How to interview a design leader.
In my leadership career I’ve led five searches, each leading to excellent hires that have since matured into principal-level designers and senior product managers. I've also been on the other side of the table as a candidate. This strategy will help you find the most capable design leader in the least amount of time.
Focus on leadership first
This is counter-intuitive—an experienced designer has to have the best portfolio, right? No. Leadership is about organizational sensibility, strategic growth, team and succession planning, and operations. Even the most talented designers struggle to perform in these roles if they don’t have the training, experience, or willingness to learn fast.
When I entered my first design leadership role, my coach told me “You’re not a designer anymore. Say goodbye to fonts and colors.” It landed hard, but she was right. My world went from long stretches at the computer, reading briefs and exploring concepts, to strategizing with senior leaders, supporting designers’ career growth, and running design reviews across dozens of teams.
Ask these questions to assess a candidate’s leadership:
Tell me about a time your usual leadership approach didn't work, and what you tried instead.
In a previous role, which other leader did you work with most closely and why? How did this relationship support the organization’s goals?
If I told you our long-term strategy was x, how would you operationalize design to support that?
Then look at design
If a design leader has held leadership roles in the past, and has many years of contributing under their belt, then their creative skills are probably solid. Remember, you’re not hiring a Creative Director, that’s a different role. Their work needs to be good, but not great. You’re looking for consistency of quality, not the occasional reach.
Ask these questions to assess their design talent:
Tell me about a time you stepped in and did the design work yourself. Why did you choose to, and what happened?
In no more than 10 minutes, walk me through a piece from your portfolio. Describe the gals of the work, your process, and the outcomes you measured.
Where is the design field today, and how would execute against our goals leveraging these best practices? What might you avoid?
There's a thread in the design leadership community arguing that leaders shouldn't be asked about their portfolio at all—the job is to structure the process, not deliver the design. I agree in theory. In practice, I've never seen a design leadership interview skip the work, and I think the reason matters: design contributors have a hard time following someone who hasn't polished their own craft. The portfolio isn't there to prove they can still design. It's there to prove they earned the right to lead designers.
