Why Does Brian Chesky Talk to Employees Who Do Not Report to Him?

Brian Chesky talks to employees two or three layers below his direct reports so he hears from the people doing the work, not only from the executives above them.

Right after COVID, executives called the move undermining, going around them, and micromanaging. Feelings had to come second while the company was in crisis and had to be saved. Letting executives own the details had already run for 12 years, and the company was doing well probably in spite of his leadership, not because of it. The company had the curse of a business model that was too good. eBay had a great business model and did not have to be great at execution. Amazon had a horrible business model and low margins, lived by execution, and won because execution compounded. The wilderness years were his own mismanagement, and the business model was lucky.

One executive asked whether the work was her job or his. It should never be either. He stays in the detail so he has the information, instead of only giving orders or only handing the work off. Every public-company board has an audit committee, and the word audit means they know every detail, so the chief executive should know every detail too. With AI, a prompt can find anything, which makes AI a way to see past the executive suite. In a company Guy Raz puts at 8,000 people, Chesky picks key projects and has the full chain of command in the room.