Brian Chesky’s new playbook

Key ideas

Chesky explains why he stopped delegating product at Airbnb and now runs one roadmap, a functional organization and personal reviews, arguing that leaders belong in the details.

From a machine transcript of the audio. Quotes link to the moment they are said.

1. 1

   Delegating the product can slow you down

   Chesky describes a paradox from his years of stepping back: the less he was involved, the slower teams moved, and each slowdown was blamed on too much involvement, so he stepped back further. He concedes that his stepping in did sometimes cause dysfunction. He now argues that, unless they are not a product person, the CEO of a product or tech company should in effect be its chief product officer, and he separates being in the details from telling people what to do.

2. 2

   Rebuild the org like a startup

   Chesky says that by 2019 Airbnb had about ten divisions, rising costs and work slowed by politics and dependencies, and the pandemic then took 80 percent of the business in eight weeks. He had every project written in one sheet, cut to about a fifth of them, removed management layers, dropped divisional leaders for functions, and asked each executive to be an expert in their domain.

3. 3

   One roadmap, reviewed by the CEO

   Chesky runs a rolling two-year roadmap with two launches a year, and apart from some infrastructure work nothing ships unless it is on it. He reviews projects on set weekly-to-quarterly cadences while a head program manager scores each one green, yellow or red. He says these reviews expose blockers and remove the need to win people over through influence.

4. 4

   Make product people tell the story

   Chesky says he kept the people but merged product management with product marketing in a smaller, more senior group that has influence rather than control over design and engineering. Work on a launch starts early with the story, which often shapes the product. Using a metaphor he credits to his co-founder Joe, he compares performance marketing to a laser that lights one corner of a room; Airbnb still uses it, and he says others need not go as far as he has.

5. 5

   Set the pace through decisions

   Chesky treats 'add a zero' more as a thinking exercise than a literal target, since imagining ten times the scale can push people to rebuild a problem from its parts. He says a team's pace is sometimes governed by decisiveness rather than hours. He reports that being hands-on meant far more work for one to two years, and that he then had more time because teams were aligned and he faced fewer bad surprises.

In Brian’s words

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