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.

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?

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.

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.

As for creativity, it often depends on our ability, and willingness, to grapple with challenging questions that can fire the imagination.

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.

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.

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,”3 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.

What am I really trying to achieve here?

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.

Our ability to question well is like a muscle. You must continually work it in order to strengthen it.

When people ask, How does one become a better questioner?, I advise them to take a few lessons from a true “master questioner”—not Einstein or Socrates, but rather the typical four-year-old child. Studies have shown that children at that age may ask anywhere from one hundred to three hundred questions a day4 (interestingly, some research shows the four-year-old girl asks even more questions than a boy of that age. She is the ultimate questioning machine.) Questioning at these early ages may seem like child’s play, but it’s a complex, high-order level of thinking. It requires enough awareness to know that one does not know—and the ingenuity to begin to do something to remedy that.

As the Harvard University–based child psychologist Paul Harris points out, young children discover early on that the information they seek can be easily extracted from other human beings,5 merely by using that certain combination of words and vocal inflection that forms a question.

If you could peer inside the mind of a questioning child, you’d get a hint as to why kids seem to enjoy asking “Why?”. Neurological research shows that merely wondering about an interesting question6 activates regions of the brain linked to reward-processing. Curiosity—the act of wondering—feels good in and of itself, and thus, questions beget more questions. Think of curiosity as a condition—“like an itch,” says the neuroscientist Chara...

What was once a hundred-per-day questioning habit among four-year-olds dwindles down to a few questions—or none—among teenagers.

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

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.

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 late founder of Apple, Steve Jobs, was one of the busiest people on the planet, yet he made a conscious effort to regularly ask fundamental “Why?” questions while making the rounds of his company’s various departments. At each stop, whether in the marketing area or accounting, “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.

The more questions you ask, the more comfortable you get with questioning. You also gain more experience in asking the right questions when you practice more and more. This is why it is important to have the curiosity of a four year old, lifelong.

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?

There is value in asking yourself challenging questions even when—perhaps especially when—you don’t have a ready answer. Just thinking about a difficult question—a tough decision, a creative problem that needs solving, a change you may want to make in your life—begins to put your mind to work on that issue and can soon start to yield insights and greater clarity.

Elie Wiesel once observed: “People are united by questions. It is the answers that divide them.”

A growing body of research shows that human connection is central to leading a happier, more meaningful life.13 Increasingly, we turn to technology as a means of generating more connections. But more is not necessarily deeper—and when it comes to life-enriching connections, deeper is better.

When you ask someone else a question, you are showing interest and providing an opportunity for that person to share thoughts, feelings, and stories. The better the question, the more it invites such sharing.

The challenge is to reach out with questions that open avenues for conversation, rather than provoke yelling.

the radio interviewer and expert questioner Krista Tippett: “It’s hard to transcend a combative question.14 But it’s hard to resist a generous question. We all have it in us to formulate questions that invite honesty, dignity, and revelation.”

Carl Sagan told the interviewer Charlie Rose: “If we are not able to ask skeptical questions15 … to interrogate those who tell us something is true, to be skeptical of those in authority … then we are up for grabs for the next charlatan, political or religious, who comes ambling along.”

we must arm ourselves with a set of critical questions—and be willing to consistently ask and thoughtfully consider those questions before rendering judgment. By employing this type of questioning, we can do what Carl Sagan called “baloney detection”17—the dismantling of false claims and slanted arguments from politicians, advertisers, or biased news sources (a skill needed more than ever in a world where the “baloney” is in abundance, and often well-disguised).

FIVE ALL-PURPOSE QUESTIONS FOR BETTER THINKING How can I see this with fresh eyes? What might I be assuming? Am I rushing to judgment? What am I missing? What matters most?

The psychologist and decision-making expert Daniel Levitin concurs: If you make decisions based on instinct, he says, “your gut is going to be wrong more than it is right.”2 So what can we do about that? When it comes to important decisions, we can put less trust in feelings and more in evidence.

Mike Whitaker, author of The Decision Makeover, advises that rather than spending time analyzing small decisions, “have fun with them.”3 Use them as an opportunity to be spontaneous or creative. Ice cream for breakfast? Go with your gut.

As we confront the various unknowns surrounding a tough decision, each question—What am I really trying to decide here? What’s most important? What critical information do I have and not have?—enables us to see a little more clearly, and helps us to step forward in the face of uncertainty.

A question is an invitation to think. It can be almost irresistible: Ask yourself an interesting question and you’ve given your mind a puzzle to solve. And when making important decisions, the more invitations we give ourselves to think, the better—because there are strong forces pulling us away from thinking at all.

When we make snap judgments, we’re relying on a limited or distorted view of a situation while thinking we have a more complete and accurate view. Based on his research of this phenomenon, the psychologist Daniel Kahneman developed a name (and acronym) for it: “What you see is all there is,” or WYSIATI. We form a story in our heads based on what little we know, without allowing for all we do not know,8 Kahneman explains.

Should I rely on my gut instinct when making decisions?, the scientific view is that you should do so only if you’re a chess master or someone with similarly prolonged, specific experience making decisions repeatedly in a particular situation. Most of us aren’t like the chess master—though we may think we are. “Overconfidence arises because people are often blind to their own blindness,”9 Kahneman writes. They “sincerely believe they have expertise, act as experts and look like experts.” But all the while, “they may be in the grip of an illusion.” Rather than ask, Should I trust my gut instincts?, the better question is, How can I override those instincts?

The first thing to do with that flashlight is turn it on yourself. The path to better decision-making begins by questioning one’s own beliefs, biases, and assumptions.

Today, if one is predisposed to believe something or hold a certain view, it is easier to seek out information that confirms that view while avoiding information that challenges it. Facebook’s newsfeed algorithm steadily feeds confirmation bias10 by exposing people to news and information that mostly aligns with their established preferences.

When the Nobel Prize–winning physicist Arno Penzias was asked what led to his success, he explained that he made a daily habit of asking what he called the “jugular question.”11 Penzias said, “The first thing I do each morning is ask myself, ‘Why do I strongly believe what I believe?’ ” Penzias felt it was critical to “constantly examine your own assumptions.”

Daniel Pink recommends regularly asking, What did I once believe that is no longer true?).

ASK THESE FOUR QUESTIONS TO CHECK YOUR BIASES AND BELIEFS What am I inclined to believe on this particular issue? Start by trying to articulate your beliefs/biases. Why do I believe what I believe? The “jugular question,” per Nobel Prize–winning physicist Arno Penzias, forces you to consider the basis of those beliefs. What would I like to be true? A “desirability bias” may lead you to think something is true because you want it to be true. What if the opposite is true? This question is inspired by “debiasing” experts and Seinfeld’s George Costanza.

In order to be able to question your own thinking—so that you can make room for other ideas and views that might conflict with yours—you must be “humble enough to admit that you don’t know something16 or that you might be wrong about what you think you know,” says Daniel Levitin.

Defined as “a state of openness to new ideas, a willingness to be receptive to new sources of evidence,”19 intellectual humility

If the “old smart” was about getting high grades, knowing more right answers, and not making mistakes, the “new smart” is measured by one’s ability to keep adapting. But to do that, Hess says, we must avoid being overly invested in our own ideas and expertise. “I must decouple my beliefs from my ego,” Hess explains. “I must be open-minded and treat my beliefs as hypotheses to be constantly tested and subject to modification by better data.”

QUESTIONS TO TEST YOUR “INTELLECTUAL HUMILITY” Do I tend to think more like a soldier or a scout? A soldier’s job is to defend, while a scout’s purpose is to explore and discover. Would I rather be right, or would I rather understand? If you place too much importance on being right, it can put you in “defense” mode and close off learning and understanding. Do I solicit and seek out opposing views? Don’t ask others if they agree with you—ask if they disagree and invite them to say why. Do I enjoy the “pleasant surprise” of discovering I’m mistaken? Finding out you were wrong about something needn’t be cause for shame; it’s a sign of intellectual openness and growth.

Overcoming the desire to “be right” takes a conscious effort, it seems. The venture capitalist Christopher Schroeder says he uses the following question to remind himself to keep an open mind: Would I rather be right or would I rather understand?

When it comes to making decisions or arriving at a judgment, the critical (or ninja) thinker strives to do so based on solid evidence while trying to remain objective and fair-minded. It takes some effort to engage in open-minded critical thinking instead of just assuming and accepting.

What is the evidence behind this claim and how strong is it? That may lead to a subset of more specific evidence questions, such as, Does this evidence come from a solid source? Is there an agenda behind it?