Just came across something interesting about how we think about leadership. Brian Chesky from Airbnb was talking about this idea that gets thrown around a lot—micromanagement. And honestly, his take is pretty different from what most people say.



So here's the thing. Everyone talks about how micromanagement is toxic, right? But Chesky's argument is that it depends on what's actually happening. He brought up Steve Jobs as an example—Jobs was known for being all-in on details. Most people would call that micromanagement. But when Chesky asked Jony Ive, who worked directly with Jobs on design, whether he felt micromanaged, Ive's answer was revealing. He said Jobs didn't micromanage him—they worked together. Jobs' focus on details actually pushed Ive to think bigger and grow as a creator. That kind of close involvement from someone you respect hits different than what we usually mean by micromanagement.

The distinction Chesky makes is actually important. It's not about whether a leader is hands-on. It's whether that involvement helps people develop or whether it just controls them. When it's the former, when a leader is genuinely invested and working alongside you, it can accelerate your growth. The Apple Watch, iPad—these came from that kind of collaboration, not despite the attention to detail but because of it.

For a company like Airbnb operating at massive scale—millions of listings, thousands of employees spread globally—Chesky argues that this hands-on approach actually speeds things up. No endless approval chains, no waiting for sign-offs from multiple layers. Direct involvement means faster decisions.

But here's where it gets interesting for younger workers. As leaders become more directly involved, middle management roles are disappearing. And Gen Z? They're not fighting it. Data shows most of them would rather stay as individual contributors than climb into middle management. Can't blame them really—middle management has become this squeezed position with less authority, more stress, and less appeal.

So the old corporate ladder model is shifting. Leaders are flatter, more accessible, more hands-on. It's changing what career progression looks like. Whether that's better or worse probably depends on the leader and whether they understand the difference between genuine collaboration and actual micromanagement.
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