Knowing the Unknown

Hal Gregersen has studied more than 200 corporate leaders.

Gregersen, the current executive director of the MIT Leadership Center, has worked with executives all over the world, from France to Helsinki, Finland. In his travels, he’s found that many CEOs and other leaders face a common challenge: overcoming a feeling of being isolated within the organization.

This morning, Gregersen shared some of their experiences as he kicked off the International Coach Federation’s ICF Converge event, held Aug. 23 – 25 at the Marriott Wardman Park Hotel in Washington, D.C. His keynote presentation, “Asking Catalytic Questions,” offered some examples of executives that have wrestled with overcoming what he calls “a dangerous disconnect.”

CEOs such as Walter Bettinger at Charles Schwab, for instance, have told Gregersen that they sometimes grow concerned that “people tell him what they think he wants to hear, and [are reluctant] to tell him what he doesn’t want to hear,” said Gregersen.

Encouraging open and honest communication with employees is obviously important for any executive seeking to avoid isolation at the top of the organization. But it also requires some self-reflection—and some acceptance of one’s own limits, said Gregersen.

“The best and most innovative leaders constantly and systematically try to figure out what they don’t know they don’t know,” he told the roughly 1,600 corporate coaches in attendance. “It’s part of their everyday work.”

Gregersen pointed to Tesla CEO Elon Musk as an example, noting that a pre-teen Musk reportedly sat down and read the entire Encyclopedia Brittanica in an effort to broaden his knowledge base.

On the other hand is recently-ousted Uber chief Travis Kalanick.

“He didn’t know that he didn’t know how to interact with one of his own drivers,” said Gregersen, referencing the now-famous viral video showing Kalanick arguing with an Uber driver; a clip that has racked up more than 4 million YouTube views and helped precipitate Kalanick’s downfall at the company.

Kalanick might be an extreme example, but “it can be tough to know what you don’t know,” said Gregersen.

The higher one flies in an organization, “and the better we become, it can be tempting to think that we have it all figured out.”

In studying leadership, Gregersen says he’s also discovered that the best leaders know the right questions to ask in their quest for more knowledge—of themselves as well as others. And that journey sometimes requires knowing when to shut up and listen.

“How long do you wait for others to answer your questions?” Gregersen asked those in attendance, noting that four seconds is typically considered an appropriate length.

“For some leaders, and for some coaches,” he joked, “this might seem like an eternity.”

The best leaders, however, eagerly ask the right (and sometimes uncomfortable) questions, and listen carefully to the responses they get. Making this kind of effort, he says, expands an executive’s knowledge, of course. But, from a business perspective, it can also help prevent learning new information about an important issue before it’s too late, according to Gregersen.

“If we don’t seek out surprises, surprises tend to find us.”