How these leading CEOs use questions to drive success

Most people don’t particularly enjoy being wrong, uncomfortable, or quiet. But, when harnessed the right way, those can be the perfect conditions for coming up with transformative questions that lead to paradigm-shifting answers.In his new book, “Questions Are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life,“ MIT Leadership Center executive director Hal Gregersen describes how the minds behind some of the world’s most successful companies used the power of catalytic questioning to prime themselves for innovation, and offers a framework for replicating it yourself. 

“These questions not only challenge false assumptions in the system, but they give people the energy to do something about it,” Gregersen said. “When you think of Rose Marcario, Marc Benioff, Jeff Bezos, Elon Musk, any of those folks, they systematically, habitually create conditions where they themselves are likely to be wrong, uncomfortable, and reflectively quiet, such that a question would emerge that they otherwise wouldn’t ask,” Gregersen said. Here’s how five of the world’s most successful executives used questions to generate groundbreaking ideas.

Rose Marcario and Yvon Chouinard of Patagonia

When Chouinard founded Patagonia, he did it with the intention of finding a way to build a business without compromising his morals. In his quest to be sure his operation wasn’t having a negative environmental impact — and maybe even a positive one — the company settled on a counterintuitive approach to competitive advantage: What if we don’t try to protect our competitive advantage, and give away our knowledge of sustainability? That way, other companies would emulate it.Current CEO Marcario pushed that question a step further: “How do we make it uncomfortable for other businesses not to follow us?” Under Chouinard and Marcario’s lead, Patagonia has embraced “radical transparency” within the firm to its extremes, to keep a questioning alive and push those ideals forward.

Marc Benioff of Salesforce

Benioff launched Salesforce on the tailwinds of a question, Gregersen said: “What if people sold enterprise software [over the internet], like Amazon sells books?” Today, questioning continues to drive the company.

An internal message board started by Salesforce employees called “Airing of Grievances” offers a candid problem-solving forum for discussion about work and community challenges at the company. When some of Benioff’s top managers brought it to his attention, they expected he might want to shut it down. Instead, he embraced it. 

Now, Benioff monitors the board to keep a finger on the company’s pulse, and even participates from time to time. He even shared it on his Twitter page as his “favorite internal Salesforce group.” 

Benioff also works to supply people with physical spaces conducive to a questioning mindset, which are called “Ohana floors.” They feature wide-open spaces and views of land and sea. “If you want people to think differently, you need to put them in a different space,” he told Gregersen.

Ed Catmull of Pixar

For Pixar CEO Ed Catmull, questions should be recursive, Gregersen said. He’s constantly questioning, “How can I build a sustainable organization, knowing that there are forces of isolation and lack of candor always at work in every level of the system? How do we fight that ongoing, because the fight is never ending?” 

“They ask and engage with that question over and over, causing a series of crucial conversations focused on building a better future,” Gregersen said.

Pixar has established a number of exercises and traditions designed to encourage raw candor. The Brain Trust, for example, puts directors in a room where they receive uncensored feedback from their peers, with the goal of establishing a deeper emotional connection to the project they’re working on. This feedback can be quite difficult because the best movies are made when a director has a serious emotional stake in the movie, and the director is often sent home for the remainder of the day, or weekend, afterward. 

Elon Musk of Tesla, SpaceX, Solar City, and The Boring Company

Musk favors “first-principles thinking,” which involves stripping away all of the assumptions that have been taken as givens but shouldn’t be, then asking “What are we sure is true?” When it came to outfitting his electric vehicles with wheels, Musk analyzed the process of producing one from the ground-up, realizing that each should cost just a fifth of what they’re sold for. 

In “Questions Are the Answer,” Gregersen writes that “Musk is very aware that people don’t normally push back so hard on what is presented to them as reality. They are “more likely to say: ‘Well, we looked at what other people pay for wheels and they seem to pay somewhere between $300 and $600. So, we think our $500 number is not that bad.’ But that just means everybody else is getting ripped off, too!’”

By asking “Is there some way we could apply that solution to a different industry?” Musk has founded companies that span the financial services, space flight, and transportation industries.