‘We used to refer to ourselves as a family’: Airbnb boss Brian Chesky is all business after emotional letter

No matter how much you like your colleagues, don’t think of your workplace as a family, says Airbnb CEO and co-founder Brian Chesky.

Chesky learned this lesson from experience, he told Wharton psychologist Adam Grant’s “Re-Thinking” podcast in May.

In 2020, at the height of the COVID-19 pandemic, Chesky penned a note to employees explaining that the company would conduct layoffs. “I have a deep feeling of love for all of you,” he wrote.

It made sense: Workplace families were a particularly popular loyalty-building concept among tech companies pre-Covid, with perks like free food, dry cleaning and in-office gyms encouraging employees to spend more time in the office than with their actual families.

But today, Chesky would frame his appreciation differently, he said: Thinking of your workplace as a family can be an effective motivational tool, but it can also make it difficult for bosses and employees alike to do their jobs.

“I wrote that letter fairly quickly,” said Chesky. “I didn’t have a lot of time, and so I wrote what I felt and that’s what I felt, and I was pretty emotional when I was writing it. And it is true that a company is not a family. In fact, we had to make that pivot.”

“We used to refer to ourselves as a family, and then we did have to fire people, or they’d have to leave the company, and you don’t fire members of your family,” he added.

How to think about your workplace instead

If you shouldn’t think of your workplace as a family, how should you approach it? Netflix CEO and co-founder Reed Hastings has a simple answer: like a professional sports team.

“You should organize around this idea that everyone has to fight for their job every year like it is in professional sports,” Hastings told Stanford University’s ‘’ View From The Top’’ interview series in February. “If you’re going to win the Stanley Cup, it’s because you’ve assembled the most amazing group of hockey players that have ever been together.”

From a leadership point of view, the family approach can be a problem when you have to reprimand someone, enforce a rule or conduct layoffs, said Hastings.

“In a family, you look after your siblings, your parents, your kids no matter what,” he said. “They go to jail, they do whatever, you’re with them.”

Using the word “family” can put bosses in situations where they can take advantage of employees, leadership development coach Joshua A. Luna wrote in a 2021 Harvard Business Review article: The more emotionally attached you feel to your organization, the more easily your manager can regularly ask you to go above and beyond like a brother or sister would.

If you don’t take on the extra work, you could fall out of favour or even get fired. Hastings’ approach is smarter, wrote Luna: The professional sports metaphor helps create a sense of belonging at work while still keeping performance and productivity at the front of everyone’s minds.

A positive, healthy workplace culture “respects the transactional nature of this relationship,” Luna noted.