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How to ask questions the way great business leaders do: CFO Summit

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NEWTON, Mass. — To succeed in an environment roiled That was the motivational message to CFOs from Hal Gregersen, executive director of the MIT Leadership Center, at the recent MIT Sloan CFO Summit. Certainly, senior financial executives understand the importance of asking questions in their line of work, Gregersen conceded to the CFO Summit audience. But, “given this trend of digital transformation, which is changing all of our lives,” CFOs need to ask better questions — and more of them — if they aim to play a strategic role in this period of business upheaval, he said.

Drawing on research from his new book, Questions Are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life, Gregersen served up a who’s who of  “certified, focused problem-solvers” to make his point — from the founder of JetBlue to the CEO of Patagonia, to Fadi Ghandour, co-founder of Aramex, a logistics company headquartered in Dubai and the first United Arab Emirates-based company to be listed on an American Stock Exchange.

“Hired According to Gregersen, a big factor in Aramex’s success was Ghandour’s ability to ask questions that elicited “passive data,” or data that he wouldn’t ordinarily hear. When Ghandour traveled for business — sometimes arriving late — instead of making a chauffeured beeline to the hotel for some rest, he insisted on being picked up “They know him, he knows them, [and] they speak candidly and pass along data that isn’t coming through official channels.”

MIT CFO Summit, great business leaders, digital transformation, CFO
Hal Gregersen, director of the MIT Leadership Center, gives a talk on how to ask better questions at the MIT Sloan CFO Summit.

Getting out of the corporate bubble where people are likely to tell you what you want to hear is crucial to good decision-making, Gregersen said. “It’s the passive data that is not getting pushed at us that allows us to figure out what we know we don’t know,” he told the CFO Summit audience.

According to Gregersen, only about 60% of the decisions made “And the only way to catch those wrong decisions faster is Driving around also figured large in another business leader profiled Rose Marcario, now the CEO of Patagonia, was a private equity dealmaker en route to a big meeting in New York when her driver slammed on the brakes. Annoyed that she was no longer making progress, Marcario looked out the window and saw the culprit was a hobbled pedestrian slowly crossing the street. The sight “struck her like a dagger in the heart,” Gregersen said. The woman resembled her mother, who had suffered from psychological problems when Marcario was growing up.

Her reaction to this encounter is an example of another condition of asking great questions, according to Gregersen: being reflective. Marcario asked the driver to drop her off in Central Park, and as she walked, Gregersen said she clarified the problem she would solve five years later when she joined Patagonia as its CFO: “‘How can I make a living without losing my soul?'”

How Pixar creates great business leaders

The third condition observed The meetings are an invention of Disney and Pixar Animation Studios President Ed Catmull, a computer scientist In his research at Pixar, Gregersen learned that some of the best movies made there are based on the life stories of the directors. So, the Braintrust sessions are not only a critique of the movie’s merits, but also a judgment of sorts on the director’s life story.

“Top-of-the-line leaders are getting feedback [in a setting] where they are wrong, uncomfortable, and they are forced to shut up and listen,” Gregersen said. 

The point of the anecdote Gregersen told the CFO Summit attendees was not that they go back to their offices and set up Braintrust meetings, but that they find ways to put themselves and their teams in situations where they can get feedback of that brutal caliber.

“As we walk into that world of digital transformation that’s full of opportunity for us, the best advantage we can take of it is by … figuring out our own path to regularly put ourselves in situations where we are wrong and feel uncomfortable,” Gregersen said. “When we do that, that is when the questions come that literally unlock answers we ordinarily wouldn’t get.”