5-ish Questions for Questioning Expert & Leadership Guru Hal Gregersen  

Hal Gregersen Interview Intellects.co

Here at INTELLECTS, we’re all about asking questions—hence our tagline “Ask and you shall succeed.” So when we scored an interview with Hal Gregersen, Executive Director of the MIT Leadership Center and the man who invented a decision-making technique for business leaders called “catalytic questioning,” we were both excited and, admittedly, a little intimidated. Gregersen is a creative thinker with a formidable track record: esteemed author, Senior Lecturer at the MIT Sloan School of Management and ranked as one of the world’s most influential management thinkers. He believes that asking the right questions can unlock brilliant ideas and launch innovations. Needless to say, we were thrilled to get a compliment on one of our own questions, below. Read on, let his brilliance sink in, and start asking questions.

“The reason we get stuck on a problem is because we’re asking the wrong questions.



Let’s say a clothing brand is trying to hone their marketing plan, and they can’t decide whether to invest in hiring a creative director to improve their branding or invest in website and mobile functionality. How could catalytic questioning help a CMO make this decision?

Hal Gregersen: The reason we get stuck on a problem is because we’re asking the wrong questions. When that happens, the best way out is to change the question. This may seem obvious, but uncovering the right question is harder than it sounds. That’s where catalytic questioning comes into play. Catalytic questions, like catalysts in the real world, dissolve false assumptions and accelerate positive change. They are big questions that change the world, both globally and locally, which is exactly what we try to do at the MIT Leadership Center

Clearly this clothing company is stuck on figuring out which direction to go. Intellectually, the CMO cares about the problem. More importantly, it matters to her emotionally. The first step in finding the right question, one that unlocks a new solution, is choosing a problem that she cares deeply about.

I’d encourage the CMO to pull a few people together–ideally people who don’t see the world the way she does–for a Question Burst. It just takes a few minutes: four, to be exact. After quickly sharing the challenge with them, follow three rules for the next four minutes. First, ask nothing but questions about the challenge. Second, don’t answer any of the questions. Third, don’t explain why we are asking the questions. After doing this for four minutes, chances are she’ll be in a better place to solve the problem both intellectually and emotionally. Likely, she’ll have reframed the challenge in a slightly new way or uncovered ideas she hadn’t yet considered.

Obviously I am not giving the clothing company CMO a set of specific questions. That’s because I have full confidence that when leaders do a series of Question Bursts they will rapidly reframe their questions and solutions to solve significant problems. The same happens when we do this as individuals, as I often do, for professional and personal issues. 

Hal Gregersen


We’re in a fascinating, enlightening, and somewhat confusing time right now when it comes to gathering information and making informed decisions. Trusted news sources are doubted; fringe news sources are influencing millions with potentially manufactured information. How can you mentor the next generation to ask the right questions when there is so much conflicting information floating around on the Internet?    

HG: The advice I would give to the next generation is quite similar to what I give to CEOs. You must actively get out of your routines and go looking for surprises. Just last week I was visiting with Tony Hsieh, CEO of Zappos. During our discussion, he invited me to stay for a week at his Airstream trailer park in Las Vegas, with this caveat: “Come without any specific schedule. Let serendipity be your guide. See what happens when you hang out by the campfire and visit with whoever shows up. Part of the magic of the park is just fortuitously meeting interesting people from all different backgrounds.” No wonder, then, that at Zappos itself, Hsieh spends a lot of energy working on “how to get employees to collide more often, having serendipitous encounters just like in the Airstream park.” It’s the only way to discover the “unknown unknowns” in our lives before it’s too late.

That’s exactly what Fareed Zakaria at CNN told me he does to get closer to the truth. Like Hsieh – but not at an Airstream trailer park – Zakaria cultivates a wide range of on-the-ground sources to get multiple versions of the truth. Otherwise, surprises come actively looking for him, exposing unexpected truths.

Today, online algorithms excel at giving us information that we want to hear. One fundamental key to sorting out truth from error is actively and intentionally putting ourselves in places with people who are strikingly different from us and our everyday routines—including our online routines. When we do that, the unusual situation can easily force us to be unexpectedly wrong, unusually uncomfortable, and uncharacteristically quiet.  When we live our lives where these three conditions are ever-present, the conditions cause us to ask new and better questions. These better questions are exactly what help us sort out truth from error. Stewart Brand, an iconic innovator for decades, told me that every day he asks himself, “How many things am I dead wrong about?” In fact, John Chambers told me in a recent interview that this question—featured in my “Bursting the CEO Bubble” article—was the only one that caused him to think twice. It’s a tough question to live by, but well worth the effort in an age of disinformation and misinformation.

Put simply, actively and intentionally getting out of our comfy routines provides the very best protection against the daily tsunamis of false information. And it’s only by getting out of our routines that we’re capable of formulating and asking new questions, ones that shine a bright light on truth and error in our lives–or for that matter, in our country and our world.

Hal Gregersen


INTELLECTS is basically our forum for networking ideas to gain new perspectives about the work we do and the work we hope to do. It’s easy for extroverts to jump in and create conversations with people different from them, but what about someone who is more of an observer? How could they create a similar experience of gathering knowledge from others—but in their own way?

HG: Great question!  Years ago I had a chance to interview Pierre Omidyar, eBay founder, for a research project on innovation and learned that he loves to learn by reading diversely and reflecting intensely. Contrast that with Marc Benioff, founder of Salesforce.com, who loves to talk face to face with people, hundreds of them, to spark new ideas. Both approaches give new perspectives, but the paths differ, and that’s ok. 

My suggestion for introverts is to actively diversify the kinds of information they’re exposed to by putting themselves in wildly different places, whether physical or digital. I recently had the chance to visit with Gen. Stanley McChrystal, whom I discovered is an introvert. Early on in his career, troops thought he was arrogant because he didn’t talk with them when they were in large groups. It wasn’t until his boss raised the issue that he became aware of the unintentional signals he was sending and decided to do something about it. Today he literally changes the physical setup in his office with the intention of helping people feel more comfortable talking to him. 

Surprisingly, the Question Burst methodology provides a great opportunity for introverts to get engaged in a group conversation. I’ve noticed that the rules of engagement during questioning create the space for quieter people to contribute. In fact, asking nothing but questions disrupts our everyday conversations so much that everyone can contribute. It’s no surprise then that introverts often ask the best questions, precisely because they have often been the best observers of the situation for months or even years.

The bottom line is that extroverts and introverts can both ask and answer great questions. The way they accomplish it might be different, but both can excel at surfacing catalytic questions to change the world.

Hal Gregersen


CMO/Marketing budgets are often impacted by shifts in the business. What questions can be asked to move great ideas back to a conversation rather than leaving them at “NO” because of budget constraints?

HG: When leaders use “budget constraints” as the primary weapon for shutting down questions or conversations, it may well mark the beginning of the end of that company. During a downturn is when we need the most creative questions and insights. That may seem counterintuitive, but it’s true. Whether it’s Guy Laliberté at Cirque du Soleil or Simon Mulcahy at salesforce.com, they both work hard to hear new ideas. Where some leaders might hit the brakes on other people’s comments or questions, they hit the brakes on their own mouths instead. They say, “Tell me more” to keep the ideas coming. 

Another terrific strategy for getting great ideas–or our organizations–back on track is asking short and simple questions. Think six words or less. “What is” questions bring us back to the basics:  What is a customer? What is a product? What is our industry? What is success? Another approach is asking three classic questions: What is working? What is not working? Why? If leaders have paid the price to build trust in their team and organization, then people will actively pursue the truth around each of these questions, especially about what’s not working. At the most innovative companies in the world, my recent research shows that leaders ask these questions ruthlessly because they are ruthless about the pursuit of truth. It’s the fundamental starting point to getting beyond “NO” to a more compelling “YES.”

Once we have a deeper grasp of what is actually going on by asking what’s working, what’s not, and why, then we can ask the classic forward thinking questions: What if? How might? Why not? These not only surface new ideas but invite good but well-hidden ideas back to the discussion table.

Hal Gregersen


The cadence of questioning and answering is something that you feel passionate about to encourage healthier conversations in business and in the workplace. Tell us about your "4-24” approach to questioning. What steps can companies take to implement it?

HG: The genesis of the 4-24 project comes from the harsh reality that most students face around the world when trying to ask questions at school: the fact that they don’t get to ask questions. The average student asks about six or seven questions in the classroom per month. The average teacher asks 350 to 650 questions every day. Students learn very quickly that answers matter far more than questions. The sad truth is that most workplaces don’t do much better when it comes to creating a culture of inquiry, or truth-seeking.  I want to turn that tragic statistic around before it’s too late.

One way of getting both adults and children to ask better questions is by making the Question Burst part of a daily routine. If we spend four minutes each day for an entire year on this, it adds up to about 24 hours of time. Consider this as a gift to ourselves of creative, reflective space where we can build better questions that help make a better world. The whole point of the 4-24 project is to get our questioning muscles back in shape. And if we do this as adults, the next generation is far more likely to do the same.

“The best organizations in the world go out of their way to foster provocative questions from every corner so that problems get solved faster and a better future gets created.”

Companies play an important role in creating a space where inquiry leads to insight and insight delivers impact. People need time and resources, aka safe spaces, to ask the right questions. In organizations, often the biggest barrier to asking the right questions and creating conversations that matter is the presence of leaders who are more committed to consolidating their power and privilege than making a better product, service, or workplace. Questions are the great equalizers in any organization because the best, most transformational questions often come from distant places, the outer edge of an organization, instead of headquarters. And that’s why the best organizations in the world go out of their way to foster provocative questions from every corner so that problems get solved faster and a better future gets created.  That’s exactly what we try to do at MIT, where colleague Bob Langer, founder of Langer Labs, perfectly frames the importance of asking the right questions for our generation–and the next: “If you think about the way you’re judged in life, I don’t think it is by how good your answers are; it’s by how good your questions are.” That’s why I do what I do. That’s why asking the right questions matters. That’s the meaning of my life. 

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