385: Unlocking New Ideas by Asking Better Questions with Hal Gregersen

Pete Mockaitis
Hal, thanks so much for joining us here on the How to be Awesome at Your Job podcast.

Hal Gregersen
Thanks Pete. Wonderful to be with you today.

Pete Mockaitis
I’m so excited to dig into this good stuff. Thanks, Janika, a listener, for connecting us. That’s pretty cool.

Hal Gregersen
Janika is exceptional at asking questions. Years ago she was a research assistant worked with me and helped me push the edge in some of my work back then and still does that today.

Pete Mockaitis
That’s cool. Well, I want to hear about different boundaries, if you will. You’ve lived in ten different states and five different countries. What are some of the key things you’ve learned from having been around?

Hal Gregersen
Oh, where do you start? Have you ever lived in – have you had the chance to live in more than one country, Pete?

Pete Mockaitis
Well, lived in is probably a strong word. I purchased groceries and I was there for a week, but I don’t know if it counts.

Hal Gregersen
I love it. I love it. As you well know traveling to a country and living in a country are two different things. The power of living in a different country is that – or even living in a bicultural family is that it doubles the probability that we’ll ask another that otherwise we wouldn’t ask and get a valuable new idea that otherwise we would never get.

All of that happens because we’re able to see the world through completely different values and lenses. One of the greatest gifts that we can give to ourselves or to those closest to us is actually a chance to live in a different place, a very different culture. They’ve been profound.

Part of that seeing the world through a different lens comes from being pushed to the complete edge of your experience. When I moved to France, I didn’t know French. At every level of my life, I was pushed to the edge. In work it was a completely new work routine. In our village and community, it was very difficult to get integrated. In our church context, it was similarly difficult to integrate.

To be truthful, Pete, for probably two or three years I was moderately to severely depressed, sometimes just wanting to pull the covers over my head and “I don’t want to get up and go to work today.” It just completely flattened me out, pushed me down. But sometimes it’s from the dirt of the earth that we sort of rise.

Out of that came some grounding, some very different ways of looking at the world and gratefully so. I never would have said that in the middle of it, but you have people who are around you who help you rethink and re-ask and reframe in ways that we’ve walked away from these five countries always with friends who are so close and deep that you can meet them 5 – 10 – 15 years later and it’s like it was yesterday.

Pete Mockaitis
Beautiful. That’s cool. What a blessing. Cool. I’m speechless. Well, let’s talk about right now your work role is the director of MIT Leadership Center. What is that all about?

Hal Gregersen
Well, the leadership center was started over a decade ago. It’s a leadership center for all of MIT, including the business school, but even beyond. I came here four or five years ago.

When I landed I ran across this … Foundation report, which basically said that the alumni from MIT have launched over 30,000 active companies. They employee close to 5 million people. They generate almost 2 trillion of revenue in the world, which is like between a ninth and tenth largest gross domestic product by county in the world. I’m like how do they do that.

We for several years literally studied MIT alumni and graduates to figure out what is it they’re doing that enables them to create this enormous change in value and approach to the world. What we landed on, Pete, was we call it problem-led leadership.

Leaders at MIT don’t step up to follow people. It’s all about what’s the challenge, what’s the problem you care so deeply about that I would love to work with you on it. That’s just how they operate. They pick big, huge problems. These are incredibly bright, smart, analytical people.

But they pick problems that are so big they cannot solve them themselves. As a result it’s this fascinating team dynamic of you’ve got this skill, I’ve got that skill. You step up; I step back. You step up; I step back. We just iterate and we bump into deep conflicts. Over time we actually solve things that other people often don’t.

It’s a fascinating way of looking at leadership. It’s all about waking up and showing up in the morning with what challenge and problem is so interesting to me that I can’t not solve it. Now contrast that with people who wake up and go to work in the morning wondering what’s the politics of the day in the workplace. That’s the antithesis of the problem-led organization.

That’s why I love MIT. This place just thrives on trying to figure out what are the world’s biggest challenges to solve. You and I both know there are big challenges out there. What’s really fascinating is that for the most part these folks are deeply engaged in actually solving some edges of the biggest problems.

Pete Mockaitis
That’s really interesting because you think of people at MIT, there are associations in terms of utter brilliance and then also maybe some of the pejorative associations of some of that if you think about a computer engineering person. I’m sure that’s pretty unfair for a large swath of the population there.

But it’s really intriguing you think that you’ve got those brains and it’s almost like the only way you can get a rush or to have some real fun with that brain is to get a problem that’s just gigantic and go after it.

Hal Gregersen
Well, one of my former executive MBA students recently I bumped into him. He works at Metro Biotech. You’ve probably never heard of the place, but they basically take blood samples of cancer – people in cancer – who know they have cancer and they’re going to get treatment, but we have to figure out as oncologists, what treatment should we give them. Historically, it’s like a guessing game.

He and others at Metro Biotech, they literally have used some of the questioning techniques you and I are going to talk about, but they are just problem solvers and questioners of the core to the point that they’ve created this ability to draw the blood of someone that has cancer and to test it rapidly in a few days with different protocols of different chemotherapy protocols and they can pretty much nail it that this is the one that will work.

At one point, they were just stuck trying to figure out a better solution to what they were doing with their technology. They literally asked nothing but questions, a method he had learned from me in class and his team. It actually unstuck in a way that got them to get a better, more accurate answer and a quicker answer.

The cool thing about that is that one of his relatives was in cancer treatment or preparing to as they were doing it. It was one of those just-in-time solutions that came by asking a different question that otherwise wouldn’t have happened. We may look at MIT people as nerds. They’re certainly bright and they’re smart, but they really do solve problems that make our lives better.

Pete Mockaitis
Absolutely. Not to slam any MIT people. Huge respect all the way around. I’ve got plenty of nerdy tendencies myself.

Hal Gregersen
No, I didn’t take it as a slam, Pete. On the one hand they’re really good at that and on the other hand, the Achilles heel often is some empathy and perspective taking and figuring out what’s going on in the room beyond the problem being solved. There are challenges too that come of it.

Pete Mockaitis
I’m fascinated by this. This cancer treatment selection knowledge that has been created, is this kind of widespread and common practice now?

Hal Gregersen
More so. They are doing it around the world. The colleague of mine, the former student, he’s running the India operation now. They’re trying to do that all over.

Another guy named Jeff Karp, who’s affiliated with the MIT system and runs Karp Labs. He was trying to figure out how can you heal a baby’s heart when you’re doing an operation when it’s moving and wet and sticky, but you’ve got to hook it together and hold it together. He actually learned by looking at slugs and other different things in the real world how to create this gooey substance that actually holds the sticky thing together. It’s amazing.

Pete Mockaitis
That’s cool. That’s cool. Well, let’s dig into this approach in terms of nothing but questions. You unpack a bit of this in your book, Questions Are the Answer. What’s sort of the broad thesis of the book?

Hal Gregersen
At the very core it’s so counterintuitive because usually when we’re stuck, we just double down and dig deeper and deeper for what’s the right answer here, what’s the right answer here. Counter intuitively, when we are operating at the edge of uncertainty, when we’re trying to figure out what we don’t know we don’t know, by definition there are not answers on that edge. We’re looking for something that isn’t there.

But asking a different question will actually unlock a new answer that we otherwise would never have seen. It’s almost by definition when we’re working in a world or on the edge of uncertainty and the unknown, questions are the answer. When we’re stuck, whether it be at work or in life, when we’re stuck, we’re just asking the wrong questions. The path out of that stuckedness, the window, the door to something better is actually that key of asking the right question.

Pete Mockaitis
Well, very intriguing. Can you maybe give us an example?

Hal Gregersen
For example, I met, when I lived in France, Andreas Heinecke, who 30 years ago – plus years ago, he’s a reporter in Germany working I think at a newspaper. His boss brings a new employee in and says, “This guy got in an accident. He used to be able to see, but now he’s blind. Andreas, could you help him figure out how to be a reporter?” Andreas is like, “What? What do I do here?”

But Andreas when he was a little kid had a hearing disability. It made it a little hard. Kids made fun of him, so Andreas was sensitive to this man’s situation. His first question was, “What kinds of tasks could this person do as a reporter,” which is a good question. It opened up some opportunities there.

Then he worked it and worked with this guy and worked the question to the point that it became a different question, Pete. The new question was “Where could someone without sight thrive at work? Not just do a few tasks, but thrive.” When he asked that question, he thought about it and he realized they would thrive at a workplace that’s dark, pitch black.

He created Dialogue in the Dark, where literally people like you and me, they pay an amount, we go to one of their exhibits all over the world and we go through the dark space guided by blind people, who are adept and professional in the dark. You and I have to learn how to cross streets, navigate restaurants, navigate buying food, navigate walking in the park, all in the dark.

What he’s done with that is he’s created this experience where as we interact with the dark-sighted people, we gain deeper empathy for others who don’t have what we have. We learn things and we have our assumptions challenged. This has happened with ten million people now. They’re one of the largest employers of blind people on the earth.

All of that came from Andreas reframing a good question, which was “What could this blind person do as a reporter?” to “Where could a blind person thrive?” Then it turned into this social enterprise that literally has made a big impact, especially for those working in it as the blind folks, but also the ten million-plus visitors who genuinely walk away having seen the world differently.

Pete Mockaitis
This is fascinating. You said the question evolved. How can we facilitate/accelerate this question evolution?

Hal Gregersen
Well, this is the tricky thing. You haven’t done it yet. Maybe you will. I think you just might. But most reporters ask me the question, “Well, Hal, what are the questions I should be asking?” which is not a bad question at one level.

I can say, “Well, Pete, I think you should start with trying to figure out what’s going on in the situation? What’s working, what’s not and why?” Then once you understand what’s really going on, it’s like, well, let’s try some prescriptive future … questions, like “What if this?” and “Why not that?” and “How might this?” and so on. Those are giving you a list of questions.

But what I discovered in interviewing 200-plus of some of the world’s most creative leaders. Jeff Bezos at Amazon, Daniel Lamarre, the CEO of Cirque de Soleil, Ed Catmull, who is the CEO and the founder of Pixar and now Disney Animation Studios, Diane Greene, who founded VMware. I can go on with a list of just amazing people, who are sustainably innovative and creative.

When I ask them, “How do you find the right question when you’re stuck?” They didn’t give me a list of questions. What they said was, “We intentionally put ourselves in situations over and over and over so that the right question for the context emerges and opens up doors and windows that would never have opened.

Now that probably sounds like, “What are you talking about? That’s just some big theoretical blah, blah, blah,” but that’s what it was. They put themselves in conditions where questions came to them that otherwise wouldn’t. They were so unique to the situation, like Andreas Heinecke’s was, that it often led to the creation of the business, some of which today are worth billions of dollars.

Pete Mockaitis
You’re putting yourself in that situation, that context, what does that mean exactly? It’s just sort of like taking on a challenge bigger than you have any idea of what you’re doing or what does that context insertion look like?

Hal Gregersen
It starts with either having a challenge or it starts with a problem or an opportunity, but then it’s putting myself in situations where I’m going to ask different questions. Here’s the conditions, at least that I discovered with these 200 people. Put ourselves in conditions where we’re wrong, not right, where the situation makes us feel a little bit uncomfortable, in fact maybe quite uncomfortable.

When most of us are wrong and uncomfortable, our instinct is to run from it, but these folks embraced it in a way that they were reflectively quiet. As a result, the question emerged that unlocked doors that otherwise weren’t there. It’s being wrong, uncomfortable and reflectively quiet. What kinds of situations do that?

I can give you a quick example. Literally, over a decade ago, it was my first interview with Marc Benioff, who founded Salesforce.com. He’s originally a sales person for Oracle. He’s doing a great job. He’s incredibly successful. He’s always at the edge of the organization, constantly bumping into customers, getting positive and negative feedback about what’s working and what isn’t.

By the end of 15 years, he’s slightly burnt out while he’s incredibly successful and he’s got this … challenge that he’s been trying to figure out, which is “How on earth can small- and medium-size enterprises take full advantage of this large enterprise software when they can’t afford it?” That’s what he’s trying to figure out. Part of that comes from his own family history of small and medium enterprises.

Anyway, he’s trying to figure it out. But he doesn’t have an answer. He takes a year-long sabbatical, but he doesn’t sit around on his behind. He does what he’s been doing for the last 15 years. He gets up, he gets out, he talks to people all over the world, rich people, poor people, government leaders, business leaders, religious leaders, just a whole range of folks from different perspectives.

He’s constantly bumping into himself being wrong and a bit uncomfortable about answers that he’s hearing and questions that are getting asked, but he’s reformulating and reformulating and trying to figure out this issue of small – medium enterprise and large enterprise software. Then he’s swimming with the dolphins and he finally gets the question, which is what if we sold enterprise level software like Amazon sells books on the internet.

He did not find that question looking in a book of questions to ask. That question today seems inevitable. It seems self-evident, but back then they thought he was an idiot when he asked it. But he’d done that hard, wrong, uncomfortable, quiet homework over and over to where the question emerged that otherwise wouldn’t.

Pete Mockaitis
The homework, when he’s talking to these people, what’s he asking these people?

Hal Gregersen
It would range from – some of those questions I mentioned earlier, Pete. I’m not exactly sure what he was asking, but my hunch would be he’s trying to figure out first of all what’s the terrain. “What’s working in your world? What isn’t?” And trying to create a safe enough space that people actually give him honest answers. That’s the tough thing.

Those are simple questions, Pete. What’s working, what’s not, and why? But creating a safe enough space for people to give you the honest answer, that’s a tough one.

When I met Marc a few years ago walking through the World Economic Forum … meetings, I was visiting with him. I said, “Mark, how do you ask the right questions?” He looked me right in the eye – he’s about my same height at six foot four-ish – and he just said one work, “Listen.” Then he was quiet.

I’m like, “What’s he doing here?” I think what Mark was doing was figuring what kind of listener is Hal Gregersen. Is it just ears? Is he all here? Is he 100% present? Then after a few seconds, he waited and then we had a 15 minute or so conversation about what does it mean to listen, ranging from Jewish Kabbalistic traditions to the whole – it was a worldwide kind of conversation about what does it mean to listen.

I think that’s what he was doing. He was posing questions. “What’s working around here? What are you frustrated with?” Then he shut up.

One of the diagnostic questions of whether or not we’re good in these conditions of raw, uncomfortable and quiet is when we ask a question, how long do we normally wait on average for someone else to answer. 1,001, 1002, 1003, 1,004, 1,005. If people are answering our questions within one to two seconds, or we’re filling in the space with some follow up question or our own answer, pretty much everybody in the room already knows the answers and the question is probably not even worth asking.

The real question are ones where it causes someone else and/or us to step back, think twice, reflect a bit. It’s usually a three-second pause rate. Then we start a conversation. It’s not just a back and forth. It’s a conversation to try to figure something out.

I’m live here in Massachusetts and one of the former governors, Deval Patrick, he once told me in an interview I had with him, he just said, “It’s the power of the pause, Hal.” He said, whether it’s working as a consultant when he was young as a Bain consultant or whether it was – I think he was at Bain – whether it’s being the governor, he said “It’s always that last one or two seconds after you ask a question that if you’re just quiet and listen and people know you care, people will start offering you information.”

Again, it might be information that can make you feel really uncomfortable and really wrong about how you’re looking at the world, but it’s the stuff that changes things.

Pete Mockaitis
That’s lovely, thank you. Now I’m curious. Let’s talk about listening well such that the other person is feeling safe. I guess one of the key is just be okay being silent for more than three seconds. That can take you fairly far. What are some of the other best practices in terms of listening well and creating that psychological safety such that folks will really tell you the truth about what’s working, what’s not working, etcetera.

Hal Gregersen
Can I come back to your question-

Hal Gregersen
-from a different angle, Pete, which is there’s this method that I discovered 20 years ago called the Question Burst. I was with a group of people. I was stuck in a challenge. We were stuck collectively. It was about some gender diversity and equity issues in the organization.

The energy was low in the room. We were just languishing. I think you know those moments. I had this instinct from what I’d been reading from some things from Parker Palmer and other folks like how – just stop everything and ask nothing but questions. That’s what we did.

It was the days of blackboards. We had three or four blackboards in the room we were operating in. I said, “Let’s just fill these blackboards up with nothing but questions for the next 10 – 15 minutes. No answers to them, no explanations as to why we’re asking the question, just questions.” By the end of that process, it was like, “Whoa, what happened here?” The energy rose. Ideas to actually solve the problem surfaced that otherwise weren’t there.

Ever since then I’ve used this Question Burst method sometimes in four-minute bursts with individuals or with pairs or with trios or in groups of five or six, where it’s even longer than four minutes at times, but the rules are no answers to questions, no explanations of the questions for a very fixed period of time.

When we do that, we get to the end of that process and 80% of the time we’re emotionally in a better place, 80% of the time we have at least one new idea, 80% of the time we’ve reframed the challenge at least slightly. It’s like an amazing vehicle by which we see things differently.

That question burst is what I did with the senior executive at a company that was trying to listen better. That’s where I’m coming back to your question on how do you listen better.

I was talking with him about a challenge, which was one of their distribution facilities, where people were packing and shipping stuff, the workers felt like they were being treated inequitably. The reality was, they were being – with their pay. The reality was they were being paid higher than market rate for that region and area.

We did this question burst. I said, “Okay, let’s set the timer, four minutes, nothing but questions, no answers, no explanations.” We got 20 questions at the end of that. Then we looked through them. I asked him, “Which questions really resonated for you that they might help you solve this challenge?” These are two of the ones that were really crucial.

First question was “How often are you in that facility,” that packaging facility. His answer was he couldn’t remember the last time he visited it. The second question was “What do you see in their eyes when they’re expressing this sense of unfairness about pay?” He didn’t know, but he knew he needed to know. The good news is he got up, he got out, he got into the world, he got into their world and he started building the trust by which he could get answers to those questions.

Pete Mockaitis
Oh yeah.

Hal Gregersen
That’s one of the biggest things is that we rarely get a catalytic question, a transformational question, we rarely get an idea that changes the world or it’s breakthrough. It rarely if ever happens sitting in our office.

Sitting in our office is a great place to be isolated, to be comfortable, to be right. That’s what offices are for generally. But getting up and out, where the situations would put us in front of people and places where we’re provoked and wrong and uncomfortable, that’s where the better questions surface.

Pete Mockaitis
I really like that. That really made it clear in terms of the being wrong and uncomfortable in terms of saying, “I don’t know and I feel like I should. I have done wrong by not getting there often enough. I’m uncomfortable by the fact that you’ve exposed this shortcoming or inadequacy in my management.”

Hal Gregersen
Yeah. Can I show you a personal experience about that?

Pete Mockaitis
Oh yeah.

Hal Gregersen
Here at MIT they invited me to do a questioning workshop or seminar with some of the local administrative staff from the floor that I’m on in the area. I did and we sat down and it’s this, again, part of the workshop is this Question Burst method. We sat in trios. We each took two minutes to explain our challenge and then four minutes to generate questions. I was the third person in the trio.

It came my turn and I explained my challenge, which was, “It’s just really hard for me to work with administrative assistants. I’m not quite sure what to ask them to do or how to get them meaningfully involved with my work?” Then it was quiet. Okay, four minutes nothing but questions.

The first question that one of the admin assistants in this trio said to me, Pete, she said, “Hal, do you have control issues?” I’m not kidding. It was like this hot dagger that just got jabbed into my heart. I felt a bit flushed. I felt awkward. It was like, man, she went right to the issue, didn’t she?

What’s beautiful about this simple process of asking nothing but questions is that it forces us to be quiet. We can’t answer. We can’t respond. We have to live with the question. By the end of it I realized I need to rethink some things that I’m doing.

Pete Mockaitis
With the question burst approach – you mentioned your situation associated with administrative assistants. Other chimed in with their questions. Are you not generating questions? Are you just receiving questions?

Hal Gregersen
You want to try it, you want to give it a run.

Pete Mockaitis
Let’s go for it. Yeah.

Hal Gregersen
Why don’t you explain to me a challenge? Here’s how it works. We explain a challenge to somebody. Here’s my opportunity or challenge. We have no more than two minutes to do that. That’s purposeful because if we explain it for more than two minutes, we start walking other people into our stuckedness. We tell them too much. It’s a two minute rule, just explain it in two minutes. Then at the end – if it’s less than two minutes, I get it, fine.

But then we just for four minutes ask nothing but questions about the challenge. Do you want to give it a run?

Pete Mockaitis
Okay, sure thing. Now what I’m clarifying is, you are the sole question generator or are we both generating questions?

Hal Gregersen
I actually do this myself alone. If I’m doing it with somebody else, both of us, Pete, generate questions.

Pete Mockaitis
All right, both of us.

Hal Gregersen
But if it’s your challenge, on average you’re probably well off to listen mostly to my questions.

Pete Mockaitis
Okay, so I’ll you do the majority. All right, well, let’s go for it.

Hal Gregersen
Okay.

Hal Gregersen
The best use of this method is to pick a challenge that is really important to you, that you’re really stuck on and that you might feel a little awkward telling the world about.

Pete Mockaitis
Okay.

Hal Gregersen
So go for it.

Pete Mockaitis
Well, I think this counts. I do feel somewhat awkward, especially telling this world about it because I want to talk about the podcast itself in terms of I’ve observed in terms of the data from the number of downloads or the engagement in terms of how deep into an episode people listen, it’s rather clear that some episodes are hits and other yeah, okay.

I’d like them all to be hits.

Hal Gregersen
Yeah, yeah.

Pete Mockaitis
Yeah, how can I make that happen?

Hal Gregersen
Okay, so the challenge is how I can make everything a hit?

Pete Mockaitis
Yeah.

Hal Gregersen
Okay, here we go. I’m going to set my timer, four minutes and we’re going to launch into it. Are you ready?

Pete Mockaitis
I’m ready.

Hal Gregersen
Here we go. Here’s the other rule as we start. I’m inviting you to write all the questions down verbatim, word-for-word because sometimes if you switch the words that I say to your words, you miss the question.

Pete Mockaitis
Okay, I’m going to typing going because I type faster.

Hal Gregersen
Okay, just type as fast as you can. Here we go.

Can every podcast be a hit? Is that realistic? What makes you uncomfortable when podcasts don’t work? What kinds of people generate the most interest? Is there any commonality across it? Whom do you most care about as an audience member? If you could influence one person on planet Earth with your podcast, who would that be? Why does having a perfect hit rate work or high success rate, why does it matter? What is success on a podcast?

Pete Mockaitis
I’ll throw out a question. What’s the mix or breakdown of guest sources in terms of where are they coming from and what proportions?

Hal Gregersen
What podcasts hit emotions the hardest? How might you create better stories? What is the arc of interaction on a great podcasts versus a not so great? Does anyone you know as a podcaster have a perfect track record? How might the podcast format make a perfect track record impossible? What metric of influence matters most to you? There we go, four minutes, done.

Pete Mockaitis
All right. Thank you. That’s cool.

Hal Gregersen
Let me ask you a couple of quick questions. Do you feel compared to before we started four minutes ago, do you feel the same emotionally? A little bit better or a little bit worse?

Pete Mockaitis
Well, I definitely feel better because a number of the questions get me thinking, “Yeah, okay. Does anyone you know have a perfect track record?” It’s like, well, no. I can see it the iTunes popularity little icons associated with their episodes is some are definitely 5x others in terms of what iTunes calls popularity. I feel better there in terms of okay, 100% is not something that I should feel bad about not hitting. There’s that.

Hal Gregersen
I hear you. I hear you.

Pete Mockaitis
I feel better there. Then I feel kind of reflective in terms of whoa, yeah, that’s heavy. Also, I’m excited about sort of ideas associated with – we talk about what generates the most interest.

It’s sort of like, well, shucks, I can just sort of put two things together in terms of we tagged every episode by the topic, subtopic and competency covered just recently. I’ve also gotten a bit more savvy with the Apple engagement data in terms of how to make real sense of it. It’s like well, why don’t I stick these two things together and we’ll see what we see in terms of some themes and commonalities.

Hal Gregersen
Okay, okay. You sound like you slightly reframed the challenge. It sounds like you got some ideas to do it differently. This is what I’m talking about. This Question Burst never solves the problem, but it creates progress and movement and that’s the point. It helps us move to a better and better question. Were any of the questions emotionally uncomfortable?

Pete Mockaitis
Well, yeah, some of them when it comes to “Well, how might you create better stories?” That gets me thinking to top, top podcasts that are really sort of narrative-story driven with sound beds and stuff.

Hal Gregersen
Right, right.

Pete Mockaitis
It’s like oh man, those guys are like the best in the world and we’re just chatting. I’m just chatting with professors. How might I create better stories? Boy, it seems like there’s quite a gap.

Hal Gregersen
I hear you. There are ways of closing that. My suggestion, Pete, around this is what you just experienced, if you did this two or three times with other people, you would not only continue to get better questions and answers, but you would also engage in a very productive way more and more people who would care about your challenge and help you do something about it.

It’s really powerful not as a sort of one-time experience, but as a pattern by which we actually create these conditions where people are wrong and uncomfortable and quiet. It’s an artificial way of doing it, but nevertheless it creates those conditions because my bet is you wanted to answer some of those questions. Am I right?

Pete Mockaitis
Oh sure.

Hal Gregersen
I hate to say it, but probably every answer you would have said, it was not going to be helpful, useful. It’s probably wrong anyways. Anyway.

Pete Mockaitis
And it’s cool, you mentioned earlier, it’s like “Hey, in four minutes, we generated 20 questions,” I was like, “Really? That’s a lot of questions for four minutes,” but sure enough I’m counting this up. We got 15 there.

It’s so funny you mentioned four minutes because I’ve just recently been noting that to be a great amount of time to sort of challenge myself to say straighten my desk. It’s short enough for me to not be intimidating, but also long enough to make some genuine progress and maybe even really feel like I’m in the zone and want to keep going. I’ve recently found four minutes to be kind of a magical time line for some stuff. How did you land on four minutes?

Hal Gregersen
Two ways. One is our sustainable attention span with full attention is a little under four minutes as adults. To me that was part of the four minutes.

The other part of the four minutes is there’s a project I found – it’s just in its nascent, early stage, but it’s called the 424 project, where literally if you or I spent just four minutes once a day trying to ask better questions about challenges and opportunities we care about, over the course of 365 days, we’ve just gifted ourselves 24 hours of our time, one full day, of just asking better questions. That to me is the other part of it.

Part of it is just sustained attention. Four minutes tends to be in one sense an upper end, but it’s also it’s kind of how might we help nudge the questioning capacity of others in the world forward.

Pete Mockaitis
That’s great. With that challenge then, you’re trying to find a new buddy each day?

Hal Gregersen
Absolutely. I was sitting down with someone who’s not only a friend, but we were doing a bit of coaching about some issues. He’s a CEO of a big organization. But his issue was quote personal. It was basically “I’ve been very close to my oldest daughter. She’s now a teenager, early teen and she’s starting to pull away with friends. How can I keep this relationship strong?” That was his problem definition.

We’re sitting at lunch having this coaching conversation and we got out some napkins, did a Question Burst, four minutes later, 22 questions later, just hear a few of the questions that we asked or I asked or he asked.

Do I listen enough or tend to act too fast? Do I push too hard? Do I helicopter too much? Do I recognize and praise what she’s best at? What talents complement yours as a father? When was the last time – what do her eyes say when she expresses concerns? What are her greatest worries? Who would she be if her last name wasn’t yours? What’s uniquely independent about her? What will you do when she gets married and moves out? What are her greatest areas of independence? These were tough questions.

Pete Mockaitis
Yeah. What I also love about these questions is that Question Burst is kind of quick and some of them I guess I’ve heard elsewhere like, “Oh, a powerful question is not one that has a yes or no answer.” Some of these do and that’s okay.

Hal Gregersen
It is okay. Some of them do, some of them don’t. They each can have their provocative element in one form or another.

At the end of this questioning process, this guy he realized – he actually got a little bit teary. He just said, “I’ve been focused on how not to lose her, but now I’m realizing that the real question is how can I support her growing and flourishing? How can I let her find her?” That’s a totally different question, but it ended up being the one that opened up a much better relationship.

The real issue just becomes how do we either at work or at home, especially at work on a productivity sort of logic, it’s not only how do I ask better questions, but how can I create a space where other people are regularly asking the tough questions to move what we’re doing forward. That’s the bigger issue.

Pete Mockaitis
This is beautiful. Hal, tell me, anything else you really want to make sure to mention before we shift gears and hear about some of your favorite things?

Hal Gregersen
It’s the point I just mentioned, which is whether it’s Ed Catmull at Pixar having a room called The Brain Trust, where directors get complete unvarnished full of candor feedback about their movies when they’re building them, where they learn that it sucks or it’s the Lion’s Den at Cirque du Soleil that does the same thing or it’s a working backwards process at Amazon, where people read documents about new ideas for 15 minutes, they shut up and be quiet and then they know the questions are going to fly about the idea.

At these innovative organizations with innovative leaders, they systematically in their own unique way always create spaces and processes where the tough questions get asked and people know what’s going to happen. When that happens, we start moving the needle. We start doing things better. We start changing the world.

It’s not just about us, but it’s about are we creating safe enough consistent spaces for our team, for our organization, for them to feel comfortable being wrong and uncomfortable and quiet so that we can ask the toughest questions, because those are the ones that unlock our biggest blind spots, the things we don’t know we don’t know. That’s the key to the future.

Pete Mockaitis

Beautiful. Now could you share with us a favorite quote, something you find inspiring?

Hal Gregersen

I love Elie Wiesel’s quote, “In the word ‘question’ there’s a beautiful word ‘quest.’ I love that word.” End quote. The questions that matter are the ones that we have to work hard for. Once we find them, they are a quest, but once we find them they open up doors that otherwise we’ll never see and it can benefit us and others.

Pete Mockaitis

How about a favorite study or experiment or bit of research?

Hal Gregersen

Actually, way, way back, Stanley Milgram’s study on obedience to authority, where common people like you and me once we get in positions of authority. In that particular study, they gave electrical shocks to people that were life threatening just because their role expected them to do that. That’s a short version of the study.

I’ve learned over my lifetime, it’s really easy for power to go to my head. The biggest inhibitor of asking questions is power and privilege. The challenge for me as a human being or for me as a leader is how do I get beyond that isolation of power and privilege and get out into the world in a way that I don’t get trapped in my bounds of authority.

Pete Mockaitis

How about a favorite book?

Hal Gregersen

I absolutely love Ed Catmull’s Creativity, Inc. He is so thoughtful about how do you build a sustainably creative organization.

There’s another book that’s a close second, if not first depending on the day, by Parker Palmer called Let Your Life Speak. It is a powerful inward auto-biographical look at his figuring out who he was and how to be whole with both the good and the bad that made up this person called Parker Palmer. It’s a profound book.

Pete Mockaitis

Thank you. How about a favorite tool, something that helps you be awesome at your job?

Hal Gregersen

I love the Headspace app. It’s a mediation app. It’s been super powerful for helping my head, my heart, my hands be more reflectively quiet. I can sometimes let anxiety and toxic worry just take over my life and Headspace has been a godsend to be able to not let that happen quite so much.

Pete Mockaitis

When you’re using Headspace, you just kind of march through the sequence that’s on there?

Hal Gregersen

Sometimes. Sometimes I start, but this isn’t one isn’t grabbing me. Right now I just started regrets because one of my challenges is holding onto regrets too long. I’ve still got to do the first exercise, which is write down all my regrets and then think about them briefly and cross them off before I go to section two. Some of them I work through, some of them I struggle with.

Pete Mockaitis

Is there a particular nugget you share that really seems to connect and resonate with folks that you’re working with?

Hal Gregersen

I love this one. I heard it from Tiffany Shlain. She founded the Webby Awards. Her father was an amazing physician. When Tiffany was growing up, her father told her over and over and over, quote, “If you’re not living on the edge, Tiffany, you are taking up too much space.” I think it’s just this invitation to push ourselves and others to the edge of whatever’s possible.

Pete Mockaitis

I love it. If folks want to learn more or get in touch, where would you point them?

Hal Gregersen

Easiest way is HalGregersen.com. There’s a contact space there. Or come visit me at MIT.

Pete Mockaitis

Do you have a final challenge or call to action for folks seeking to be awesome at their jobs?

Hal Gregersen

At the end of Stephen Hawking’s recent book, Brief Answers to the Biggest Question, his final chapter is on super intelligent – AI becoming super intelligent. He has a dystopian view of the world that it will take over.

My challenge and it’s why I’m not doing what I’m doing, it’s my next project, how can we nudge the questioning capacity of the world forward so that we as a human race, we will always ask the better questions compared to AI or super intelligence. Because if we don’t learn how to do that, we will lose that game. But I’m convinced somehow or another, we can continue to ask the better question.

Pete Mockaitis

Well, Hal, this has been a ton of fun and powerful, transformative. I think that a lot of question bursting is going to be popping up across the world. It’s been a delight. Please keep doing the great work you’re doing.

Hal Gregersen

Thank you Pete. You too. I appreciate it.