Big Ideas

Using the Power of Questions to Think Deeper, Act Faster, Create Better

As a journalist, questions are Warren Berger’s stock-in-trade. But what struck him when he interviewed software and product designers was the way they used questions to launch their creative process.


“They asked, ‘Why isn’t this situation working as well as it could?’” Berger told Convene. “Or, ‘Why isn’t there a product that does X, Y, or Z?’ ‘What if you took this existing thing and you redesigned it so it worked better?’ They were always trying to frame the right question to solve.” Asking “stupid questions,” one designer told Berger, was an important part of his job, “because no one else will ask them.” That notion “got in my head,” Berger said. “I started thinking, well, if questioning really is at the root of design, then more broadly, you could say it’s at the root of creative problem-solving and creating new things, new possibilities.”

Learn More: Listen to a podcast where Senior Editor Barbara Palmer and Editor in Chief Michelle Russell discuss so-called “dumb” questions

Fascinated with the power of questioning “as a way of looking at the world,” he spoke to more than a hundred business innovators, scientists, artists, engineers, filmmakers, educators, designers, and social entrepreneurs, and distilled their ideas into a practical “why/what if/how” system of inquiry — the backbone of A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas. Recently published, the book has received acclaim in media outlets including Fast Company, Fortune, Harvard Business Review, The New York Times, and The Wall Street Journal, among others.

We were born, Berger says, to ask questions, but that instinct gets squelched as we move through the education system and into the workforce. One possible reason, he writes in the book, is that “questions challenge authority and disrupt established structures, processes, and systems, forcing people to have to at least think about doing something differently.” Which can be a luxury in today’s fast-paced business environment, where, Berger writes, “We operate on autopilot — which can help us to save mental energy, allow us to multitask, and enable us to get through the daily grind.”

But getting through the daily grind is not the same thing as getting ahead. We can only innovate if we learn how to form and tackle what Berger calls “big, beautiful questions.”

Just what is a beautiful question? And how can it transform business — and the meetings industry in particular? Here’s what Berger told Convene.

Did you initially plan to focus exclusively on innovation in the book?

My whole initial focus was, where does questioning fit in that area of innovation and design and problem-solving? What is the role of questioning? Then as I got into it, I realized there is so much interesting stuff with questioning. It pulled me into the idea that questioning is not just about your business. It’s about your life. Then I got into the education part, realizing that if you’re going to talk about questioning, you have to go back to childhood and the fact that we start out as natural questioners.

It started to move in all of these different directions as I was working on it. And really one of the challenges in the book was to not go in too many directions. I eventually just said, okay, I’m going to break it down into four parts. I’m going to try to convince people why questioning is important and why it is underappreciated. I’m going to talk about education, and the fact that we start out questioning and then we seem to question less and less as we get older, and [the traditional] education [system] may be a part of that. Then I’m going to talk about what this all means in business, because questioning is so important in business. Then I’m going to wrap up by talking about questioning in our lives. So that was sort of the way that I came at the book.

You define a “beautiful question” in the book as a big, ambitious question that can be acted upon. That’s an important distinction, because that doesn’t necessarily mean that it can be answered.

Exactly right. I wanted to make a distinction between the kind of questions I’m talking about and philosophical questions, because I didn’t want to get into [questions like], “Why are we here on Earth?” or “What is the meaning of life?” I don’t have any problem with those kinds of questions, but to me those are different — they are spiritual or philosophical. They’re not questions that you’re going to necessarily act upon to bring about change. They are just questions that you may ruminate on for your whole life, but they’re not actionable.

One of the ideas you discuss in the book is how important it is to frame things the right way during brainstorming — or “question storming,” as you call it; changing the phrasing from “How can we…?” or “How should we…?” to “How might we…?” Yet you say that this approach doesn’t work on problems that are too broad or too narrow. Can you elaborate?

Well, first of all, “How might we…?” is a really interesting brainstorming approach that I discovered was being used at Google and at [the design firm] IDEO. What they figured out was just by using that language it seemed to open things up — using the word “might” gave people permission to explore and to not feel that they had to come up with the answer, that it was more of an open process of considering possibilities. It seemed to free up the conversation, that it’s really effective. That is one thing: getting the language right.
Then — this comes back to being actionable — you want to take on a problem or a challenge that you can begin to move forward on. Therefore, you don’t want your “How might we…?” question to be too unrealistic, like, “How might we create world peace tomorrow?” — because there’s nowhere to go with that. It’s too big. It’s too ambitious. It’s too broad.

There also are questions that I think aren’t ambitious enough: “How might we paint the walls a nicer color in our office?” or even “How might we raise the profit margin by .5 percent this quarter?” To me those questions [involve] things you’ve got to deal with in everyday business life, but they’re not really the kind of questions that are going to get people inspired and excited.

So the sweet spot is somewhere in the middle, where you’re thinking about something that is ambitious in terms of maybe a new way of doing something for your company or your industry or your business. It’s a new spin on something, but it’s not so outrageously ambitious that you can’t begin to take steps on it. That’s what you’re looking for when you’re getting together as a group. You’re saying, “How might we find a way to get our customers more engaged in X?” You’re trying to find that nice, middle ground that is both ambitious and actionable.

You say in the book that questions that are good for running a business — like, “How much is this going to cost us?” or “Who is responsible for this?” — are not necessarily good for leading it. Because they lack ambition?

Exactly. Those are the questions businesses are used to asking: How long is it going to take? Who is going to do it? Those are all practical questions that have to get asked at some point as part of doing business, but you don’t have to worry about those questions because somebody is going to ask them. It’s just the natural process of doing business.
The questions that don’t get asked are the ones that aren’t practical, because no one is forced to ask those. Those are optional, right? Those are the questions that go by the wayside. Like:  “What if we were to step back and think about this process of what we’re doing and try reversing the order of it, or try doing it in a slightly different way?” One of the things I say to businesses is the “what-if” stuff is really important.

The idea of structuring your questions in why, what if, and how can be really helpful. It’s a good tool to think about when you’re doing this kind of questioning, because whatever it is in your industry or your business, everybody has challenges they have to deal with. You almost have to start with “why,” because you have to understand what the challenges are and why they’re there, and why they represent the problem or an opportunity — like, “Why hasn’t anybody solved this before?”

Then you want to move to “what if.” That’s when you really start to use your imagination. You understand at that point that there’s a challenge in front of you, and now you’re going to use your imagination to say, “Okay, what if we try this? What if we tried something different?” I love that stage, because anything is possible. It’s a great way to do brainstorming at the early stages.

One of the things you can do with “what-if” questions is you can take ideas from other industries or whole other disciplines. You say, “What if in the meeting-planning industry, we borrowed a technique from Hollywood?” or “What if”— and I see Silicon Valley startups doing this kind of thing — “we applied that technique when we roll out a new program? What if we did it the way these startups roll out their new companies or their new products? Is there an idea we could borrow from them and bring it into the industry?” So when you’re doing that kind of “what-if” questioning, you can do all that kind of combinatorial thinking. It’s really wonderful.

Then the third part to me is that at some point you want to get into “how” questioning. This is where “How might we…?” can be very effective. The “how” is where you start to introduce a little more practicality into it in terms of, “What are the steps that would actually get us started on this? We have this idea, this possibility, but it’s just an idea right now. So what do we do to begin to make it real? What do we do to begin to test it out and experiment?” To me, that’s all in the how stage. It’s trying to figure out, “How do we get started? How do we test it? How do we make this thing work? How do we put the parts together of this idea?” Then, “How do we know if it’s working once we get started?” So that is the third big cycle of questioning. I think if people use that “why/what if/how” cycle, you can apply it to almost any problem in your business.

What if your workplace culture doesn’t encourage that kind of questioning?

Most people understand [its value] once they get exposed to this idea and if you point out to them that there’s a lot of evidence that this works. One of the things I do in my book is point to the fact that you can look at all these innovations in the recent business world. But you can also go back decades. I started with Polaroid from the 1940s, and it was a “why/what if/how” kind of scenario that led to that innovation. Then you look at all these billion-dollar tech startups, anything from Instagram to Square…. They started with questioning, and their ideas were fueled by this kind of “why/what if/how” questioning. Airbnb is another.

I think that the way you get this into a culture is by showing people, explaining to people that there is real value in doing this kind of questioning within an organization. You’re going to surface ideas that never would have been surfaced otherwise — and there are actually multiple benefits to it. It gets people engaged. Even if they don’t think that it would excite them, once they start doing it, they get excited. Suddenly that five-year-old that is still inside all of us comes out, because we are drawn to questioning. That’s why we did it so much when we were five years old. It’s a thing we were born to do, but we’ve gotten out of the habit of doing it. We’ve suppressed that tendency.

Once you allow people to tap into that, they almost always really enjoy it — they find it energizing and motivating. If you can get [people] working in a company to think of some interesting questions, they will get very invested in those questions, and they will want to work very hard to try to find the answers. So, this is not only [about] innovation, it’s about motivation.

How can using “why/what if/how” kind of thinking set an organization apart?

I think any large organization has to do this kind of thing. They have to question some of the assumptions and ways they’ve been doing things, because it will zap energy out of the organization if there’s that feeling of staleness. Especially today — we live in a time of innovation and people expect change. They expect new things. They want novelty. They want freshness. That all relates to questioning.

The first step is, you have to question what it is you’re doing right now. What works about it? What doesn’t work? Is it still relevant? Is what you’re doing as relevant now as it was five years ago? If not, why? What’s changed? How do you have to adapt to those changes? Staying fresh and contemporary and innovative requires that you ask these kinds of questions on a regular basis, and you even have to go to the core of your organization or your association in terms of things like the mission statement and question that. A lot of times people are operating by mission statements and values and vision statements that were created a long time ago. And they might not have been updated, or they might not make as much sense now, or they might just need freshening.

You talk in the book about the value of mission questions over mission statements. How do you think turning your mission into a question would be perceived by members of an association or customers of a company?

I think in most cases they would love it. The difference between the way someone receives a statement versus the way they receive a question is pretty significant. A statement is something that is thrust upon us. Most of us don’t react that well to statements. Sometimes we are skeptical of statements. Sometimes we just resist them, and sometimes we ignore them. And one of the problems with mission statements is they are not very credible. I went through the mission statements of lots of companies, and they were pretty horrible. I mean, first of all, they usually don’t say anything. But more than that, what they do say sounds arrogant and it sounds insincere. Usually it sounds like an ad slogan, and not even a good one.

So the problem with mission statements is that right now, for the most part, they are just not very effective. They’re not going to rally anybody. They’re not going to convince anyone to get excited, and that’s supposed to be their purpose — to rally people around the idea of this organization. So considering that, it doesn’t hurt to go back and look at them and see if there’s anything that can be done to improve it. When you change a statement into a question, a lot of things happen. Suddenly some of the arrogance goes out of it, because you’re no longer saying, “This is what we do. We are the best at blah, blah, blah.” You’re asking, “How might we get to be the best? How might we do a better job of this? How might we be the ultimate X, Y, or Z?”

That is much more humble. It’s also much more engaging to the members of the organization or the association or anyone who collaborates with the association, because it says, “This is an open question. It’s a journey. And you’re invited to go with us on the journey and help us answer the question.”

I think that one of the best ways you can reach out to people is through questioning. Salespeople know this. Salespeople often use questioning as a way to align with their prospect and a way to make the person that they’re selling to feel as if they are part of the process that leads to the sale, as opposed to being sold something. A mission question changes the relationship between the person who is putting out the question or the statement and the people who are on the other end of it.

The education community has embraced your book. Conferences are in the business of delivering education to adults. How might a conference create more of a culture of inquiry?

I think there needs to be some reinvention there, speaking as someone who speaks at conventions, and also attends them fairly regularly. There is a need to shift the model in various ways. Amazing things can happen. Go back to the creation of the TED conference some years ago when Richard Saul Wurman — one of the people I interviewed for the book — created it. He just said, “I’m going to reinvent — I’m going to question everything about the way people behave when they give speeches at conventions and meetings. I’m going to question everything from, why is there a podium? Why are they standing behind a podium? Does that make sense? Why do they go on so long? What if we had a strict [time] limit and cut them off?”

So he basically questioned all the conventions of people giving business speeches. And it was amazing what happened when he did that, because it created this fresh, new approach to giving a speech. I think that kind of thing has to be done on a regular basis with all types of education, conventions — any time when you’re presenting ideas to people, you have to question the format and say, “What can we do differently? How can we shake it up?”

I think a lot of conventions now are just too locked into two kind of things: One is the person standing up and giving a long keynote; the other is the panel of four experts with a moderator — which, by the way, in my personal opinion, those don’t work. I’m sorry. I have seen so many panel discussions and I have seen very few that work. So there is something that needs to be changed about that particular format.

Keynotes are okay, but even there I think you need to shake things up, and you need to try to inject some new ways of doing it. You need to figure out, how can you get the audience more involved? How can you get the people up out of their chairs onstage? How can you introduce visuals in a different way? How can you break it up more? Why does the questioning have to be at the end of the talk? Why can’t the questioning be in the middle or at the beginning?

You have to think about those kinds of “whys” and “what ifs” about the way these things are structured, because right now a lot of them are just too familiar, and people go into their seats, they’re pulling out their smartphones, and they’re barely paying attention. It’s definitely a field that really should experiment and should be trying a lot of different things.

In terms of what we can learn from education and questioning and how it can apply to this type of education that happens at gatherings and conventions: Smaller groups work better. Large rooms are sometimes not as good. That is a thing to keep in mind. Another is, engagement is really important. Interactivity is really important. If you can find a way to get people to interact with what’s going on onstage, it’s going to improve the situation. It’s going to improve their learning, and it’s going to improve their engagement level. I think that what we are seeing in schools is, if you give the students a chance to engage with the subject material, ask their own questions, get them involved on that level, it makes a big difference.

You write about how important it is to be better observers and listeners in order to ask better questions. How can meeting professionals become better on-site observers during their own events?

I use the term “contextual inquiry” in the book, meaning that you go into the context that you’re trying to improve or change or learn about — you go into that world and then question it from within. That’s really important.

The example that I gave in the book was a hospital that wanted to improve their service to patients. And the way that the firm that was helping them — the way they learned about it — was to have one of their people go in as a patient, and observe the experience laying on a gurney, being in a hospital room, and getting that observation from within the context. Then they are able to ask questions that they would never normally ask. Like one of the questions that came up in that situation is, “I’m always looking at the ceiling of the hospital, because I’m always on my back. What if hospitals could do something interesting with their ceilings?” These are things you never learn unless you put yourself in the shoes of the people who are using your service or your event.

To me, that’s the only way to do it. One of the least valuable things, by the way, is questioning people after the fact. A lot of times, questioning people after the event, you’re not going to get great insights from that. You will get obvious stuff, but where the insights will come is from is sitting in the middle of it, trying to experience it in much the same way as a participant would. Make sure you are in the back of the room, not the front of the room. And just try to put yourself in their mindset. Try to see the event not as a planner or an organizer of such an event but as an attendee coming for the first time. Most of us have that imaginative skill, that ability to step out of our own role and see something as if we were not steeped in it, not a professional.

That’s where you will tend to get your best insights. Then, make a note of whatever questions come to mind as you’re doing that. Look for inconsistencies, patterns, things that maybe don’t make sense, things that are odd and jump out at you. A good, good question comes from that.


Using the Power of Inquiry for Meetings Industry Breakthroughs

In A More Beautiful Question, Warren Berger maps out a process of inquiry to spark game-changing ideas for products and services. Here’s how Berger’s “why/what if/how” method of inquiry might be applied to tackle one challenge faced by meeting organizers: Why is it so difficult to track attendee engagement? While organizers can easily keep a record of who attended each session and collect their feedback via surveys after the event, that doesn’t truly capture their behavior and the quality of their interactions with presenters and fellow participants. What if:

› There were a way to help meeting participants make valuable connections and to customize their educational experience at events?

› A tool could store each registrant’s historical meeting-attendance data, helping attendees to recognize others they’ve met during past events as well as those who share their interests and challenges — enabling them to automatically exchange their contact information on site in a way that integrates their social-media profiles?

› Attendees could access a feature on this tool or device so they could register and pay for a special event, eliminating the need for paper tickets?

› Meeting professionals could access data that captures attendee behavior during the event for internal use — i.e., which sessions were most popular and had the greatest interaction, which topics lit up the social-media-sphere, who visited which booths and had a meaningful exchange, and how many connections were made with fellow attendees that had the potential to help them address a business concern or meet a need? This would help validate the value of the event to the organization’s leadership and inform future programming.

Michelle Russell

Michelle Russell is editor in chief of Convene.