Chesky noted that having a broad mix of people and personality types working within your company is crucial. This is important from a diversity and representation standpoint, but he also points out that different people have different skills on a strategic level.
"You can break people down into three different phases. There's phase one people, who are builders, there's phase two people, who are scalers, and there's phase three people, who are large-scale people," he said. "You need to have a diversity in the company of all three, and they need to respect one another and not really fight one another, and I think that at a lot of companies, there's a culture war between these stages, and I think that's very dangerous."
One of the main tenets of Chesky's management style at Airbnb is a very hands-on approach to leadership. Rather than focusing solely on the high-level aspects of managing a multi-million dollar company, he makes a concerted effort to immerse himself in Airbnb's day-to-day operations. Every Sunday, for example, he sends out an email to the company with whatever is on his mind, which leads to staff replying to him and opening dialogues about various elements of the business. "I always wanted to have a pretty flat organisation, where anyone could come up with an idea," he said.
"I say, 'walk the park'. It came from Walt Disney; Walt Disney used to walk the theme park every single day when he was building Disneyland," Chesky explaied. "You don't manage just by metrics, you manage by visibility, by walking around. You'll often learn as much in the hallways and popping into meetings as you will through your chain of command."
Like many other Silicon Valley leaders, Chesky is also a big proponent of taking risks and 'celebrating failure'. Just because something isn't a success right away, he warned, doesn't necessarily mean it's a bad idea it could just be down to poor execution. As evidence of this, he pointed to Airbnb's 'experiences' offering, which went through two prior iterations before achieving the desired success.
"The problem is, so much of innovation is an enemy of what people want in an organisation, which is clear decision-making, lack of churn, all these things a clear process. And the problem is, sometimes innovation is not a clear process. Sometimes it breaks or undermines your processes, and you need to have, I think, some tolerance for that."
