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Career Life Stories: Bob Baxley, Advisor

Bob Baxley, a film-maker turned design executive whose experience was shaped by household names like Apple, Yahoo, and Pinterest, shares the most interesting design challenges of his career and hones in on a surprising void within design today. He also reveals the number one quality he looks for in design candidates and highlights the difference between scaling influence and managing others.

1. What led you to an early career in design, and how did you get started?

To be honest, I fell into it at a time where design as a career wasn’t widely available. When I got started in 1990, the field wasn’t well-known and hardly anyone was even talking about UI design. At the time, it was known more as HCI (Human Computer Interaction), or like at Apple, Human Factors Engineering.

I’ve found that most of the people in design are refugees from some other career. After having talked to a lot of design leaders, I conclude that there are three primary backgrounds from which UI/UX designers hail from which are architecture, graphic design, or film-making like myself. What’s interesting is that people from each of those backgrounds have very different strengths and weaknesses when it comes to design. Architects tend to think about UI design as a system, whereas graphic designers tend to focus on the aesthetic, and film-makers often prioritize the story.

Bob Baxley Design Executive

2. Which of your roles as a practitioner did you find the most interesting or surprising from a design perspective?

I worked on very different problems at each company, and I only went places where I fell in love with the problem.

The Apple Online Store is probably the marquee experience of my career, in part because of what was happening at the company while I was there. I started about nine months before the iPhone was announced, and I left the Apple Store about the time that the iPhone5 came out; to provide some context, Steve Jobs passed away just after the iPhone 4 announcement. To be at the company at that moment in its development felt historic. I firmly believe I was at the greatest company in the world at the greatest moment in its evolution. It was a little bit like getting to go to the moon. Beyond that, the e-commerce problem space is interesting because you’re connecting things like search and social with the realities of inventory and logistics; at the end of the day, a breakdown in UI design implementation has real-world consequences in terms of payment gateways, shipping, customer satisfaction, and sales.

The role that surprised me the most was at Apple Retail where we were trying to figure out new pieces of software to use inside the Apple stores; specifically, I was working on future ideas point of sale in the stores. The thing that surprised me about is that it was the first time I’d ever worked on true human-to-human interaction that was mediated by technology. I had to fundamentally understand the specific interaction we were trying to facilitate, and then the technology had to be out of the way. In all of my previous experiences, the technology had been front and center because the interactions were human-to-computer. Apple Retail was an unexpected challenge, and it opened me up to all that technology was enabling behind the scenes at places like restaurants, stores, and at Disneyland in particular.

The most interesting problem space I worked on was Yahoo search. Search fascinates me because it is the smallest possible UI which provides the greatest amount of functionality. As a user, search seems so simple, but it’s incredibly nuanced and complex.

3. Over time, how have you seen the landscape change for designers?

The big shift in UI design coincided with the rise of the smartphone and more specifically with the advent of the Appstore in 2009. No one was really paying that much attention to UI/UX until the rise of the Appstore. Suddenly, consumers were interacting with software thousands of times per day from their pockets, so any friction points were amplified. In mobile, when you’re touching the phone all the time, fiction just isn’t tolerated by consumers.

If you think about the Appstore as an expression as human creative and technical energy, I’m convinced there has never been a greater concentration of human effort in all of mankind. It absolutely dwarfs any other innovative era.

4. What design skills or type of experience seem to be the most “in-demand” today?

My impression is that far and away, the number one skill across all industries is design management. Companies are struggling to find designers who are ready to go into management, much less who have already had management experience. What makes someone a good individual contributor as a designer in terms of temperament doesn’t necessarily translate well into management. Designers talk about wanting to be an equal partner to engineering and product, but I suspect it’s going to take a while for that to happen on a broad scale because there really don’t seem to be many designers who genuinely want to do the politicking, socializing, and worrying about the business that is required at the C-level. Some do and do it very well; however, they seem to be more of the exception than the rule right now.

In the last couple of years, from an anecdotal perspective, it seems that more companies are starting to see design more as a function that fits inside either product or engineering. To ensure design still has a voice at the table, some companies are tapping Chief Product Officers with strong design sensibilities to be the advocate and champion for the design function at the C-suite table.

Another department that’s trending due to an emphasis on ‘how to scale design’ is design operations; design operations is a way to scale the overall output of larger design teams by offloading aspects of production such as final assets along with their multitude of resolutions and formats. These teams also work to maintain design standards and create various tools to simplify the creation of prototypes, mockups, and more. Finally, design operations teams tend to also include design producers who help to manage schedules, internal communication, and other tasks that ensure everything runs smoothly.

5. How are design teams usually structured within an organization?

It’s culturally specific so it varies from company to company. Sometimes design reports to product and sometimes it reports to engineering. Another thing that varies is whether design is centralized or distributed. In centralized teams, designers usually report up into a head of design, and in a distributed organization, designers typically report into each of the point products. Some companies create a “platform team” which is supposed to advocate for standards and best practices which design teams might arbitrarily follow.

Additionally, some companies bias toward unicorns that can do interaction, information architecture, product design, user research – basically the full-stack. Other companies bias more toward hiring for specialized skills as they build multifaceted teams.

6. In your experience, what qualities make a great designer? What are the personality traits you tended to look for in candidates?

The simple answer is that I always look for something which I call ‘equipoise’ which, to me, is a nice balance between confidence and humility. The designers I liked to hire had to have enough confidence to put their idea out there and advocate for it, but they had to have the humility to listen to feedback and understand that they might be wrong. Designers that are to humble give up on their instincts too quickly, and designers that are too confident are impossible to communicate with because they can’t take feedback. 

Designers are one of the few functions within an organization that ever faces the blank page. They get very ambiguous requests and are the first people that start to give them detail. Because, in a way, design is an artistic expression there is this element of vulnerability that you don’t find in other functions which makes that confidence-humility balance that much more important. It’s frankly just more fraught with emotion.

Design leaders must understand how to manage passion, whereas most other leaders get to manage numbers. Trying to advocate for yourself or your team on the basis of passion and not come off as emotional is very difficult. One caution is that passion and frustration are two sides of the same coin. If you don’t manage it properly, passion can flip to frustration very quickly.

7. Do you have a favorite interview question?

Imagine that in three years you’re leaving this job. What is it that you want to be able to write on your LinkedIn profile or resume to get your next job? What are the 3-5 bullet points do you hope to get out of this job over the next couple of years?

This question was a way for me to understand what a candidate wanted to learn about, because as a manager, if I could understand what someone wanted to learn then I could start to figure out their curiosities and passions. From there, I could think about the types of problems and projects I could put them on that would excite and motivate them.

8. What advice do you have for young professionals who desire to become a design leader?

If you want to be a leader, then go be one. You don’t need a promotion or to be manager to be a leader.

When I talk to people who tell me that they want to go into design management, I always try to understand why. A lot of times they think it’s the only growth path that’s available to them, so I try to get them to clarify if they’re looking to scale their influence or if they’re looking to help other people.

If you want to can scale your influence, then you can do that by having better ideas and getting better at selling them. Design is great, because if you have a great idea on Monday and have a good sketch of it on Wednesday, I’ll get you in front of the CEO on Friday. Getting access to sell your idea is not the challenge – the challenge is not having any great ideas.

If someone truly wants to be a manager, though, I make sure they understand that the role is about managing other people’s careers. Some of the best managers I’ve known have been parents. Through the parenting experience, you come to realize that management isn’t about power but about unlocking another person’s potential and that there is an intense satisfaction that comes from seeing someone else succeed.

Beyond trying to get people to clarify why they want to be a manager, I also try to get them to clarify the problems they like to work on and the business models that resonate with them morally. Some companies make money by advertising, or by being part of the transaction flow, or by selling a product, and I think these revenue models resonate ethically for people in different ways.

Finally, I make sure the person is clear on the stage of company that is the best fit for them. Some people are great at the 0 to 1 problem; others are good at 1 to 10 and then others 10 to 100 and so on.

9. As we wrap up, what resources (books, blogs, podcasts, events) would you recommend to folks who want to expand their knowledge about design?

Design literature has gotten so far in the weeds with different tools and processes, and I tend to think we’ve lost sight of what it means to create great work and to really love what we’re creating. I sadly think that design has sort of been captured by business, so if I were to point people in a direction, it would be toward content related to becoming better at crafting stories. Story-telling is a skill that I think all designers could improve.

I also enjoy documentary podcasts like Slow Burn about Watergate or The Thread from OZY. Beyond those, I read a lot about philosophy, history, behavioral economics, historical creative figures and what their routines and work-lives were like.

For now, I’m trying to get away from the mechanics of design and back to the poetry.

10. Finally, what is the best way for people to connect with you?

LinkedIn would be the best way to connect with me.

If you’re interested in connecting with Bob, please follow this link to his profile.

If you enjoyed our conversation, you can also check out others interviews in our Career Life series: Elain Szu from AccelTerence Lim from UdemyDan Portillo at Greylock, and Caroline Ingeborn at Toca Boca.

Bob Baxley is a design executive, advisor, and mentor who works with companies and people who care about making great software. Over the course of his career Bob has served in a variety of leadership and individual roles for some of the leading companies in Silicon Valley including Pinterest, Apple, Yahoo!, Claris, and others. The work created by Bob and his teams has been seen and used by over a billion people around the world. A proud liberal arts major, Bob holds degrees from the University of Texas and Stanford Universtiy. A published author, Bob and regularly speaks about design to audiences around the world.