to production like it's all about getting rid of ambiguity and so the more ambiguity that can be removed upstream the faster designs 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 a space to think it'd be creative and explore advice there just how to navigate that well if you go back to my example the script and storyboard script 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 there's always a tendency of 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 you know let's is a point of pride there's no way I'm to go execute that exact thing so that so you're right like pms have to give you the space to operate and I think a lot of what they're trying to achieve could be done in more informal ways conversationaly and whiteboards uh things like that but yet you need you need to narrow the problem for the designers you know they need constraints they don't need they don't need a tiny little box but they they need constraints you know they can they can terms of like you don't you don't give them an airport tarmac you and you don't even give them a football field it gives them something more like a basketball court you know they're 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 counter intuitive lessons on building product design and building teams leadership is there as they're another very counter intuitive lesson you've learned about building products hiring leading teams that goes against common startup wisdom the thing I would say is it you should wait as long as possible to draw a picture like uh and in that I think that pushes against all the JNAI 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 isn't 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 that looks even slightly realistic much less something that comes out of one of the JNAI tools you know 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 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 is your first order thinking and I think there's a way you can stay in these things conceptually and conversationaly 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 taken 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 go okay well that's interesting let's table that what else we got you know there's one story that's kind of related that's useful and 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 it's just yeah yeah but we just have to make it blue it's like well we're not making it blue and a couple days goodbye and I saw the home page and the link had been made blue because she had got around me and she got an engineering and just made it blue and I started the hallway again I was like you know what the house 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 just 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 a more prominent one of which is making it blue you know which is the thing that came to you first because you're not the designer like it that'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 what's the problem with the thing and then let us solve it don't don't jump to it and tell us this is what we're supposed you know don't tell us this is just exactly what we're supposed to do and again it I do the same thing on the roadmap like you decide to 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 respect this advice about not dry quickly and not making that primal mark which I love that term is I met I'm curious to 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 that's on that do you discourage people from doing that for you 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 mean I haven't played with it a lot myself because I'm not an operational role right now but you know presumably it's really useful at cranking out that actionable prototype which you can click and you know experience and I've said for a long time that an interactive idea needs to be expressed interactively so we're not talking with our hands so 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 you know ideas start off pretty fragile and the best idea is 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 them like the little plant and in the Pixar movie Wally you know you've kind of you've got to give that little guy a little space a little time some water and some nourishments 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 it'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 will also say that you know everybody when they when they look at a prototype what they're focusing on is the visual and textual expression and so as soon as you produce something in high resolution the feedback you're going to get is going to be back colors and shapes and like these these presentation layer things which are very loosely related to usability and value right it's it's like it's like focusing on the special effects of a movie that has a really bad story and so it it thoughts about we used to use what we call block frame diagrams which were even simplified versions of wireframes it was just big chunky blocks if 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 you know we had to talk about conceptually what it was and so we were trying to build up this firm foundation where we could go from the block frames to 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 and it initially it made the product team really nervous because we would be sitting in these block frames to wireframes for sometimes weeks and they'd be like when are we finding and see the cops and then what would happen is because we had such a robust design system what's we locked down on the on the block frames we could send it to an agency and they could do the full high-res cops like in a day you know they'd be exactly what they were doing instead of 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're 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 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 gnai tools it's this seductive thing of hey let's just go let's go make the competency 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 it'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 to see she's one of the cpo's at Microsoft I really there's many cpo's she has this concept of demos before memos and just like promsets written here d's you should just be prototyping all your and so it's interesting to hear that 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 it's 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 then frankly that you're proud of and that you're using just 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 you know I mean I look there's a there's a counter argument that's you know you can say oh it's like Darwinian evolution and we're just going to spend 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 head of 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 you know what the blind spot was or what my strengths and weaknesses were I'd seen some prompts about that stuff and what I was really fantastic what I was what's a what's an outdated mindset that I'm holding on to that's not still serving me and it came back with this a very polite prompt or a 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 that was really useful I asked to sew in my blind spots that was also useful I use it for a lot of exercise input that's useful and they exercise that I've gone through most recently was I 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 chat to PT 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 helping me with this task and so we've just gone through that process and and it's been really useful for me it's no substitute for a therapist or a real coach or anything like that is not a human being it doesn't care about me I'm not saying that you should use it instead of these other options you need a human being as well but it's been very good at reflecting back to me things that I think have been floating around in my undermind and so I there's there's a 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 have heard this is your unconscious or something like that but I think of your undermined as the part of your brain that's processing information before it gets a language and then when you go to consciousness you've turned it into language in languages into full universe of things you can think languages what you can think in English and if you talk to multi-lingual speakers they'll tell you that they can think things in other languages than what they can think in English so if you always 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're undermined how to work in a compiled code and it could do a lot of stuff that you can't really do in the interpreted code which moves slower and it's kind of has different orientations when we call that consciousness so I was feeding chat GPT all this stuff over the last year so and there are all these patterns in my undermind that had been going into that that I wasn't able to express with conscience conscious language and so when I started asking it questions I think what it was doing was it was statistically reflecting patterns back to me that already existed in my undermind but because it was putting them into language my conscious mind could now recognize them and respond to them and so again I found it as a sort of a life coach I found it very useful is a mirror back to things that I was probably already thinking and it helped me clarify my thoughts it's not pushing me into 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 Colone episode that I did recently he has okay well linked 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 yeah she's helping achieve a thing and then forward yeah and then also and it's important element of say you don't want like you say you don't want to be busy but something you just create keep creating busyness for yourself maybe you do want this so anyway we'll link that up so there's a lot of good stuff there yeah that's great okay one final question before we get to a very exciting lightning round this is one that we that I don't think you have any idea I'm going to ask you and so I'm curious where this goes this is a story that Jeff Redford suggested I ask you he told me that you're obsessed with space you love talking looking researching space telling stories about space there's a story that you share about this guy named John Hobolt does that ring a bell oh yeah totally okay share that story and because I think there's something really powerful here for people building products so I should clarify I'm also I am a fan of a 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 to ever and I think it's an incredible there's there's a profound number of leadership lessons and individual lessons to be learned from that program and I've done multiple talks about this I could go on for hours that's to be so here we go the particular question you're asking is John Hobolt so John was I can't really 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 present Kennedy goes to Rice University I believe it's 19th September or May 1962 they give us the famous moon speech we choose to go to the moon up because it's easy but because it is hard that whole thing which I also have to say and maybe you'll link to this in the show notes as well everyone should go watch that talk that it 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 ways that's 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 are NASA are like you know we've we've only recently put Alan Shepherd into space and he just went up and went down I mean that was like almost like a blue origins type thing that was just up and down we didn't even do a lap around the earth like the Russians did it with Yuri Kagan and now we're talking about going to the moon like nobody knows how to go to the moon and there were three different options for going to the moon one at the time one was to build a big giant rocket and just go straight to the moon it's called director sent and the main advocate for that was Warner von Braun who was the main rocket guy in the world a little bit of a complicated past but nevertheless Warner von Braun's a big guy he's got the president's ear yeah he's like let's build a big giant rocket go to the moon people are like yeah the problem is when you get to the moon the rocket's still super big so like 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 he spent two spacecraft into earth and then you you link them up in our orbit then what it 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 earth the moon surface and back up and that spacecraft is truly a spacecraft it only flies in space which means the engineering requirements around it are profoundly different because it doesn't have to survive uh re-entry into the earth right and so is 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 them I mean there's just a lot goes on and so a few bolts had uh come across this paper from a gentleman named Yurik and Drauchach who was uh 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 could think about going to the moon but Yurik and Drauchach in 1918 is on the planes 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 that he's figuring right this paper John discovers it years later and John tried to sell lunar orbit rendezvous it's not going over it NASA and so eventually he decides to go around all the hierarchy and he sends a very famous memo to one of the top guys at NASA the memo starts somewhat as a voice in the wilderness and then it goes on and there's points in there where he's really emphatic and 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 stuff that he just made the case and you know it was I mean Yurik's whole career a 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 champ in the idea and and he was another year so after that famous memo which he 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 rodive but eventually they do and even with down brought himself was very complimentary to that to he evolved 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 weight 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 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 Yurik had brought this idea to the world and it just sat around and then somebody discovered it and dusted it off was able to push forward and it came through and then maybe the third lesson is like ideas need champions and then each champions will want 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 yeah I love that you summarize the takeaways two way the way so the like to me the takeaways and the lessons here is one is coming back to your Pinterest board in the office say the hard thing to is be patient you know it may take a little bit of time for an idea to like a radical idea especially to president and stick and get adoption so if you're you know pitching a big new product idea like give don't assume and 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 p.m. I hear a lot of people say that they're reluctant to post on social media or LinkedIn or something because like well I don't want to be you know don't be self-promoting and I try to council them and like look it's not about self-promotion like it's a like there are ideas that you care about that you want to see succeed in the world and so get out there is an advocate of the idea it's it's not about you but the idea and 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 so there's I like that drum roll yet it is 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 gonna recommend the first ones 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 like and it will give you an insight I think into the designer mindset that is like when you understand typography I think you understand where designers come from and the best designers I know are just total type nerds so highly recommend elements of typographic style second book Zen in 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 cohesive whole which I believe is the main challenge facing most software teams they they create something that's highly fragmented instead of a single hole so Zen in the art of motorcycle maintenance and then the last one is a book called Time in the Art of Living by Robert Grooton it's just a very interesting collection of sort of impressionistic views of time and how time passes and what time means that's very different from the others and it's not something probably gets recommended on your show to often but I think it will I think it will help people in their lives in a powerful way I think these are all brand new entries in the in this question next question you have a favorite recent movie or TV show you really enjoyed so I really enjoyed several 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 it was definitely interesting watching 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 just to death but she was like what I thought ever it's super fascinating and then I'll throw one other in there which is not something I've recently seen but something I had to recommend for everybody which is Lawrence 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, character, 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 the 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 and love that movie. Next question you have a favorite product that you have recently discovered that you really love. You're focused on recent and I'm just gonna push back. Now here's not the terribly recent the stuff that I go back to I give you a couple of nerdy. I have a Lika M6 scam 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 like a cameras they're I've seenly expensive but the thing about like a cameras is you show up different when you shoot with a Lika. 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 throw up 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 the digital SLR you just take a whole bunch of pictures and hope something's gonna turn out. I think these cameras are very useful metaphor for being conscious about how the tools you pick are gonna impact the thing that you produce. Once you go into Figma you've made a decision about the thing you're gonna produce. If you stay in a sketchbook you've made a different decision you know if you go into something else you've made a different kind of decision. So I say the Lika M6 with film because of that and then the 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 a bitica is really fascinating it's a it's ultimately it's a habit tracker and task management but it's fundamentally a game it's a role playing game where you create a character and your character revolves and can buy armor and go on quests and things as you check off your habits and stuff and it is the most interesting expression of shifting conceptual models that I've ever seen so if you think about a conceptual model it's sort of the software equivalent of a genre in a movie and so like once you say it's a project man of a 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 it's a you know social media you're kind of in a certain genre but these are different genres and habitica is really interesting because it mixes genres it mixes role playing game with what 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 those two genre mashups are really interesting when you come to a rom-com you have a certain expectation of what can happen a rom-com suddenly if somebody suddenly got shot a rom-com you would like that would not make sense to you in the same way that if somebody made a really funny joke in a genre movie it wouldn't make sense so I think a bitic is just the most interesting example I've ever found is somebody really doing it fascinating mashup of conceptual models which is sorry this is a little stop it's just it's an unexplored and unexploded possibility of software ideas I love how profound this lightning around to herity is the the point about like a changing the way you even think about the photo is so interesting have never thought of it that way you mentioned Star Wars have you seen Amdor by the way I know but my life everybody's raven about it okay it just yes I've been watching basketball so I just haven't had the spare time yet but 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 you find useful in work or in life yeah so there's three quotes that I come back to all the time they're repeating most of my talks first of all I've already used which is design is clear thinking made visible by Edward Tufty second one is from the American landscape photographer Ancel 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 carbs 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 fight plenty of photographs that like tingle your senses with 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 I think I love that this connects back to the by coding apps and prototypes that people build they you know you can do it really quickly but they won't go too far potentially yeah not to hit on the stool they're amazing okay they are they are at like always AI stuff is profoundly amazing and I I will encourage people like what are the most amazing things for me about this moment in AI is it this the kind of AI we're experiencing has been theorized for well over 50 years so there is a vast not 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 what it means to be human so like there's so much stuff you could be reading to help you process this moment and in 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 as we grow a lot talking around soon we get self-driving cars all over San Francisco yeah really really start it's a future yeah it's a future let'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 into which and you know is going to be useful like here's a robot law that we gotta be thinking about yeah I just just to go back to this idea of how once you what you create an expression of something people baseline off of it I recently got to hear Henry Modisett who's headed to design it a proplexity give a talk and one of the things he said that just really struck me was that people's conception of AI was founded by was put out there by Hollywood years ago so this idea that that AI is going to take stuff over and is ultimately like really dystopian and malevolent towards humans and stuff like that it's actually something that's created by Hollywood and we're all like and now we're like trying to outlive how you know it's stuff like that and so it's just just just a great example of somebody put the concept out there and planted that seed and people's heads and now we're struggling to get people off that baseline and to look at it with fresh eyes that's a that's a really good point yeah it's it's much more entertaining to watch AI trying to kill us all not just everything's amazing a great job yeah okay final question I know you're a huge sports fan in particular your big warriors fan so let me just ask you this say we're running the warrior say we're the owner of the golden state warriors what would you 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 stuff is on the court and off the court you know if you listen to the so the local announcers they're always like these non-steff minutes really matter you know like like I look at that and like that's not that's not really a team then right that's like stuff and you know it's like stuff and the in the in the band of Maryman and the warriors are bigger than that right and most of these basketball teams are bigger than that it's 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 organizations uh 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 you know a singular I don't even you know I've been calling me generational players but bigger than that you know he is unequivocally the greatest shooter in the history of the game and he's one of only two or three players is 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 know that you can't have the whole franchise built around just him I love this hot take a great way to end it Bob I kill us into all day this is so fun and interesting in so many ways on so many levels uh two final questions we're can fix funny online if they want to reach out and maybe learn more about what you're up to and how can listeners be useful to you uh so bobbacksley.com's the easiest place right now it's just a bento site but I'll get some more stuff up there uh in the coming 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 published pretty much every day on LinkedIn so that's an easy way to find me you know I'm happy to 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 Liny it's it's about these ideas it's about the idea that software matters you know that we're making something for people on the other side of the glass and that it's a way that we show that we care and that we should care so I wouldn't it's 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 know I talked about this earlier like the digital world not safe for our kids like have we kind of done something wrong so I just I hope people take that responsibility more seriously and try to help clean things up a little bit I think we've we've made a dent in that Bob thank you so much for being here thank you so much Liny it's been 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 podcast Spotify or your favorite podcast also please consider giving us a rating or leaving review as that really helps other listeners find the podcast you can find all past episodes or learn more about the show at Lenny's podcast.com see you in the next episode