Are you asking yourself the right questions?

How to spark catalytic questions that lead to breakthrough insights

This article was written for the Tony Robbins blog by Hal Gregersen, executive director of the MIT Leadership Center, and was inspired by research and case studies contained in his new book, “Questions are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life.”

About 20 years ago I was leading a brainstorming session and we got very stuck discussing something that many organizations struggle with: how to build a culture of equality in a male-dominated environment. With a few minutes left till everyone had to leave, we had done a lot of talking, but the energy level in the room was essentially nil.

Glancing at the clock, I resolved at least to give us a starting point for the next session. “Everyone,” I improvised, “let’s forget about finding better answers. Let’s just write down better questions we could be asking about this problem. Let’s see how many we can generate.” They dutifully started to throw out dozens of questions. To my astonishment, the room quickly reenergized. Instead of trudging out at the end, people left excited. And with good reason: among the questions scribbled down were a few catalytic ones that deeply challenged assumptions and opened up potential new solutions.

Brainstorming for questions, not answers – a process I now call a “Question Burst” – wasn’t something I’d tried before. It just occurred to me in that moment and I have since used it in hundreds of sessions, with constant refinement. Over the years, I have learned that it creates a different kind of space where the usual rules and norms are suspended and different behaviors encouraged. This small-scale exercise has also convinced me that breakthrough questions aren’t just a product of superior cognitive processes going on inside people’s heads. To a great degree they’re a matter of creating the conditions where we can become a little more wrong, uncomfortable, and reflectively quiet. It’s in these settings that we encounter surprising, new questions to help solve our most vexing problems.

Recently I did some coaching work with the CEO of a global organization. We started out with typical work-related issues, but at one point the discussion took a turn toward home. The CEO expressed concerns about his eldest daughter, who was just turning thirteen. For all those years, he had cherished his close relationship with his daughter, but as the teen-hood transition became real, he felt her pulling away. We decided to do a Question Burst about his concerns. Here are some of the questions we generated in four minutes

  1. Do I listen enough or tend to solve too much?
  2. Do I push too hard?
  3.  Do I hover too much?
  4. What is she the best at?
  5. Do I recognize that enough?
  6. How is she better than you?
  7. What do her eyes say when she expresses concern?
  8. How can you slow down to see what you’re missing?
  9. What does your schedule say matters most to you?
  10. What are her greatest worries?
  11. How well do you know who she is?
  12. Who would she be if her last name wasn’t yours?
  13. What is uniquely independent about her?
  14. When do her eyes sparkle?
  15. What are her greatest areas of independence from me?
  16. What has she learned lately from her own experience?

His review of the questions afterward immediately turned into a deep conversation about the role parents play in the lives of daughters and how parents can do too much hand-holding as children grow, robbing them of their own journeys. By the end of our conversation he had arrived at an approach he felt good about: “I had been focused on how not to lose her, but I now realize the real question is how to support her growing and flourishing on her own. I need to let her find her.” His insight, painfully brought to the surface, brought tears to my eyes then, and does now as well.

If you are looking for new insights to solve a problem you care about, you may want to try out the Question Burst exercise. Here’s a brief user’s guide sourced from my new book, Questions are the Answer.

Step 1: Set the Stage

Select a challenge you care deeply about. Perhaps you’ve suffered a setback, or you have an indistinct sense of an intriguing opportunity. How do you know it’s a problem ripe for a breakthrough, given the right unlocking question? It’s probably a good candidate if it “makes your heart beat fast,” as Intuit CEO Brad Smith put it.

Next, invite a small group to help you consider that challenge from fresh angles. Bringing others into the process provides a wider knowledge base and helps maintain a constructive mindset. Include two or three people who are starkly different from you in terms of their “insider” understanding of the problem and general worldview. They may well generate compelling questions that you would not because they have no investment in the status quo.

With your partners assembled, give yourself just two minutes to lay out the problem. Once you’ve gone to the trouble of engaging willing helpers, it would be a pity to pollute their minds with your preconceptions before you’ve gained any benefit from their thinking.

Before launching into question generation, clearly spell out two critical rules of engagement. First, ask people to contribute only questions. Explain that those who try to suggest solutions will be redirected. Second, explain that no preambles are allowed. Explanations and details, short or long, mainly guide people to see the problem in a certain way – the very thing you’re trying to avoid.

Now, do a quick emotion check. Are your feelings about the challenge positive, neutral, or negative? Jot down your baseline mood. You’ll do it again after the session is over.

Step 2: Generate the Questions

Set a timer and spend the four minutes collectively brainstorming surprising and provocative questions about the challenge. No pushback is allowed on others’ contributions. Capture every question verbatim and ask your partners to keep you honest on this; otherwise, you might unconsciously censor something you don’t want to hear. As you’re writing, add your own questions to the mix.

Once the timer goes off, do another quick emotion check. Are you more positive about the challenge than before? If not, try rerunning the exercise. Or try again tomorrow. Or try it with different people. Remember that this exercise not only sparks valuable new questions but also provides a positive emotion boost 85% of the time, making it more likely that you will make progress.

Step 3: Unpack the Questions

On your own, study the questions you jotted down. Select a few that intrigue you and strike you as different from how you’ve been going about things. A few criteria can help as you consider each question: Is it one you have not asked or been asked before? Is it one for which you honestly don’t have a good answer? Is it one that evokes an emotional response, positive or negative? In other words, subject the questions to a surprise test, an honesty test, and a gut-check test.

Finally, commit to the quest – the pursuit of at least one new pathway you’ve glimpsed – and do so as a truth seeker. Set aside considerations of what might be more comfortable to conclude or easier to implement, and instead focus on what it will take to get the problem solved. Devise a near-term action plan: What concrete actions will you personally take in the next three weeks to find potential solutions suggested by your new questions?

That’s how the Question Burst works. The exercise helps people gain energy, reframe problems and uncover new solutions to achieve powerful, positive results more than 80% of the time – because it consistently creates the special conditions where catalytic questions can thrive. And that makes all the difference.

About Hal Gregersen

Hal Gregersen is Executive Director of the MIT Leadership Center, a Senior Lecturer in Leadership and Innovation at the MIT Sloan School of Management, and the founder of the 4-24 Project. A Thinkers50 globally ranked management thinker, he is the author of Questions Are the Answer: A Breakthrough Approach to Your Most Vexing Problems at Work and in Life (HarperCollins, November 2018).

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