Taste, quality and what it actually takes to build software people love (w/ Bob Baxley)

A lot of SaaS products ship fast and skip the thinking. This episode is about what happens when you don't, and why that actually matters for growth.

Bob Baxley spent 35 years designing software at Apple, Yahoo, Pinterest, and ThoughtSpot. Products he worked on have been used by hundreds of millions of people. He's one of those people who has spent a long time thinking carefully about what makes software genuinely good, not just functional, and why so few companies get there.

In this conversation, we get into how to build a culture where quality is the standard, how to get your whole company to care about design without a single presentation, and how the decisions you make at the conceptual level shape everything downstream.
 
🧠 What you'll learn in this episode:

0:00 - Why the tech industry is in a speed race and what that means for product quality

7:37 - How Bob fell in love with computing at 11 years old and why that shaped everything after

12:31 - Why timing matters as much as talent when it comes to what you can build

13:58 - How economic pressure from VCs is changing the pace of design work inside companies

24:36 - The real difference between sales-led and product-led companies, and why it never changes after founding

27:05 - Why design teams have hurt themselves by hiding their process from the rest of the company

30:00 - How Bob's team ran an internal influence campaign at ThoughtSpot using weekly Loom videos

35:49 - What a head of design actually does on a sales call and why it worked

37:42 - Design tenets vs. design principles, and which one actually helps teams make decisions

42:30 - What choreography over control looks like in practice for a design leader

47:51 - The difference between micromanagement and being in the details, and why it matters

54:55 - How to think about quality within constraints instead of chasing world class as a target

1:00:46 - Why taste is hard to compete on, and which layer of the market you actually need to nail first

1:01:15 - A simple exercise to raise the taste level of your engineering team

1:06:08 - The three stages every market goes through before design becomes a competitive advantage

1:12:36 - What it really means to design for the person on the other side of the glass

1:16:57 - Why user research needs to be a ritual, not a one-time sprint

1:20:44 - The Post-it note observation that turned into a multi-billion dollar company

1:24:29 - Bob's favorite apps and what they got right at the conceptual model level

💡 Actionable takeaways from Bob

Steal these quick wins:

1. Run the "three favorite apps" exercise with your team

Ask everyone to name their three favorite apps .Not the ones they use most, their actual favorites. Getting your team to sit with that question starts a real conversation about what quality actually means versus what just has good distribution. 

2. Show the work before it's done

Bob's team at ThoughtSpot made a 22-minute Loom video every week for 35 weeks, showing projects at every stage and sent it to the whole company. It shifted how every department understood and valued design work, without a single big presentation or formal pitch. If your team feels invisible inside the company, this is a low-cost way to change that.

3. Replace your design principles with tenets

Principles like "be clear" or "feel responsive" don't help anyone make a decision because nobody argues the opposite. A tenet is a hard-edged statement your team agrees on once so they stop relitigating the same debate. 

4. Go watch your users outside the context of your product

When Bob was asked about ZenMaid, his recommendation was to visit cleaning business owners and understand how they think and run their business, not just how they use the software. Watching how someone actually works, before you introduce your product into the conversation, gives you better ideas than any feature interview.

5. Ask an LLM you've been using regularly: "What outdated mindset am I holding onto that's no longer serving me?"

The answer Bob got shifted how he thought about control and leadership. His suggestion is to run it with an LLM that has enough context on you to give a real answer, not a generic one.

What is Love At First Try?

A SaaS product design podcast for non-designers. The Love At First Try Podcast explores how SaaS products become unforgettable.

We unpack the idea of taste in product and brand design, deconstruct what makes beautiful products beautiful, and show how to merge growth with delight.

If you’re a SaaS founder, CEO, or developer building products people love, this is for you.

Jim Zarkadas (00:00)

Hey, I'm Jim, and this is the Love at First Try podcast, a podcast for SaaS CEOs and developers that truly want to learn more about design and care about it, but there are no designers that find it too complex. In every episode, we discuss how to design products that become sticky and unforgettable. We dive into the topics of taste, UX, growth, and conversions, and we share practical tips and frameworks you can add into your development process. Enough with the intro, so let's dive into today's episode.

Jim Zarkadas (00:28)

thanks a lot for joining me again. It's an honor. And I love that we have the chance to discuss today and go deep into all these topics that we both have in mind. And we always start the podcast with a quick intro. I did not make the intro. I always ask the guests to introduce themselves and tell a bit of their story and what they're currently working on. So yeah, if you can elaborate on this, that will be amazing and hear your story from you actually. That would be a cool one.

Bob Baxley • Silicon Valley (00:53)

Yeah, well first off, Jim, let me say thanks for having me. It's a real honor and privilege to be here. So I'm looking forward to the conversation and for all you out there listening, I appreciate you joining in and hope it's a useful conversation for you as well. My name is Bob Baxley. I'm a software designer who lives and works in Silicon Valley. I moved here in 1990 when I was 27 years old. I'll let you do the math and what that means. I've been working in the industry for 35 years, started on desktop products, so I used to work for a company called Clarisse, which was a wholly owned software subsidiary of Apple, still is actually. And there I worked on the first couple of versions of Clarisse works, had some work in McDraw and some other products there. From Clarisse, I eventually over the course of those years moved into management, spent some time as director of design at Yahoo, where I led the team that worked on Yahoo search products, most notably launched Yahoo Answers and helped design the original version of Yahoo Answers.

Then had the chance to join Apple in 2006, which was a very fortuitous time to join what would become one of the most important companies in history. I joined about nine months before the phone was announced and I joined leading the design team that worked on the Apple online store. So if you ever went and bought Apple hardware at apple.com, that was the part of the product that I worked on. I know all of you went and configured your $15,000 Mac Pros and see how juiced out you can make things. ⁓

Jim Zarkadas (01:48)

Mmm.

Bob Baxley • Silicon Valley (02:17)

Obviously it was an amazing experience working on the online store, did that for six years, and then worked on the corporate side of Apple retail for two years, which was also absolutely fascinating. A very unexpectedly fulfilling experience, ⁓ understanding retail and designing products that are used inside the stores by the employees. It's a ⁓ fascinating aspect of design, working on employee experiences, and I'm so grateful to have had that opportunity. It made me see the world and experiences, whether that's restaurants or theme parks and movie theaters, whatever, it just opened up my eye to a whole different part of the economy and a different type of design and experience. From I Left Apple in 2014, I believe it was, went to Pinterest during a high growth period of that company, was there from 2014 to the of the middle of 2016. Then spent a few years kind of wandering around trying to figure out what I wanted to do and how I felt about tech.

This was between like 2016 and 2019. But then I decided I wanted to get back in the game and was fortunate to find a role leading design at an enterprise software company called ThoughtSpot. I was there for just over four years. And that actually got me a lot of exposure to what it was like working for a company that was largely based out of India. Although the company had been founded here in Silicon Valley and most of the execs in our headquarters were officially here.

Jim Zarkadas (03:13)

Hmm.

Bob Baxley • Silicon Valley (03:38)

The bulk of my team and virtually all of engineering was located in Bangalore and various parts of India. So I did get to travel to India, especially after the pandemic and the quarantine, I spent seven trips to India in 18 months, which is not something I would recommend, but it was quite memorable and meaningful to me. I left ThoughtSpot two years ago this month. And to be perfectly honest, at 62, I'm trying to figure out what to do now.

Jim Zarkadas (03:53)

Hehehehehe

Bob Baxley • Silicon Valley (04:04)

I wish I could give you a clear story of what I've been doing, ⁓ yeah, after 35 years in tech, it's a little murky as to what you do next. So that's where I'm at right now.

Jim Zarkadas (04:14)

Yeah right.

Yeah, like a beautiful story. It's always a challenge like deciding what to do next. It's a yeah, it's such a deep thing and so so personal on where you find meaning and yeah, it's a it's a very tricky one. I went through a phase like when I I went through a similar phase actually when when I I quit one of the companies that I was working for in the past. I was at a point was like, ah, maybe I want to become a kite surfing instructor like I'm into kite surfing and I really love it. I'm like, what if my life wasn't into tech? What would be that version of team for example?

Bob Baxley • Silicon Valley (04:41)

Mm-hmm.

Jim Zarkadas (04:46)

So I didn't do anything like that because then you start thinking about all the consequences. Okay, maybe I'm gonna live in an island and I don't want to this and that and so on. But it's a very interesting process to go through because I feel like it really helps you kind of learn yourself kind of a deeper and understand what you truly want versus what you don't want.

Bob Baxley • Silicon Valley (04:47)

Yeah.

Yeah, I think I'm a little fortunate in that, you know, the first time I saw a computer, I was 11 years old and it was a very early stage ⁓ Heath kit computer that a friend had built with his father was based on the original Intel 8. I think it was 4044 chip or something like that. And I just fell in love with computing. You know, I remember the moment vividly and you know, it was almost 50 years ago and I remember it like it was yesterday and the only thing I can compare it to is you'll occasionally hear like Broadway stars talk about how they were a little kid and they went to go see a musical and just being up near the stage and seeing all the actors and the singers and stuff. And they were just sort of moved by the whole theater experience. They knew that's what they wanted to do with their life. Like it's sort of like that for me. I just fell in love with computing. And so like I love tech in a really deep way.

Jim Zarkadas (05:46)

Hmm

Hmm

Bob Baxley • Silicon Valley (05:56)

I don't necessarily love the tech industry as it's operating today, but I love computers. And so I, I don't fantasize about going and being a kite surf instructor or really anything else. The thing I struggle with is, you know, at this point in my life, how can I best engage with the industry to be, ⁓ to be useful to other people and to give me opportunities to grow and continue to learn and stuff like that. And, know, to the, to your earlier point, I do think we're at an interesting inflection point where a lot of folks, especially if they've been in the industry for a while, but think even some people trying to get started, they're looking at the industry and saying, this really what I want to be a part of? And am I going to do what's needed to do to make this transition to more of an AI-based work environment? ⁓ And I think there'll be a lot of people just decide to opt out. And to your point, there are economic consequences to that, but there's also some happiness and stability consequences to that as well. So I think there's a lot of people, at least in my circle, that are trying to make that understanding of the value prop. I could be leading a very different life than the one I'm leading. What does that mean?

Jim Zarkadas (07:03)

Okay. Since you mentioned like, would love to go into that topic. I'm really curious. So two questions, three, but our first one is what is the thing that made you fall in love with tech? Like what do you say that you have like a deeper connection with tech? So I would love to tap on that and understand how would you describe it? And the other part is like that you said the separation between tech and the tech industry and people kind of opting out. So what is the thing that you're seeing that doesn't feel right and why you've seen people in your search like opting out with the whole AI transition and so on. So yeah, these two topics would be really lovely to go deeper into.

Bob Baxley • Silicon Valley (07:35)

Yeah. Yeah. Yeah. Well, let me go back to the story of how I fell in love with computing. So again, I think for many people, maybe many people in the call, they may not remember the first time they saw a computer. Maybe they remember the first time they saw an iPhone or something like it, but you know, the computers and stuff, that kind of technology has been around long enough that you kind of have to be close to my age to have a clear memory of the first time you saw a computer.

Jim Zarkadas (07:51)

Hmm.

Hmm.

Bob Baxley • Silicon Valley (08:01)

But in I think it was 1976 or so, maybe 74 when I saw it, ⁓ there weren't that many computers around. mean, was, I mean, the word computer existed, but only in kind of the mainframe corporate type of the word. There wasn't really this idea of personal computing. And ⁓ my particular story, I was at my friend, Clint Wilkinson's house, and I knew him and his family through the church we went to. This was in Dallas, Texas. His father, ⁓ Tom, was an engineer at Texas Instruments and was sort of like your classic nerdy Apollo era kind of engineer with the white shirt and the pocket protector and the whole thing. And so it's not crazy that Tom and Glenn had were building things together, you know, and so Heath kit was a company that operated the United States that would sell you the stuff you needed to assemble electronic components. So you'd buy stuff in a kit, you'd put it together yourself. Hard to believe I know, but he would buy things like oscilloscopes or radios or in this case, a really early primitive personal

And so on this particular day, I'm over at the Wilkinson's house and I go in Glenn's bedroom and it's a total disaster and a mess and everything. But down at the end, he has on set up on a piano bench. He has this black and white monitor and then this metallic box that's got like a keypad on it and a little LED type rate. I read out like a calculator. And then for the first time in my life, I saw a ⁓ typewriter like a typewriter keyboard that was not part of a typewriter and it was connected to this metallic box through a cable. And again, I think it's probably pretty hard for many people to put themselves into that moment and realize how novel it was. But honestly, I'd never seen anything remotely like this. so Glenn sits down on the ground, he starts typing some things onto the keyboard and they show up on the monitor, which is also something I had never seen before. Like TV was a broadcast medium. The idea that you could generate an image, they would show up on something that looked like a TV monitor.

Jim Zarkadas (09:28)

Yeah, yeah.

Hmm.

Bob Baxley • Silicon Valley (09:57)

was completely new to me. And so he would type a letter and it would show up on the monitor. And I could kind of get my head around that because it sort of felt like a video typewriter. But then he typed two or three things and the screen started printing out a whole bunch of stuff. In retrospect, what he did is he ran a basic program, basic being a programming language. He executed a program and the program spit out a bunch of extra stuff. But again, in my mind, I had never seen anything like that ever. I had never witnessed something where you typed a few things on a keyboard and a whole bunch of other stuff came back in response. And in that moment, I think some part of my 11, 12 year old brain sort of said, my God, like that's a like there is something different and magical and miraculous happening inside that metal box. And I do not understand it. ⁓ I also don't understand humans. ⁓ But and they're also interesting. But I think there was something about the metal box that blew me away.

Jim Zarkadas (10:57)

I totally get it. Yeah. Yeah, totally. Yeah

Bob Baxley • Silicon Valley (10:57)

⁓ yeah. And then, you know, I, I subsequently,

the, the school that I was going to at the time, one of the, some, one of the parents actually bought an early Wang computer, which is against like kind of a primitive PC. And I learned in the sixth grade, I learned how to program in basic, which is a, ⁓ an early stage interpreted computing language, very similar in structure to Python. and it turned out that my brain, just the way it was structured was very well suited to programming.

And so I fell in love with the concept of programming. And so by the time I'm 13 or 14, I was just absolutely in love with computing. And then it turned out that my, you I just wasn't in a place economically that my parents could afford to buy me an Apple II, which would have been the obvious thing to get. They did take me to the computer store in Dallas, Mr. Micro out in Richardson, Texas, just outside of Dallas. I still have the brochure in my closet right over there. I still have the brochure that I picked up that first day for the Apple II, which has an Apple on the cover.

Jim Zarkadas (11:30)

Hmm.

Love it.

Bob Baxley • Silicon Valley (11:56)

with the headline, simplicity is the ultimate sophistication. And I think on that, and I remember that visit to Mr. Micro really clearly as well. I think that that visit as well is when I fell in love with Apple and when I somehow got attached to Apple. And then, know, through, mean, it's a longer sequence of events, but I eventually discovered software design when I was 27 and I was working for Clarus in Dallas as a sales rep which we could talk about the value of starting your career in sales. We could talk about that as well. But I started out in tech and sales basically. And then it turned out that they had a UI job that they had opened in California to work on this product called Clarus Works. And I came out and interviewed for that. And because I had previous experience running a graphic design studio, it turned out I was a good fit. And in 1990, I was a good fit to become a UI designer. And that's how I kind of got started and moved to California.

Jim Zarkadas (12:23)

Mmm.

Got it. That's a hello story. Right?

Bob Baxley • Silicon Valley (12:55)

So yeah, it's a lot of random stuff that has to do with things I bumped into and just, you know, in just the reality. And I think this is important for everybody to keep in mind. Like the opportunities that life's going to bring you are highly dependent on the year you were born. You know, you don't you don't get to be Steve Jobs if you're born in 1982. Like you get to be Steve Jobs if you're born in like 1958. I think it's probably over and that's probably like 54, you know.

Jim Zarkadas (13:10)

Yeah, that's a good point.

Hmm

Yeah, that's something that I'm experiencing more and more like, since I started like getting into entrepreneurship, that's something that I started realizing, like the power of timing. Because many times I want to feel like, no, it's all about like the effort and coming out with smart ideas and being consistent and all these things. Sure. But also there is a timing aspect like that, that sometimes just happen only once in a specific time. Yeah, that's a very good point. And talk about, yeah.

Bob Baxley • Silicon Valley (13:43)

Yeah, most all of this happens only once.

you don't get to invent that, you don't get to be around for the advent of the web again. Like that was a one-time event, you know?

Jim Zarkadas (13:47)

Yeah.

That's very, true. Talking about one time events, like it's perfect past to jump into the tech industry and the AI stuff. And I'm curious there, what is the thing that you see on the tech industry and you're not like happy or excited about with, and what is kind of a, what are you seeing the tech industry that in terms of the direction that is maybe changing? So I'm curious to hear your thoughts on that part and what you see from your circle, ⁓ from people and how they react to that and how they feel.

Bob Baxley • Silicon Valley (14:22)

Yeah, well, look, I think the pressure with generative AI is for everybody to move faster. And I think companies have understandably and I try to be really non-judgmental about this. I have deep feelings about it and how I want to behave as a designer. So I do have like my own personal interest in things, but I also try to set that aside when I'm looking at what's happening in the industry because I don't want to cloud it by what I wish it was. I just try to be open-minded about what it actually is.

In the industry right now, there's enormous amounts of money to be made. So there's incredible economic pressure coming from executives and from VCs and investors and stuff. So there's just enormous economic pressure. People care mostly about how to make as much money as quickly as possible. And that means you just have to move fast. Moving fast is not what design is set up for. Design is this contemplative, know, let's take a moment, think about it, try to create something that I'm proud of and it's going to last. And that works sometimes, but it probably doesn't work for a lot of companies today because the idea of design is that I can sit and I can take in all this information. I can pause, process it, and then come up with a solution. But that really only works if the foundation that you're working within, that the solution, the foundation that the solution has to live within is going to be stable.

So for example, if we were really going to design something from the ground up, it could take us, well, let's take Figma, for example. It took them three years to go from starting the company to like having something they could show to users. spent three years to build that. Like there's no way you could spend three years today building the first version of a product because the foundation on which you're building would be completely different by the time you were done in three years. So, you know, in an era where the reality of the tech is changing so quickly,

Jim Zarkadas (15:59)

Mmm.

I see.

Bob Baxley • Silicon Valley (16:16)

It may be that the smartest strategy is just to move as quickly as possible and see where it's gonna go. And to not really have a big vested interest in what the outcome is, ⁓ that is profoundly unsatisfying as a designer. And I'm not at all convinced it leads to good outcomes for users, but it's not an irrational business strategy, sadly. ⁓ And so I think that there are people who worked in a different era of design where you did have the opportunity to sit and think and make something you were proud of, make something that you loved, something that had meaning and that you could of express yourself through and that you could really touch and improve people's lives on the other side. I there's a long period that that's kind of what design was. And that's not really what the tech industry largely is right now. The tech industry is just a speed race right now. And so I think there's a lot of people that really like working the other way that simply don't want to work the new way.

Jim Zarkadas (16:43)

Hmm.

Bob Baxley • Silicon Valley (17:12)

⁓ which again is a perfectly rational choice on their part. So I don't criticize anybody for deciding they don't want to play anymore. That's totally rational. I think the people that are screwed are the people that kind of want to play, but they want to play by the old rules. And so they're trying to play, but they're trying to function in the old way, but they're living in a new environment. And that's just, you're just going to be roadkill in that scenario.

Jim Zarkadas (17:18)

Exactly. ⁓ Yes.

Fully agree. I'm curious on what you're saying on the speed part. So you're describing like how design used to be that you can go deep, like take your time, think and make something that you're proud of. Like what are the things that you're saying? I'm not sure if you have like a very specific examples of like maybe products or design stories of.

What is the new version of design that doesn't feel that has the deep thinking for you? Is it that you need to see that feature like next day, that this is the pressure that you've seen in the industry or...

Bob Baxley • Silicon Valley (18:11)

Yeah, so again, I haven't been in a regular operating job in two years. So everything I'm telling you is by anecdote and talking to other people inside other companies and reading people's LinkedIn posts. My sense, and some of the people I've been mentoring have recently gotten jobs and they just talk about the velocity of requests and demands coming at them and how in the past, if they were gonna do, you know, a design for a feature, they might expect to get a week or two weeks to be able to show a first draft of that feature. And now it's like a PM might bring them a question in the morning and expect an answer within a few hours or certainly by the end of the day. ⁓ And they're dealing with more and more engineering teams and just the velocity at which they're expected to flip things around. Because I do think there's this sense that you could just feed an AI engine something like a PRD and it's going to produce some screens. know, now, yeah, right. So you know that that's not true. but there are a lot of people who ⁓ aren't close to the rubber that still think that's the reality, right? And there's also a lot of people that just think that's good enough, you know? And I know a lot of what your agency does is growth design. You know, I think growth design's a really interesting model for where design in general might be going, which is my understanding of growth design when we did it pretty intensely back at Pinterest, which again, was a while back, but still.

Jim Zarkadas (19:17)

Quality standards.

Bob Baxley • Silicon Valley (19:31)

You know, we were running dozens and dozens of experiments all the time. And the thing that I realized with growth design, it was to not hold on too tightly to what you want the solution to be. You have to kind of know directionally. I want it to kind of be like this, but you have to be able to entertain a lot of wiggle room and say what might get there and be willing to try variants that maybe don't feel right to you, but end up performing really well. And so it's it's this, you know, most designers like they get really attached to the solution, like if you think about graphic designers, like Paul Rand did one version of the next logo. Like he didn't even show Steve Jobs alternates. It's like, this is the version. And by the way, you owe me a few hundred thousand dollars. ⁓ Like that doesn't really fly today. ⁓ And so I think, again, the people that are buying the design just want something that's good enough as quickly as possible. And that's, again, I just think that's profoundly unsatisfying to most people.

Jim Zarkadas (20:03)

Yeah.

Hmm.

Bob Baxley • Silicon Valley (20:31)

who in their heart are designers.

Jim Zarkadas (20:35)

Yeah, yeah.

It's a very interesting one. want to share some like some thoughts from my side as well on this topic from the experience that I've seen. So one thing that I've seen when comes to tech industry is that there is a difference between bootstrap companies and VC fund companies. Like it's something that I've really seen and experienced personally. We work mostly with bootstrap companies as a team. And it's not that they're super lifestyle driven or something like they are more lifestyle driven even like the CEOs are like, Hey, this is a beautiful job that I created for myself. I don't want to just sell and you can multimillionaire, I already feel like a multimillionaire because I have the life that I was planning for. what the bootstrap companies have is very solid culture on, because it always starts from the leadership and not so much pressure from investors, VCs and all these things. And with the VC companies, I see like that's constant pressure, like faster, more like, more people. And I'm like, we want to move faster. Let's have 10 more designers. No, but design doesn't work this way. I don't care. want 10 more designers. And I'm like, they don't get it. And then you have people that are more like, ⁓

People like to say if you're like into insurance some insurance let's say brokers that are starting a SaaS product They're not really product people that's something Steve like was saying a lot I've seen it in many interviews that he gave that like you have to be a product person It's a very specific type of person like in terms of the thinking and the culture that you have So that's something I've seen in the industry in terms of the difference That's why I'm a huge fan of the bootstrap companies and then on the speed

That's something I'm kind of experiencing a bit on. Suddenly I find myself multitasking more between many projects, but it's also like the teams are growing. So maybe we're reaching a point where we need more designers, let's say, and it's not an AI problem. like with AI, it's really, I feel like it really comes back to the leadership culture. Like how do the top people in the company think? Because this just kind of is going to expand to the whole company, right? It's like a family. The parents set the vibe in the culture and this has a big impact on the family. So I really see companies in the same way.

And if it's just like typical executives, AI is going to make them super delusional, if that's the right word. And they just think that suddenly there's this magician that can create solutions. Like what you said that you can just give a PRD and you get something. Yeah, you're going to get something, but it's not the right solution. And if you're satisfied with that, then maybe you don't need a designer. Maybe you can just go and see if this kind of a trust, like, or however you see it, like maybe you can call it good enough. ⁓ But I feel it really comes down to like the culture of the company and how, like what are the quality standards? I feel is one of the things that are going to dictate a lot on how designers work and everything. And how I've been experiencing AI is a, I feel like liberated in a way that suddenly I can build, like by build I mean that I can, I've been always saying that my problem with Figma and all design tools was that it was too much of a drawing and I come from an engineering background. I'm like, I'm building a product. Like it's built, it's like building that bottle. I want to the material. I cannot just create sketches and then hand over to an engineer.

Bob Baxley • Silicon Valley (23:37)

Mm-hmm. Yeah. Yeah.

Right. Yeah, you have to be able

to work in the medium in which you're creating. Yeah.

Jim Zarkadas (23:49)

Exactly, and that's something that I find

really beautiful and find myself jumping between Figma and Claude and like Depending on the face that I'm into on the design, the levels, what are the details that I want to work on? So fine

It's very interesting with AI how the design process is changing and how personalized it can also become to every designer because you can just build your own workflows and everything. But yeah, when it comes to the AI companies, because you mentioned the GenAI and the VCs, yeah, I feel like there's a lot of madness over there where like, hey guys, you really need to slow down and think more. And I feel like it comes down to also what you said, the economic pressure, that there are crazy bets on AI right now money-wise, and they want them to work. And also, the side that I've been experiencing and makes me sad as a human, like as a part of society, is the marketing side of AI. I'm like, guys, this is not a nice world to live in. Too much clickbait, too much ⁓ trying to scare people, a lot of FOMO. I believe that B2B could be better than the trusty B2C content where people always try to steal your attention, but it feels like it's becoming a bit similar. And I feel like the economic pressure is one of the big reasons actually.

Bob Baxley • Silicon Valley (24:51)

Yeah

Jim Zarkadas (25:01)

we see also this kind of this this madness because they just need crazy crazy returns on that. ⁓

Bob Baxley • Silicon Valley (25:01)

Yeah, yeah.

Let me try to unpack two things in there. The first one is your split between Bootstrapped and VC funded. ⁓ A different way to think about that is between companies where the product exists to fuel sales. it's like most B2C companies, the sales team is actually driving the bus. I think as designers we go, well, is it product led or engineering led? I think the bigger question is,

Jim Zarkadas (25:11)

Yeah, yeah.

Bob Baxley • Silicon Valley (25:34)

Is it product in the whole, you know, the largest sense of the word product, not the role, but is it product led versus sales led, right? Does the sales team driving the bus telling the product team what they need to develop because then they can do more sales, right? And that's probably 90 % of companies. But then there's another group of companies, which you're saying are bootstrap companies, which I think is true, but it's not always bootstrap companies where the product exists and sales is in support of the product. Like we're going to make the product we love.

Jim Zarkadas (25:41)

Hmm

Yeah, true.

Bob Baxley • Silicon Valley (26:02)

and the sales team's job is to go and sell it. And that's how Apple works, for example. Yeah, so like, not to pick on anybody, but if we look at like Salesforce, for example, it seems to me as an outsider that Salesforce is largely driven by their sales team and that they're adding features and manipulating the product in order to address the needs of their users, of their paying customers, which is largely the same for Zoom. mean, almost enterprise, almost all enterprise companies operate that way. But then there's a small group of companies, maybe Airbnb. I actually think

Jim Zarkadas (26:05)

Yeah, to get the message out there. ⁓

Yeah, 100%.

Hmm.

Hmm

Bob Baxley • Silicon Valley (26:31)

Pitch was one of these, one of your local companies. ⁓ Apple for sure, but also Lego, Leica, Patagonia, there's plenty of other companies in the economy where they make something that they care about and then it's the job of the sales team to go sell it. And so I think as a designer, you have to be really cognizant of which kind of company you're signing up for because they do not change. If the founding principle of the company and the founders of the company don't believe in product and don't believe in design, they will never graft it on.

Jim Zarkadas (26:32)

Mm-hmm.

Yes, these are beautiful examples.

Bob Baxley • Silicon Valley (27:00)

It will never happen. Amazon, Microsoft, Google, they will never ever, ever be design driven. They just will never make that switch. So that's kind of one thread. The second thread I want to talk about is, ⁓ you know, the executives just coming to the design team and say, you know, just spit something in the AI and like, let's see what comes out. I think design and I learned this at ThoughtSpot. I think the industry has done ourselves a huge disservice by not really showing our process in the rest of the company.

Jim Zarkadas (27:01)

Yeah.

Mmm.

Bob Baxley • Silicon Valley (27:29)

designers tend to like they take in all the information and then they tend to go into their library like environment and they sit together, you know, and they throw around ideas using really kind of strange words and vocabulary. And so it's all kind of very secretive and stuff. And then they come out with two or three solutions, which if they're good solutions look really obvious. So if it's a really great UI, when you first see it, you're like, well, yeah, of course, like how hard could that be? You know, that's so obvious.

Jim Zarkadas (27:29)

Mmm.

Yes, true.

Hmm.

Mmm. Yeah.

⁓

Bob Baxley • Silicon Valley (27:58)

Of course, it's only obvious once you actually see it, but we don't really show all the other things that we threw away. So for example, when I was working on the Apple online store, we introduced a buy online, pick up and store feature. We did 82 different versions of that. We had 82 numbered versions of that feature. And when it finally shipped, it was two radio buttons in the cart. Do you want to pick it up or do you want to ship it to your house for each item? That was basically what the feature came down to.

But it took us 82 versions to get there. Now, if the executive team and the rest of the organization understood all the different permutations we were going through and all the different arguments, they would have thought really different about the design process. But what they mostly thought is that they told us some requirements and then something magical happened and then we spent all our time drawing them. And of course, like drawing them is not the issue. And we just don't, I think again, as a design community, we haven't really let people in to understand the debates and the things that we're considering to get to the solutions. So everybody from the outside thinks it's super easy. So then they're sort of like, it's natural then that they would think, why can't AI just do this? It all seems pretty straightforward to me. So I think this is one of those things where we've probably hurt ourselves by not letting people into the messy middle, know, not letting them see that.

Jim Zarkadas (28:59)

Hmm.

Yeah, yeah, a hundred percent. And that's something that I've experienced as well sometimes. Like one of the things that I'm trying to do is to do like more collaborative design. like one thing that I, and it's actually on the first part that you said between like sales driven and product driven companies, a hundred percent. I find it way better categorized as a bootstrap and VC funded. A hundred percent agree on that. And on the second part, yeah, I, I fully agree. And like on this one, thing that I tried was doing more design workshops, so includes more of the team to design together. You lead the session, but they're part of the process and they can see like, see the deep thinking and everything. And it's something I'm actually a big fan of. And I realized in the past, I was afraid, but it was like, no, I cannot sell them all these ugly designs that I'm creating. Like they have to see the final cool thing. But actually once I started experimenting with the workshops, I realized design is getting better. It's more fun and the whole team also enjoys it more. And they can have a, a, a decent impact and like a meaningful impact that word that I was searching for on the solution. So fully, fully agree on that part. I'm communicating better and even when it makes sense to make them part of the process, I feel that is a good one also to embrace.

Bob Baxley • Silicon Valley (30:25)

One of the tactics that we did at ThoughtSpot that I thought was really powerful is one of my co-leaders, he had this observation that we were basically all on TV now because the company was remote, kind of distributed. And so we communicated a lot through Slack and Zoom and things like that. He's like, okay, so we're all basically on TV and we have all these internal communication channels, which we should sort of treat like social media. And we should basically run an influence campaign inside the company.

And so what we started doing, and we did it for about 35 weeks, and then I just kind of ran out of steam, but we would make a video every week that was about 22 minutes long, and we'd make it in Loom, and the video would start. I'd kind of introduce what the team was working on that week, and then the group was divided into three different, what we called studios. So smaller teams working on different parts of the product. So I would talk for a few minutes, and then each one of my studio managers would go through, and they would describe what was happening in their studio. And they would show projects at whatever level of fidelity they were at.

Jim Zarkadas (31:10)

Mm-hmm.

Bob Baxley • Silicon Valley (31:21)

Sometimes it was like these really simplified block frame diagrams, sometimes wire frames, sometimes high res prototypes, sometimes nothing but words on a whiteboard, know, whatever it was, they would just kind of expose what they were working on, what the issues were. And then I would come, so each one of them would go and then I'd come back at the end with some sort of design story, which I typically took from the Apollo program or something. And so we would send that to the whole company through a Slack channel every week. And you know, out of a company of 600, the first couple of videos got like maybe 400 views.

Later, it would be down to like 150 or 200 views, but they became known inside the company to the degree that like the sales team started to understand what we were doing. And they would, know, some of the sales guys would come up to me at company meetings and they would start talking to me. I'd have no idea who they were. And then they would invariably say, I know you from the videos. And so I kind of became like this sort of internal YouTube star. And what everybody realizes they would, they would see all the ideas that we're playing with and all the variants and they developed a much better appreciation for the level of ambiguity we were trying to work through and the level of thoroughness that we were using to arrive at our solutions. And it completely shifted how they thought about what the team was doing. We never had trouble getting head count after that. We didn't have trouble getting a seat at the table. All that went away. And in fact, design at ThoughtSpot became, at least at that point, one of the four competitive pillars of the company. So when you would see our sales presentation, you'd see design as one of those things.

Jim Zarkadas (32:23)

Hmm.

wow.

Bob Baxley • Silicon Valley (32:46)

And as the head of design, I started getting invited to sales calls to help close deals or convince teams on what was going on, things like that. like we, we just through those videos, we dramatically raised the profile of design by showing the messy middle. And I'll, I'll, I'll share a little aside that might be useful. About two years ago, I saw this prompt on LinkedIn to try on chat GPT and I ended up running it. And the prompt is, ⁓ what is an outdated mindset that I'm hanging on to that's no longer serving me? Let me repeat that. And I suggest everybody run this at home with an LLM that you've been using a lot so it understands you a little bit. What is an outdated mindset that I'm holding onto that is no longer serving me? And what it came back with in my case was it said, given your age and your profession, it's not surprising that you're really attached to the concept of control, but that's not the world we live in anymore.

Jim Zarkadas (33:17)

Hmm.

That's a good one.

Bob Baxley • Silicon Valley (33:40)

and it kind of went through and explained it better. And it eventually had this phrase, which was meaningful to me, though I know it's just statistically derived, but the phrase was, you need to emphasize choreography over control. And I now kind of really take that to heart, choreography over control. And I think when I was in operating design roles, I wish I had held onto that a little bit more. And the design leaders that I see that are being really successful, I think they're better at being choreographers and not trying to like just

you like hammer down the control so much. And certainly being at Apple, like you were supposed to control every last single little pixel, right? And I think that's actually what's culturally been challenging for Apple in the era of AI and probabilistic computing over deterministic computing. They can't control it the way that they're used to controlling everything else. ⁓ And so at ThoughtSpot, I think I got a little bit more hands off and I got more comfortable sharing with the company all the stuff we were gonna throw away.

Jim Zarkadas (34:29)

Hmm.

Bob Baxley • Silicon Valley (34:38)

you know, and I was more comfortable letting them see behind the screen, right? And it helped them understand and appreciate and ultimately respect a lot more of what we were doing.

Jim Zarkadas (34:49)

Yeah, it's a beautiful story and yeah, the prompt 100%. I'm gonna do it after the podcast. I'm really curious now.

Bob Baxley • Silicon Valley (34:56)

You'll be shocked. Yeah. I've done a couple of workshops now where I just, where the workshop, the only thing I plan for the workshop is the prompt. And so you get a bunch of people around the table and you give them the prompt and then they all input it. And then you just watch their faces one by one where they're just like, my God. And then you just see where the conversation goes. it's, you know, every time it's been magical, absolutely magical. Yeah.

Jim Zarkadas (35:04)

Nice.

Yeah, one thing that I wanted to comment on is a beautiful example of how like a thought spot, like we're talking about a common of 600 people, how sewing the value of design and the process can look different between a team of 20 versus 600 and how you need to kind of really be systematic and think about it and about what ways would work.

Yeah, and I'm curious, you mentioned that you started being invited in sales calls. That's something I haven't heard before about having a head of design at a sales call. And I'm curious, what would you mention as a designer over there? Would you present the solution, of a pitch, the thinking around it, or what does a designer do on a sales call? I'm curious.

Bob Baxley • Silicon Valley (36:13)

Well, so we were trying to sell that a competitive advantage of the company was that we had superior design. So I think we needed to have a way of explaining how our design team worked and how that was different from what other companies were doing. So I had a presentation, which I gave many times, which talked about the history of the company and why the company will talk to it had a couple of stats about how design can increase the value of a company slides. Honestly, I don't really believe that McKinsey study and some of these other things. I absolutely don't believe those numbers but we throw them around because people like numbers. And then I would tell the story of our founder, a gentleman named Ajit Singh. ThoughtSpot was his second company, he's now onto his third. And Ajit, you he'll tell you, like I grew up, he grew up in rural India. He's got a degree in chemical engineering. And early in his career, he worked for the American company Honeywell. And during his tenure at Honeywell, they did a couple of engagements with IDEO. And by seeing IDEO and what they did, he just fell in love with design.

Jim Zarkadas (36:45)

Yeah.

Bob Baxley • Silicon Valley (37:10)

And so every company he started had this appreciation of design right at the beginning. And so I tell his story to kind of say, you know, design is in the DNA of the company. It is in the founding of the company. That is why I am here. If it wasn't a design living company, led company, you wouldn't have a guy from Apple working here. So we're trying to convince the customer that design matters and it's deep in the company. It's not just a one-shot deal. And then we go through our design process, how the team works.

Jim Zarkadas (37:11)

Mm-hmm.

Bob Baxley • Silicon Valley (37:39)

⁓ We would show some mechanics of the tools we use because that was typically kind of interesting. We had this whole concept of tenants. So we would talk about design tenants versus design principles, which is always interesting to people. Design principles tend to be things like, ⁓ you know, we're saying for clarity, it should feel secure, it should feel responsive. They're all these single words, which are all great, but they're not useful for making design decisions because nobody would ever argue the opposite. You know, nobody's like when you're looking at design.

Jim Zarkadas (38:04)

Mmm.

Bob Baxley • Silicon Valley (38:06)

Nobody's ever gonna say, you know, it's too clear. We should make it confusing. And therefore, principles is sort of a nice North star. They don't help you make decisions. Tenants, by contrast, is something I learned at Apple. And tenants are these hard edged statements that help the team know that when they come to a fork in the road, they should always go left. And so the story from Apple is that when they were working on keynote early on, the guy who was leading keynote sort of asked Steve, Steve Jobs, how should we think about keynote?

And Steve said, I want you to keep three things in mind. One is it should be difficult to make ugly presentations. Two, ⁓ you should have cinematic quality transitions. And three, you should optimize for innovation over PowerPoint compatibility. And so if we just push on that last one and you think about a team that was struggling with whether to do innovation or PowerPoint compatibility, if they had to confront that issue time and time and time again with every feature, they would eventually divide into two groups and they would gouge each other's eyes out. And I saw that happen at Yahoo. I know how that works, right? The team would repeatedly have the same debate over and over and over again until it just calcified. And so the concept of a tenant is you just decide once and for all and you don't revisit the issue. And so at ThoughtSpot, I started to pay attention to like, are the debates we kept having over and over again? And we just created tenants to address each of those. And the three tenants we had, I'm pretty sure I can remember now, let's see, the three tenants we had was the first one is users,

users should have to opt into complexity, right? So whenever a dialogue box opens up or a window opens up, do show like the full mass of things you can do or do you show a simplified approachable version and then people can turn on knobs and buttons? Given that our product was supposed to be sold to business users and not to train data analysts, we felt that we should start with a simple version of the feature and let people turn things on. But that's a decision and there's a rational decision to do it the other way.

Jim Zarkadas (40:00)

Mm.

Bob Baxley • Silicon Valley (40:03)

If for example, you're Tableau where your market is trained data scientists that want to be able to see the whole thing right from the beginning. But you know, once you make that decision, users should have to opt into complexity. There's a whole lot of downstream debate that goes away. So that was the first one. The second tenet was ⁓ documentation is a failure state. And we use that one a lot. That was if your instinct is to explain it in the docs or to hide it behind a little eye with a circle, you know, if you had to have explanatory text, you didn't have the feature right. Like nobody wanted to be trained on the software. And we just kept hammering that over and over. Nobody wants to learn your software. You're just another tab in somebody's browser and all they want to do is go home to their children and families, right? Like stop making demands of the users. And so that all got expressed through this tenant of documentation as a failure state. And then the last one was the entire product should look and feel like it came from a single mind, right? And that was our attempt to create a product that was a unified, cohesive, coherent, singular experience, which is radically different from what most enterprise companies do, where they are very content to have a highly fragmented experience, where you're clearly moving from one team to the next. And the reason they go for the fragmentation is because it allows them to deconstruct the product into individual design and product teams and let those teams operate independently. But they eliminate a lot of friction by not making the whole thing work together.

Jim Zarkadas (41:13)

you

Bob Baxley • Silicon Valley (41:29)

which was just not how we wanted to function. Like we wanted the whole product to look like it came from a single mind and to be a coherent whole. But that meant that we had to balance every feature with everything else going on in the product and that creates friction and takes more time to reconcile those issues and stuff. ⁓ like once we would, you were asking about the sales calls, when we would take these customers through these tenants and they could understand our thinking, you can imagine that's a very different kind of conversation in a sales call.

Jim Zarkadas (41:55)

Mmm, yeah, the core principles,

yeah.

Bob Baxley • Silicon Valley (41:59)

from what they were having with any other company. ⁓ You know, actually a lot of those conversations led to invitations for me to talk to design teams at other companies and things like that. Cause then they're design leaders who get really interested in what we were doing and how we functioned and stuff. So, yeah.

Jim Zarkadas (42:02)

Mm.

That's a beautiful story. Now, yeah, everything

makes way, way more sense. More sense. Yeah. And I really love also the idea of like, don't just explain like how it solves your problem, but talk about the philosophy. Like it could be your unique point of view on the market and like how you're actually building this product. And yeah, it just makes so much sense to me. I love the approach. And you mentioned something before the choreography versus control, right? And I'm curious.

You already started the story, but I'm curious about another example of this topic, like just a simple example where you can explain the difference between these two. How do you act in the one way and the other? How does it look like?

Bob Baxley • Silicon Valley (42:55)

I mean, just at a personal level, for example, with the choreography control stuff, I've just gotten much more open about sharing things on LinkedIn that maybe aren't complete. I haven't kept up with it, but there was a couple of weeks when I just sort of made videos and put them up there, not really knowing where they were going to lead. And they ended up being some of the best performing stuff I'd ever done. So, yeah, I think a lot of time it's giving yourself up to the idea that you don't know what the result's gonna be. And I think as a designer, that can be pretty hard. If you think about design, let's see, I think this is right. If you think about design presentations, a lot of times designers come in, they try to explain everything before they show you the work. If you think about portfolio reviews, a lot of times they're trying to set up, this is the business problem and this is the input I got and blah, blah, blah, blah, blah. And then eventually they show you the work. And what that whole thing is about is they're trying to eliminate the risk of you not liking the work.

Jim Zarkadas (43:44)

Hmm.

Bob Baxley • Silicon Valley (43:51)

They're trying to pre-sell it so that by the time you show it, the time they show it, you're already bought in. And I think that's a way of trying to control the room and control how people are gonna respond. Because if you just walk in and you go, well, this is it, here's the thing. You don't really know what's gonna happen. And so I think you have to be prepared to think on your feet and kind of choreograph your response to the room when you just show the work. Now, one of the things we learned at Apple is that none of the executives would ever sit through their setup.

Jim Zarkadas (43:52)

Exactly.

Hmm.

Bob Baxley • Silicon Valley (44:20)

Like they just don't care. Like none of them would let you set work up because they knew that you didn't get to set the work up when the user saw it. So, you know, they wanted to have the user's experience of it, which is just show me the thing and I'm going to respond. I'm going to respond and then we're going to deal with it. So it was I think it was very frustrating a lot of times when candidates would come to present their portfolios from to me. And I was always just like, stop it. Show me the cops. Where are the cops? You know, that's I was sort of famous for that. The woman that ran ⁓ design ops for me at Pinterest. She used to just laugh about all that time, laugh about that all the time. Because one of my lines was shut up and show me the comps. I don't care. I don't want the setup. I don't need to explain the business. Just show me the comps.

Jim Zarkadas (44:57)

Yeah, yeah, yeah, yeah, I fully, fully hear you. I fully hear you. And that's a good one actually. From a personal point of view, like on my side, I've been experiencing like what you described of once you get into entrepreneurship, you have to start being way messier than you are as a designer. And it feels like I now need to develop two sides of myself. The one, like the designer that has like a very clear vision and everything. And then the entrepreneurial, which is more of the mess around and find out kind of a way. Even like the podcast, this podcast, an example, you could try to make it like perfect control, everything on the experience,

We can just keep it simple and just go and be like, yeah, I'm just going to publish a nice conversation and that's it. So it's something, yeah, that hits home. Like I totally understand what you mean. And it's it's a very interesting one. And also in the world of growth design with A-B testing where sometimes like the interesting thing with growth design, what I, why I love it so much is because it's a big challenge to your ego as well. Like A-B testing. I don't believe this.

Like I believe in A-B testing, but I don't believe in outsourcing taste and thinking and decision making into A-B testing. It's like you just need to figure out the right way to use it. And it's a strange feeling when you run an A-B test and it feels uncomfortable. was like, let's see, is it going to work or not? Before the A-B test, can be fully, fully confident. And sometimes, yeah, like you may have full confidence and faith in solution, but the market can prove you in a different way. That's why I mentioned also the entrepreneurial part, yeah.

Bob Baxley • Silicon Valley (46:12)

Yeah.

Jim Zarkadas (46:27)

Yeah, now...

Bob Baxley • Silicon Valley (46:28)

Yeah, look, I think designers need to get more comfortable with ideas like choreography and improvisation, things like that. You you need to think of yourself like more like you're in a jazz band than like you're in a symphony orchestra, right? You're not playing from the dots. You're not performing the same thing every time. ⁓ It's also, again, when I do portfolio reviews, when I was a hiring manager, you know, I would interrupt designers all the time when they were presenting. Like I wouldn't just sit there and let the lecture go on. I was always stopping them, asking them questions kind of poking on the work a little bit, which again, I'm sure some of them thought I was just being rude. What I was trying to do is to test how good they were at thinking on their feet and how well they could respond to criticism or observations in real time, because that's a critical part of the job. And some of them could respond to that better than others.

Jim Zarkadas (47:05)

Mm.

Hmm.

Fully, fully agree. 100%. 100%. Okay, let me think about the next topic. I want to dive a bit deeper into the Apple and Steve Jobs kind of a time of your career on this one. And some topics that I have in the notes is...

The like that's under Brian for the CEO of Airbnb has been talking about recently the difference between micro management and being in the details, right? And I'm curious about your experience on this topic from the different companies that you work with and how you describe these two, these two versions. What does it really mean to have leadership that is truly into details? you in while I was doing my research, like on other podcasts you've joined and things you've shared, like one of the things that you shared, I think it was about Avelia, that the C-level, that the executives there have really, really good taste, for example. And I'm really curious on how does, from your experience, leadership that is really into the details looks like, and how does that collaboration with design look like as well.

Bob Baxley • Silicon Valley (48:15)

Yeah.

Well, look, so your first question was micromanagement versus into the details. And to me, micromanagement is I'm telling the my boss is telling me how to do things, right? They're micromanage me at the micromanaging me at the methods level, right? They're telling me how to do my job. Whereas an executive that's into the details, they're critiquing my output, but they don't say anything about my process. Right. And I think that's an important distinction. Once somebody gets into your process, they're kind of they're into your business. It's sort of like I'm gonna do things my way, leave me alone and judge me by what comes out the other end. So I think that's a useful and important distinction. Micro-managers will make everybody crazy. ⁓ Somebody who manages the details just looks like they're paying attention. ⁓ So at Apple, there's just a culture of everybody's paying attention to all the details all the time, because that's what matters. And so it's not just that.

Jim Zarkadas (48:53)

Hmm. Hmm.

Exactly. Yes.

Bob Baxley • Silicon Valley (49:10)

executives, whoever they were, were like judging everything and asking all these detailed, pointed questions all the time. Instead, everybody in the company, everybody you interacted with was asking stuff all the time because they all had a vested interest in the company producing something that was as high quality as could possibly be. Like the bar was world class for everything, everywhere, all the time, which also can be quite maddening. And there's only a certain type of person that survives at Apple for a long time because to work in that high performing environment is incredibly demanding. But like one of the stories that I like to tell is at least at that time, when I first started working there, you go to Cafe Max, the cafeteria there at the company, and you would get a pizza, and the pizza would come in kind of your standard square cardboard pizza box, and it would have a big box of oil, you know, have a big plot of oil underneath it. And eventually the pizza guys invented their own pizza box.

And it was made from a different kind of material. It was round and it was rippled so that the pizza not only stayed warm longer, but also the oil dissipated in a different way. And it was an all around better pizza box. My understanding is they got a patent against the pizza box. I haven't confirmed that one way the other, but that was my understanding at the time. And so that's an example of somebody deep inside Apple just asking themselves, how can this be better? And the entire company is that way all the time.

Jim Zarkadas (50:28)

Hmm.

Bob Baxley • Silicon Valley (50:31)

There's plenty of stories of Steve asking some pointed detail about something on the online store. was on occasion, I was in email threads where he had gotten an email from a customer asking about something and he or somebody on his team would be forwarding that off to the different groups around the company to get them to work on it. you some of your, you or some of your listeners may have read with Tim Cook's recent announcement of stepping down. He talked about how he starts every day at I think 5am reading inbound customer emails.

Jim Zarkadas (50:56)

Yeah.

Bob Baxley • Silicon Valley (51:00)

Like that's something that I don't think people realize the power of that for Apple, both in the case of Tim and Steve, because they both had very public email addresses. Steve at Apple, Tim at Apple. It's pretty straightforward. And Apple has, you know, Apple has an army of fans and users around the world that fortunately hold the company to very, very high account. And so when design fails, you've got all these people that are sending notes into the executive teams to the CEO and those CEOs then are escalate those.

Jim Zarkadas (51:12)

Yeah.

Bob Baxley • Silicon Valley (51:29)

So Apple's in this really interesting feedback loop with its user base, where the user base is forcing the company to maintain a high standard. And as annoying as it was, we eventually did get to something like that at ThoughtSpot as well. Because we were competing on design, it mattered to the company. And as the team became more well known through the videos and other means, if we came up with something that people didn't think was up to snuff, they would call us out. Yeah, they would push back.

Jim Zarkadas (51:47)

Hmm.

Yeah.

Bob Baxley • Silicon Valley (51:59)

You know, there was times

when I'm like, Oh my God, I have to take more comments from the peanut gallery and it would be very frustrating for me as an individual. But then I tried to call myself by saying, well, look, it actually means they care, you know, and I would say that I know there's a lot of frustration with the liquid glass release and people, people thought it was really bad, but just like ask yourself the mere fact you can be this disappointed in this upset tells you how high regard you have for Apple, right? Like there's really not another company that could release a design that was that was that far off the mark where you would care that much, you know, like if like like if Google mess something up or, you know, Facebook messes something up like, yeah, yeah, of course they did, you know, I mean, another one like so I think Steve did that for Apple and holding Apple to account around design, I actually think Tim's though amazing job doing that around the issue of privacy for the company. And so people inside the company now realize that privacy is sort of an existential value and that if they flub that up, it's a real issue. So just again, do the thought exercise. Imagine that there's a data leak and all your Instagram credentials get shared. You'd kind of go, yeah, kind of expected that. Now imagine that happens to your Apple accounts. You're be like, whoa, whoa, whoa, like, wait a minute. I can't believe those guys messed it up. Like you're gonna be upset in a very different way. ⁓ So I think as a design leader, you know, there's an opportunity for a lot of design leaders to say, I want the...

Jim Zarkadas (53:00)

Hmm.

Mmm. Mmm.

Bob Baxley • Silicon Valley (53:25)

I really want the company to be so into what we're doing at design that I'm going to be getting feedback from everybody around the company because they care that much. Again, it's pretty annoying. It's level. It's not. But I do think it's a good signal that people care and that what you're doing matters.

Jim Zarkadas (53:36)

That's a beautiful one. Yeah, it's not a fun environment. Yeah.

Yeah.

Yeah, yeah, 100%, 100%. On this one, I have one question with the world class part, because it's something, it's a personal challenge that I have like all these years and I'm not, I can't tell if there is a solution or what is the solution. So I'm really curious about your experience. So the challenge is you want world class quality, right? Like that's what inspires you. That's what you aim for. That's what you're here for. Like you want to this level of quality in your design, but then there's the real life constraints of. timelines, ⁓ the resources, resource management. So money and time, like how much buzzard do you have? How much time do you have and the velocity you need to move with. So one of the principles, I'm not sure if you know Basecamp, ⁓ Jason Freed and DHH, like it's a really cool company and they have the SEPA book and one of the principles is flex the scope and keep the deadline fixed. So

Bob Baxley • Silicon Valley (54:30)

Yeah, of course. Yeah. ⁓

Jim Zarkadas (54:41)

It's a principle that I kind of ⁓ love because the more time you give something, the better you can do. And it can be also bit of a dark hole that goes against business principles where you need to make progress. But I don't know. I also sometimes I'm like, you know what? Screw the deadline. We need to make it better. Like this is not up to our standards. So

I'm not sure if there is a process in the end or if it's just all about gut feeling and personal intuition to learn where you draw the line for every project you work on because not every project has the same significance, for example, for the company and for the customers and so on. So yeah, I'm curious about your thoughts on this topic because it's a, I think it's a challenging one for many designers out there as well in companies.

Bob Baxley • Silicon Valley (55:20)

Yeah, so look, world class might be the wrong standard. World class is a result, it's a consequence of a lot of things. I think at the individual designer level, you have to realize that the constraints that you have, the timeframe within which, and constraints could mean both constraints of the project and how many resources you have. One of those constraints is time, like how much of an investment can you make in this thing? And so if you think about the information you have at the moment, the amount of resources you have, all these different factors, is the thing that you produced

Jim Zarkadas (55:26)

Mm-hmm.

Hmm.

Bob Baxley • Silicon Valley (55:49)

the best work that you could do given all those factors. Like, are you proud of your effort? If we think about it in sports terms, if I go and I'm gonna try to set a PR running a 5K, if I'm feeling great and I'm feeling in a great day and I set a PR, well, that's terrific. If I'm older or I'm injured and my time is less, I still put in my best effort. I should still feel great about that race, even if the final outcome maybe wasn't as good.

Jim Zarkadas (56:17)

Hmm.

Bob Baxley • Silicon Valley (56:17)

And I don't know if that's a perfect metaphor, but I, you know, with every design that you produce, I think you just have to constantly be asking is that, but is this the best I could do given all the circumstances or at some point, did you just fold at some point? Did you just get too tired and you just gave up like, and when it comes to deadlines, it's sort of like, did you run through the tape? Did you do everything you could given the time you were given or did you sort of slack off because the deadline didn't seem like enough. And so you just didn't take the effort seriously.

Jim Zarkadas (56:27)

Hmm.

Bob Baxley • Silicon Valley (56:46)

And I've always tried to hold my team more to account of did they do the best they could given the resources and time and everything else that they had. And then I looked to the company, you know, I've never argued with people about headcount. I've always told executives, know, the company funds my team at the level that they're comfortable investing. My job is to give you a good return on that investment. So if you want to give me 10 heads, I'm going to give you 10 heads of design effort. If you want world class design, I'm telling you that's probably more like 15 to 20 heads.

Jim Zarkadas (56:46)

Hmm.

Bob Baxley • Silicon Valley (57:15)

But you can tell me that doesn't matter. That's not the most important thing. And I'm going to trust that because you're running the company. So again, my job was always do the best I could with what I had. Sometimes that was world class. If the company was set up in the right way and all these other factors, but it being world class was a consequence. I couldn't control that. What I could control was at the best we could do at the time with resources we've been given. And so I think that's the thing that maybe people need to focus on.

Jim Zarkadas (57:16)

Hmm.

That's a really good one.

Bob Baxley • Silicon Valley (57:42)

I'll also say on the deadlines thing, because you said, you know, if I had more time, I could make it better. Actually, you couldn't. There's a point where more time becomes really a negative factor. ⁓ So I can't which artist it was. I can't remember who it was, but they said, I don't need more time. I need more deadlines, you know, and John Lasseter from Pixar, he had a great line, which is our movies are never finished. They're merely released. ⁓ So I always think that the trick is to set a deadline that gives you enough time, but not quite.

Jim Zarkadas (57:58)

Mmm.

Bob Baxley • Silicon Valley (58:10)

And that's actually probably where you're do your best work.

Jim Zarkadas (58:12)

the pressure, the healthy pressure, yeah, yeah, yeah, to have the idiom.

Bob Baxley • Silicon Valley (58:15)

I mean, you look at the Beatles, just for one example, it's top of mind. Everything the Beatles did from their first album to the rooftop concert and Abbey Road, actually, that whole thing, like all those albums, everything, all those tours, the movies, the TVs, like the whole kit and caboodle of the Beatles, it's like seven years, you know? I don't think the Beatles get better if you give them 14 years. I think they got a lot done in seven years. And then unsurprisingly, they're completely burnt out and spent and all needed some downtime.

Jim Zarkadas (58:31)

Hmm.

Bob Baxley • Silicon Valley (58:42)

And then amazingly went on, three of the four of them went on to have amazing solo careers as well. ⁓ But I don't think you, and the same is true of many other musicians. have this of one decade or less period where they just cranked an amazing amount of stuff. And I don't think it gets better because they have more time.

Jim Zarkadas (59:00)

Yeah, that's a very good one. It's that ⁓ at some point and after it doesn't really add value anymore and doesn't have any impact. And I really like your perspective on this. It's very, very helpful on the always understand like the constraints and judge the outcome based on that. It's something, and also try to maximize, like do your best effort and try to maximize the return over kind of the constraints that you have. ⁓

Think about like AI event right now and how can you improve design quality? So just want to start like a personal thought on this one to ⁓ thinking that like investing into design, especially for a boot shop company, it's something you can prioritize you can do, but it's very tricky in general because it can be very expensive and you can do it up to certain extent depending on the growth stage that you are as a company. And one of the things that I've been thinking a lot about is how can we have more impact without being in control fully of the design? Like with AI, how can we, for example, a small detail, how can we write a UX writing guidelines, like some guidelines for AI when developers build stuff to at least have better copy, more human centered copy, like things that are easier to read and understand. And just kind of a fine small piece of work and add value without being the person that has to design this whole thing. And a topic that I'm personally, I find very fascinating and I can't say that the industry is going to do this or something, but I feel there is something they're worth exploring is how can you train your engineering team to be more design centric? So I always think how can I have an impact versus control everything? One way is to have my own design projects, but another way would be maybe to do like design hackathons with the developers and teach them about basics of design thinking and this way impact the culture and make engineering to ⁓ see better UX let's say to production. So it's a very interesting one. And what you said that I need more deadline.

is not time. It's also very interesting because once you have the constraints, it's very clear boundaries on how creative you can get. yeah, like you need these limits to start thinking about solutions, otherwise can get really, really chaotic. yeah, these are some kind of a personal thing that I've been experiencing on my side on that topic, which is,

Bob Baxley • Silicon Valley (1:01:11)

Well, I think so one of the questions you hit in there, I think is really interesting, which is how do you raise the taste level of your engineering team? ⁓ And one of the reasons that I have not been a supporter of this argument that taste is what's going to save design and taste is what's going to differentiate products is because I don't think that the user base is particularly sophisticated. So I don't think the user base values taste. And if the user base doesn't value taste, I don't know how you compete on taste. And I just remind people that if you look across the world, most of the most popular products are not the highest quality. If you think that Americans, for example, have great taste in food, then you have to wonder why McDonald's is the most popular restaurant in the country, right? Those things don't align. ⁓ If you look at Instagram, you get the sense that not that many people have particularly good taste in photography. They may be getting good at the production values of photography, but I challenge you to remember any picture you've seen on Instagram.

Jim Zarkadas (1:01:46)

Hmm.

Hmm

Bob Baxley • Silicon Valley (1:02:08)

other than with friends and family. They just have no meaning. Whereas in your head, you could probably pull up 10 Pulitzer Prize winning news photographs. So the quality of the photography on Instagram, even though it's kind of this nice eye candy stuff, it's not good photography. It's completely absent of meaning. So when we look at software, like to users, the engineers, to executives, do people really understand what's a great software experience?

Jim Zarkadas (1:02:12)

Mm-hmm.

Bob Baxley • Silicon Valley (1:02:36)

And an exercise that people could run is get a small group of engineers. You can't do it in a big room. But if you have like five people, five, maybe 10 people, just go around the room and ask people, can you name your three favorite apps? I'm yet to meet a designer that can name their three favorite apps. Like usually when I ask that question, people are just stopped in their tracks and they're just like, ⁓ I don't know. And then they open their phone and they start highlighting things that they use all the time which has nothing to do with whether or not it's a good product. They just happen to use it all the time. That's like usage and whether or you think it's well done are two completely different things. I think Box Goldberg Variations is the most amazing piece of music ever written, but I don't listen to it every day. ⁓ So I think just by calling people's attention to, you actually watching software and thinking about what's good and getting them into that conversation of what are your three favorite apps and then why.

Jim Zarkadas (1:03:13)

Mm-hmm.

Bob Baxley • Silicon Valley (1:03:30)

And as a design leader, you could probably facilitate the discussion. And you don't really have to tell them why A is better than B. You just have to get them to start asking those questions. And they'll sort of start to develop their own natural philosophy. They've just definitely thought about it before. So I think that's one part. users don't. And again, I've never met a designer that can answer that question. So if you're listening at home, you know, and I'm not going to put you on the spot here, Jim, but if you're listening at home, just in your own head, most of you people are designers for goodness sakes. I mean, if you were musicians or filmmakers, and I asked you what your favorite album was or what your favorite movie was. I couldn't get you to shut up about it. Like you would go off. You wouldn't name. You wouldn't be able to name three because there would be so many candidates. And yet all of us have spent decades working in tech and off the top of our head, we couldn't. We couldn't name three products that we really like because they're so well done. Like that's just a crazy gap ⁓ that I that so I think, you know, the design industry

Jim Zarkadas (1:04:09)

Hmm.

Bob Baxley • Silicon Valley (1:04:30)

I think all of us just need to realize when we talk about taste, where is the general level of taste and how do we raise that? Even in graphic design, I mean, I live in the United States, graphic design in the United States is just for crap. It's horrible. Go to Japan, actually graphic design in Japan is pretty challenging. Software design in Japan is absolutely horrible, like shockingly bad in Japan and they sort of know it. You go to Europe, graphic design's incredible, industrial design's incredible. So when we talk about

Jim Zarkadas (1:04:49)

Mm.

Bob Baxley • Silicon Valley (1:04:59)

taste is the thing that's gonna separate software design from everything else. Like, I don't know, man, got people who develop some better taste. And how do we do that?

Jim Zarkadas (1:05:09)

Yeah, yeah, there is a lot of hype also about taste. what is the new mode, the taste of the new mode and all these things. Like, I don't get like, we work on this one, not that you mess with, we work with B2B Saz, right? And one thing that I love B2B Saz as a designer is that I find many super ugly products that make many millions. ⁓ And why do I like this as a designer is because...

It's been a big lesson for me that good design is subjective and what people need, like what people need is not always like amazing UX. And amazing UX sometimes comes down to is this part of the product strategy, for example, like Linear, one of the designs, like a very design-centric companies on the product management space, they position as the best kind of a UX in the market. It's like their unique differentiation.

Bob Baxley • Silicon Valley (1:05:48)

Yeah. Yeah.

Yeah, totally. That's totally their competitive advantage.

Jim Zarkadas (1:05:57)

Whereas like when it to JIRA and other ones, people don't use it for this reason. It's just a difference. So also like on the taste and design, it really comes down. Another thing is like the business strategy on how do you position on the market? Like Zenmade, one of the teams we're working with, we're positioned as the easiest to use in the market versus like Madecentral, like a competitor. They're super complex, but they're very robust. So they're more like for bigger companies, it's more like enterprise in the cleaning business. So that's something an observation that

like in the past and I fully agree on everything you mentioned the taste, the taste topic.

Bob Baxley • Silicon Valley (1:06:33)

Well, so I gave a talk years

ago about how every company and actually every industry, start out by competing on functionality. And then once functionality has commodified and equalized, then they start to compete on business things. So business things conclude like distribution, pricing, know, customs, enterprise sales, ⁓ know, supply chain optimizations, all the business stuff. And then after all the business value has commodified, then finally you can start competing on design. But you can't compete on design unless you have all those other things down, right?

Jim Zarkadas (1:06:40)

Hmm.

Bob Baxley • Silicon Valley (1:07:02)

So if we look at Google, again, it's nothing against Google, but if you look at Google, they largely compete on functionality. Like none of us use Google because we think they have an incredible UX. We use Google because they have incredible capabilities, which is fantastic. They haven't had to move beyond that because nobody else can reach what they can do functionally. Then we look at Amazon. Why do we use Amazon? We use Amazon because they're crushing it on the business stuff. Like their distribution network, their supply chains, their delivery, like they are just crushing it on that.

Bob Baxley • Silicon Valley (1:07:30)

There are many, many other much better e-commerce experiences and many places where I can replace most of the functionality of Amazon, but I can't replace the delivery times, the availability. They just nailed it on all this business type stuff. And then you have companies that have to compete on design and Apple's a good example here. They have to have all that functionality. Apple wouldn't be able to survive if they didn't have parity on functionality with most everybody else. And then they've got all the...

Jim Zarkadas (1:07:48)

Hmm.

Yeah.

Bob Baxley • Silicon Valley (1:07:59)

the business stuff, they have incredible supply chains, incredible ops, they've got incredible retail stores, it's incredible value for what they're delivering, they've nailed all that stuff. And so now they get the opportunity to compete on design, because that's how they're to differentiate themselves. And it works really well for them because they these 35 % margins on consumer electronics when their competitors are getting 5%. Like that's that's the value of design, you think about like how much more profit margin they're able to generate, even though they're less than 50% of smartphone sales around the world. Last time I looked, they were like 110 % of ⁓ revenue from smartphones because the Android carriers take more stuff back than they take in. I don't think that's quite right anymore, but still, if you look at their market share versus sales share, they make a ton, or profit share, think it's market share versus profit share. They make the vast majority of profits in smartphones, ⁓ even though they only have 50 % of the market from a market share perspective.

Jim Zarkadas (1:08:40)

How about again?

Hmm.

Bob Baxley • Silicon Valley (1:08:55)

And it's because of design. Like if they were just competing on the business layer or the functionality layer, they wouldn't be able to get those kinds of margins up.

Jim Zarkadas (1:09:03)

Yeah, it's a very good one. Also like the perceived value and how you can grow your margins like through a better experience because you're focused like on qualities like how do you compete on the market? Is it like that you have people that appreciate quality versus people that just want to solve the problem don't really care? ⁓ Yeah. Yeah, it's a very, very interesting one.

Bob Baxley • Silicon Valley (1:09:23)

That's what saying, like user benefit. Like at some

point you have to look at how the users are responding and do they, is taste something that's gonna matter? Like design probably doesn't make the difference for everything. Now you and I as designers, we may, you I have a very strong moral position that we should be designing things for the human environment and that we should care about the people on the other side of the glass. You know, I think the Golden Gate Bridge is a better bridge than the Bay Bridge because it's so superior aesthetically.

Jim Zarkadas (1:09:43)

Mm-hmm.

Bob Baxley • Silicon Valley (1:09:50)

When I look at the Golden Gate Bridge, my heart is lifted, my soul feels better. Every time I drive across that bridge, I look out the sunroof so I can see those towers. Every single time. I've done it hundreds and hundreds of times and still I do it. The Bay Bridge, it's a perfectly great bridge. I mean, it functions as a bridge. It gets me across some treasure island in San Francisco quite well, but it doesn't lift my soul in any meaningful way. So I personally very much want to live in a Golden Gate world.

Jim Zarkadas (1:09:55)

Right?

Exactly, just functioned

Hmm.

Bob Baxley • Silicon Valley (1:10:20)

But I can also understand that there are many other people that are reasonably satisfied with the Bay Bridge world.

Jim Zarkadas (1:10:27)

Beautiful analogy, beautiful example. yeah, yeah. really kind of, this really hits kind of in a deeper way. Like I really recognize all the feelings that you've described. like I, as a designer, like if you ask me, why are you investing your life energy into design? Because as a human, like I have this creative energy, I could invest into something else. Like why product design is, I always like, it sounds really cliche, but I strongly believe that great design, let's say better design or great design can make the world a

better place because design is really about care and love, right? It's really what you describe. Like if I think about urban design, since we started discuss because before we started recording about Amsterdam, like one thing that I love about the Netherlands, originally from Greece, the way, I grew up in Athens in the south ⁓ part of Europe. Athens is a really messy city, no plan, no structure, just kind of a lot of buildings thrown in there. Amsterdam has a lot of structure and now we bought a house in the new neighborhood close to Amsterdam, which is newly built. And you can see that there were people that really thought about the details. What's going to be the ground exactly? Like what kind of rocks are we going to use? What's the color of the bricks of all these houses you're going to build? How are we going to make a playground and the house around? How are we going to create a more social environment? And if you use design in a good way, it just makes life so much better. And it's like the quality of life itself. It makes you feel things. It makes you develop better habits. That's why for me, if I would get out of product design, I would love to get into urban design, honestly, like design environments people can leave because that's where it can truly make a difference in their lives.

Bob Baxley • Silicon Valley (1:12:02)

Yeah, look, I completely feel the same way. And design is how we show empathy and care and support. And

I always describe it as the people on the other side of the glass. And one of the things I like working on software is that, you I've worked on products have been used by a billion people. Like, nobody knows who I am. Like how many other industries could I work in where I could touch a billion lives? None. Like this is it. And so I try to always keep in mind that people on the other side of the glass, unfortunately, because we work at a medium that's also intermediated, so we never see the audience.

Jim Zarkadas (1:12:20)

Yes, yeah.

Bob Baxley • Silicon Valley (1:12:32)

It's very easy to lose track with the fact that there's a billion people on the other side of the glass, which is, think, what makes it so easy for companies to make bad choices on behalf of their user because they just don't see the downstream benefit. And to go back to my story about working in Apple retail, that was really the only time in my career when I could go watch somebody use something that I had worked on and see them operating it in real time in the wild. And so it created a connection between my decisions as a designer and the impact of their life. Like I could see that connection in a very real way. ⁓ You know, not too long ago, I had the privilege to get to talk to the design team at Toast that make the handheld point of sale system for restaurants. And I was telling them, like, you know, tonight, all of you are gonna be at dinner with this grandma in Ohio. And she's gonna be at dinner with her two grandsons and the bill's gonna come due and the server's gonna bring over the Toast device and they're gonna hand it to her. And she's either gonna know what to do or she's not. And if she knows what to do, she's going to look like a hero to her teenage grandsons. And if she doesn't, they're going to grab it from her and go, here, grandma, me show you how to do that. And she's going to feel like an idiot. And so which one's it going to be? Because you guys are going to decide like you're you are at that table with this lovely grandmother in Ohio. Are you going to make her life better or not? And I think I mean, I couldn't really see them because we're on Zoom. I think it had an impact on them. You know, I think it drew them back to the reality of what they're working on.

And so I try to remind designers of that all the time, engineers and product people too. I think it's just very easy to lose sight of that. Again, because we're not in real space with our audience. You kind of forget they exist and you get caught up in your own needs and your own demands of shipping on time and hitting this deadline and making this profit margin and blah, blah, blah, blah, blah. And you forget that you're like actually hurting people. And I think if people could, I think if the creators of software could understand

Jim Zarkadas (1:14:21)

Hmm.

Bob Baxley • Silicon Valley (1:14:28)

directly the damage that they're doing the confusion they're injecting into people's lives the frustration that they're injecting the people's lives. I think they'd be a lot more careful.

Jim Zarkadas (1:14:36)

you

So I know we're a bit over time, but if you're okay, I would really want to go a bit deeper into this. Like I had it on my agenda. the, the, the topic is how can you become truly more user centric when you're not the user, right? Because when you design, say for the Apple store, you have the benefit of being like, you can actually use it in itself or yourself. I'll bring an example of a team that I'm working with. like using this example, working brainstorm a bit of a few ideas is ZenMaid.

Bob Baxley • Silicon Valley (1:14:44)

Yeah, yeah,

Jim Zarkadas (1:15:07)

So it's scheduling software for cleaning businesses. So imagine like a cleaner that is transitioning to a cleaning business owner, they're hired three, four cleaners and they're using a software to manage the counters, send invoices, collect payments, pay their team and essentially run the whole business. They spend hours every day using that software, right? So they really rely on this to run their business. And one of the challenges that I have on design is that I'm not a cleaning business owner.

but I need to design for them and I need to empathize with them and, and, and fill them. And I've been looking into creating rituals. I'm a strong believer of habits and rituals and not just doing one time user research, you do a bunch of interviews and then you disappear for the full year. But actually how can I build rituals that are going to bring me closer to them? One was that we have a really good customer. We've been working for years and she's joining our design course. So we have at least one person. Many people say, no, like this is not a good idea because this is not statistically correct.

Bob Baxley • Silicon Valley (1:16:01)

Yeah, yeah. No, that's a great idea.

Jim Zarkadas (1:16:05)

and so on, but it really changed our minds because you can get at least one perspective. One is better than none in this case. And can tell yourself if it represents most of the customer audience. So that's one of the rituals we found that was a really good contribution with also low complexity, because we just paid them for a few hours per month to join us. But I'm curious, how do you approach this topic and what are some rituals maybe you've seen or you develop a set of thoughts, like the comments that you

worked in the past on how to become truly user user centric. And just another quick example before I pose is we, we have this idea like Amar and Alex, the, the, the CEO, the city of the company that we should go and rent a van and just travel through the States of U.S. and just visit, clean business owners and just kind of talk to them about ZenMate and so on and see how they're experiencing it. And

I feel as a designer, want to do something like that. Just go and shadow some of them or just go and fly and spend one week doing only this thing, hang out with cleaning business owners, observe their lives, how they use the software, where they get frustrated and just do it as a fun experiment for a week. So yeah, that's just an example that I wanted to share and I'm really curious to hear about your thoughts ⁓ and yeah, the mindset you have on this topic.

Bob Baxley • Silicon Valley (1:17:22)

Yeah,

so look, your instinct on it being a ritual is totally the right one, right? And I think everybody needs to cling that. Research is not a one-cling to that. Research is not a one-shot deal. It's gotta be something where you're refreshing that all the time. So ideally it's something weekly or bi-weekly, but you need to be kind of in constant contact with your audience. ⁓ So there are a lot of different mechanical ways we could talk about doing that. One of the things we started doing at ThoughtSpot, ⁓ which was wildly more useful than I expected it to be and is generally accessible to people that are working in bigger companies,

Jim Zarkadas (1:17:40)

Mm-hmm.

Bob Baxley • Silicon Valley (1:17:51)

Almost all enterprise software company, once they get past a certain size, is going to have what's called a customer success team. And so this is a group that sits inside sales that goes and works with customers to help them adopt the software and make sure that it's working well. Those customer success people are incredibly good proxies for your users because they're seeing what the audience is dealing with and all these different points in the software and they already work for your company. So we took some of those folks and we learned...

I'd been there a couple of years before we realized that for every major project, we really needed a customer success person on the design team, as part of the early team, to help us shape the product. Because they would understand how people were using the feature and what functionally what was going on. They didn't necessarily help us build empathy with what the users were dealing with, but they helped us understand functionally what the product needed to do and what our solutions were and weren't appropriate. So they were a great proxy for the knowledge that we didn't have about the problem space.

Jim Zarkadas (1:18:37)

Hmm.

Bob Baxley • Silicon Valley (1:18:47)

So that's kind of one technique. At Airbnb, I know the gentleman who runs all the product and marketing there, Hiroki Azai, Hiroki and I used to work together at Apple. And I heard Hiroki on an interview and he said that Airbnb, they'd been able to collect an enormous number of short videos from hosts and guests who have stayed at or rented Airbnbs, talking about their experience with Airbnb and what it meant to them. And so they've got like hundreds of these things and they can go in at any moment and just watch this enormous collection of two or three minute videos of people talking about what the service means to them. ⁓ That's not gonna tell you a lot about a particular feature, but it's gonna help you understand people's relationship with the company, which I think is also a very important kind of emotional conduit back to your audience. So that was another interesting technique. In Apple retail, because it was a real life environment, I would routinely just drop and go into one of the stores and just sort of sit and hover and sort of be a voyeur watching the store, not necessarily talk to anybody, but just kind of watching what was going on. So that was a useful way to maintain a touch point. And then one other technique you might consider, and you mentioned going on a road show to talk to people about how they were using the product. I might encourage you to expand that and just go try to talk to people that are in the business and try to understand the mindset of a cleaning operator owner, of a cleaning company owner.

and what they're thinking about, kind of outside the constructs of your particular software. Because as soon as you're asking about your particular software, you're naturally, some part of you is gonna be curious, but some part of you is also gonna be defensive, because you're gonna want them to like the software. And they're gonna say things differently because they wanna please you. There's just a social thing that happens in those interactions that keep you from getting ⁓ unbiased feedback. And so when you go into an environment with somebody who is in the space and you just try to develop an understanding of their mindset outside what the technology is doing. I think you'll get better ideas down the road. It won't help you design a feature right now, but it will help you down the road. There's a great story. can't remember what the company is, but they're a company that, it's a multi-billion dollar company that helps companies in the United States, helps medical clinics in the United States negotiate between Medicare and their billing system. And yeah, and I...

Jim Zarkadas (1:20:51)

Hmm.

yeah, I've seen them. Yeah, yeah. I don't remember the name, but I've seen that one.

Bob Baxley • Silicon Valley (1:21:09)

Yeah, if I remember the insight for the company is they were just going and watching in doctor's offices, all the billing clerks. And what they noticed is they all had these post-it notes all around their monitor. And on the post-it notes were all these obscure Medicare codes that they had to input for different procedures. And so one of their insights was, could we create a piece of software that would eliminate the need for these post-it notes? Like that was kind of the whole idea, you know? And that turned into like this incredible, you know, multi-billion dollar company. So there's something...

You know, some of the techniques, the last technique I mentioned is it's sort of in the vein of ethnography, which is a technique used from anthropology. ⁓ So I think there's an enormous value for designers and actually engineers and others just to go in and take an anthropological approach and do some sort of ethnography study without talking about the technology. Like just put all that aside and just go see what people are trying to accomplish.

Jim Zarkadas (1:21:42)

Hmm.

Mm-hmm.

Yeah, exactly.

Bob Baxley • Silicon Valley (1:22:04)

And it's likely that out of that, one, you'll develop a greater empathy and understanding for the mindset of the user and the problem they're facing. But you also might come up with technological solutions to the work they're trying, the work they're doing and the tasks they're trying to accomplish that are not merely ⁓ electronic simulations of what they're already doing, right? You might be able to conceive of completely different ways of achieving the goals that they have using technology that they couldn't describe or think about themselves.

Jim Zarkadas (1:22:34)

Yeah, I fully agree on everything. I really agree and like love what he says, like don't focus on the product, actually expand the scope and see how the product fits into their life and understand them more as a human and as a business owner. Like how did they run the business? What are some challenges? And yeah, like look at the whole picture. Don't focus. Yeah, exactly.

Bob Baxley • Silicon Valley (1:22:53)

It just kind of watch them like just yeah,

again, if people would go spend a little time just studying some of the methods of anthropology and I'm not saying anybody is going to be I'm not trying to compare this to academic anthropology, which is a completely different endeavor. I'm just saying that there's some of the techniques that anthropologists use ⁓ that could be useful in some sort of primitive form. Another great story is when the team at Pixar decided to work on the movie Cars, ⁓ they knew that they wanted to kind of capture this Route 66 style of the American West and the American road trip. And so what they did is they took a bunch of people and they did a road trip along what used to be Route 66. And they visited all these old places and they drove through those deserts and drove along those roads. And that then turned into the visual look and the places that you think of in the movie Cars. mean, that's where the idea for something like the Cozy Cone comes from, or Radiator Springs. They went and they did the road trip. So there is something super powerful

Jim Zarkadas (1:23:43)

I see.

Bob Baxley • Silicon Valley (1:23:51)

for you guys that you would have by doing a road trip and going in these people's environments and in their offices, following them as they go on their nightly routines to do the cleaning and office buildings and whatnot. Like really walking a mile in their shoe. ⁓ You will definitely come up with better solutions that you would otherwise have never thought

Jim Zarkadas (1:24:10)

Yeah, I'm taking some notes while we're discussing as well on this. Yeah, I feel like maybe this is the year to go and give it a try. I fully agree. Super. Thanks a lot for all the insights. And last quick question, and we can wrap it up, is what's your favorite app and why? Like you mentioned that it's something you ask all designers, and it's fine because I ask every guest, what's your favorite SaaS because we're mostly into B2B SaaS, but as I to be a SaaS. And for me, what you said that people...

keep bringing like products that they just use all the time. Like for me, I would say like, what is a product that makes you feel something like a level, like a decent amount of excitement and kind of a wall effects in the last, I don't know, like month or year that comes to your mind. there anything.

Bob Baxley • Silicon Valley (1:24:54)

Yeah, so I have this one little practice to some at home. know, I so I look at apps that I think are doing something interesting and novel and that show me that they're thinking harder. So although the product I think has kind of dropped off is not nearly as successful as I would have hoped it would have been. ⁓ One of my favorite apps from a while back is Pitch, which is an online slideshow produce production tool. ⁓ Yeah, pitch.com from the guys that did Wanderlist. Yeah, I think they're based out of Berlin, if I recall. And what I really liked about Pitch

Jim Zarkadas (1:25:14)

the feeds.com, yeah.

Bob Baxley • Silicon Valley (1:25:23)

is they did at least back up and try to reconsider what it meant to create a slide deck in the modern era. And so the way that they created collaboration at the level of a slide, for example, like that's just kind of an interesting little feature that you could assign a slide to somebody I thought was really interesting. I also thought it was really interesting. They had some mechanism where if you reordered a list, they would switch everything around for you. So like if you had a bullet list, you could grab bullet five up to bullet two, and it would push everything down and re-number everything.

Jim Zarkadas (1:25:29)

Hmm.

Bob Baxley • Silicon Valley (1:25:51)

It was like, they actually paid attention to how people are manipulating objects. Yeah. so I really appreciated the care that they had put in. This is one where they lacked key functionality for me. The way that they treated master templates and the way that they treated transitions wasn't ⁓ what I needed. So I've still am kind of wedded to Keynote. But I thought that the pitch team, ⁓ I thought they did some wonderful design in terms of reimagining how you could accomplish some of these tasks inside the tool. So that's one example I use of a product that I think in certain ways got things really right. And then another one that I really like is a product called Hobitica. And Hobitica is a to-do manager and task list type thing. ⁓ So there are lots of to-do managers. Almost, well, most of them you just, you know, you make a list and you check stuff off.

Jim Zarkadas (1:26:22)

Hmm.

Love it.

Bob Baxley • Silicon Valley (1:26:43)

some of them maybe have some sort of gamification where they give you an award after you've teffed off a certain number of things or something like that, which interest what's interesting about Habitica is rather than gamifying your habits and your to do stuff. It actually is a game at its core. It is the conceptual model of a role playing game and the gameplay is doing your habits, your daily habits and checking things off your to do list. And so in the case of Bidoka, when you start the tool and ask you, do you want to be a warrior, a healer, or a mage. And then you have to give yourself a name. And then as you do your things and mark them off, you get points. You collect gold and mana and stuff like that. And if you don't do things, then you lose your life force and stuff like that. Eventually you can go down different levels and you work way up these levels and you can buy armament and you can eventually collect eggs. And then you can go out on ⁓ quests with your friends. So if you have other friends in the tool, you can get four or five people together and you go on the quest together and you eventually get to take on a boss when you've collectively you've made a certain number points and if people don't do stuff and the team fails things like that. what I love about Habitica is that they flipped the conceptual model. So it fundamentally is a game. And again, the gameplay is doing your habits in your in your to-do list versus trying to gamify what is fundamentally a habit tracker. And so, you know, I describe it as they yeah, they blended conceptual models in a really interesting way. And I think a conceptual models like a movie genre.

Jim Zarkadas (1:27:46)

Hmm.

That's a good one.

Bob Baxley • Silicon Valley (1:28:09)

And so if we look at a film like Star Wars, like what's really interesting about Star Wars is that Star Wars mixes the genre of a space movie and a cowboy movie. And so Star Wars is basically a cowboy movie set in space with World War II dogfighting scenes in the middle, right? And so what George Lucas is doing is he's blending these different conceptual models or genres to create something new. And I don't think much software, I actually haven't met any software teams that think deeply about the conceptual model of what their product is. Like fundamentally, what is this thing and how do we want it to be, how do we want the user's mind to represent it? They just fall into whatever the first idea is. Like most products have kind of a, there's an obvious conceptual model, but it's typically not the best one. And people don't really design at the conceptual model level very well. And I think that's a huge miss because if you get the conceptual model right or you do it interesting,

That's when you can really point the user in different directions. And I think the conceptual, I think designing at the conceptual level, at the conceptual model level, may be the key differentiator in products moving forward. know, cause if you think about, if we just look at to-do managers for a moment, like if you choose Things, which is another app I really like, if you use Things versus Apple Reminders versus it's the Omni to-do thing or Todoist, like all these different things, they're slightly different conceptual models on how to manage your day. And functionally, they're all kind of the same, but again, conceptually, they're slightly different. And so we all have our preferences because that concept fits us slightly differently. ⁓

Jim Zarkadas (1:29:50)

That's a beautiful insight

It's that's a beautiful example.

Bob Baxley • Silicon Valley (1:29:51)

Yeah, it's like you mentioned Basecamp earlier, like what's really the difference between Basecamp, Asana and Monday. And it's, I mean, they could

just kill each other over features, but that's not really it. All three of them have slightly different ideas about how teams work together and how they should get work done. This is honestly, this is one of my biggest disappointments with Slack is that Slack was this interesting moment when they could have really shifted inter-office communication and done something really magical if they had spent time to really think about it and take a philosophical approach as to how inter-office communication, inter-group communication should happen to benefit collaboration and productivity. And they didn't really. They stumbled into this internet relay chat thing and then they just built a bunch of stuff on top of it. And so now we have Slack and is Slack better than email? Maybe. Is Slack the best way any of us can imagine communicating? Not really. I think it was just a

Jim Zarkadas (1:30:32)

Yeah, I think so.

Bob Baxley • Silicon Valley (1:30:47)

You know, and I love that team. I love Stuart. Like I've got a lot of respect for what they've accomplished, but it's I don't know. Like, you know, I look at them like I don't know how to use Slack and people are like, what do mean? I'm like, I don't, I don't know what Slack wants me to do. Like I don't know how to, I know how to operate the user interface, but I don't know how to really use Slack to maximum effect inside a company. What's a conversation versus what's a channel like blah, blah, blah, blah, blah. And it's just, yeah, it's a smorgasbord of things without a real point of view.

Jim Zarkadas (1:30:58)

Yeah, like it's really what you said like that the point of you and like on slack I also recognize the feelings like just it's really kind of a heart for my productivity when I when I open stack. It's always busy. I'm like, but I cleared my inbox like all the messages yesterday. Yeah, but it's still busy and it's so hard to focus and it's really what you said is like

Yeah, it's the approach and what do you define as success? Like with Slack, do you want to just be better than email or do you want to find really one of the most productive ways for people to do work and communicate, which is two different approaches.

Bob Baxley • Silicon Valley (1:31:51)

Yeah, well, so that's, mean, they're an interesting example,

because they didn't really set out to redesign inter-office communication. They were creating a video game, and then they created this internal comms tool because they were all remotely, you know, they were a remote distributed company, or distributed group. And so they invented this internal tool, and then it seemed pretty cool. And then Stuart did what Stuart did with Flickr too, which is he just pivoted and he said, well, forget the video game, let's go do this other thing, you know.

Bob Baxley • Silicon Valley (1:32:17)

Yeah, that's the thing. credit to him, they sold it for whatever it was, like $25 billion or something, and he's living a great life now. ⁓ Yeah, I got to work with him briefly at Yahoo after the Flickr acquisition. He's a terrific guy, deserves all the credit and all the success he's had. ⁓ But I still think Slack was a missed opportunity.

Jim Zarkadas (1:32:24)

Yeah, for sure.

I totally hear you. Super. Thanks a lot for today.

We had a really, really beautiful episode, like so many great insights. And I can't wait actually to show the recording with the teams because also like with the Zenmei team, it's something that I feel that they're going to really love. like the depth of what I really like in our conversation and use like the depth of your thinking actually. And also like when I asked you about the apps, like which app do you like? It's how, how, like what are the things that you appreciate as a senior designer as well? Like the, the, the mental models that they're using, the product strategy, the approach, and what makes you feel something versus somebody else that is not into product.

design that's always interesting with the guests is that depending on the background there are different things that make them feel connected or excited about a product ⁓ so yeah thanks a lot for your time that's been really really really nice

Bob Baxley • Silicon Valley (1:33:14)

Yeah, my pleasure. Thanks for having me, man. This is great.