A More Beautiful Question: The Power of Inquiry to Spark Breakthrough Ideas

by Warren Berger

I think of this brand of questioning as a subcategory of Why questions that could be considered “challenger questions.” They have a certain attitude about them: restless, rebellious, skeptical of convention and authority. As in: Why should we settle for what currently exists? And why should I believe you when you tell me something can’t be done?

One of his chief tasks is to teach them “to understand that the incumbency has an interest in maintaining the status quo. To question well, you must have the ability to say, ‘It doesn’t have to be that way.’”

George Carlin had a lifelong mistrust of authority, Kelly Carlin noted, and his advice to parents was “Don’t just teach your children to read. Teach them to question what they read. Teach them to question everything.”

Another common counterquestion that challengers can expect to be hit with is some version of Okay, genius, how would you do it better? An interesting assumption is built into this question: that if someone is going to challenge the existing ways, then he/she had better have an alternative ready. But it’s important to ask Why and What If questions even if we don’t yet know the How. Getting to a better alternative may be a long process, but it has to start somewhere—and that starting point often involves questioning the status quo.

Assumptions and biases of our own may be embedded in the questions we ask. One of the ways to find out is to subject those questions to . . . questioning.

“Everything that’s ever happened to you or occurred to you in your life informs every decision you make—and also influences what questions you decide to ask. So it can be useful to step back and inquire, Why did I come up with that question?”

“Every time you come up with a question, you should be wondering, What are the underlying assumptions of that question? Is there a different question I should be asking?”

Questioning one’s own questions—as in, Why am I asking why?—might seem like a circular exercise, bound to lead nowhere and yield dizziness. But there are practical, constructive ways to do this, and they can help produce a more insightful or more informed question. They range from simple practices such as “the five whys” to more exhaustive methods such as contextual inquiry, wh...

people are inclined to look for the easiest, most obvious explanation for a problem. On top of that, “we tend to personalize things that are really systemic.”

The five whys28 can be used outside of business, as well. IDEO has used it to address a number of behavioral issues.

“I’ll ask myself, As a doctor, what am I really good at and not so good at? Then I’ll go to a deeper level of questioning: Why did I want to become a doctor in the first place?”

You might broaden a question to make it more applicable to more people, and therefore more significant. For example, the Airbnb founders could have limited the scope of their question to Can we set up an online accommodation-sharing system in San Francisco?—but they quickly broadened it to Can this idea work worldwide? On the other hand, as Machover notes, to move forward on a big question sometimes it’s necessary to break it down into smaller, more actionable questions—as in, Before we try to do this thing worldwide, how might we make it work in our own backyard?

While you can do much tinkering around the edges of a question using such methods, perhaps the best way to question a question is to take it out into the world with you—and see if the assumptions behind it hold up when exposed to real people and situations. Often, what seems to be the right question in one context proves to be the wrong one in another.

Contextual inquiry is about asking questions up close and in context, relying on observation, listening, and empathy to guide us toward a more intelligent, and therefore more effective, question.

In the business world, IDEO has32 been a pioneer of this type of research. As the design firm was being formed twenty-odd years ago, its founders, including the designer David Kelley and his brother Tom, realized that to solve human engineering problems (such as, How do we make gadgets that fit into people’s lives?), the company would have to employ the kind of psychological and behavioral inquiry normally done by social scientists. So the firm hired psychologists and other students of human behavior and began to develop its own methods of observing people.

IDEO understood that to question effectively, one couldn’t do it from inside the bubble of the company, or in artificial settings such as focus groups. To understand how people live, you have to immerse yourself in their lives—watch them in their kitchens, follow them as they go to the supermarket, and so forth. The company’s researchers sometimes go to great lengths to experience things firsthand.

To do contextual inquiry well, you don’t need a team of trained researchers. What’s required is a willingness to go out into the world with a curious and open mind, to observe closely, and—perhaps most important, according to a number of the questioners I’ve interviewed—to listen. Listening informs questioning.

Paul Bennett says that one of the keys to being a good questioner is to stop reflexively asking so many thoughtless questions and pay attention—eventually, a truly interesting question may come to mind.

Contextual inquiry requires a commitment to the question you’re exploring. It’s one thing to ponder questions in your room, or within your own company’s offices, or in online surveys; it’s another to go out there and, as Novogratz says, “spend time sitting on the floor with people, listening to them as they tell you about their lives.”

Confronted with a problem that was larger than themselves, they decided to make that problem—and the question that defined the problem—their own.

“productive obsession.”35 It will surface, recede, then surface again. It will invade your dreams as it embeds itself in your subconscious. You’ll wrestle with it, walk with it, sleep with it. And all of this will prove helpful during the What If stage of inquiry.

struck. In Westergren’s case, ideas and influences began to come together; he combined what he knew about music with what he was learning about technology. Inspiration was drawn from a magazine article, and from a seemingly unrelated world (biology). A vision of a new possibility began to form in the mind. It all resulted in an audacious hypothetical question that might or might not have been feasible—but was exciting enough to rally people to the challenge of trying to make it work.

If the word why has a penetrative power, enabling the questioner to get past assumptions and dig deep into problems, the words what if have a more expansive effect—allowing us to think without limits or constraints, firing the imagination.

“In order for imagination to flourish,37 there must be an opportunity to see things as other than they currently are or appear to be. This begins with a simple question: What if? It is a process of introducing something strange and perhaps even demonstrably untrue into our current situation or perspective.”

The Pandora What If question certainly introduced something “strange” into the world—Westergren’s notion that you could take the whole vast universe of music and break it down in a genetic manner struck many (especially musicians) as an off-the-wall idea. But the beauty of the What If stage of questioning is that it’s a time when off-the-wall ideas are welcome.

coming up with original ideas or insights—the kind of lightbulb moments that can lead to imaginative What If questions—often involves the ability to combine ideas and influences, to mix and remix things that might not ordinarily go together. Einstein and others have referred to this as “combinatorial thinking”; in this book, I’ve been using the term connective inquiry to focus on the questioning aspect. Whatever one calls it, this mix-and-match mental process is at the root of creativity and innovation.

in coming up with fresh ideas, we don’t have to invent from scratch; we can draw upon what already exists and use that as raw material.

connecting those bits and pieces in a clever, unusual, and useful way, resulting in (to use a term that seems to have39 originated with the British designer John Thackara) smart recombinations.

Smart recombinations are all around us. Pandora, for example, is a combination of radio station and search engine; it also takes the biological model of genetic coding and transfers it to the domain of music (a smart recombination often takes ideas or influences from separate domains and mashes them together). In today’s tech world, many of the most successful products—Appl...

People have been combining and recombining ideas for as long as there have been ideas, but in the Internet age, the opportunities and possibilities for creating “mashups” seem limitless.

“The creative act is no longer40 about building something out of nothing but rather building something new out of cultural products that already exist,”

Smart recombinations are inspired in all sorts of ways. Sometimes they are the result of cold calculation (How can we combine this moneymaking thing with that moneymaking thing to make even more money?); sometimes they’re a product of serendipity.

“The nature of innovation [is that] we build new ideas out of existing ideas.” Murray cites Einstein, Walt Disney, George Lucas, and Steve Jobs as prime examples of innovators who “defined problems, borrowed ideas, and then made new combinations.” They did it, Murray says, by combining things that didn’t seem to go together and by borrowing ideas “from faraway places.”

Innovators who are good at connecting are inclined to take something they’re working on—say, Walt Disney’s planning a new amusement park—and begin to think analogously: What if this amusement park could be like a movie, brought to life? “In doing this,” Murray explains, “Disney takes his original subject, an amusement park, and lays a metaphor on top of it and begins to see the whole thing through that ‘movie’ metaphor—so he creates it with storyboards, and the employees become cast members, and so on.”

To forge those illogical connections, Murray advises, “You must quiet the logical mind.” This is confirmed by the latest neurological research, which suggests that the human brain is a connective-inquiry machine that never sleeps. It is constantly sorting through seemingly unrelated bits and pieces and inquiring, What if I put this together with that?

Why does X have to be the way it is? What if I try to think of a different way of doing it?—it’s a form of divergent thinking,43 and it triggers some interesting activity in the brain, says Dr. Ken Heilman, professor of neurology at the University of Florida’s College of Medicine.

start by thinking of the brain as a forest full of trees. “Think of a neuron, or a nerve cell, as one of those trees,” he says. In this analogy, the cell body forms the tree trunk; there are major branches, known as axons, and smaller branches, dendrites, that extend out to the farthest reaches. “In the brain, some of those trees are closer together than others, and the branches communicate with each other.” As this happens, “neural connections” are formed, which can produce new thoughts, ideas, and insights.

Zhong’s research has found that we can’t necessarily control the brain’s search for remote connections—much of which happens in the unconscious mind—but we can provide impetus and help guide that search by focusing on a problem to be solved, a challenging question to be answered. “Having that goal or that question you’re working on is very important,” Zhong confirms. If your conscious mind puts a big question out there, chances are good that your unconscious mind will go to work on it.

Moreover, if you have a curious mind—and if you actively ask questions and gather knowledge to sate that curiosity—this also can aid in connective inquiry by providing “a plethora of raw materials to be connected,”

if your curiosity has been focused on a particular problem, and you’ve been doing deep thinking, contextual inquiry, questioning the problem from various perspectives and angles, asking your multiple Whys—it all becomes fodder for later insights and smart recombinations.

So even though it can initially be beneficial to approach a problem with a beginner’s mind, as you progress to imagining What If solutions, it’s useful to have some acquired knowledge on the problem—preferably gathered from diverse viewpoints. It also helps to have a wide base of knowledge on all sorts of things that might seem to be unrelated to the problem—the more eclectic your storehouse of information, the more possibilities for unexpected connections. (Heilman points out that people who are well read and well traveled, those who have diverse interests and a broad liberal arts education, are developing “a whole series of different modules that can enable more connectivity and more creativity.”)

This is why I’m a proponent of reading anything and everything, as long as there’s a decent set of mental models to process what’s real from what’s fiction.

But before undertaking conscious efforts to spark connective inquiry, bear in mind that it seems to thrive when we’re distracted or even unconscious. So the best thing may be to take your question for a walk. Or take it to the museum. Or, if you’re feeling lucky, take it to bed.

“So I came up with a process whereby I would always answer the more obvious questions first. Then, as my anxiety would lessen, I’d start to answer more of the questions that required real thinking.”

When you’re anxious, he learned later in his professional research, your brain tends to be less creative and imaginative. “You want to attend to the outside world, not the inside,” he said. “And you’re trying to get to answers that are the simplest. But when you’re relaxed, you go the other way—you’re able to go to the inside world.”

In the more relaxed state, neural networks open up and connections of all kinds form more freely.

it’s important to spend time with challenging questions instead of trying to answer them right away. By “living with” a question, thinking about it and then stepping away from it, allowing it to marinate, you give your brain a chance to come up with the kinds of fr...

people often come up with more novel ideas or solutions when they’re relaxed or distracted—in what Zhong calls a state of inattention.

it may be best to move back and forth between focused attention and inattention.

“I’ll just relax on the couch or walk around and do a lot of thinking: What if I combine these different ideas to solve this one problem? I just let it incubate and see if I can connect these different ideas somehow.”

He said that when he is working on a difficult problem, he sets aside time, right before going to bed, to review all the pertinent issues and challenges. Then he goes to sleep and allows his unconscious mind to go to work.