Warren Berger Tells How to Ask a ‘Beautiful Question’

There are questions that Google can answer, but there are others that require a different, much deeper kind of search. Those questions fascinate Warren Berger.

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To stay ahead in my ad agency, I read a lot of books that purport to have "the answer" to some problem or another—how to improve your business, find happiness, and so forth. But I just finished a book that takes a very different approach. It is entirely focused on questions, not answers. And I found it to be profound and eye-opening.

A More Beautiful Question by Warren Berger is about the importance of asking thoughtful, ambitious "beautiful questions"—the kind that can bring about change in the world around you. A fair amount of the book is focused on the need to ask deeper, better questions in business—which really resonated with me. I went through a process of tackling a lot of ambitious questions when I envisioned "movement marketing," wrote the book Uprising and started my own challenger ad agency StrawberryFrog.

But Berger also writes about how questioning can help us solve problems and work through difficult challenges in our daily lives. In today’s fast-paced world, a lot of us are rushing around and doing things without taking the time to ask the critical Why and What If questions that can guide us in better directions.

Recently, I spoke with Berger about the importance and the art of asking ”Beautiful Questions.”

How did you become interested in questioning—and how does one tackle a subject as big and broad as questioning?

As a journalist I’ve been asking questions my whole life. But it was only in recent years, as I was studying innovators and how they think, that I came to realize a lot of people who come up with breakthrough ideas start by asking great questions—the questions no one else is asking at the time. So I thought, why aren’t more of us asking these kinds of dynamic, powerful questions? And that led to my own years-long “inquiry into inquiry.”

And you’re right, it is a big subject to take on. Questioning is like breathing—it’s something that seems so basic, so instinctive, that we take it for granted. But there’s a lot we can all learn about how to question, and really do it well. So I sought out people who are “master questioners”—innovators, entrepreneurs, teachers, artists, basement tinkerers, and social activists who question conventional thinking daily. I was also curious about what’s going on in our brains when we question, so I interviewed leading neurologists. I studied the way comedians, in particular the late George Carlin, use questioning to challenge assumptions and see the world differently. And I spent time at a fascinating place called The Right Question Institute, where they are developing techniques to help children and adults become better questioners.

At one point in the book, you say that today, the value of questions is rising while the value of answers is declining. Why is that?

In a world of rapid change, answers quickly become outdated or obsolete. But great questioning leads you to new and better answers. Questioning is important for a number of reasons. It’s a critical starting point of problem-solving and innovation—whether we’re talking about business or social issues. Thoughtful inquiry can help us begin to see and understand the challenges around us more clearly. Questions also spark the imagination. And we’re now learning that questions (versus declarations) can help us motivate ourselves—while engaging the interest and support of others. Learning how to act on our questions can lead us toward solutions and creative breakthroughs. Einstein understood this; so do the people running Google and lots of other innovative endeavors.

The book is also filled with stories of breakthroughs that began with a question. What do you consider to be some of the more interesting examples?

The cell phone started with a question. So did The International Red Cross and the Olympics, as well as the Internet. Questioning gave us car windshield wipers and instant cameras—the latter can be traced to the question, “Why do we have to wait for the picture?,” asked by the 3-year-old daughter of inventor Edwin Land, who would later start Polaroid. Companies such as Netflix, Pixar, and many others can be traced back to a “founding question”—though my favorite, just because it’s so odd, involved a college football coach who asked, “Why aren’t the players urinating more?” That question led to the realization that the sweating players weren't replenishing fluids well enough, which in turn led to the creation of Gatorade and a $20 billion sports drink industry. So while it may have sounded like a weird question, it turned out to be a beautiful one.

How do you define a "beautiful question"?

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The term is inspired by this line from the poet E.E. Cummings: "Always the beautiful answer who asks a more beautiful question." The way I define a beautiful question in the book is: "An ambitious, yet actionable, question that can begin to change the way we think about something—and might serve as a catalyst to bring about change." For example, when someone steps back and asks, Why are we doing things the way we've been doing them the past 20 years—what if we tried a whole new approach? That's a beautiful question. These kinds of questions challenge assumptions, and take a fresh look at things that maybe are being taken for granted. But the key word is actionable—I'm interested in questions you can act on, to possibly bring about change. I make the case that we should all try to formulate our own beautiful questions and then take ownership of them—"How might I begin to do X or Y, to bring about a desired change in my life?" Generally speaking, a beautiful question cannot be answered quickly on Google—a different, much deeper kind of search is required.

In the book, you say that questioning is under-valued and under-taught. Why isn’t there a greater appreciation of the importance of questioning, and why don’t we teach it?

We have an education and business culture that tends to reward quick factual answers over imaginative inquiry. Questioning isn’t encouraged—it is barely tolerated. In both classrooms and workplaces, questioning may be seen as a challenge to authority. And it can be perceived as a sign of weakness—an indication that one “doesn’t know.” In schools, we teach to the test, with much of the focus on memorization of answers. But we’re realizing now that memorization of answers is not all that big a deal when you’ve got facts at your fingertips on your smartphone. The more important thing is, do you know how to look for the right information, and how to evaluate it? That’s where questioning comes into play.

You also point out in the book that people who question tend to be very successful, in business and elsewhere.

Yes, research from the business consultant Hal Gregersen shows that the most innovative business leaders—the late Steve Jobs, Jeff Bezos and the like—tend to question everything. And it is through constant inquiry that they find new opportunities. So this points to an interesting dichotomy, which I explore in the book—society does its best to discourage questioning, but those who ignore that and remain inquisitive often end up running our most creative and successful businesses while coming up with game-changing ideas.

How can we get better at questioning?

The Right Question Institute maintains that questioning is like a muscle; the more you use it, the stronger it gets. And based on observing what “master questioners” do, there are certain behaviors that seem to lead to better questions, such as paying close attention to details of everyday life and work, looking for interesting patterns and inconsistencies; refusing to accept conventional wisdom about what can and can’t be done; and being willing to ask fundamental questions, even ones that may seem naïve. Perhaps the most important thing you can do is take ownership of the promising questions you raise by trying to act on them, moving from why to what if to how.

Scott Goodson is the author of Uprising and founder of StrawberryFrog.