An Interview with Joshua Goldenberg, Head of Design at Slack

Recently, we had the opportunity to interview Joshua Goldenberg — Head of Design at Slack and design advisor to Affinity. Prior to Slack, Joshua served as Head of Design at Palantir from 2011 through 2016, where he built the design arm of the company. Before Palantir, he designed Oscar-nominated software at Lucasfilm. Here’s what he had to share about his inspiring journey across all corners of the design world, from print to product.

Can you describe your path to what you’re doing currently?

My interest in visual things started at a very young age. Even as young as a fifth or sixth grader, I was taking as many art classes as I could, and paying more attention in those classes. By the time I was a high school senior, I had managed to engineer my schedule as a senior to be almost all art classes. In retrospect, I don’t know how I graduated, but I got exactly the right amount of credits. I was doing a metal sculpting class, a ceramics class, AP Art, Photography, and Commercial Art. It was like, Gym and five or six art classes. I deeply cared about artmaking — they weren’t blow-off classes for me, and I was super engaged.

After high school, I decided to go to San Francisco Art Institute as a painting major — which, at that time, was what I thought I was going to do with my life! I got there and I loved it, but it didn’t take me very long to realize that painting wasn’t a great opening career move.

It just so happened that I had a friend who had started a record label in Los Angeles, and that I was living with someone who had a really killer Mac with a lot of software on it. So I started using Photoshop to make digital art and started to experiment with type. I had no understanding of what being a designer was. My mindset was that I was making art with a computer. This guy who started the label in Los Angeles came over one day and saw what I had created. He told me that he wanted to use it for his label. He paid me for it and I was like, “Wait a second… I could do this for a living.” That was how it started.

Shortly after that happened, I dropped out of art school after nine months as an 18-year-old and tried to “make it” as a one-man design studio for the next five years, which was pretty rough. Not knowing what I was doing at all and without any formal training, I had to figure out that you’re not supposed to send a printer Photoshop files with the text embedded as pixels. I had to learn about basic things like vector-based art, typography and how to do pre-press. I wound up working with a weird mix of random local businesses, and then a bunch of music industry stuff that was spread out all over the country. This was all around 1994 to 1998.

During that time, the web (or at least the commercial web) was coming into being, and I was learning HTML and CSS. At some point, I was sitting exactly between print and web design. I realized that I was getting bored and I wanted to work on more complex things. Working on more complex things meant that I should be working with teams, instead of being by myself all the time. So I went to work for my first design agency in 1999, which was VSA Partners in Chicago (a great agency). I thought I would be there for a long time (like many of the other people who worked there) because it was such a great place.

But it happened that after 7 months, I had befriended a brilliant engineer (the technical director) and he was leaving with a few other people to start another agency that would be a little more technology-focused, and potentially more product-focused. I didn’t fully understand what that meant back then — it was really a time before you could build products on the web. But I had learned what it was like to work with a great engineer, and the idea lit me up. I was like, “I’m going with this guy because I actually want to be close to a great engineer.” I was more interested in being a designer paired with an amazing engineer.

So the five of us started an agency — right as the dot-com crash happened. That was hard. There was a sudden, massive drop in people spending money on agency work, and a lot of the potential web stuff we were going to work on dried up. It was really hard, but the experience of working with that amazing engineer was great and taught me what it was like to have awesome partners in engineering. It also gave me a taste of working on apps, even though it was still too early for modern JavaScript and web applications, and was way before smartphones and app stores and modern software distribution.

In late 2002, I came back to California and became a freelancer again. I contracted with two agencies and became both a designer and a creative director — working for agencies in Chicago and in California. I did that for a few more years until I began to realize that I didn’t want to work on marketing-focused work anymore. That was my exit from the agency world.

Around 2006 or 2007, product design as a role in software had become more of an idea in the design zeitgeist, and I landed some work with a product studio called 80/20. I worked on a redesign of Second Life with the Linden Labs team, a team of engineers and product folks, and the problems were complex and interesting. That was what made me fall in love with working on tools and software. When that ended, I knew I wanted to move fully into the space as a product designer, and focus on challenging interaction problems, with deep engineering teams. And that realization led me to understand that the only way to really engage with problems like that was to join an in-house team and be able to iterate on a problem from the inside

Around that time I had a friend who was working at Industrial Light & Magic (ILM), and introduced me to the folks in Research and Development there. I wound up working on a stealth team inside ILM that was ultimately directed by George Lucas. He had carved out a budget to work on a pre-visualization system — he basically wanted to see if we could get rid of storyboarding by hand, and do it entirely digitally. We used a relatively low-fidelity real-time game-like engine, and built a bunch of tools to support editors and directors and previs artists to be able to quickly sketch out shots and sequences in filmmaking. Working on this was a lot of fun, and there were a lot of really interesting design challenges. I worked on that tool at ILM for a year and a half — and once it became stable, there wasn’t much design to do for it, so I started to work on the broader visual effects pipeline of ILM.

After doing that for another year and a half, I realized that I wasn’t a great fit for visual effects: I wanted to work on a team that was focused on making the tool the absolute best it could be, as opposed to making the production the absolute best it could. The software and the design weren’t secondary to me. So I started looking. I had an old friend who was an early hire at Palantir, and he asked me to come talk to them. Right around the time that I was thinking about leaving ILM, I spent a day with folks at Palantir and totally fell in love with the problems they were working on. I was one of three designers in a company of almost 400 people, which was a wild period of time. They were growing so fast. I was doing design work, but also figuring out how to build a design team, how to recruit, how to onboard, how to design an intern program and college hiring program, how to allocate and rebalance teams, develop design process, and a ton of other things focused on design leadership. I ended up building a team that was (at its peak) 40 people over the course of four and a half years. There was a lot of change and transition, but the team was a great team full of wonderful people, many of whom I still talk to.

After those four and a half years, I felt ready to do something else. So I started putting feelers out. I probably met between 18 and 20 different companies and founders. I really wanted to get a sense of how current startup founders were thinking about design in their organizations, how they were structuring design teams, who those teams reported to, and what their hiring plans were. I went through everything from really small startups to 400-person companies. I wasn’t really looking at anything bigger than that. And randomly, a couple of friends in enterprise venture capital introduced me to Stewart Butterfield and Brandon Velestuk at Slack.

I had set two principles for myself when I left Palantir. One was that I wanted to work on something that I had more of a first-person relationship with: meaning something that I would use every day. The other was that I wanted to work at a place, where design already had a seat at the table. After spending time meeting the team at Slack, and realizing it was a product and a company that I’d love to work with, I joined in April 2016.

You mentioned that creativity was just a huge part of growing up, and that you recognized this from an early age. Did your parents encourage you in that direction?

They were really supportive of everything I wanted to do creatively. On the visual side, it turns out that both of my grandmothers were artists. There are still pieces of theirs hanging at my parents’ houses. One of my grandmothers did many different kinds of painting, and my other grandmother did wonderful charcoal drawings.

There was a time when (during my last two years of high school, I think) I took over the garage as an art studio and worked on some big fun pieces that, in retrospect, I would never hang up. But they were totally supportive. They were initially weirded out by the idea of me going to art school because they were thinking, “How is this going to apply career-wise? But whatever, it’ll probably work out.” I had a lot of encouragement from them.

There is a part of me that wishes that I had known what design was, instead of just what art was. Design was harder to access when I was much younger. The awareness and design literacy wasn’t as prevalent as it is today. It’s very different now. You can connect with design as a high school student much more easily than one could when I was a kid. I wish that I had that — because I wonder how much more I could have been shaped by design if I had encountered it as something completely distinct from art at a much younger age.

Who has had the biggest impact on you as a designer?

I was a print designer first and, for a long time, there was a group called The Designers Republic. They had a huge influence on my work. They did so much of the foundational design and shaping of what electronic music looks like today.

Anselm Kiefer probably had the biggest influence on me as a painter. Also in design, I grew up in the age of Raygun and David Carson, and I was attracted to more organic and dirty things, as opposed to the Swiss work I would probably gravitate towards more now. I was attracted to design that felt like the art I liked, partly because when I was younger I really only understood design through the lens of painting and visual art.

Who has had the biggest impact on you as a leader?

One great manager I had was a woman named Terri Tomcisin at VSA. She was a really empathetic, kind manager who gave great feedback, and also gave me my first real job — at that point, I had worked by myself for a number of years as a freelancer.

Michael Lopp — the VP of Engineering at Slack — has been writing books and blog posts on management for years. We worked together at Palantir and I had read a bunch of his work before I met him. His writing is more engineering-focused, but everything applies to design — in terms of working with people, interpersonal situations, giving guidance, and being a good listener. That had a pretty big influence on me. He’s a good friend who I work with every day, and his work had an influence on me before I even met him in person. And, I’m really fortunate to get to work with a ton of great leaders at Slack, like Stewart and April Underwood.

Have there been points in your career when you had to take a really big risk to move forward?

Definitely. The points that stand out: when I realized I wanted something bigger than design for marketing. At that time, there wasn’t quite a name for product design yet — before apps and app stores. Software was still distributed on CDs at Best Buy. The space just wasn’t nearly as big. But I had the intuition that software was going to explode, at least on the web.

It was still really early, so figuring out how to work on software in a non-marketing sense — and instead, in a purely tools sense — was hard. That felt extremely risky. I had no qualifications to be really doing product design at that time, but I thought it was something I could be good at. I had a sense for interaction design that had come from thinking about user experiences throughout my marketing projects. I took a risk by switching to something I had to build knowledge and credibility in, and also found people willing to take a chance on me, only having worked in adjacent design areas. I’ve made it a point since to try to enable the same chances for other designers.

Do you think your background in studio art and more traditional graphic design disciplines had an impact on you as you shifted into product design?

Yeah, and I’m not sure that it’s necessarily good either. Let me separate those things out because there’s a subtle distinction.

Having a graphic design background is, for sure, a very good input for being a product designer. I would encourage anyone to do that. To anyone in school who can dive into a mix of computer science and product design while getting a formal, foundational education in typography and graphic design layout (those are the things that inevitably carry any design discipline forward really well) — I would totally encourage it.

But coming from a fine arts background is a little bit different because it actually teaches you anti-patterns for design which you have to undo. Understanding composition and color and spatial relationships and negative space are all valuable. You develop your eye. But while art and design look like they’re really close together, they’re actually really far apart when you zoom all the way in. You have a need as an artist to put some part of yourself into everything. You have to learn how to undo that as a designer because that’s just straight up not what design is. When you become a designer, you figure out that you’re actually here to solve someone else’s problems. Often, the best thing you can do is to take yourself out of it. The thing you’re making has to be used by other people. It’s so different, at that point, from being an artist. You have to undo imposing your own will, aesthetics, and creativity into everything.

There’s a bridge. The bridge between these two sides is developing a sense of taste. And obviously, that’s important and very hard to teach.

What are the best and worst career decisions you’ve made?

That’s hard to say. I regret working alone for so long. My resume is kind of weird-looking. I was mostly an individual contributor for like 15 years. Even when I was doing creative-director-type of work, I wasn’t a manager in the sense that people didn’t report to me, and I wasn’t helping them with career development. I worked as an individual contributor for a really long time, and that ultimately had value because I stayed so close to the work for so long. But only after long periods of time as a freelancer did I learn I wanted to be on a team, focusing deeply on solving problems.

The actual worst decision I ever made — and I couldn’t have possibly known this — was probably starting an agency six months before the dot-com crash. That was horrible timing.

The best decision I ever made was almost certainly switching to product. I think it really saved my interest in and passion for design. I was so burned out on marketing — and I don’t have anything against marketing in general — but doing random agency work, I couldn’t get the thought out of my head that I was just helping people sell things that I didn’t care about. Even then, I think I would have felt differently if I had moved to an in-house team sooner, but, I had the strong sense that there was more I could be doing with design — and I found it. Making that switch was the best career move I’ve ever made.

How do you push through the worst of times?

That’s a good question. I’m pretty patient. I’ve been able to think about things on a slightly longer timeframe. Developing that sense of patience has helped. I’m ruthless about taking breaks. If I’m frustrated with a problem, I’ll go for a walk. If I’m frustrated with something longer-term, I’ll take a vacation. I’ve identified the things that help me unplug and reset. I’m good at knowing when I need to do that, and going out and doing it.

What advice would you give to somebody starting out in product design today?

First, be a graphic designer too. I have definitely said this before, but foundations in information architecture, information design, layout, typography, prioritization of how things read… these are supremely important to being a great product designer. Oliver Reichenstein said that 99% of web design is typography. That is largely true of software design too, whether it’s deployed on a web browser or not.

The second piece of advice is much harder for someone to just go out and practice, but you have to remember that design exists at the very top of the stack. That means it’s the thing that every discipline in a company can see and touch — and therefore have opinions on. No one is ever going to walk up to an infrastructure engineer look over their shoulder and say, “Hey, you should probably change that line of code.” If that happened, it’s going to be an engineering manager who is intimately familiar with the particular problem on the screen. But designers can experience that 8 hours a day, because our work exists at the top of the stack and it’s there for everyone to see and comment on, regardless of their design literacy.

And to be clear, that’s ok. But, that means we have to be way more resilient than a lot of other disciplines to feedback, and to be adaptive in a way that is extremely demanding. It can crush people who aren’t used to it, and it can burn people out. You have to figure out how to manage it and consistently be really open to feedback all the time. You also have to synthesize it in a way that not just includes people, but also gives yourself a chance to put all the pieces together in the way that you think is best — because you are the actual professional who does this for a living. You then have to reflect that back out in a way that’s persuasive.

It’s a whole set of really hard things that are somewhat unique to product designers, on product teams. That’s a lot to become good at. Great designers take feedback from everywhere and pull it all in and wind up with something that’s better for the sake of the feedback that it received — whether that’s from users, research, peers, or stakeholders. But it is not design-by-committee. This is a hard distinction for many people.

What kind of legacy do you hope to leave?

When I think about that, I think about my kids. I hope that my kids are wonderful people who are satisfied in their lives and contribute good to the world. As a professional, I hope I’ve left behind things that people love to use. As an organizational leader, I hope I’ve helped advance and develop other leaders and managers who’ll go on to lead organizations that feel well cared for, are healthy, and produce great work.

If you’re interested in learning more about what we’re up to at Affinity, come check our website out at affinity.co.