Design: Challenges Of Scaling, Creating & Being Human

As a long-time Apple executive and a former Head of Product Design at Pinterest, Bob Baxley is a seasoned design expert. With nearly three decades of experience behind him, Bob is now enjoying retirement, mentoring and advising companies about design and challenging the education industry to promote design courses at university level.

Speaking to Winter Circle as a member, he explores the shifts in the industry: why design no longer needs to justify its seat at the table, how it’s more important than ever for designers to connect with their users and why that little-known tech company in Cupertino can still teach other executives a lot about really knowing their product.

Reflecting on his legacy and a memorable moment with Steve Jobs, he simply says “we’re not building cathedrals and pyramids, we’re building sandcastles on the beach. Everything I’ve worked on has been washed out to sea after a few years. I think people get caught up in thinking they’re creating something that’s going to last forever. It doesn’t.”

How have you seen the design industry shift over the past decade or two? I would have thought that design has in some ways come more to the fore than it once was – is that an accurate assumption?

The iPhone X has just come out, 10 years after the initial iPhone. The App Store came out about 18 months after the first iPhone and my sense is that we didn’t really start to design software in a meaningful way until the advent of the Apple App Store and until smartphones really started taking off. That created enormous demand for high-quality software because people were using apps a lot.

To my mind, we’ve only seriously been designing software for maybe eight years and during that time, there has been an enormous shift. If you looked at the industry before then, you’d see designers talking about how hard it was to justify design as an activity to their executive teams, to get a seat at the table. Fast-forward less than a decade and I’m hosting panels about scaling design at large companies, talking to the Chief Creative Officer at SAP and the VP of Design at Walmart Labs. Design is not trying to justify its seat at the table anymore.

I can do the math and work out something I’ve worked on has touched a billion people.

We’re at a point now where we’re trying to develop standardised methodologies and techniques as well as ways of communicating to allow the profession to scale. We’re developing professional infrastructure. Almost every other profession already has professional groups, university programmes, mentoring programmes, they know how departments are organised, they know what specialities look like and what career levels look like. We’ve come a pretty long way considering it’s only been seven or eight years, but there’s still a long way to go.

What would you say are the main trends in the industry – what is everyone buzzing about?

What I see in the online chatter is that there seems to be a lot of evolution and interest in design tools, as well as ideas on how to collaborate. I’ve seen quite a bit of emphasis lately on design leadership and the more prominent writers in the field, like Julie Zhuo at Facebook, write mostly about management issues.

The conversation around design management is indicative of a profession that is trying to scale. When you only had three or four people in the design department, you didn’t think about what it means to be a great design leader. That’s increasingly a discussion – how you hire, how you recruit, how you figure out the culture, how a design team interacts with product and engineering. More and more, designers are wrestling with the question of whether they want to stay individual contributors or take a management track. When you think of traditional designers, like graphic designers or even industrial designers, usually they’re leading really small studios and they don’t have to wrestle with the idea of becoming VP and leading a 200-person department. Designers still think so much [about design]. Their currency is their craft.

Let’s talk briefly about what you’re excited about in the space…

The thing I’m most interested in right now is trying to understand the impact of tech on people’s daily lives and on their mental wellbeing. I think all of us feel a bit of anxiety in how much time we spend on our phones and how distracted we see ourselves and our colleagues. As an industry, we have to own some responsibility for that and to start thinking about our impact on each other. There’s a book called iGen about the impact of smartphone culture and social media on teenagers. I have a couple of teenagers and I can confirm it is very real. The anxiety that these kids are carrying through their daily lives, trying to keep up with their phones and Snapchat, is pretty debilitating.

Our recent interview with a Head of Product at Google touched on how we don’t even see technology anymore because we’re so immersed in it – it’s omnipresent. How do you think design feeds into this?

That’s a weighty question. One of the biggest problems I’ve seen is that not many designers actually see people using their software. When I was at Yahoo a long time ago, I remember thinking it’s impossible for us to understand that right now, as we’re sitting in a meeting, there are 40 million people interacting with the Yahoo network. But we don’t see any of them because we’re creating Yahoo by ourselves, one screen at a time.

I don’t believe that tech executives take responsibility for the user experience.

There’s a bizarre paradox when you’re designing software, that your work reaches more people than any creative pursuit I’ve ever been able to identify. I can do the math and work out something I’ve worked on has touched a billion people. If you just get a couple of pawprints on Facebook, you’re touching 2 billion people. That scale is unprecedented. But as a designer, you never see that. You’re completely isolated from your users. You have no way of comprehending the fact that you’ve created something that’s been used by hundreds of millions of people. A sports star can go to a stadium, a movie star can go to a theatre but it’s really rare for people working on software to ever see a mere mortal actually use it.

This was really driven home to me when I was working on Apple retail because some of the software that I worked on was used in the stores. That was probably the first time when I could actually go to a place to see people interacting with what we’d built. We would sit around and watch people use stuff inside the stores – it was eye-opening. I think there’s a huge risk right now and I think that’s one of the reasons software feels a little out of control. I think it’s really hard for a 24-year-old designer working in San Francisco to have any appreciation of what it’s like to be a 62-year-old trying to get a boarding pass in Heathrow.

As you said, everyone has a responsibility to have these conversations around bridging the gap between technology and people. How do designers and companies remember this when designing and developing products?

I think one of the biggest risks here is the fragmentation of any user experience. Think about a user in an overall day and how many different products they’re having to interact with. For a user, [a day] is a profoundly fragmented experience. There’s cognitive friction, where the user has to adjust all the time and use a lot of energy to navigate all these different systems.

A classic example of this is ecommerce. If you go to an ecommerce site, typically there’s one team that designs the merchandise, another team that designs the shopping cart and another team that does checkout. For a lot of sites, you can actually feel when you get handed off from one site to the other, you can feel when you’re transitioning from one team to another.

There are people who spend five years of their careers working on checkout and that’s all they ever see and that makes it hard to realise that’s actually just one minute of a 10-minute experience. I don’t know anybody in any large company that can even begin to have a handle on what a user’s experience looks like across the whole journey. I don’t know any ecommerce company that looks, in totality, at the overall experience from homepage to thank you page.

Is there a solution? How does a design leader or a company take a holistic view of everything?

I’m probably not in the mainstream here, but I don’t believe that tech executives take responsibility for the user experience.

Except for everybody’s favourite tech company in Cupertino, California, there’s no other tech company where the executives feel like it’s their responsibility to provide a great [user experience], where they feel that they’re personally responsible for the creative output of their team. I think most tech executives feel that they’re responsible for creating the environment where the team can do the work but they’re not responsible for managing the work itself.

Over and over, you’ll see executives who actually don’t know how to look at their creative team and say what’s good and what’s bad. They ask did you run the numbers? Did you do the metrics? How did you get to the solution? Tell me about the process. That’s a fundamentally different way from how truly creative companies work.

Design is about the only activity in a company where your job is to start with a blank page and figure out what to do.

If you look at Apple, Pixar, Disney or any movie studio, the studio heads are responsible for the creative output of the company and they get fired if the movie sucks. No tech executive gets fired because the product sucks – it just doesn’t work that way because nobody thinks they’re responsible if the product sucks. What I saw at Apple, and I’ve seen this in some other places, is that the executives do, by definition, have the 40,000-foot view. When I was in meetings with Ron Johnson or Jennifer Bailey, they were always asking the harder questions about how everything connects.

When it comes to designers transitioning to management and becoming senior leaders in a company, is there friction in merging these creative minds with business issues?

It’s definitely a challenging transition. Design is a portfolio profession. The challenge is when you move into management, you move away from your portfolio. A lot of people understand that and it’s part of their reluctance to move into management. I think designers in bigger companies are starting to realise the power of having a great leader and a great manager and so they’re starting to look for that. The trick with being a design manager is that you have to bridge between the different modes of thinking in a company.

Design is about the only activity in a company where your job is to start with a blank page and figure out what to do. There’s an emotional vulnerability to that, even if you’re mature enough to not connect your work with your self-worth. Even if you can pull those two apart, there’s just a natural human anxiety of staring at the blank page and being the person that has to come up with the original idea. Design managers who can manage that creative anxiety have a unique and powerful skill.

When you’re working for organisations that are on the forefront of design, is there pressure to keep innovating and keep delivering the ‘next big thing’? And does that pressure effect a designer’s ability to solve the problems and have the headspace to be creative?

If we’re talking about Apple when I was there, it was a really mature company. Apple knew what Apple was about. There was a very narrow expression of the brand. If you look at Apple marketing materials, for example, there are two typefaces, three sizes, two colours so it’s a narrow band. That pulls a lot of variation out and reduces the number of variables. At Apple, there was a tonne of pressure to do the best work you could for that particular little feature or interaction but you didn’t have this huge blank canvas to navigate. You go to a startup and everything is in flux. The colour scheme, the typography, the name of the company, the voice, the brand – it’s all in flux. That’s a much bigger challenge as you’re trying to balance all these things and that makes it harder to do excellent work in one particular area.

You have to perform. Design is pretty close to performance art. You have to bring your game, present your work, stand up there and take the arrows if your ideas are bad.

Some designers make it and some don’t, some enjoy the intensity and some don’t.

Touching on your time at Pinterest, what advice would you give now to other executives, particularly in startups?

I think the trick as an executive is to find out what stage of a company or a startup you’re most effective at. I was effective at Pinterest for a particular phase of its evolution. I probably wouldn’t have been effective if I had been there before that time and there was a point where I probably wasn’t the right person anymore, when the company got bigger and the needs changed.

Frankly, that’s part of what changed for me at Apple as well. I really enjoyed Apple when it was the underdog but once Apple became the big dog, I don’t know if that was really my environment as much. Some executives scale, and I actually think that’s the miracle of someone like Mark Zuckerberg. To be able to turn him from a Harvard undergrad to a bonafide global leader in eight years is transformational personal growth.

A lot of executives along the way don’t make it, they don’t evolve at the same pace or in the same direction as the company and you see companies where the founders don’t evolve with the company and they tend to not be particularly successful, especially on the design side. The examples of that are Yahoo, eBay and Twitter – all companies where the founders moved out really early and to this day, those companies struggle with who they are. I think the big learning from Pinterest is if you want to go play in a startup, figure out what phase of the startup you’re probably best suited to and nail that.

Some designers make it and some don’t, some enjoy the intensity and some don’t.

Looking back at your time at your career, was there product you worked on that you think had a lasting effect on the industry?

We did a big redesign of checkout when I was on the online store at Apple. The Apple Store app came out around the same time as the iPhone 4 and it was the first time the online store had to really collaborate with retail because we were going to have features for both channels in the app. The executives of those two organisations were incredibly talented, larger-than-life personalities and for me, trying to navigate the two of them and harmonise their needs was a great interpersonal leadership challenge.

I had to manage this while trying to get my team to do their best work but there was a lot of trust in the team, people were doing really solid work and we had a really good review cadence. We were able to take our work all the way up and present it to Steve. He really liked it and actually looked me in the eye and told me we’d done a good job, which was a nice moment.

But the legacy I have is the people who worked for me who had a great time working together. And then there are all of these different people who have used software that I’ve worked on. I like to think that when they were using it that it worked well for them and they had a good experience. If I made their lives easier for that brief little moment, then that’s something.

Overall, I look back on 27 years of designing software and I think I did some good work at the time but we’re not building cathedrals and pyramids, we’re building sandcastles on the beach. Everything I’ve worked on has been washed out to sea after a few years. I think people get really caught up in thinking they’re creating something that’s going to last forever and it doesn’t.

Everything is changing all the time.

Design is very ephemeral.


Bob Baxley is a Winter Circle member, former Head of Product Design at Pinterest and former Senior Manager of Design & Product Management at Apple.

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