What was the moment that you knew that you wanted to work in design?
It dates back ‘til I was about four years old. Back then, I became obsessed with Mac Paint on my grandmother's Apple computer, and never looked back. I had a serious interest in art and computers ever since I can remember, and it's all I ever wanted to do. Throughout high school and college, that's all I focused on.
Still today, the intersection of design and technology is where I put my focus. Every year it's like an onion that keeps unfolding, getting more interesting.
How did you get to where you are now?
It's been a decent journey. I grew up on the south side of Chicago in the states. Art and technology wasn’t a popular topic when I was young. Most of what I know has been self initiated, spending a lot of time learning how to do things. Eventually when I got to college I earned degrees in computer science, fine arts and psychology.
My first job out of school, I was hired as a software engineer at a small consultancy in Chicago and that was my foot in the door. From there, I practiced design through developing interfaces. We contracted a lot of unique clients which gave me a broad exposure to different design and technology problems. Over time I became interested in working in a more proper design organization.
In Chicago, there weren't many agencies I was interested in working at, so I started my own in an attempt to make the studio that I've always wanted to work for. Around that time I realised that I had been traversing this fuzzy art and technology world for a while and I felt compelled to write a book about breaking down creativity, making it more accessible to people that weren't traditionally trained in design. So I wrote the book, which led to an adjunct professor role at the Institute of Design in Chicago.
I taught and ran the studio for a while which was some of the most productive and rewarding times of my career. Then shortly after that, I got a call from Uber, and for the last two or three years I've been out in San Francisco working at Uber.
Is there anything that you would do differently looking back?
Yeah, I would've asked for more help. Like I mentioned, early on I was very self started, it eventually became a point of pride to the extent that it even made me a bit spiteful that I didn’t have much support or mentorship.
“People are very willing to help you and mentor you. You just have to ask.”
Eventually, I realised that people are very willing to help you and provide mentorship. You just have to ask. Back then, I was a little too proud to ask (and probably still am). If I had to go back to the beginning, I would have just asked for more help.
What did your teachers think of you back when you were at school?
In college my teachers would often tell me, "You're good at math, you should stop doing this art stuff, and focus on math and science." But then my art teachers would say, "Hey, you're good at this art stuff, you should stop focusing so much on math and science, and think about a serious career in art."
This was always a source of tension for me because my professors didn’t really understand how technology and design would come together at that time. Frankly, none of us did, the concept was still nascent.
What was the biggest challenge you've faced so far?
"Running a business produces the kind of stress that nobody should have to experience. That by far has been the biggest challenge to date. Working at Uber is also very challenging, but it’s the good kind. The scale and complexity of the work we do is what keeps me engaged."
Uber had a rough year in 2017. Our presence in the media was constant and it was hard not to get distracted by it. Being on the inside, I saw the good parts. I witnessed first hand the impact that we're having from a social, environmental and an economic perspective, and how we change people's lives. Our digital world impacts the physical world in a unique way.
Internally, we've always seen Uber as a force for good, although externally it's been probably described as the opposite. It’s been a challenge to show the world through design, policy, and communications that we're trying to do the right thing. I feel that we’re finally in a position to show the world what Uber is, and it's potential.
Aside from those challenges, what's it like to work for such a big corporation?
Coming from a small shop, I was used to operating in a studio mentality. Working for Uber and making that shift to big company, was a huge culture shock for me. The idea of not being the ultimate owner and having to weigh in all of our decisions with numerous stakeholders...it seemed ridiculously slow compared to what I was used to.
Then over time, I realised that Uber has a responsibility to go to that much rigour. Because unlike a 10 person studio - where you can put anything out in the world with relatively low risk - at Uber, there are millions of people's livelihood at stake. So when you put things out into the world, you have to strive for excellence.
Ultimately, I wouldn't trade it now because the impact and the reach Uber has far exceeds anything I've done in the past.
Just to get a little perspective, what's the structure like?
There's a little over 300 designers spanning across Uber. Which seems big, but very quickly you'll end up working with a lot of people so it doesn't stay big for too long.
"In general, we aim to hire versatile-ists, people that have a broad set of interests but also have the depth to go deep in any given area. As a result we have a healthy balance of product designers, design engineers, service designers, and visual designers."
Since we operate in over 600 cities, we also have design teams distributed in a handful of offices around the world. As a part of shipping products globally, we also have a need for a variety of specialized skill sets. These disciplines include teams of very talented UX researchers, conversational designers, cartographers, data designers, and motionographers to name a few.
Personally, this has been a great experience. In the past I didn’t have access to so many different types of highly-talented folks. I feel like I learn something new from the team every day.
What makes a day a good day for you at work?
I like to do focused work in morning when I'm feeling most fresh. Then in the afternoon, I usually jump around teams to check in on the work and do critiques.
I love helping people develop ideas are in a very early state. It bothers me when people have good ideas but they don't necessarily have the right skill set to let those ideas blossom, so it gets killed. I get a lot of excitement out of helping people develop their ideas into real tangible concepts and let them run the course.
What frustrates you the most about your current design process, and how are you trying to change it?
The Design team, like the rest of Uber, has been maturing over the years. As a design organisation goes from 10, 20, 30, 40, 50 people to 300 people, other things need to change as well in terms of process, roles and expectations.
Our growth happened so fast I don't think we've quite matured into the world class design organisation that I hope that we'll become.
"Sometimes it can get frustrating when you have an idea of how things should work, but we're still in the process of transitioning out of old ways of working."
How do you communicate the future of the brand to your team?
This is a good question because we just went through a huge rebrand. It took us about a year to conceptualise and deliver. The last time we went through a rebrand, which wasn't actually that long ago, we received feedback that we could have done a better job integrating brand and product. This time, it was a conscious decision to make it a product driven brand redesign.
Throughout our time working on the new brand, we created many notional designs that represented the way we wanted to express brand in product. Aside from the basics like color, composition and typography, we needed to develop frameworks and systems around concepts like safety, transportation and trust...which can be tricky concepts to articulate.
A lot of the artifacts that came out of the rebrand became the seeds for what our ideal app should look and feel like. Then we worked with a bunch of product teams to educate them on the new brand goals and stress test it.
What's your creative sign off process like?
Probably not that much different than you might expect. There's a lot of review sessions, and strategic discussions about what’s the right thing to work on. We typically evolve the solutions a few times before we arrive at a good place to ship. But that's really where the design work starts because we learn a lot very quickly through experiments and user studies. As we gain more information from our markets we revise pretty quickly afterwards.
What's your biggest learning from managing design teams?
When I was just starting out managing, I’d get frustrated when I’d put people in positions to accomplish tasks, regardless of their skill set, and be disappointed if the outcomes weren’t great. I quickly realised not everyone is at an equal skill or experience level. It sounds pretty obvious in retro, but I didn't know how to tune myself to make sure that I was setting people up for success.
It’s important to understand every individual on the team, what skill sets they have, what they're good at, and how they're looking to grow. As a manager I try play matchmaker between the right projects, right people, and the right growth opportunities. Whilst, also looking out for the strategic opportunities that align with their personal goals. This helps to develop a good rapport with team mates, and also establishes trust on both sides - you as the manager to the individual, back to you.
"Great working relationships yields great work."
Great working relationships yields great work. Making sure that people are always in a position to succeed and keeping their best interests in mind has worked out pretty well for me.
What's the role of prototyping like at Uber?
As designers, we have a plethora of tools in our design tool belt, and it's important to know when to bust out the right one at the right time.
"I believe in a 'right tool at the right time' approach to design."
Communicating the work and knowing which fidelity to use is sometimes just as important as the work itself. Sketching, Post-It notes, wireframes, high fidelity, motion - they all play a part in the process of moving an idea forward.
"Prototyping specifically, is critical for us in our product design process because it helps us uncover flaws and inconsistencies early on. Today, digital products are so complex, I don't think it's practical, maybe impossible to spec out designs for every permutation and edge case with static design mocks."
Often times a design will change hands 10 times before it gets into production. If we rely soley on static mocks much of the intent gets misinterpreted. Then in production, we realise, "Oh there's all these edge cases that we missed." and we have to double back to refine them. It's a really inefficient way to do it. Prototyping accelerates that process for us.
What are your thoughts on the future of design tools?
This is something I think a lot about. I work closely with our design platform team at Uber, who’s charter is creating designing systems at scale. Part of their charter includes design tooling and automation. We're always speculating how the relationship between design and engineering evolves over time, and which aspects of that process will become automated.
I think this topic is at a unique moment in time. A lot of community-inspired projects have inspired some new ways of thinking about the developer / designer workflow. I think we’re right on the verge (finally) of unlocking a step change in design tools and workflow. I’m excited to see what the next 1-2 years brings.
What's the best advice that you've ever been given?
Early on, one of the mentors saw that I’d get frustrated presenting work to stakeholders. Especially when it didn’t go the way I hoped and I’d complain that they didn't understand my ideas. His advice was:
"You have to recognise who's at the other end of the table."
For me that meant, know your audience. When you're presenting work, or you're in a position of critiquing work, it’s important to realise that every person is in their own moment, journey, career, and every project, similarly, is on its own stage, journey and life cycle.
That’s a complicated way of saying, every project is filled with a mixed bag of people with varying experience. The feedback you give or get should be tempered for that particular situation.
That has been one of the strongest pieces of advice that rang true for me.
Could you remember some of the worst advice?
I have to think about this….It's easy to remember the best advice. It's hard to remember the worst. In general, people tend to discard the bad.
My first job out of school, I was hired as an entry level software engineer. Given I was passionate about design, I would periodically “get caught” tweaking the UI's of the software I was working on, trying to make that more consistent, more aligned and whatnot. I say “got caught” because as an engineer, that really wasn't my job.
At some point, one of the senior engineers pulled me aside and said, "You should really stop doing this design stuff and focus on becoming a better engineer."
Luckily, I never thought of myself as much an an engineer, so I took it as a compliment that people noticed that I was making the UI's better.
What are you watching on Netflix right now?
I find Chef’s table ridiculously inspiring. I have some friends that are chefs, and I've always had a sense that the work they do is similar to the type of work we do in pulling together tastes, and threading together unlikely connections to create something unique, and the experience around that.
That's really what that show is all about, and I find it incredibly inspiring. It's food. It's obviously not design in the digital sense, but I can't help but think it's exactly the same type of mentality. I find a lot of truth in that show.
What are you reading right now, or what would you recommend?
I just finished reading 'Creative Selection', it was written by one of the original iPhone creators, Ken Kocienda. It was just published recently, it's been a hot book at Uber, and probably all throughout Silicon Valley. It's the book a lot of us really wanted to read. It's a peek behind the curtain of what it was like at Apple during a very special time.
There's something to be said about their process and how they relied on good taste to make a lot of decisions, rather than data. That was a nice message to remind us that we don't need to be completely beholden to data to make good decisions. Some of the things that matter most just can't be measured with data.
Whose work do you follow and admire?
This might sound kind of weird, but I have a pulse on things happening in the game development world. I'm always impressed by people that are writing custom pixel shaders, and interesting graphic effects for video games. I find inspiration in that because the work is very organic and quite different than the type of work that we typically see for UI product design.
Periodically, I'll find inspiration in this work and try to apply it to a concept we’re working through.
Sometimes in a weird way, I'll find inspiration in those really bizarre screen effects in how I might do a transition, or I might do a piece of motion in something I'm working on. It's not any one individual, but as an industry, I'm usually following along.