What motivation reveals about CEO readiness

Airbnb CEO Brian Chesky has a question he likes to ask founders about their companies: “Why do you deserve to exist?” It’s a provocation that’s not about market share, pitch decks, or investor appetite, but rather necessity. “The best generic answer I’ve ever received was, ‘if I don’t do it, no one else will,’” he recently told the tech news podcast TBPN. It’s a striking question that more CEOs—or those aspiring to be—should be asked and even ask themselves. Leaders are often evaluated on their ability to ...