According to Business Insider, Figma co-founder and CEO Dylan Field admitted on the “First Time Founders” podcast that he was initially a “bad manager” across the board. Field, who started Figma in 2012, said he had to learn a completely new skill set while under pressure from VCs to ship a product, with Figma’s beta not launching until 2015 and a paid plan not arriving until 2017. He credited hiring his first manager, director of engineering Sho Kuwamoto, as a major turning point. Field’s story mirrors those of other founders-turned-CEOs, like Duolingo’s Luis von Ahn, who micromanaged until he had 50 employees, and Asana’s Dustin Moskovitz, who finds management “exhausting.” Despite the struggles, Field ended on an optimistic note, saying management skills are “very learnable.”
The Founder’s Management Gap
Here’s the thing a lot of people don’t get: leadership and management are not the same job. Dylan Field nailed it when he said you can be a good leader and a bad manager. He thought being a visionary founder meant he was “good to go.” Turns out, nope. The day-to-day grind of knowing where your team is, building real relationships, holding consistent one-on-ones, and creating accountability? That’s a separate muscle. And most first-time founder-CEOs haven’t developed it. They’re often brilliant product thinkers or coders suddenly responsible for people’s careers and well-being. It’s a brutal, humbling transition. Basically, you go from being responsible for code to being responsible for humans, and humans are way more complicated.
The Pressure Cooker of Time
Field’s story about taking five years to launch is wild in today’s “move fast and break things” climate. Can you imagine telling your investors today that the beta is three years out and monetization is five? He’s right: “You’ll be dead.” But that immense time pressure creates a horrible environment for learning soft skills. When you’re racing against the clock, who has time for thoughtful one-on-ones or relationship building? You’re just trying to survive. It creates a vicious cycle where the founder, who is already a weak manager, has zero bandwidth to get better. The product might eventually thrive, but the team culture can suffer for years. It’s a classic case of the urgent drowning out the important.
The Micromanagement Trap
This is where Luis von Ahn’s comment is so fascinating. He says founders *should* be micromanagers up to about 30 employees. I get the logic—early on, every detail matters, and you need intense hands-on control to set the standard. But his admission that he took it to 50 employees is the real lesson. Letting go is incredibly hard. When you’ve poured your soul into every pixel and line of code, delegating feels like losing control of your baby. The shift from “doer” to “empowerer” is maybe the hardest part of the founder-to-manager journey. Von Ahn’s current role as “culture carrier, mascot, and tough decision maker” shows the evolution. You go from controlling tasks to shaping the environment where tasks get done.
So, Can You Learn It?
Field’s final point is the most crucial: this is all learnable. It becomes muscle memory. But how? For him, it was hiring a real manager, Sho Kuwamoto, and learning by observation. That’s a powerful move—bringing in someone who already has the skills you lack. For others, it might be an executive coach, a peer group, or just brutal self-reflection after burning out a few early team members. The common thread is acknowledging the gap. The worst founder-CEOs are the ones who never admit they’re struggling with the people part. They blame the team, the market, anything but their own managerial growing pains. The good ones, like Field, say, “Oh, for sure, I was bad at all of it.” And that’s the first step to getting better. You can watch more of his conversation here.
