There’s a quiet tension in design careers that doesn’t get talked about enough: the moment you’re nudged—sometimes subtly, sometimes not—toward management. It’s framed like a choice between two tracks: either you keep designing and risk stagnating, or you shift into leadership and start climbing. But the way that choice is framed is misleading. It makes management sound like a promotion when, in reality, it’s a shift in craft.

I was listening to Mig Reyes on the Dive Club Podcast recently, and he said something that cut through the noise: you shouldn’t go into design management until you’ve really excelled as an individual contributor. That might sound obvious, but it’s not how the industry works. Many people are promoted before they’ve gone deep. The result is a layer of managers who are disconnected from the very thing they’re supposed to lead.

I’ve worked under a few creative directors over the years—smart, articulate, seasoned—but it was clear they hadn’t touched modern design tools in a long time. Maybe they once knew Photoshop or Sketch, but they’d long since detached from what today’s design practice actually looks like. And that’s a problem. Because part of a manager’s job is to teach—not just high-level thinking, but hands-on execution. Sometimes, the best way to unblock a junior designer isn’t with a pep talk, it’s by showing them exactly how to solve the problem in Figma.

It’s not unlike football. The best coaches—people like Pep Guardiola or Jürgen Klopp—weren’t just players; they were leaders on the field. They understood the rhythm of a match from inside it. And when they became coaches, they weren’t just strategists—they were translators. They knew how to take what they’d learned on the pitch and give it back in a form their players could use. That’s what a good design manager does too.

The risk of stepping into management too early is that you haven’t seen enough. You don’t know what advice to give because you haven’t lived through the edge cases. You can’t always predict the second-order effects of a decision. And worse, your team can tell. It’s not about ego—they just want to know they’re being led by someone who understands their world, not someone who’s permanently drifted above it.

Personally, I’m drawn to the relational side of management. I like the conversations, the pattern recognition, the chance to help people grow. But I never want to be the kind of leader who can’t open the file. Staying close to the work keeps me honest. It’s a reminder that design isn’t just something I used to do. It’s something I still care about.

If you’re thinking about moving into design management, the question to ask isn’t “Am I ready to lead?” It’s “Have I gone deep enough that I have something to give back?”