Airbnb's Brian Chesky says these 3 mistakes made him a 'terrible CEO'

Founder instincts and CEO demands

Chesky said that starting a company came naturally to him, while leading one required a different set of abilities. He recalled developing a founder’s instincts as a child by designing toys, taking them apart and persuading friends to buy what he was selling.

As Airbnb grew into a global travel company, he said, he had to learn how to manage people and guide the organization. Chesky told Guy Raz he had been a strong founder but initially a poor CEO.

Choosing and guiding executives

Chesky said advisers urged him to hire highly experienced executives and then leave them to work. He later concluded that a young company needed people who were only somewhat ahead of him in experience, and that he needed to stay closely involved.

When his own judgment conflicted with an executive’s experience, Chesky said he usually deferred, which he later viewed as a mistake. He also said some executives came from companies where they had managed established operations rather than built them.

Avoiding hard conversations

Chesky said he struggled to hold colleagues accountable when their work fell short. He found it difficult to decide when to give direction and to have direct conversations about performance.

He described himself as conflict-averse and said he sometimes failed to act when an employee was not succeeding. At times, he took over employees’ work, which could deny them room to improve or leave him supporting them in an unsustainable way.

The cost of saying yes

Chesky said another mistake was not saying no often enough, leaving the company without a clear focus. He likened executives with competing priorities to passengers in a car who each want to travel somewhere different.