Good questions: A conversation with leadership expert Hal Gregersen

Great leaders ask great questions about what they don’t know they don’t know, says new executive director of MIT Leadership Center

October 10, 2014

Hal Gregersen updated

Hal Gregersen

Hal Gregersen, co-author of The Innovator’s DNA, joined MIT Sloan this year as the executive director the MIT Leadership Center. In an interview, Gregersen discussed the importance of questioning, how he connected with an MIT Executive MBA class, and how photography informs his own inquisitiveness.

What is it about questioning that is so central to successful leadership?

For nearly 20 years, Harvard Business School professor Clayton Christensen and I have been trying to figure out what causes great leaders to ask the right questions. During the last few years we’ve interviewed about 100 senior leaders from around the world for a forthcoming book and so far the answers have been intriguing. We asked Stewart Brand, who started the Whole Earth Catalog decades ago, how he surfaces such incredible questions. He said, “Every day, I wonder how many things I am dead wrong about.”

When we interviewed A.G. Lafley, the chairman, president, and CEO at Procter & Gamble, he shared the same thing but in different words. Every Monday morning he wakes up asking himself, “What am I going to be curious about this week?” Which really means, “What don’t I know? What am I missing?”

In senior executive roles, the toughest challenge is figuring out what they don’t know they don’t know. This creates the most dangerous blind spot, but many executives are not actively working to uncover it. That’s why Kodak dove under. That’s why Nokia dove under. And the global list goes on where senior leaders failed to explore the crucial blind spots that came back to destroy their companies. It’s a dangerous emotional space for most executives to enter, and they avoid it at all costs. A critical question for any executive to answer is “How long ago did someone ask you a question that caused you to feel uncomfortable?” If the answer is more than seven days, it’s time for a leadership shake-up, because the bad news that you need to hear is likely not making it your way.

Is that type of inquisitiveness based on talent and intuition, or can it be learned?

I taught Leading Organizations to the MIT Executive MBA class this summer, and it was a powerful learning experience, both for me and many of them. At the beginning, some were skeptical about why I asked them to keep a questioning journal about all the questions they had related to the course content, as well as any insights gained. During class we also practiced a methodology that I call “ catalytic questioning.” Each student identified a professional challenge for which they honestly did not have a solution but wanted one. They shared their challenge with two other peers in class and then spent four fast and furious minutes brainstorming nothing but questions about their challenge. Almost everybody walked away with a different perspective or angle on the challenge, as they uncovered new questions that they’d never considered before. And those new questions were just like keys that unlock a door; only in this case they opened up entirely new avenues of action. I’ve found the same response working with thousands of executives around the world.

Most leaders know that asking the right questions makes a difference, but they’re hard-pressed when it comes to teaching anyone else how to do it. That’s the core of what I’m trying to achieve through The 4-24 Project, which is a non-profit organization I founded dedicated to keeping questioning skills alive so individuals can pass this skill onto the next generation of leaders.

How will you continue your work on questioning at MIT Sloan?

I believe that powerful insights come from deep interactions across disciplinary boundaries. MIT is world class when it comes to technology and science, and then you combine that with a world-class business school—it’s unbeatable. Before joining MIT, I thought, “There must be some really incredible things going on there.”

After joining MIT, I discovered that data backed up my hunch. MIT alumni have started or lead companies that collectively account for the 11th largest economy in the world. Now my hunch is that to do what they’ve done, MIT alumni must have been asking different, better questions. Based on my brief interactions with students, faculty and alumni so far, I believe this is one of the core capabilities that leaders gain from an MIT experience. Now I’m hoping to figure out what it is that we can do to bring in the right people and then equip them to go off as better questioners, ultimately creating even greater value.

Recent photography by Hal GregersenRecent photography by Hal Gregersen

You have incorporated your work on questioning and innovation into your work as a photographer. What can executives learn from the pursuit of photography and other arts?

Every 4-year-old on the face of the earth is both a great artist and a great questioner. And all of us were once 4 years old, so we have it in our genes to ask great questions and to be great artists. Photography is my art of choice. I fell in love with a camera at the age of fifteen and have been smitten ever since.

Thousands of pictures and four decades later, my photography work has come full swing into my leadership work. The mere act of photographing helps us see things that we wouldn’t otherwise see and that’s core to creating the right questions. If we don’t see new things, we won’t get new questions. The trick is using the camera to unlock new insights into leadership challenges—especially the things we don’t know we don't know about ourselves, others and our organizations—as well as create beautiful images. That’s what we tried to accomplish recently in a unique workshop co-taught with Sam Abell, a 30-year National Geographic veteran, through the Santa Fe Photography Workshop. We brought together a small group of senior executives from around the world who love photography and taught them how to ask better questions as leaders and photographers. It was thrilling to work with Sam, and weave the power of photography into the heart of our leadership. After four intensive days of working together, each of us, including myself, walked away transformed. Powerful stuff.