Airbnb CEO Brian Chesky has an 'email problem'; does not remember the last email he wrote

Airbnb CEO Brian Chesky can barely recall the last time he sat down to draft an email. In fact, he believes the broader working world would be better off stepping away from email altogether – or using it “not very often”.

Speaking in an interview with Time, the billionaire founder admitted that he rarely creates messages in his inbox from scratch.“I don’t know if I write an email a week. I respond to emails every day because people email me. But I’m trying to think of the last time I, like, drafted an email,” Chesky said.

The ‘problem’ Brian Chesky has with email

Explaining his disdain for the format, Chesky described email as an outdated medium that feels like a chore compared to more direct, personal alternatives.“I just find it inferior to almost every other form of communication," Chesky explained, adding, “Email is subject-based. Text message is person-based. Text messages are much faster. It’s contextual. You feel a deeper connection. The person doesn’t have a subject line. When you get a text message, it doesn’t feel like work to respond.”As text messages pop up as immediate phone notifications, Chesky said he is far more likely to get a quick response by texting his 8,200 employees.

If an issue arises, his preferred approach is to call, text, or meet someone face-to-face.Chesky ranks his communication preferences in clear order:

While texting may feel more casual and human to a boss, receiving a ping from leadership outside typical working hours often feels like work to employees, regardless of the app. Chesky dismissed pushback over communication preferences, arguing that “everyone has a right to run their company how they want.”

He noted that he tries “not to text people when I think they’re with their family unless there’s a crisis,” but acknowledged that his own work-life balance is likely far more “blended” than that of the typical employee.Chesky is not alone among chief executives who lean into continuous connectivity:Farmer J, the founder and CEO of London’s healthy fast-food chain, told Fortune he has never activated an out-of-office auto-reply, even while away on his honeymoon.Nespresso UK & Ireland CEO Anna Lundstrom told Fortune her team can reach her across platforms, including WhatsApp, Microsoft Teams, LinkedIn, and email, noting her phone is within reach from the moment she wakes up because she would “always rather know something than not.”Uber CEO Dara Khosrowshahi stated on the Diary of a CEO podcast that weekend emails are “part of working hard,” adding that if he does not receive an answer on Saturday, he follows up on Sunday with a question mark asking what is going on.