Airbnb CEO Brian Chesky discusses early leadership mistakes

Airbnb CEO Brian Chesky has identified three specific leadership mistakes that occurred during the company’s transition from a startup to a global organization. Speaking on the ‘How I Built This’ podcast, Chesky noted that while he felt naturally suited to the role of a founder, he initially struggled with the responsibilities of being a CEO.

Chesky highlighted three primary errors in his early management approach:

First, he followed advice to hire highly experienced executives and give them significant autonomy. He later concluded that for a young company, it is more effective to hire individuals who are only slightly more experienced than the founder and to remain closely involved in their work.

Second, he noted a tendency to defer to the experience of older, more seasoned executives, even when his own intuition suggested a different course of action.

Third, he identified challenges in managing competing priorities and making difficult personnel decisions as the organization scaled.