Why You Should Micromanage
What Mickey Drexler taught me about caring out loud
I found myself crouched under folding chairs, picking up napkins, adjusting pillows, and nudging trash bins into place. We were organizing a major event, and my event manager caught me mid-reach. "We're the hosts," I told him. "A napkin on the floor ruins the experience." He looked puzzled. I had a full team helping, yet there I was, doing what looked like grunt work.
From the outside, I must have seemed obsessive. Maybe I was exaggerating. Worse—was I micromanaging? I wondered if I was a control freak.
Have you ever felt that tension?
Then I prepared for an interview with Mickey Drexler—thanks to a generous introduction from our friend Mike Cerre (thank you, Mike)—the prince of retail, the force behind GAP's cultural dominance in the '90s, and later the turnaround of J.Crew and now Alex Mill. That's when I got my answer.
If you grew up in the '90s, you remember GAP. It wasn't just a clothing brand—it was a vibe. Commercials with swing dancers in khakis. Soulful music. Minimalist design. Cool without trying too hard. Drexler curated and engineered all of it. And when Steve Jobs needed someone to help launch the first retail store for Apple—the one that would become the blueprint for every brand that followed—he called Drexler, who served on his board of directors for 17 years.
In multiple interviews, Drexler has said it outright:
"I'm proud to be a micromanager."
The words gave me a jolt. Aren't we told micromanagement is bad? If you've ever taken a leadership course or sat through a management seminar, you've heard the gospel: give people autonomy, trust your team, delegate outcomes. I've taught it. I believe it. So what was I getting wrong?
But slowly, the more I read Mickey’s interviews, the more I started to understand. It wasn't who Mickey was micromanaging but what Mickey was micromanaging.
“I’m proud to be a micromanager—for what a customer sees, feels, and hears. I micromanage, but I provide leadership. People know what is important.”
That wasn't the sound of a control freak. It was the sound of a leader who pays attention. For Mickey, micromanaging the details is a form of care. As he put it, "If the bosses don't care about the little stuff, who's going to care?"
He continued: "I care about every letter to a customer. It's not about doing someone else's job—it's about teaching how you actually need to be when you run any business. I wish more people paid attention—to the loud music, to the prices, to the small stuff. So how do I do it? There are team members. I'm inspirational with them—or I teach."
Then it hit me: Mickey doesn’t micromanage people. He micromanages experiences. And that’s a huge difference.
When I shared that observation with him, he agreed. “I had the best customer training course in the world. I was a customer.” Then he told me a story. The morning of our conversation, he walked into his usual café. It was freezing. The music was blaring. When he asked the staff to adjust it, they hesitated. “The boss likes it this way,” they said. Drexler shook his head: “That’s the problem. The boss isn’t thinking about the customer.”
When I shared that observation with him, he agreed. "I had the best customer training course in the world. I was a customer." Mickey noted how often he encounters spaces where the environment feels off—too cold, too loud, poorly tuned to the customer. When he asks for adjustments, the response is often: “The boss likes it this way.” For him, that’s the problem. “The boss isn’t thinking about the customer,” he said.
Talking to Mickey, I felt understood. If you've ever been with me in a restaurant or a café, you've probably seen it—I'll ask to dim the lights, lower the music, soften the atmosphere. Not to be difficult. Because I care how a space feels. We were both obsessing over the same invisible details—the ones that quietly shape how a moment feels.
The Twitch of Doubt
Micromanagement has become a taboo word in leadership culture. It's shorthand for insecurity, for mistrust, for bosses who can't let go. And it's true—micromanaging people can create bottlenecks, sap morale, and signal fear. But not all micromanagement is created equal. What Drexler shows us is a distinction rarely made: the difference between micromanaging outcomes versus micromanaging details that shape the experience. One is about control. The other is about care.
This isn't old-style management. Brian Chesky, co-founder and CEO of Airbnb, demonstrates the same idea: "My philosophy is you start in the details. You're involved in every single thing. You hire great people, and you're in all their details, and over time, once they develop muscle memory and they prove that they understand the system, then you can gradually let go." Every creative leader practicing Business Artistry—the leadership philosophy I explore in keynotes and teach in executive classrooms—knows the importance of being in the details.
It's a principle echoed by leaders across industries—attention builds trust, not just products.
Designing Trust, Not Delegating Blindly
Both Drexler and Chesky remind us that great leaders don’t just delegate—they model standards. That doesn't mean doing the work for your team. It means setting the tone, obsessing over the customer-facing moments, and showing what "excellent" looks like. Drexler doesn't micromanage emails because he's picky—he does it because a single badly written message erodes the brand. He's not adjusting the music volume because he's bored—he does it because curating atmosphere is a strategy.
This is trust-building through clarity. Micromanagement, done right, isn't about distrust—it's about teaching care.
The Invisible Signature
Think of a great meal, a striking boutique, or a perfectly paced product launch you experienced. Behind each of these is someone who sweat the invisible stuff—the stuff a customer might never notice consciously but would feel if it were missing. Apple, Disney, Braun—these brands were not built by "hands-off" leadership. They were built by leaders who embedded their vision in every corner of the customer journey. From how a zipper sounds to the weight of a shopping bag, every detail says: we care.
The conversation with Mickey made me reflect on that moment with my event manager—the napkin under the chair. After the event, we debriefed. I explained why I'd done it—not to take over, but because every detail shapes the guest's experience. That moment stayed with him.
And maybe that's what Mickey meant when he said, "I'm inspirational with them—or I teach." You lead by example, and you don't just do the thing—you unpack it. You show why it matters. That's how people learn what to notice, what to care about, and how to lead by caring out loud.
The one meaningful move for you: Sweat one detail your customer will feel but never see—and let your team watch you care.
Have a meaningful weekend,
NIR
If helping your team create with meaning is on your mind, this is exactly what I speak about. Curious what that could look like in your organization? Let’s talk.
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