Airbnb’s Brian Chesky became a billionaire by knowing how to find the right question, says leadership advisor

• Some of the most successful people got to where they are not by having all the answers, but by knowing how to find the right questions, according to SYPartners CEO Jessica Orkin. It’s an increasingly important business strategy—and survival skill—amid growing uncertainty about the future.

What’s made billionaires like Oprah Winfrey and Airbnb CEO Brian Chesky so successful? The ability to ask the right questions, believes Jessica Orkin, CEO of leadership consultancy SYPartners.

“What we’re finding again and again is that the most transformative leaders are those asking the most courageous questions,” she said at Fortune’s Most Powerful Women summit in Riyadh, Saudi Arabia, last week.

With AI disruption and geopolitical uncertainty making planning a challenge, no leader can have all the answers. But what every entrepreneur and corporate CEO should be getting better at is asking the right questions, Orkin said.

“These are questions that are not just about strategy,” she added. “They’re bigger than that…They’re questions which, by the act of asking, changes the field of what’s possible.”

By way of example, she noted that Chesky, when starting Airbnb, could have asked a question like, “How do we monetize a spare room? A second house?” Instead, he asked, “What if travel was about belonging?”

That deeper question “created an $85 billion business and has revolutionized hospitality around the world,” she said.

Cosmetics brand Sephora found a powerful question as well, she noted. “They could have asked, ‘How do we sell more makeup globally?’ But instead, the question became, ‘How can we help people around the world define beauty for themselves?’ So instead of chasing a universal standard of beauty, people were able to create theirs. 

As for Oprah Winfrey, Orkin said, she “could have asked, ‘What’s next for me after television?’ Instead, she asked, ‘How can I help other people find their purpose as an expression of my own?’ And this launched new platforms, new communications, and a global tour that filled arenas.”

Of course, Orkin added, finding this question is not easy.

“Standing in the uncertainty is hard. We have been trained as leaders, find the direction, point our people at it, and run as fast as possible. And so this requires self-reflection. It requires knowing your own purpose, the purpose of your organization.”

The search for the right question is made all the more difficult, she noted, by the deadlines and other pressing matters that business leaders contend with on a day-to-day business. 

But Orkin insists it’s crucial. 

“Questions are often thought of as a soft skill, but they’re not—particularly today, particularly in such a time of transformation, such a time of unknown. They are a survival skill.”

This story was originally featured on Fortune.com