How Does Brian Chesky Get Honest Pushback?

Brian Chesky gets honest pushback at Airbnb by keeping people who can afford to tell him the truth, then by taking the opposite side of his own idea so the team has room to disagree.

Most of the people willing to tell him the truth have been with him more than 10 years, including his co-founders and a few who do not need the job and can risk getting fired. In London last week, he and the team landed on a new company tagline. He texted his CMO and two creative leads that the line was final and he did not care what anyone said. After sleeping on it, he saw he had sucked the oxygen out of the room. The next day he told them they had two weeks to find a better tagline and said he thought a better one existed.

They finished in a week, half the time he gave them, and told him the original tagline was the right one. Taking the counter position gave them permission to disagree. If people agree every time he flips his position, they are still not comfortable speaking up. Sometimes he asks for an opinion before he gives his own.