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

Great business leaders are willing to endure all sorts of pain when they ask questions, says Hal Gregersen, who spoke at the MIT CFO Summit. That's how they solve problems.

NEWTON, Mass. -- To succeed in an environment roiled by new digital business models, asking questions matters more than having all the answers. But not just any questions. The most successful business leaders ask questions that are designed to prove them wrong, are likely to make them uncomfortable, and will drive them to reflect on their behaviors and beliefs. That's how they become great problem-solvers.

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 by FedEx to run the business in [Arab hotspots], he got so good at it that he started a competitor," Gregersen said of Ghandour, who stepped down from Aramex in 2012 and now oversees a technology venture capital fund.

Passive data

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 by one of his Aramex truck drivers.

"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 by great business leaders are right, but what sets them apart from their less high-achieving peers is they catch the wrong decisions faster.

"And the only way to catch those wrong decisions faster is by actively seeking passive data," he said.

Soul-searching reflection

Driving around also figured large in another business leader profiled by Gregersen during his CFO Summit talk.

MIT CFO Summit, great business leaders, digital transformation, CFO
At the MIT Sloan CFO Summit, Hal Gregersen's slide on three conditions that help business leaders ask better questions.

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 by great business leaders is they put themselves in situations where they are susceptible to being told they are wrong, Gregersen said. At Pixar, directors participate in the Braintrust meetings, where they meet to discuss the current movie Pixar is working on.

The meetings are an invention of Disney and Pixar Animation Studios President Ed Catmull, a computer scientist by training, and they can be "devasting, difficult, but absolutely necessary, " Gregersen told the CFO Summit audience. 

[We need] to regularly put ourselves in situations where we are wrong and feel uncomfortable. When we do that, that is when the questions come that literally unlock answers we ordinarily wouldn't get.
Hal Gregersenexecutive director of the MIT Leadership Center

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."

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