Excerpt: Why Question?

Excerpt: Why Question?

The Book of Beautiful Questions focuses on four key areas: How to Decide, Create, Connect, and Lead. This excerpt is from the Introduction to the book, titled “Why Question?”

I am a questionologist.

You may be asking yourself: Is that really a thing? I asked myself that very question a few years ago. Then I did some research, which turned up hundreds of different types of “ologists,” ranging from the acarologist (who studies ticks and mites) to the zoologist. But searching among the Qs, I found no entry for “questionologist.” And this led me to inquire, Why not? Isn’t the study of questions as worthy of classification as the study of ticks and mites?

My questioning then advanced from the “Why not?” to the “What if?’ stage—as in, What if I just declared myself a questionologist? I did so in, among other places, the pages of the New York Times. And to my surprise, no one questioned it.

I have been using the term ever since, as I visit companies (including many Fortune 500 businesses), government agencies, such as NASA, and schools from grade-school level through university. I have been invited to various gatherings of farmers, accountants, artists, scientists, soldiers, political operatives, Hollywood agents, Danish pharmaceutical executives, and Australian school teachers. The interest in questioning crosses all lines, it seems.

And it should. When we are confronted with almost any demanding situation, in work or in life, simply taking the time and effort to ask questions can help guide us to better decisions and a more productive course of action. But the questions must be the right ones—the ones that cut to the heart of a complex challenge or that enable us to see an old problem in a new light.

My new book, The Book of Beautiful Questions, contains many such questions—hundreds of them, covering everyday situations that range from getting out of a career rut to strengthening personal relationships. The book is about asking thoughtful questions at the right time in order to make the best choices when it matters most. It is aimed at creators, problem solvers, and decision makers. I believe that we have at our disposal a natural tool to help us think and “hack” our way to more successful outcomes. That tool is the humble question.

I first began to appreciate the value of questions years ago, when I worked as a newspaper reporter. For me (and for journalists in general), a good, pointed question can serve as a spade for digging and unearthing bits of the truth of a story. Through the years, I tended to think of a question primarily as something you ask others in order to extract information from them. I’m sure that attorneys, pollsters, psychiatrists, and other “professional questioners” think of questioning the same way.

But my work as a journalist also brought me into contact with inventors, entrepreneurs, business leaders, artists, and scientists, who often were the subjects of my writing. I found that many of these people tended to use the questioning tool in a different way—their questions were often directed inward. They might be trying to solve a problem or create something original, and in doing so, were likely to begin with questions that they asked themselves: Why does this problem or situation exist? What are the underlying forces, the larger issues at play? What might be an interesting new way to come at this challenge?

This type of questioning helped lead these creative thinkers to original ideas and effective solutions. And this observation formed the basis of my previous book A More Beautiful Question, which made the case that questioning is a starting point of innovation. In that book, I showed that inventions from the instant camera to the cell phone, and startup businesses such as Netflix and Airbnb, could be traced to a “beautiful question”—one that shifted the current thinking, opened up a new possibility, and ultimately led to a breakthrough.

After the book came out, as I conducted press interviews, gave speeches, and engaged with audiences of readers, I found that while many agreed with the premise of the book and its “Ask more questions” message, there also seemed to be a hunger for something more targeted and specific. People wanted to know which questions they should be asking with regard to a particular problem they might be facing or a goal they were pursuing.

When I spoke to business leaders, for example, they tended to be most interested in questions that could help in running a company, whereas those at creative gatherings wanted to know how to ask questions that could spark ideas. Likewise, with people seeking to improve personal relationships or with those grappling with difficult decisions about whether to accept a job or pursue a new passion—all were seeking the questions that might help them make better choices or achieve the best results in a specific situation.

To me, any question that causes people to shift their thinking is a beautiful one. The questions in my book are intended to do that—to remind you to slow down and think more, to broaden your perspective, to see past biases, creative blocks, and emotional reactions. In so doing they can help steer you in the right direction at critical moments when you’re trying to 1) decide on something; 2) create something; 3) connect with other people; and 4) be a good and effective leader. These are the four broad themes of the book. In my conversations with readers and with audiences at my speeches, these four areas seemed to come up most—they are very much on people’s minds.

How can questioning help us decide, create, connect, and lead?

In each of the four featured areas, questioning plays a central role. Decision-making (or at least, good decision-making) demands critical thinking—which is rooted in questioning. It has been suggested that critical thinking is in crisis today, as evidenced by a growing collective inability to distinguish fake news from the real thing (or real leaders from fake ones). We can blame the media or Facebook or the politicians themselves—but ultimately, it’s up to each of us to work through the hard questions that enable us to make more enlightened judgments and choices. Asking oneself a few well-considered questions before deciding on something—a candidate, a possible career or life change, an opportunity that you or your business may be thinking about pursuing—can be surprisingly effective in helping to avoid the common pitfalls of decision-making.

As for creativity, it often depends on our ability, and willingness, to grapple with challenging questions that can fire the imagination. For people within an organization trying to innovate by coming up with fresh ideas for a new offering or venture or for an individual attempting to express a vision in an original and compelling way, the creative path is a journey of inquiry. It often starts with identifying a singularly powerful “Why?” or “What if?” question (so many well-known creative breakthroughs, in business and the arts, can be traced back to a question of this type). But it doesn’t end there. Knowing the right questions to ask at each stage of the creative process can guide the creator forward—steadily advancing from early stages of finding an idea to the final challenges of getting that idea “out the door” and into the world.

Our success in connecting with others can be improved dramatically by asking more questions—of ourselves and of the people with whom we’re trying to relate. Surprising new research suggests we become more likable to others by asking questions—as long as they’re the right type of questions, asked in the right way. (When asked the wrong way, questions can be confrontational and downright annoying.) While many of us tend to rely on generic “How are you?” questions, more thoughtful and purposeful questions can do a better job of breaking the ice with strangers or bonding with clients and colleagues. They also enable us to forge an even stronger, deeper relationship with the people closest to us. And—worth noting in these polarizing times—questions can help us understand and begin to relate to those who see the world very differently.

Lastly, leadership is not usually associated with questioning—leaders are supposed to have all the answers—but it is becoming increasingly clear that the best leaders are those with the confidence and humility to ask the ambitious, unexpected questions that no one else is asking. Today’s leaders—and I’m referring to not just top corporate executives but team leaders of any type, as well as civic leaders, social advocates, “thought leaders,” family leaders, and educators—are facing unprecedented challenges in a world of exponential change. They must ask the questions that anticipate and address the needs of an organization and its people, questions that set the tone for curious exploration and innovation, and questions that frame a larger challenge that others can rally around. Mission statements are no longer sufficient; the new leader must pose “mission questions.”

Within each of the four distinct themes, there are different types of questions that tend to be most effective. Many of the decision-making questions are designed to help you work through your own biases. Creativity questions are more exploratory and inspirational. Relationship questions tend to be empathetic. Leadership questions are more visionary.

But what ties them all together is this: The simplest and most powerful thing that happens when we ask ourselves questions is that it forces us to think. This might involve something as simple as pausing before making a decision or pursuing a course of action to ask, What am I really trying to achieve here? That very basic question, in and of itself, encourages you to think more—and that’s a good start. But there’s much more you can do if you’re armed with more sophisticated, situational questions. You can use them to prompt or remind yourself to look at that situation from multiple perspectives or to challenge your own assumptions about it. When we do this, we tend to open up more possibilities and options—which means we’re not only thinking more about a particular challenge, we’re also thinking about it in a more comprehensive and balanced way.

See all the excerpts »

Find out more about The Book of Beautiful Questions »