The Secret Art of Micromanagement with Airbnb CEO Brian Chesky

For Brian Chesky, the learning never stops. As the co-founder of AirBnB, he had to transition from an impassioned entrepreneur with a brilliant idea into a CEO responsible for thousands of employees. To make the hard decisions necessary for AirBnB to survive the COVID pandemic, a cataclysmic event for the travel industry, Brian had to lean into the skills and thinking he’d learned and practiced for over a decade of leadership.

I’ve watched Brian grow as a leader for years, and so I was delighted to sit down with him for a conversation on what people get wrong about great leadership. He shares with me the difference between micromanagement and “eyes on” leadership, why leaders should fight the instinct to be liked, and why an existential crisis is the best thing to put a company’s values to the test.

⏰ Timestamps:
0:00 The difference between founders and CEOs
2:46 The worst business advice Brian ever followed
6:46 Why numbers are not the language of business
8:29 When to command and when not to
12:32 What is micromanagement?
15:55 What bodybuilding taught Brian about leadership
17:52 How Airbnb survived COVID
21:27 Brian’s first actions during the pandemic
25:42 How to stay humble and growth-minded
30:35 Hire according to your values
33:55 Strong cultures versus weak cultures
39:18 A new vision for Airbnb
41:42 Brian’s succession plan