Add a Little Wonder to Your Life: The Case for Asking Big Questions

“We don’t ask ourselves the big questions enough these days.”

Michael Bungay Stanier is the author of The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever, and the Senior Partner and Founder of Box of Crayons. Michael recently chatted with Neil Pasricha, author of the New York Times bestseller The Happiness Equation: Want Nothing + Do Anything = Have Everything and Director of the Institute for Global Happiness, about the power of asking questions.

This conversation has been edited and condensed.

Michael: Your TEDx Talk “How do you maximize your tiny, short life?” wasn’t really a talk. As you said, it’s a TED Listen—the whole thing was just questions. It was a very different experience than a usual TED Talk, when somebody comes [out] and goes, “I’ve been thinking of this awesome idea and I’m now going to show you it with full slides and a bit of whiz-bang.”

You’re more about “I’ve been wrestling with these questions and I want to share some of those questions with you.” What made you go there?

Neil: TED is this incredibly interesting group of people from all walks of life and all backgrounds—entrepreneurs, venture capitalists, people running non-profits—but they sit silent all day.

I thought, “How do we get them to be the participants?” The original idea was to have people yell out answers but I realized I couldn’t manage that! So I let the answers sit in people’s heads.

Michael: Which was a good call. It’s more powerful as an experience to watch.

Neil: It’s the same reason why I didn’t do PowerPoint slides. When we have nothing to hook our minds on and we’re in a chair and there’s nowhere else we can go, then our brains either do one of two things: You either totally opt out or you’re so engaged you’re almost having a transcendent experience. I was aiming for the latter. I just think that we don’t ask ourselves the big questions enough these days. None of us do—myself included.

Michael: Was there one question that particularly resonated for you?

Neil: Most of them! I tried braiding together three themes. One was community, the capstone question being “Who are you in this with?” Then time. Not how we measure time but how we make time feel longer. So the capstone was “How will you measure your life?” And the third was impact: “How well do you know your grandparents’ grandparents?” and “How well will your grandchildren’s grandchildren know you?” The point being not very well … and they won’t.

“What is the single biggest thing you’re giving to the future of our species?”

So oh no, life is infinitesimally small already and now it feels smaller. But the last point was: What is your baton? What is the single biggest thing you’re giving to the future of our species?

I still don’t know the answers, but I just feel like life is so small. It’s over in the blink of an eye. And everything we consume, wear, see, drive to work in, ride on, walk on top of—every one of those things came from someone else who, maybe 100, 1,000, 10,000 years ago, contributed to this amazing thing called a wheel or a shoe or a suture or a song… and so, partly what I was trying to do is [ask], are you thankful enough for how much crazy, ridiculous, incredible stuff you’re using today which someone just gave to you? Pasteurizing the cheese [you’re] eating. The process that made [your] coffee. The guy laying the pipe underneath the city to give the water [you] drink.

And how can you be one of those overly impactful people in the next [hundred], thousand, or ten thousand years?

Michael: I read a quote like, “Questions are the portals of discovery,” and I love that, because [when] you ask the right question, a doorway opens up into new and different futures.

But the challenge is how do you sit with the question? Because, to your point, there’s that awkwardness and tension. You open up a space of ambiguity and uncertainty. It’s much more comfortable to go with what we know or what we think we know.

Neil: Totally. Think about a boardroom meeting. How often is the entire room sitting in silence? Pretty much never. Yet André Perold, a famous Harvard professor, used to tell me: “The only time everyone is thinking is when no one is talking.” Imagine if a CEO said, “Hmm, what should we do about this new competitive entry? Wait, no one answer for a minute!” No one does that.

Michael: One of the questions I think is really powerful—and really hard to answer—is, “What do you want?”

“It’s the LinkedIn profile-ification of the world. We try to distill our gigantic, ambiguous, complex selves into these narrow buckets: what degree, what job title.”

Neil: It is extremely challenging. As a dad, I still pigeonhole my kid all the time without letting that question simmer. We were at the subway station and he saw the train operator sticking his head out of the window when the subway drives into the platform. He said, “I want to be that guy when I’m older.” So I say to friends, “You know, my son wants to be the subway train driver, the head-sticker-outer guy.” And right away what he wants to do is narrowed to, first of all, an occupation. Then I create permanence around that.

It’s the LinkedIn profile-ification of the world. We try to distill our gigantic, ambiguous, complex selves into these narrow buckets: what degree, what job title. It’s because we don’t give ourselves space to really surround ourselves with the root questions: “What do you want? Who are you? What do you want to become?” They’re huge questions, they’re not easily answered, and they’re also dynamic.

Michael: And related to this is the question, “What do I not want?” It’s not just what can I have. It’s what can I not have or let go of or move away from?

It’s so easy to chase what [it] looks like you should have. I think of my life and I’m like, “Okay, I don’t own a house, I don’t own a car, I don’t have children.” It’s not that radical, but it’s different from a lot of the expected ways to live your life. And it comes from sitting down and asking, “Wait, do I want to buy a house? Why would I buy a house? What’s making me want the house?” My wife and I don’t actually want a house. It’s not the thing we want at all. But, if you don’t ask that question—“What do I want? What do I not want?”—you’re not questioning what’s influencing you to buy or chase or pursue, and you can chase empty goals.

Neil: I agree. So how do we ask ourselves more big questions? Especially in the corporate [world], it’s easy for everyone below the top level to be doing without asking. I worked at Walmart for ten years. We had dramatically disruptive businesses through our marketplace. But it wasn’t talked about.

How do you miss things like that? If you’re asking those questions, then you’re going to miss getting disrupted.

Michael: Part of it is having people who pull [us] aside, hold [our] feet to the fire a little bit and ask [us] the questions. Because I might not be asking them myself. And then when I don’t have an immediate answer, they come back a week later and say, “So, where did you get with that?”

Neil: Yes, and if you are indeed the average of the five people around you, then at least make sure those five people are very diverse from each other. Look around and make sure you’ve got the oldest friend in your life, plus the newest friend, plus somebody you met at work. Because they aren’t deep into your world like you are. If I say, “Oh, my book made the bestseller list!” they don’t say “Congrats!”… they say “Why did you write a book?” And then I’m like, “Hmm, wait a minute…”

Michael: Exactly. That comes from different people with different perspectives who see you through a different lens, and therefore ask different questions about how you are in the world.

“If you are indeed the average of the five people around you, then at least make sure those five people are very diverse from each other.”

Neil: That’s a fantastic way to do it. The other thing you can do is be conscious of putting it into your calendar.

There used to be an old document people at Walmart used to forward around, like, “Questions that leaders should ask themselves.” Somebody at work printed it off and photocopied it for everybody. And I saw some of the executives put it up on their office wall. It was a list of questions: “Where are we going? Do my people know where we’re going? Am I getting asked enough questions from my direct reports? Do I know who my best performer is?” It was these kinds of questions, and they hung them up on the wall. Put it somewhere where you bump into it.

Michael: Marshall Goldsmith hires somebody to call him every single day… He’s got the five questions that matter to him. “Did I write today? Did I do my press-ups today?” And so on. And he literally hires somebody whose only job is to call him up every day and ask him those questions.

He says something like: “I’m too cowardly to create the time to sit down and answer these questions myself.” And I totally understand that, because I have this same streak of cowardice and slipperiness. I’ll find a way of avoiding doing this work. So he literally pays somebody, kind of that external accountability piece.

Neil: Because you know the call is coming, you’re going to go to the gym.

Michael: Right. And if this is the 17th time in a row that you’ve answered “No” to that question, either you’ve got to get your act together, or you should find a different question. So maybe this isn’t a question that matters… or maybe it matters a lot.