The Quest to Ask Better Questions

Warren Berger's next book will look to improve the very act of asking.

Warren Berger's next book will look to improve the very act of asking.

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In his previous book, Glimmer: How Design Can Transform Your Life and Maybe Even The World, Warren Berger, co-founder of the New York writing collective The Marmaduke Writing Factory, sought to understand the ways that great designers create. He found at least one common trait: Designers are very good at questioning everything.

"Like the old joke—How many designers does it take to change a light bulb, and the designer's answer is, Does it have to be a light bulb?—designers question why things are done a certain way, and whether there might be a better, more interesting way," Berger tells me.

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Questions are sometimes better than answers. So Berger looked beyond the design world to understand the power of questioning to spark change, innovation, and progress. The result will ultimately be a book titled A More Beautiful Question, published by Bloomsbury.

There is questioning with gravitas (as in, is there a deity?) and questioning with insignificance (as in, can I borrow the car?). But Berger focuses on what he calls "Beautiful Questions"—borrowing from the e.e. cummings line "Always the beautiful answer, who asks a more beautiful question." There are, Berger explains, "certain kinds of catalytic questions that can lead to game-changing answers and results. These are questions that, once raised, tend to get people thinking in a different way—and can trigger a process that leads to some kind of a breakthrough."

Questions have literally moved mountains, powered rockets, and instantly developed images. Berger points to when Edwin Land was taking a photograph of his four-year-old daughter with a standard camera. "She wanted to see the results right away, and he explained, no, it takes a few days," he says. "But she wanted to know, Why do we have to wait for the picture? And this question got Land started on the journey that led to the creation of Polaroid instant photography."

Berger, who has only just started his journey, wants to track down the results, good and bad, of fundamental questions. "You see this a lot in Silicon Valley, for instance, where so many of these radical new ventures can be traced back to a great question," he says. But he is also interested in people who are asking, "What if we rethink the way schools work?" or, "Why are we designing prisons this way, when we could be doing it that way?"

This theme has a Talmudic side. A question is a spiral that leads to more questions. But when does Berger stop questioning and settle for some answers? He explains that deep questioning can be the first step in bringing about change—but you also have to begin to act on those questions at some point. Berger is less interested in philosophical or existential questions that are basically unanswerable. "I'm aiming for something a bit more practical," he says. "To me, a Beautiful Question is something that should feel important, meaningful, profound—but also potentially answerable and achievable. Once you've set your sights on a question like that, the idea is to really tackle it. These are usually very difficult questions to answer. You can't look it up on Google or—you have to grapple with it. You may spend months or years 'living the question.'"

A great question tends to evolve. "In studying innovators," Berger says, "I've found that once they take on a big question, they often proceed through various 'stages of inquiry' that gradually lead them toward an answer. They may not always get to the answer they want, but they do arrive at something." He has labeled these stages as "speculative inquiry," "contextual inquiry," "constructive inquiry"—all steps in a process that keeps the questioner moving forward on the journey.

Berger is also trying out an idea called "collaborative inquiry," tapping into the ideas of young people interested in the subject. "I'm used to working alone in my cave as an author, but this idea is so big and challenging, I just felt like I didn't want to go on this journey by myself." So on his website he asks people to submit their own "Beautiful Questions" and invites them to join him in the investigation. "I'm asking a team of selected collaborators, not a random 'crowd,' to help me as I put together the answer. As the book's author, I'll still make all the decisions and do all the writing—but hopefully the team will unearth some great raw material that I could never find on my own. I'm very conscious of the fact that I'm asking people to do something for nothing, so my hope is that I can make it an enjoyable, enriching experience."

As the questions grow, will the answers change Berger's thesis? "I started off with the thesis that one had to learn how to be a better questioner," he says. "But now I'm starting to think it's about re-learning—because the truth is, we all start out as questioners.

"The average 5-year-old questions everything. Yet research shows that many of us begin to question less and less as we get older. Is it the school system, which tends to prize memorized answers over creative questions? Is it because we feel social pressure to 'seem smart?' Or maybe it's a business culture that discourages employees from questioning entrenched corporate policies and practices? My book will try to answer these and many, many other questions about questioning. So now maybe you can see why I'm going to need help."