July 9 / 52 MIN

Bob Baxley: What it takes to build a connected workflow

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Bob Baxley

Bob Baxley

Author, Speaker & Design Leader
About The Episode

What do Yahoo, Apple, and Pinterest have in common? Silicon Valley design vet Bob Baxley.

With extensive design leadership experience under his belt, Bob knows a thing or two about bridging the gaps between teams to help champion a connected workflow.

In this episode, Aarron and Eli tap Bob’s insights on productive design reviews, getting in sync with engineers, and what it takes to build key relationships with executives—all in the name of making products people can’t imagine living without.

Key takeaways:

  • Tactics for leading effective design reviews
  • Strategies for better alignment with developers and building key partnerships with execs
  • Gaining more empathy for people using our products outside the tech bubble


Bob Baxley is a designer, advisor, mentor, and advocate that has built, managed, and led teams at some of Silicon Valley’s most notable companies. With a career spanning three decades, Bob’s work at Apple, Pinterest, Yahoo!, and elsewhere has touched hundreds of millions users around the world through search, social media, e-commerce, fintech, and productivity apps. Currently, Bob advocates for programs and organizations that are helping to recruit and inspire the next generation of designers.

Design Executive, Advisor, Mentor, and Speaker Bob Baxley on what it takes to build a connected workflow

The following is a complete transcript of this episode of the Design Better podcast. Enjoy the episode!


Bob Baxley: Right at the very beginning, the VPs felt they had a lot of opportunity to move the design around and what they wanted in the app and what they wanted the priorities to be, so they had really strong input right at the beginning, before there was any work committed, before any final comps had been done, before any designers got attached to any ideas.

Narrator: This is the Design Better Podcast, where we share lessons and insights from today’s foremost design leaders. We hope the conversations and stories you hear help you transform your design practice and build remarkable products.

In our third season, we’re exploring the connected workflow: how designers work more effectively and efficiently with their engineering and product counterparts. We’ll talk about how building key partnerships throughout an organization can help you ship better products, faster.

This podcast is hosted by Aarron Walter and Eli Woolery and it’s brought you by InVision, the digital product design platform powering the world’s best experiences.

Aarron Walter: Bob Baxley has led teams at some very design-forward companies, including Apple and Pinterest. Along the way, he’s learned a lot about the mechanics of leading great design teams to launch products successfully. We chat with Bob about design reviews, who should be involved, and what’s the best fidelity of work to show to make them productive. We also speak about getting aligned with developer partners and building key partnerships with executives. We learned a lot about maintaining a connected workflow from Bob and hope you will too. Thanks for listening.

We also wanted to share a fun, easy way to get more from the Design Better Podcast at home. The Design Better Podcast is available as an Amazon Alexa skill for Echo Dot and more. Say, “Alexa, play the Design Better Podcast on TuneIn,” and you’ll hear our latest episodes. Thanks for listening and now we’ll start the show.

Bob Baxley knows a thing or two about design leadership, and how to build well-connected teams. See Bob spent over eight years at Apple, serving in leadership roles for their retail and E-commerce teams. And as Director of Design, he led teams working on a broad range of applications including the Apple online store … maybe you’ve heard of it. As well as the transactional areas of iPhoto and GarageBand.

Most recently Bob served as the head of Product Design at Pinterest, where he built, led, and managed a multi-faceted design team responsible for both the consumer and business-facing elements of Pinterest.

Bob is now an advisor, a mentor, a speaker, and personally I think he’s just a minch. As well the author of Making the Web Work. Bob Baxley, welcome to the Design Better Podcast.

BB: Aarron, thanks for having me. Eli, great to see you. How are you guys doing today?

AW: So Bob is someone we have talked with quite a bit over the years, and he knows the Valley and the Bay Area and the design industry like few others out there. And Bob, you’ve been involved in the Design Leadership Forum, facilitating conversations.

And for those of our listeners who don’t know about the Design Leadership Forum, it’s a group of design leaders that get together at special events to have moderated conversations. Bob has moderated many of those conversations, discussing the challenges that most design leaders face, and it’s a great way to learn faster together.

Bob, at the many dinners you’ve directed the conversation, can you talk about maybe a theme or two that seems to be recurring, that you hear a lot of design leaders struggling with, and what’s happening inside of design teams?

BB: Well, first of all, Aarron, thanks for including me in some of those dinners. They’ve been so much fun to be a part of and to connect with the community. You know, I think that thing that I’ve taken away from the dinners the most is that we’re kind of inventing the profession as we go along.

So a lot of design leaders show up, and there’s not a standard playbook. And I think people kind of want there to be, they expect there to be, and I think they maybe get a little frustrated that they’re having to figure things out. But it really speaks to how new the profession is.

And we don’t have the multiple decades of figuring out processes and what not, that people in engineering might have, for example. I mean, they’ve been writing code at scale for a long time now. And I still think that we’ve only really been designing software since the advent of the App Store, which people kind of forget. But the App Store released around the same time Obama was sworn in for his first term, and I’m sure there’s many listeners who remember that vividly and probably think it wasn’t all that long ago.

So we’ve really only been involved in serious software design for maybe a decade. And what I’ve seen mostly in the forums is just the sense of community is really strong. And to have these leaders come in and be able to hear other people talk about similar problems and similar challenges, I think it helps them feel that they’re not alone and they’re not isolated.

When the reality is, in their companies they may be the only people really seriously thinking about these issues. If you go into engineering, there might be multiple engineering managers or directors trying to work through the problems. But often times the design teams, the people leading those teams, are really at the avant garde of building those organizations.

So in terms of themes, there’s a lot of just practical things about working with engineering, working with PM, hiring strategies. There’s a lot to stuff about interacting with executive staff and how to try to get CEO buy-in, and things like that. It’s a lot of sort of navigating, you know, I hate to use the word politics but it’s sort of navigating the politics in power structure companies and finding a way to …

You know, we talked for many years about getting a seat at the table. And having a seat at the table and actually being part of the conversation is sort of a different thing. And so I think a lot of these leaders feel that like, “Yeah, there’s a seat at the table but what does it mean for me to occupy that now? And how do I need to interact with the other people around the table?”

I mean, from dinner to dinner I tend to try to focus on some of the higher level philosophical ideas. Sort of what we’re doing as a profession, and how we’re bringing more designers in, do we love the products we’re working on. My experience has been that sometimes people like to talk about that stuff. But there’s also a lot interesting and probably the most passionate conversation around some just pragmatic, practical things. Again things like hiring strategies, you know how to do employee reviews, things like that. Which again, I think just speaks to how new we are in all this and how we’re having to figure it out collectively.

AW: Let’s talk a little bit about that engineering, designer relationship. Because that one is so critical, not that it, you know, the relationship between product and design is not as critical, but it seems to be a place where there’s often friction, or if there’s something that’s gonna lost in translation it’s usually right there.

In your experience, personally in your career and maybe also what you’re hearing from design leaders in the industry, what are they doing, what are the strategies they’re employing to have tighter alignment with engineering, to have clearer communication lines so they can ship better products?

BB: I’m not sure if I have a great answer to that ’cause I don’t know so much from talking to other designers leaders where they sit on that spectrum. For me personally, I always found it to be beneficial to realize that the engineers, like the designers, wanted to build the best product possible.

Like I went into every meeting and every review thinking that everyone in the room wanted to create something that they would be excited and proud to show their parents. And so, I think when the designers get into this mindset that the engineers are maybe trying to cut corners or aren’t totally bought into the design, they’re maybe not realizing the full scope of things that the engineers are having to deal with.

So as a designer, what I often push myself and my team, was to just make sure our specifications were as clear as possible. Personally I was a huge advocate of producing written specs. I don’t see that being as popular in companies that are trying to iterate design really quickly.

When we were designing something like the online store at Apple, you know we’re taking tons and tons of credit card transactions, billions of dollars changing hands, people expected products to be delivered on time, correctly, things like that. There’s not a lot of experimentation in something like the check out system for a major E-commerce system. There might be some marketing experimentation but you’re not really messing around to see what happens with some of the check out flows.

So in that project in particular we wrote a really extensive spec that detailed every last variation and we tried to get the engineers to help us understand every quarter case they were having to deal with. We made sure all that stuff was thoroughly documented. I tended to use kind of engineering language so I wanted to express things to engineers and if then statements, made sure that they understood the conditionals. And I think that they ended up respecting that mode of communication that we were trying to pre-preemptively answer all their questions.

One of the other dynamics I saw at design driven companies, like Apple and Pinterest, is that the engineers came in feeling like they had to do whatever the designer said. I’m sure that’s pretty unimaginable in some environments but at Apple particularly it was very design-led. Same thing at Pinterest.

And so I think the engineers had a hard time knowing how to push back and ask questions. And often there’s a lot of ambiguity in the design that the designer just hadn’t thought through, or they unintentionally left that ambiguity. And so it was always delicate to find that moment when we really wanted engineering to start driving the process and asking us all the questions and telling us everything we had missed.

AW: So Bob, when you were at Pinterest, since the focus of the product wasn’t maybe quite as transactional, was there more room for experimentation there, or did you pull on a lot of the same strategies that you’d used at Apple?

BB: Yeah. No, Pinterest was a world away from Apple in terms of process. So Pinterest is, you know, it operates in a way that I understand companies like Facebook and Google operate. It’s very metrics driven, a lot of experimentation. Particularly in the new user flows, which is an area where I think it makes a lot of sense. At any given time, and I haven’t been at Pinterest for a few years, so I can’t speak to what’s happening at the company now, but in the time I was there, you know there could be 90 different experiments going on at any given time.

And so there was definitely a culture of, “Well, let’s see. You know, let’s state up a small bucket test and see what happens.” So there was a lot less opportunity for design oversight ’cause you couldn’t really get a handle on all those different experiments as a design … someone who felt like maybe they were supposed to be the creative director of some of that.

And then I think also it sort of confused a lot of the conversation in the company. ‘Cause nobody ever really knew exactly what any given user was seeing. So I thought it ended up being a little bit confusing. ‘Cause when I logged into the site I might somehow have gotten into some test and I would be seeing some things a little bit different.

So you know, it’s this funny thing, and I noticed this at Apple too but at a different scale. You know, ’cause designers are always working on the next release and sometimes the release after that. You start thinking in your head that’s what’s actually going on. And we did stuff at Apple but didn’t release for 12 or 18 months. And because we were going to the online store and actually looking at the real user experience every day, we started thinking our designs had already shipped. And I think that’s one of the risks of the whole experimentation thing. You just lose track of what customers and users are actually seeing.

And there’s a lot of people in company that are having to live that day to day. Whether they are on the phone, or the executives, or engineers having to fix bugs with things that’s happening in production. So I think that’s been a risk, and something I suspect happens a lot in companies. Designers just get really out of touch with the production reality.

AW: So, it’s interesting that … So some companies like Automattic, I know where you have to actually spend time you know, in customer service so you have that touch on the product. Are there opportunities around that you see for designers to remain connected?

BB: Yes. So again when I was working on the online store, part of the online store operation was not really the website but also the call center. And so, and I’m sure this exists in most companies … There’s a mechanism where you can sit and incorporate a dial into an 800 number and eavesdrop on calls. And that was always just revelatory, to get on a call, listen to somebody try to explain someone some novice, you know how to configure a MacBook Air. And have to really listen to the questions that these people had.

So just listening to the calls was phenomenal. And that happens in any company. I mean, all these companies have customer service organizations that I’m sure you can listen in to calls. Actually going and sitting with customer service people was also amazing. Again the Apple call center wasn’t too far from here, there was one in Austin, another one out in Sacramento. And so we visited those multiple times. And being able to see the dynamic of what the agents are dealing with, as you’re listening in to the call, is really, really educational. You know, it’s kind of real time user feedback with actual users actually using production, you know. It’s just incredibly eye opening.

And then for me the experience that was surprising and, you know not to oversell it, but like literally changed my life, was working in Apple retail and being able to go into the stores and talk to the specialists in the stores and see transactions in the real world in real time with software systems that we had worked on.

And that experience, of designing those systems … And I was working on some things in the store that customers would see but when I was in retail, I was mostly working on things the employees themselves saw. So inventory tracking systems, point of sales systems, real time sales reporting systems, things like that. So that gave you a sense of what happens inside a store to create that experience. And all the sort of back of house, and all the stagecraft and theatrics that makes those experiences so great for customers.

And I say it kind of changed my life because since then, I have not been able to look at a restaurant the same way, you know Disney Land is a completely different experience to me. You know, if you’ve seen the movie Field of Dreams. You know, there’s that scene towards the end where Timothy Busfield walks out on the ballpark and he’s suddenly able to see all the ball players, right. And he’s sort of like, “Where did all these ball players come from?”

You know, it was sort of one of those moments. When you’re like, “Oh my goodness.” Like I go into these situations all the time and there’s all this stage craft happening to create this dinner for me. So it gave me a real sense of the craft of pulling that stuff off and it created a lot more empathy for me with the employees.

You know, sort of the frustration in my family when I travel these days, it’s not uncommon for me to start talking to the agents, the gate agents. You know, and ask them if I can look around the counter and see the systems they’re working on. You know, ’cause there’s a crazy amount of extrapolation that those people have to do. They’re working with these old command-line systems and they’re trying to hold a real time conversation with you. And that’s a tough job.

You know, one of the things we talked about at Apple, and I think Apple started to do this. You see it in other retailers that have gone to handheld point-of-sale systems, is for a long time there was this idea there is an employee-facing experience and a customer-facing experience. And one of the things I pushed really hard at Apple was that we really have to stop talking that way. Employees are people too. And if you can do stuff to make the systems easier for them, you can lower their cognitive load which frees up mental resources for them to focus on the customer experience.

And it’s much easier to have a, whatever, 20 person engineering design team making a really stellar point of sales system and off loading all that stress and confusion and tension from a, what is it about 80,000 person sales force, you know. But companies often don’t think that way, they don’t really have enough design resources to invest in that kind of back of house stuff. And so there’s a culture I think in a lot of companies where the employees can just make up that cognitive gap.

AW: Bob, when you visited these call centers or you visited retail stores, was that something that you did with your design team or would you go with product and engineering partners as well? Was that a cross-functional activity?

BB: Yeah, we did both. Some of the stuff was design team going out and looking at like a Palo Alto store. I mean, again, one great thing about Apple retail is you can always come up with an excuse to travel. Like, “Oh, we just have to go to the Fifth Avenue store. ‘Cause that’s the only 24 hour store. So it’s the only place we could possibly do this visit. I guess we’ll be in New York for the week.”

And living here in the Bay Area, this is one of the highest concentrations of Apple stores. So we can go visit lots of different store environments. If we as designers just kind of casually wanted to go see something on an afternoon, there were other times where we did more structured projects in New York. We did a really interesting role playing exercise with a bunch of the geniuses from the New York area. And we’d ask them … you know we’d set up different software scenarios and we’d have kind of cartoons of what a customer interaction would be like. And try to get their input on whether or not that would make sense.

We did a lot of … Again in the context of Apple retail, we did a lot of storyboarding. There was apps … the technology, so we didn’t show them screenshots so much. We talked a lot about the interaction what we wanted to have and then we were going to try to figure out the technology after that. And I think we sort of got into the same place that Airbnb sort of famously got into, with their Snow White project, where they have the story boards of what they want the host and guest experience to be.

So to your question, yeah there was times we went out just really informally. Which I think any designer can do on any day, again you’re picking up the phone and listening to a call center, just going out on the street and talking to people. Or you can do it more structured, and certainly if you can take engineering and product, that’s always …. It’s incredibly eye opening for engineering I think.

I vividly remember there was a usability test I did way early in my career, when I was at [Clares] working on that project. And I had been haggling with an engineer for weeks if not months about some particular feature related to printing or something. And we had like two users come in, which was way too few, but we just had a couple of people come in. And we had this engineer sit in the room with us while we did this usability test. And, you know the users’ struggled with the thing.

And to my earlier point, you know engineers wanna create great work too. He saw this person struggle, it was a huge moment of insight for him. He literally got up out of the room, went back to his cube and started changing the code.

So yeah, that really drove home for me the power of just connecting back to people that are actually using the software. A point I should have made a second ago too is that, when I look at the younger generation of designers, the thing that I see missing from them the most is they just haven’t done their 80, 120, 200 hours of sitting and watching actual users use actual software. It’s really rare. I tried to do it a little bit at Pinterest and Apple but didn’t get a lot of traction. I think it’s invaluable for designers to sit and watch users use other software, just use commercial software.

So I remember one time at Apple, where Apple didn’t do any usability tests, so it wasn’t something we could kind of make a big fuss over. But we did up organizing a small test with a, you know a bunch of engineers came. And we didn’t have users go through our software. We just had them go through checkout on Amazon and … I can’t remember all the sites, eBay, stuff like that. We just watched them go through a bunch of different sites. And it was really eye opening. ‘Cause stuff that you think didn’t really mattered that much, like delivery date, turns out to be enormously important to people. But you don’t get that insight until you actually see them.

And then is used to joke, you know we all need to spend more time with just mere mortals. ‘Cause it gives you an appreciation for how complex most software is. And we all just take it for granted. ‘Cause for one, we’re all kind of tech nerds and we live it and we love it ’cause it’s our livelihood. But we’re also just kind of all adept to it ’cause we’re swimming in it, morning, noon and night.

And you take people who, you know live a life where technology isn’t at the center of things and this stuff is really confusing. Just watching people try to manage the new credit cards with the chip instead of the swipe. I mean you see people all the time, it’s … We’re kinda getting through it now but there was a solid year in there where you would be sitting at Safeway or something and you just watch people struggling with the little stupid point-of-sale system.

And you just have to scale that across the dozens, hundreds, thousands of interactions that people are having in a given day or a given week. Personally I think that’s a lot of what leads to the sort of heightened sense of anxiety and stress and loss of control. And you know obviously there’s a lot of reasons for that right now.

But I think it must be incredibly difficult emotionally to go through your day and not be tech savvy. I think you would feel victimized all the time by these systems, that it’s somehow gotten into your head that these systems are smarter than you, you know. And there’s not attribution for this stuff. So you don’t know who to blame.

I’m lucky ’cause I know the people that designed a lot of the software I use, so when I hit a rough spot with it, I’m kind of the crazy guy in my basement yelling at people by name. Because I know who did it, you know. And it gives me a certain bit of control ’cause I realize there’s a human being behind it. But if I’m not a tech guy, if I’m my in-laws and I’m 72 years old now and I just got an iPhone and I can’t figure something out, or God forbid I can’t figure out the new feature on the ATM, or the check in kiosk at the airport, or the parking meter they just installed on my street. It just must be so frustrating and so anxiety-producing.

Again I think those of us that swim in tech all the time, we have totally lost sight that we’ve created a very rarefied world for those of us who are members of that club.

Kind of joke that we’ve turned the whole world into Disney Land and the mobile phone now is this virtual fast pass. You know, and you can see it at TSA Pre, you can see it when you check into a hotel, you can see it when you get a rental car, you can see it when you’re picking up an Uber instead of taxi. Like there’s all these systems that those of us in the know, understand how to navigate. But if you don’t know how to navigate that stuff, like you’re not getting the fast pass. You know, you gotta wait in the long line and see all these other people cutting by you and you don’t know how that system works or even that is exists. And that is just gonna create a lot of resentment.

AW: It reminds me of this SNL skit, came out about a year or so ago, with the Amazon Alexa Silver, I don’t know if you guys had watched that? But where the premise was that Amazon came out with a device for older seniors who are having trouble with Alexa. They were kinda shouting her name, “Odessa! Alyssa! Alyssa!”

But it kind of brings up a point though is … I wonder, Bob, what do you think about these kind of more emergent interfaces like Voice and maybe artificial intelligence enabled interfaces machine, Harmony enabled-

Eli Woolery: Natural user interface.

AW: Yeah, natural user interface. Will those types of things help or will you just get more kind of entrenched, those of us who are adept at it and leave the rest of the folks behind?

BB: Well, I’ll just be honest right upfront, say I don’t know. You know, I think that we … One thing I pointed out, is you and I both I think made this mistake of equating older people with technology non-proficient people. And I have teenagers as well and they have plenty of their friends that are not technology efficient.

So I think we’ve gotten to a place where it’s not a generational challenge. It’s you know, it’s how much time people wanna spend swimming in these systems, you know. And if you’re kind of a nerdy guy, a nerdy girl, growing up playing a lot of video games then yeah, this virtual world probably seems pretty natural. But if you’re not, you know it’s still pretty hard. You know there’s plenty of kids in high school, they’re having trouble with Google Docs, and figuring out Google Classroom, and all the systems they have to navigate. I mean, I don’t know how old your kids are but you know, all the systems they have to navigate in high school, much less college, is crazy.

So you’re asking about machine learning and AI enabled interfaces and I can’t say I have any kind of an opinion ’cause I haven’t seen one, so I don’t really know how to think about that part of it. The voice enabled things, interesting, because there’s so little affordance to what those systems can do. And it’s gonna be a massive cultural shift for people to realize all the things that they could ask a computer to do for them.

So the people that I see using Siri and Alexa and stuff like that, it still seems kind of like a novelty to me. I mean, I know there’s a lot of excitement around voice activated systems kinda taking over and I know there’s some stuff going on in offices now, where they’re trying to be prepared for people being able to talk to their computer. And I saw some of the stuff at Adobe MAX, where they’re talking about voice commands for some of their products. And personally I haven’t really made the adjustment to using voice and I can’t say exactly why. It just seems kind of unnatural to me and I don’t really know what I can ask.

So there’s some novelty cases like, asking Siri to dial a phone number, or you know look up a sport score is kind of fun. I just got an Apple watch so being able to do a message with an audio transcription is kind of fun. Doesn’t really replace a lot of the other stuff I’m doing though.

AW: I think it’s a valid point about the discoverability of an interface like Voice and it’s the same for Command-line, that you have to know what you can do to gain power with the system. What’s interesting to me though is that I hear this conversation at parties all the time, “Hey, did you know you can ask Alexa to tell you any word in Japanese?” Or, “Did you know that you can say, ‘Hey Siri, show me the flights overhead right now,'” and it will show you every airplane over your head.

This is a recurring theme that I people you know, sharing these novel approaches and they’re not necessarily tech people that are talking about this. So it feels like it’s wonderful in the truest sense of the word that it’s creating wonderment for people. These super powers they didn’t know they had through a natural interaction versus a UI.

BB: Yes, to hear you talk about it that way, yeah. It’s definitely an interesting cultural phenomenon, what you just described sounded like a bunch of video game people describing Easter eggs. You know, “Did you know if you do Mario this way you can get four extra coins or something?” You know, or like Pokemon Go, all that kind of insider tips and tricks.

You know for these systems we’re building that people’s lives are really … the quality of their lives could be really dependent on their knowledge of these systems. I don’t know if I’m totally comfortable with you know, people having to remember all that stuff or point it out to each other at parties. I don’t know, I guess I have mixed feelings about it.

Some of the stuff, like when I look at Slack, which is obviously an enormously successful product, tons of people use it and love it. You know, it is like a Command-line interface and I feel like we’re back to NASA relaying nouns and verb commands to the Apollo astronauts. You know, it’s just … it’s so much insider baseball. And I do worry that there’s a whole lot of people that get left behind by that. Like a whole lot of people get left behind.

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AW: So let’s talk a little bit about the design review process. I know it’s something that you’re particularly passionate about because it really … you saw at different types of design reviews in design teams from your time at Yahoo and Apple and Pinterest and various other places in between as well.

This season of Podcast we’re exploring the connected workflow of how these different aspects or different teams, different groups factions who work together to create very complicated systems, trying to make them not so complicated. Make software that’s very powerful and easy to use. Meet some goals for customers and meet some goals for business, how they interact together and communicate. And it feels like the design review is the center of that. How does a design review power the interactions in a software design team?

BB: Yeah, so I had two major experiences with design reviews. One would be during my time at Apple and the other at Pinterest. You know the way I talk about the Apple reviews at this point is, the company was at a different point in its evolution. ‘Cause I was there as the iPhone shipped and sort of the ramp up to the iPhone 5 or so. So the company was in a very focused, hyper-growth environment. And Steve Jobs was still there and a lot of what happened inside Apple was getting work up to Steve to get his approval. And the company was sort of organized that way.

And the company’s, you know and this is true today, you know the company’s strategic competitive advantage is design. That is what Apple lives and dies by as a company. And there’s not many companies like that. So I think, one of the things that maybe I didn’t calculate on properly was trying to take that Apple design review ethos and put it into an environment like Pinterest. Where, you know Pinterest design’s really important … I don’t know if the company lives and dies by design, so much as they live by content and new users and growth and they’re trying to define a whole new environment. So there’s a lot of experimentation that goes into that.

So I think trying to use the rigidity of the design review process we had at Apple in the environment of Pinterest, maybe wasn’t such a great idea. So what we used at Apple, I don’t know how it applies to other environments. It was incredible for the six years when I did it when I was on the online store.

And the routine there was, everything was structured around a week. So we came in on a Monday, we had the team meeting, talked about the projects we were in-flight, what people were gonna deliver that week. On Tuesday we had a two-hour team review, just designers but the entire design team. So everybody had to show what they were working on, everybody got to comment, everybody took notes. Then you had the rest of Tuesday and Wednesday to improve your work. And then we came back, we did the same thing on Thursday. So another two hours, the whole team, everybody got to comment. And then on Friday afternoon, from 4 to 6 PM on Friday, we sat with our VP and her executive team and we reviewed the work from the week for another two hours.

So it’s a really intense process. Like, people had to show their work every 48 hours basically. I came to describe the process as a little bit like Saturday Night Live, where Monday we sort of threw around some ideas as to what we might think we’d have for the week. On Tuesday we sort of had like the initial run through the sketches. On Thursday we had sort of a dress rehearsal and on Friday was the show at the executive team.

And you know it actually, as intense as it was, it sort of lowered the pressure because every Friday there was a new show. And so if we bombed on Friday or one of the sketches didn’t go well, it’s okay ’cause we’re back next week.

What I saw in a lot of other companies is designers tend to only go to the executives when they have something good and ready. And by that time they’re so invested in that date, and you can’t get the date really quickly right. So they don’t …. Often times you see people wanting to schedule exec reviews until they’re really ready. And by then, it’s not always that hard to get the meeting but the work is already so baked that the executive doesn’t have a lot of room to influence it without providing a big set-back to the team.

So for us, staying in touch with our executive decision makers, you know every week for two hours kept us really closely aligned with them and gave us really important visibility and feedback into all the different parts of the business, the engineering contingencies, things like that.

The team that did that you know, the store at that point was doing billions and billions of dollars in revenue. It was the, I think at the time, the second largest online store on the web, second only to Amazon. And the people we had designing the store was a team of eight. So there were eight designers working on the store. One of them was me, who didn’t actually produce anything, and one of them was a producer, who just kind of helped managed all the schedules and stuff.

So you actually had six designers actually sitting at their desk drawing the pictures. Producing an online store that had 12-and-a-half thousand storefronts in 30 some odd countries, just for the web presence. And then you had the mobile app, and then you had other project we worked on and other systems that never got to see the light of day. I mean, the volume of work we turned out was unbelievable. And that team, like we still get together for lunch every quarter or so. I mean it’s like we all went together to war or something. And everybody’s kind of scattered into the winds and worked in a huge variety of companies now. And they all talk glowingly about that time. And how intense it was but how incredibly productive it was.

Again, I haven’t seen that play out to other companies and I don’t know how well it would work in other companies. One of the things I thought was really important was everybody seeing all the work. ‘Cause you just got so much different feedback from different people that were and weren’t involved in the project. I think that was huge.

And then just the rhythm, that you were expected to show your work all the time. And so you kinda couldn’t really sit at your desk and stew and get all worried about it. And then I told the team over and over, it’s like the goal of the review is to come to consensus around ideas that we wanna see executed. So that by the time that you go back to your desk, your main job is to actually draw the pictures so that we can then look at them and evaluate them as a team. That, if you ever found yourself sitting at your desk by yourself with your headphones on stressing ’cause you felt like you had to figure it out on your own, something was really broken.

So I think for the team it was useful ’cause it helped them … You know, kinda isolated what they needed to do at any given moment. And again, they didn’t feel like they had to carry the weight of the world on their shoulders and sit and solve these big, massive problems by themselves. I use this football metaphor, “You know, nobody wants a Hail Mary pass, we all just need a bunch of three yard runs up the middle.” So like, “Don’t try to impress me, like let’s all stay together and march down the field in sync.”

You know, Steve had a great line in an interview, I think with Wired or something, where they … The interviewer was saying something like, “Your job must be so much fun, just to sit here and have these designers bring in all this great work. And you just get to kind of see it and comment on it.” And he’s like, “No, it doesn’t work that way at all. Like, if anybody ever brings in anything that surprises me, something’s wrong in the process, right. Like, we need to be really hand in hand or, you know, luxed up week after week.”

And so I actually found it to be an incredibly intense process but again, super productive, very predictable and highly efficient. Again, if you think of the scale of that team and how much we were able to produce, I’ve never seen anything remotely like it. And of course that wasn’t just our team, that was at the time, that was every team at Apple. They all worked that way. Like the number of people working on the OS or working on iMovie or iLife, it would stun you how small those teams were.

I don’t know if that’s still the case, I haven’t been at Apple in many years so it might be different now. But you know, again at that moment in time it was incredible.

AW: Can you unpack what you said about that Jobs said, “If you show me something and it’s a surprise, then we have a problem.” What’s at risk if designers present to executives something that is a surprise?

BB: You know, I always assumed that designers weren’t working with complete information. That there was always more stuff about the business, the engineering contingencies, and particularly at Apple because there was no way as an individual employee we knew everything that was happening in the company. So because of the secrecy in the company, you had to walk into every meeting with an executive thinking that they were calculating on way more variables than you would ever be aware.

So I guess I never walked into those moments trying to you know, surprise. I mean, and surprise is like, “Oh, I come up with something completely out of left field that they didn’t expect.” You know, it’s not that we didn’t bring in solutions that they smiled about, you know or said we’re clever, or were a different way of thinking about it. But I think we never came in and tried to solve a problem that we hadn’t been in sync with the week before.

Right, so a lot of the design reviews at the executive level. I mean, we talked about the design deliverables as a way to define the problem we were trying to solve. And so we walked out of every Friday meeting with a better idea of the problem we were trying to solve, in terms of all the constraints and the deadlines and all the, you know, legal contingencies and commerce contingencies. Like, every week we had a better understanding of that. And so the solution we brought in the next time was ever tighter to solving that problem.

So I think that the executives might have been impressed or maybe a little surprised, amused maybe, with the way that we solved the problem. But they were never … We never tried to go in and redefine the problem. I might compare it a little bit to like chess. I’ve been playing a lot of chess lately, the World Chess Championship is going on right now so I’m having fun watching that. And in chess the problem’s pretty clear. I mean, you can look at the board and everybody knows that’s what’s happening. But great chess players, they make a move and they find a solution that nobody else quite saw. You know, and that’s when you kinda go, “Wow, look at that. That’s amazing.” But I wouldn’t say that’s a surprise.

I mean, you see with jazz musicians as well. You know, you’ll see somebody doing a riff and some band member will look over and kind of give a big smile like, “Wow, I didn’t think about doing that. That’s a really interesting solution to the problem that we set up as a band.”

And so again, when we were presenting design solutions to the executives, we might find clever solutions but we were never trying to wholly redefine the problem.

AW: So Bob, you mentioned that this review process might not work at other companies just because of the way that Apple’s structured, and its history and the way that Steve Jobs ran it during the time that you were there. When you moved over to Pinterest, were you able to adapt the review process at all, or how did you approach it differently when you were there?

BB: Yeah, so we tried a couple of different things. And again I’m not quite sure where they’ve landed now. We did institute a weekly design review at the exec staff, which I think was really good. I don’t believe they were doing that before I got there. That actually ended up going to twice a week. So the teams head a steady cadence in which to get to the executives. And we did do all team reviews, if I recall we eventually broke down so that we had, like the growth team would have their review, and then the core product team would have their review. And then the business tool review would have their review.

And in those reviews you would see the designers plus engineers plus PM, all together making collective decisions. You know the big difference in those reviews, is there’s no one with the moral authority to make a firm decision. So, at some of the talks I give I have this phrase I use called “the path to yes.” You know, what’s the path to yes? ‘Cause all designers need to know what are the hoops they have to go through to get something approved.

And at Apple there was a really clear path to yes. And it went right up the chain of command. And at the time, again, I assume this is still the case at the company, that the people above you were all phenomenally talented. Like if our VP made a decision I wouldn’t sit around questioning whether that was the right decision. I mean, she was incredibly gifted in making these design decisions.

And as you worked up the food chain with whoever, Eddy or Phil or Tim or certainly Steve, like the decision making capabilities of these guys was unbelievable. When we went into review after review at the executive level, where they would look at something and point out something we had missed, we’d been staring at it for four months and they’d look at it for you know, a minute, and point something we had missed. So there was sort of a moral authority to make decisions that stick, that doesn’t exist in a lot of companies.

The other thing I used to say about the path to yes, I use this metaphor of, “The path to yes should look like a mountain.” You know it can look like a really dangerous, treacherous mountain where you could fall. But at least with a mountain you can see the summit. And the designers know, “Oh, I have to go through this set of things to get my work approved.”

And a lot of companies I think the path to yes looks more like cave diving. You know, spelunking where you go in the cave and you’re sort of feeling your way around and you can suddenly go through a little hole that opens up a whole other cavern. And you didn’t realize you’re actually had to go involve legal representatives from Germany, because they had this thing called the Works Council over there. Like you know, you don’t know how many groups you could stumble into that suddenly think they have a say in it.

And when I use this metaphor in my talk I also like to point out that whenever we see photographs of people cave diving, it always looks really spectacular. ‘Cause they’ve lit up the cave so you can take the picture. You know, and it looks amazing but then I’m kinda quick to point out, “You know, the cave only looked that way for about a hundred and twenty fifth of a second. Most of the time, it’s pitch dark.”

And I think that’s the reality in … You know, I worked at Yahoo a long time ago and that company had a very confusing leadership cycle, leadership structure. And it was definitely cave diving man, like you had no idea how to get stuff approved, who you had to talk to. And it created so much stress and anxiety and inefficiency for the team. I mean, it made people nuts. In a couple of cases like almost literally. So I used to joke there’s nothing worse than taking a bunch of smart, talented people with a lot of ambition, put them in a situation and then give them no mechanism for making a collective decision. They started clawing each other’s eyes out.

So, you know, I don’t know how many companies like … You know, if you go like talk to a CEO or even talk to design leaders, you just put the question to him, “You know, what’s the path to yes for one of your designers?” I don’t think many of them could answer. And you know, at least at Apple I used to tell my team all the time ’cause you know, they talk about wanting to work on bigger strategic things and I’d always say, “Well, the thing about doing big strategic work is you have to have big strategic ideas. So what I can assure you, is if you have an idea over the weekend and we can work on it a little but this week, I can get it in front of a VP on Friday and we can get it evaluated. So I want you to feel like there’s a path to yes if you have something that needs to go down that trail.”

And I think that’s much more empowering for people than you know, “I came up with an idea and I guess I have to go shop it to these six people and maybe somebody will champion it. But it don’t really know who.” And they just get into this whole political thing of trying to sell the design. It pulls you more into the personalities and the politics than the quality of the ideas themselves.

AW: I think a lot of companies that we’ve spoken with, the cadence, that level of access to executives, is harder to come by. You know, it’s not a weekly interaction with an executive. Some situations it is. And one way we’ve heard design leaders trying to solve that, Laura Martini comes to mind, she’s a Googler on the analytics team. She always talked about bringing the right people into her design review process early on, and there’s some vulnerability in that too that her team wasn’t presenting perfect finalized designs. They were presenting early ideas, stuff that was rough, sometimes sketches.

Also, Geoff Teehan over at Facebook, I’ve heard him say basically the same type of thing. That VPs and executives at Facebook, they actually love seeing sketches, and-

BB: Oh yeah.

AW: … it’s the most enjoyable part of the week, is to be able to look at these sketches, these early ideas because it invites participation. So I wonder if you could talk about that and your experience both in your personal career but then also your observations of lots of other companies and design leaders you’ve spoken with. How do people bring the right people in at the right time?

BB: Yes, so at the beginning of projects, like if I think about the Apple store app for a second. Like we had a partner that was on the Apple retail side and then we had an engineering lead, and this was pretty early on. I started working on this around the time the iPhone 3G S was out and the target was for the app to come out with the iPhone 4.

And so app development at Apple was just sort of ramping up. And there was one young engineer who was really excited about doing the app. So we had Scotty involved early on, and Cory over from retail, a handful of designers from the online store side. And then you know, we got a lot of buy-in both from Ron Johnson, who at the time ran Apple retail, and Jennifer Bailey who was running Apple online store at the time.

Yeah, I mean just an interesting story, you talk about sketches and stuff and trying to bring the right people. We knew that we had to have executive buy-in, that we had to go those two VPs in there, the SV and VP, and their teams engaged. And so the decision to make the Apple store app, was literally Jennifer looking at me one Friday after design review and saying, “You have to start designing an app now. You know, I can’t be sitting here in six months and tell Steve we don’t have an app. Like, go design it now.”

And that was kinda all the input there was and so that weekend I went and started looking through a bunch of things on the app store, which I hadn’t paid a lot of attention to until then. And one of the insights I had that most of the apps had five items down in the tray and that those items tended to be nouns. And they kinda dictated the functionality and sort of the scope of the app. And so I felt that if we could get some agreement on what those five objects would be, that would provide the basis for the design. And give us the executive buy-in we needed at the very beginning.

So instead of trying to go in with sketches or anything like that, we just brainstormed it out what those five objects could be. You know, clearly one of them was gonna be “carts”, you know one of them was probably gonna be “stores”, one of them was gonna be you know whatever the catalog we were gonna call it. Maybe one was gonna be “featured.” I mean, there was only so many nouns that would work.

And we got all the interested parties into a room, there’s probably 20 people in the room. And I just stuck big pieces of paper up on a white board with magnets. And we just sat there and over the course of like 15, 20 minutes we just tried out different words, put them in a different order, and then we all kinda looked at it and said, “Yeah, okay. That’s it.” And like, “Yeah, okay. That was it.” And that was it for like the next six or seven years.

And you know, right at the very beginning the VPs felt they had a lot of opportunity to move the design around and say what they wanted in the app and what they wanted the priorities to be. So they had really strong input right at the beginning, before there was any work committed, you know before any finals comps had been done, before any designers got attached to any ideas. I think this notion of trying to get the right people in the room at the beginning … I used to use this metaphor, it was like planting red wood garden. You know, that there was ultimate flexibility in where the trees were gonna grow right at the very beginning. But if you let it grow too long things got really difficult to move around.

So I love what you were saying about a woman at Google and sketches and stuff. Like that was something I noticed and I tried to push at Pinterest and Apple as well. Like, “Everybody put Photoshop down, just back away from your computer for a minute and let’s just sketch some stuff out.” You know, we’d spend a lot of time doing whiteboard sketching as a team or just having people sit and draw stuff. Like while we were trying to come up with a new feature for price filtering or something on Pinterest like, “Let’s just draw 10 pictures, like just sit and sketch out 10 ideas. And then we’ll weed them down.”

And that actually came from something I saw when I was working at a graphic design studio, way early in my career. And we had a new job come in for a logo and the head of the studio brought in like the four designers. And he said, “Okay, everybody just sketch some ideas.” And they sketched for like maybe 10 or 15 minutes. And between the four they came up with I don’t know, like 50, 60 ideas. And then they just started looking through them and you could throw a bunch of them away really quickly. You know, but after like no time at all you were down to like two or three maybe four really promising ideas. And it was like, “Okay, take those and flesh those out and let’s see what happens.”

And it really drove home for me that famous saying you know, “If you wanna good ideas, the challenge is to get a lot of ideas.” And I think when people start sitting down and they’re immediately in a tool, whatever that tool might be, but they start producing comps, they start getting attached to that. And then there’s like this emotional connection that builds up and it ends up being costly for them to switch from one thing to another. When at the beginning it’s like, “What can you do that is as loose as possible that can convey the idea with a minimal amount of effort?” So that you don’t feel bad about throwing the idea away.

You know, is used to talk to my team about you know, “Try to be really lazy and think about what’s the minimum investment I can make to convey the idea accurately and let’s focus on that. And then once we get an idea that we love, then we’ll go all in and we’ll really invest in helping to nurture and grow that idea. We’ll bring the army, we’ll bring it to life. But at the beginning, let’s keep things as loose as possible.”

You know sorry, to your question about who are the right people to bring in. You know I used to use this phrase kinda what I’d call “creative technologists,” that were a certain type of engineer that could see beyond the code. And see more how the mechanism and the medium of a computer and algorithm-based decision making could be brought to bear a particular situation.

And so I, in every company I’ve worked in there was always a handful of people that you knew across the organization that I would refer to as creative technologists. You know, and they were the people that were noticing parking meters and ATM kiosks and came in on the weekend talking about video games. And you know, they just had a different view of technology that were always really interesting to bring in at the beginning of projects.

AW: So Bob, one last question for you before we wrap up here. Are there any books or podcasts right now that you are enjoying or helping you out?

BB: On the design side? Yeah, I listen to a ton of podcasts so I got podcast recommendations for days. Thinking with the design lens, I think the book I’d recommend right now is Zen and the Art of Motorcycle Maintenance. Which is an interesting inquiry about philosophy and the notion of quality and how we think about objective versus subjective reality. I’m highlighting massive portions of the book ’cause I think they apply a lot … Also, it’s a lot about technology and the dehumanizing effect of technology. And how we get distanced from the people who are making all this stuff.

Like the lack of attribution in technology I think is a huge issue. I think it really dehumanizes the creators and it dehumanizes the consumption experience that the customers have. So, Zen and the Art of Motorcycle Maintenance, you know, really different kind of design book but a really interesting and powerful read for me right now. And I urge people when you read it to take … It’s one of those books that there’s a lot there.

So I’ve got into this habit of reading a book like that really slowly. So I’ll read like one chapter a day. And the chapters are only like four, five pages. So you know, it’s gonna take me like six months to read it but when you spend that much time reading a book like that it sits with you, it becomes kind of part of your life in a really different way than just trying to power through the 300 pages or whatever. So if you’re gonna read that one, take your time.

On the podcast front, probably the most interesting one I’ve read that I’ve been listening to right now is called Everything is Alive. And Everything is Alive is an interview show where they’re interviewing inanimate objects. So the first episode was an interview with a soda can and it’s all … I think it’s scripted or at least it’s ad-libbed by really, really gifted comedians and actors. And so the soda can’s talking about where he lived in the grocery store and how he got taken out to kids’ soccer games, but he was the soda can that never quite got consumed. You know, kinda what that whole experience was. And how at the end, the host finally says, “Well, do you want me to open you and drink you?” And the guy’s like, “Well yeah, that’s why soda cans exists. So if you can do that that would be awesome.” And so there’s this whole thing about him being consumed at the end.

There’s an episode about an elevator, there’s one with a lamppost. And I think it … You know, that one’s been really powerful for me ’cause one of the things I try to do this year is really try to imagine the world from other people’s points of view. And so for part of the year I was really kind of obsessed with the idea when I was talking to somebody, they were seeing me from their eyes. You know, and I was seeing them. Even though we were in the same space having the same conversation we were having two wildly different experiences of it.

And it’s somewhere in the year that actually got translated over to animals. That I start noticing my dog more and just like really wondering, “What’s going on with my dog?” You know, and thinking about what a completely different experience of the world that he has. And the stuff that he’s smelling and that he’s thinking. You know, we live in the same house, we know all the same people. We go on the same walk, we spend an enormous amount of time together. And we are having wildly, wildly different experiences of life.

There’s a really interesting article about octopuses, you know, and how intelligent they are and how amazing they are. And just trying to imagine the world from an octopuses point of view. So somehow this podcast came along and it kind of just took that to another level. You know, so now you sort of … Now you sit and you think about your car you know. Your car’s sitting in the driveway, just kind of cold. Wondering when you’re gonna come back and drive it around. You know, like, “What’s it mean to be a car ’cause all I really wanna do is get out on the freeway and go fast. God I’m just stuck in traffic all the time and it’s kind of bummer, and when are you gonna fix that dent, man I look bad. Could you help a brother out.”

Anyway, so Everything is Alive is a podcast I go for and Zen and the Art of Motorcycle Maintenance.

AW: Perfect, those are great. I’d love to go back to Zen, because I read it as an under-grad and need to spend some more time with it.

So Bob, thank you so, so much for being on. It’s wonderful having you and we really appreciate you being here on the show.

BB: Thanks guys. I appreciate the opportunity, love the podcast. I’m glad you guys are out there doing this stuff. Thank you so much for the time.

AW: That concludes this episode of the Design Better Podcast. That concludes this episode of the Design Better Podcast. Thanks so much for listening. If you’re hungry for more stories and lessons to continue to level up your design practice, visit www.DesignBetter.com. You’ll find ebooks, videos, and articles on design that you and your team can use to learn more about design thinking, building world class operations, facilitating enterprise design sprints, and so much more. If you enjoyed this episode, please leave us a review on Apple Podcasts, and share this podcast with have friend or teammate interested in designing better today. Thanks so much for listening.


Meet Your Hosts

Aarron Walter
VP of Design Education

Aarron Walter is Director of Product on the COVID Response team at Resolve to Save Lives. Previously, he was VP of Design Education at InVision, and founded the UX practice at Mailchimp where he helped grow the product from a few thousand users to more than 10 million. He’s the author of a number of books, the latest of which is a second edition of Designing for Emotion. Aarron’s design guidance has helped the White House, the US Department of State, and dozens of major corporations, startups, and venture capital firms.

You can find Aarron on Twitter and LinkedIn.

Eli Woolery
Director of Design Education

Eli is the Director of Design Education at InVision. His design career spans both physical and digital products, and he has worked with companies ranging from startups (his own and others) to Fortune 500 companies.

In addition to his background in product and industrial design, he has been a professional photographer and filmmaker. He teaches the senior capstone class Implementation to undergraduate Product Designers at Stanford University. You can find Eli on Twitter and Medium.

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