What I learned from Staff Design

This week I published the 8th and final interview for Staff Design, an interview series exploring how experienced designers navigate the individual contributor career path. This project that started out as a personal itch to scratch has been thoroughly satisfying, but I'm relieved to put it behind me. Here's what I learned during the past four months of building and interviewing.

Escaping the meta of product design

Understanding the meta skills of product design has always been fascinating. But it's easy to get stuck in the meta: thinking constantly about design and its surrounding people, processes, career paths, and for lack of a better word, drama.

Mid-way through this project, a trusted friend told me: I think you might be on the verge of taking design too seriously. Focus on the work, not the meta. What do customers want?

That conversation pulled me back from the brink of getting lost in the meta game. I show up to work to solve problems for customers, and design is a means to that end. Focus on the work.

I don't mean to diminish the importance of career tracks, titles, and the very real impact that can be had by spending just a few minutes strategizing about what you really want to accomplish as a human. But in all of my experience in the last decade-ish of building software, I can clearly track the most meaningful periods of growth to the times when I was heads down, building.

As long as you're in a place where management values people who do the work, rather than pontificating about it, then that's probably where more meaning and satisfaction can be found than in any interview, podcast, or Twitter thread.

The meta game of building sustainable side projects

When I hit publish on the eighth interview this week, I felt a wave of relief. It was over. It wasn't relief because this project was particularly hard work, but rather because it had become a multi-month stretch of thinking about the meta. I realized at this moment that the only reason I made it to the end was because of how intensely I'd front-loaded the effort to interview, transcribe, edit, and develop this project back in December and January.

I wrote about this briefly in my playbook for shipping side projects, but front-loading work seems to be the only way I get shit done. I recorded all 8 interviews by mid-January, before the first interview was ever published. This made the following weeks much less stressful.

As I look back at some of the interviews, I do find myself cringing at my own intensity in the questions I asked. From the outside, it must appear that I have an axe to grind with management, but that's not the case. I'm relieved that many of the interviewees offered sage advice and helped me to grapple with my own ideological inconsistencies. More on that in the next section.

I almost wish I'd named the project something else. I think the name Staff Design overemphasizes the titles section of this project, rather than some of the more interesting conversations about everything else that is confusing and challenging about being an experienced individual contributor product designer.

My takeaways on the individual contributor track

I learned something new with every interview in this series. The guests who shared their stories each brought a unique point of view, history, and work experience. It's very hard to boil eight interviews and tens of thousands of words into a single takeaway, but if I had to try, it would be something like:

Career ladders matter until they don't.

What I realized through each conversation was that these constructs – career tracks, level documents, performance reviews – are just scaffolding. They are here to nudge us along, until we're good enough that the nudging isn't really the point any more.

And I think that's the biggest reason that the individual contributor track is confusing, frustrating, and scary for many designers today: that scaffolding doesn't go very high.

So do I reject career tracks or titles? Of course not. They are wildly useful tools, and perhaps the best tools we have right now to make sure people are being compensated fairly for their skills and value that they bring to an organization. I really enjoy writing about this stuff, like how to write better self reviews.

But I'm also leaving this project less scared of what's at the edge of the scaffold, mostly because it seems more clear that there is no answer to seek. We get to decide for ourselves how to spend our time, what kinds of problems to work on, and who we want to be surrounded by as we build.

That's damn exciting.

What's next

It's time to take a break. It feels so good to have a project in the world that just exists. I don't feel compelled to make this a weekly series from now until the end of time. I'm looking at you, Design Details.

If this project ever revives, the format will be seasonal interviews with different groups of people, still talking about the individual contributor track and product design.

For example, I would like one season to interview managers, directors, and heads of design, to learn about what they've discovered through designing career tracks in their organizations. Another season might be with designers who reject career tracks entirely: people who go on to start their own companies, freelance for life, or pursue alternative roles. There's probably room for many seasons to interview designers who swing on the pendulum between designing and managing, learning the skills of both roles over time.

The written format for interviews is fun, but I wonder if the project would be more engaging and useful for people as a podcast or series of videos. In the future, I'll explore different ways for the interview format to facilitate the most insights per minute.

As a final note, this project only means anything to anyone because of these incredible designers who were generous with their time and ideas. Thank you once more to Wilson Miner, Vivian Wang, Salih Abdul-Karim, Jessica Harllee, Yitong Zhang, Anita Lillie, Rasmus Andersson, and Karla Mickens Cole for answering my questions.