In May 2020, travel stopped almost overnight. Airbnb’s co-founder and chief executive Brian Chesky announced that 1,900 of the company’s roughly 7,500 employees, about a quarter of the workforce, would lose their jobs.
What he did differently
Chesky’s letter, published on the company blog and read to employees by video, explained the company’s financial position, how the decision was made and who was affected. It set out the support clearly: 14 weeks of pay plus one week for every year of service, 12 months of health insurance and help finding new jobs. It was widely praised as transparent and humane.
What he learned
In 2024, Chesky reflected that describing the company as a “family” had been a mistake: “You don’t fire members of your family.” Even a well-handled message can carry assumptions worth revisiting.
Lessons for founders
- In a crisis, specifics are respect. People need facts, reasons and what happens next, not just sympathy.
- Deliver hard news yourself. The founder’s voice matters most when the news is worst.
- Review your own language. Words that feel warm in good times can ring hollow in bad ones.
The takeaway
Most founders will one day have to share bad news. Chesky’s letter shows that the way it is delivered can protect trust, even when the news itself cannot be softened.
Sources
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