MIT Sloan Executive Education innovation@work Blog

At the CHRO Summit, Hal Gregersen made people uncomfortable, and that's a good thing

Hal Gregersen at CHRO Summit

MIT Sloan's Hal Gregersen gave the morning keynote at the Chief Human Resources Officer (CHRO) Summit in Boston on June 7. "Banish Your Blindspots by Asking the Right Questions" was the theme of his talk, and he asked attendees to examine not what they knew, but what they didn’t know. "What are the uncomfortable questions in your work and life that you are not asking yourself or others?" he asked.

Gregersen is the Executive Director of the MIT Leadership Center and a Senior Lecturer in Leadership and Innovation at the MIT Sloan School of Management where he pursues his vocation of executive teaching, coaching, and research by exploring how leaders in business, government, and society discover provocative new ideas.

His best-selling book, The Innovator's DNA: Mastering the Five Skills of Disruptive Innovators, flows from a path-breaking international research project (with Jeff Dyer & Clayton Christensen). They explored where disruptive innovations come from by interviewing founder entrepreneurs and CEOs at 200+ of the most innovative companies in the world.

You don't know what you don't know

Walt Bettinger, President and Chief Executive Officer of Charles Schwab, said during his interview with Gregersen, "When you reach the upper echelons of management, people start telling you what they think you want to hear and are too afraid to tell you what you really need to know."

Of his 200+ interviews, Gregersen found this sentiment to be a common theme: many leaders reported that they found themselves precariously protected from "bad news" within their own companies. A "dangerous disconnect," Pixar Founder Ed Catmull called it. Being in this "isolated tower" prevented these leaders from getting a true sense of corporate performance, innovation, culture, morale, outcomes, and other critically important information.

Every answer has a question that unlocks it

Gregersen explored how the most innovative leaders recognize their isolated positions and create intentional, formulaic strategies to fix this. Namely, they sought out new information by seeking out new people, places and experiences, and asking some candid questions of themselves and others. They sought out people and situations that made them:

1. Unexpectedly wrong
2. Unusually uncomfortable
3. Uncharacteristically quiet

Every month, for example, Jeff Immelt, now the former Chief Executive Officer of GE, invited one manager in his company to come to a family dinner at his home, and then they spent the next day together at work talking through that manager’s work challenges. This is just one way Immelt sought out new information within his company, and encouraged his employees to communicate candidly with him.

Bettinger will approach random staff members and ask them, "If you had my job, what would you be focused on right now?"

SAP’s Co-founder Hasso Plattner will wake up and ask himself every morning, "What am I dead wrong about? How can I fix that?"

Another great example comes from Founder of Spanx Sara Blakely’s father. As Sara was growing up, her father would go around the dinner table and ask everyone, "What did you fail at this week?" If she said hadn't failed at anything that week, her father would tell her that she wasn't trying hard enough. Not only did that create within her a high comfort level with facing failure, but it gave her permission to be wrong.

Zip your lip

And lastly, many of these leaders used the power of silence to help them discover new things.

"Quiet time is the most important thing to help me frame the right questions," said Diane B. Greene, a senior vice president with Google Cloud. "When I'm faced with a problem or challenge I want to solve, I get in my sailboat by myself, and spend the day in silence out on the water until some answers float up to me."

When Gregersen asked Salesforce's CEO Mark Benioff how he sought out new, candid information, he replied, "I listen." Simply staying silent and giving your full attention to another person's answers can be surprisingly effective, and using the power of the pause to draw out an increasingly honest answer. "If you ask a question and wait three or more seconds, you're asking a question that requires actual thought from someone," Gregersen said. "If you wait less than three seconds, then you’re just expecting them to tell you what you think you already know."

In short, if you're always right, always comfortable, and always talking, beware--there's a very good chance you don't know as much as you think you know.

Learn more from Gregersen

Gregersen teaches more on this and other leadership and innovation topics in his popular program, The Innovator's DNA: Mastering Five Skills for Disruptive Innovation.

You can also check out his program, Leadership and the Lens: Learning at the Intersection of Innovation and Image-Making, which uses photography as a tool to help you discover your leadership instincts and strengths.


How many layers are between you and your staff?
How easily can they come and speak with you?
Do you give people permission to give you honest answers?
How long do wait for others to answer your questions?
How often do you seek out strikingly new places or new people?
When was the last time you were dead wrong about something?
When was the last time someone asked you an uncomfortable question at work?
If they aren’t coming to you with those uncomfortable questions, then who are they asking instead?


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