The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead

by Warren Berger

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.

While there are many “answer” books available—the ones declaring, “Here is a four-step solution to your problem, and you can remember it via this four-letter acronym”—the philosophy behind this book is different. I am suggesting that we must figure out our own solutions and answers to the complex, individualized challenges we face, in work and in our personal lives. And 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.

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?

More Beautiful Question, which made the case that questioning is a starting point of innovation.

So with this book I focus on sharing productive questions and questioning strategies that can be applied to everyday situations.

The questions featured come from a variety of sources. They derive from ideas and insights shared by entrepreneurs, life coaches, kindergarten teachers, cognitive behavioral therapists, chief executives, psychology professors, and neuroscientists, as well as an FBI counterintelligence agent, an acclaimed novelist, a venture capitalist, an improv performer, a Pulitzer Prize–winning playwright, a Nobel Prize–winning physicist, a U. S. Marine officer, a hostage negotiator, a risk-management specialist, and others. I tried to include a range of perspectives on how questioning can be used in various situations.

To me, any question that causes people to shift their thinking is a beautiful one.

These questions 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.

Decision-making (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 traps of decision-making.

Surprising new research suggests we become more likable to others by asking questions2—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.)

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.

Mission statements are no longer sufficient; the new leader must pose “mission questions.”

The simplest and most powerful thing that happens when we ask ourselves questions is that it forces us to think. More specifically, when we’re working on questions in our minds we’re engaged in “slow thinking,”

the term used by Nobel Prize–winning psychologist Daniel Kahneman to describe the kind of deliberate, effortful cognition that tends to lead to better decisions, choices, and actions.

This might involve something as simple as pausing before making a decision or pursuing a course of action to ask, What a...

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.

Our ability to question well is like a muscle. You must continually work it in order to strengthen it. Even if you feel that you already have a knack for questioning, there are many ways to improve. There are approaches to learn, from “speculative inquiry” to “appreciative inquiry,” which I’ll cover throughout the book. There are techniques for building a better question and for sharing it with others—including nuances involving tone and phrasing. And there are also ways to encourage others around you to question more (particularly important if you are, or aspire to be, a leader).

But in order to do any of this, we must overcome what seems to be a general reluctance to ask thoughtful questions—of others and of ourselves.

What are the five enemies of questioning?

Foremost among what I think of as the “five enemies of questioning” is fear. Though many young children start out as fearless questioners, they gradually get the message—from teachers, parents, other kids—that asking a question carries risks, including the risk of revealing what they don’t know and perhaps ought to know.

To ask a question is an admission that 1) you don’t know, and 2) you do care—doubly uncool.

Fear of asking questions can be particularly strong in the workplace, as employees worry: Will asking questions make it seem as if I don’t know how to do my job? Will it annoy my colleagues and supervisors? Or worse, will it threaten them in some way?

If fear is the first enemy of questioning, running a close second is knowledge. The more you know, the less you feel the need to ask. But the problem here is twofold. First, we can easily fall into the “trap of expertise,”9 wherein knowledgeable people begin to rely too much on what they already know and fail to keep expanding upon and updating that knowledge. This is particularly perilous in times of rapid change. And there’s another problem with depending too much on our existing knowledge: To put it bluntly, we don’t know as much as we think we do.

This brings up the third and fourth enemies of questioning, which are related to each other: bias and hubris. In terms of biases, some of them are hardwired in us; others may be based on our own limited experiences. But in either case, if we are predisposed to think something, we may be less open to considering questions that challenge that view. The book’s second section, on decision-making, looks at some of the ways we can use self-questioning to better understand and challenge our own biases and assumptions.

The relationship between humility and questioning is interesting—if you lack the former, you’ll probably do less of the latter.

The last enemy of questioning is time (or the supposed lack of it). We just don’t seem to make time for questioning—starting in school.

“Some people see things that are and ask, ‘Why?’10 Some people dream of things that never were and ask, ‘Why not?’ Some people have to go to work and don’t have time for all that shit.”

We’re under pressure to make quick decisions and render snap judgments, and to do, do, do—without necessarily asking why we’re doing what we’re doing or whether we should be doing it at all.

“I always asked why we’re doing things the way we’re doing them,” Jobs said.11 As Jobs took on the role of the inquisitive four-year-old wandering the company, it had a powerful effect on him and those around him—forcing everyone to reexamine assumptions.

How might a four-year-old see this situation?

The fear of asking questions in front of others can only be overcome by doing it, one question at a time.

ARE YOU A BEAUTIFUL QUESTIONER? ASK YOURSELF THE FOLLOWING Am I willing to be seen as naïve? Am I comfortable raising questions with no immediate answers? Am I willing to move away from what I know? Am I open to admitting I might be wrong? Am I willing to slow down and consider?

What if I find that I have no ready answer for the serious questions I ask myself?

So the trick is to become more comfortable living with a question, working on it, learning from it—and knowing that you don’t need to have an answer right away.