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

by Warren Berger

This 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 thinkers, creators, problem solvers, and decision makers.

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. 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.

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.

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.

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.

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.

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 Charan Ranganath.7 And that condition often leads to the action known as questioning, which is how we scratch the itch.

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.

ASK

Elie Wiesel once observed: “People are united by questions. It is the answers that divide them.”12

On the most basic level, questions help us understand, and empathize with, other people. 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.

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.”

these are difficult times to make sound judgments because the sheer amount of information coming at us puts a strain on our ability to evaluate it. “We’ve become less

critical in the face of information overload,”16 Levitin says. “We throw up our hands and say, ‘It’s too much to think about.’ ” When that happens we can end up making important decisions based on emotions or “gut reactions” rather than evidence or logic.

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?

We’re subject to inherent biases, false confidence, irrational risk aversion, and any number of decision-making pitfalls. Katherine Milkman of the University of Pennsylvania’s Wharton School, who has researched and written extensively on decision-making, says: “The science simply doesn’t support the value of following your gut1—in fact, it supports exactly the opposite approach to decision-making.” 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.”

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. But the decisions that matter—in your business or your career, in personal relationships or financial investments, in the voting booth—are worthy of more thought.

Questions enable us to “organize our thinking around what we don’t know,”4 says Steve Quatrano of the Right Question Institute, an inquiry research group.

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.

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.

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.

USE THESE FIVE QUESTIONS TO DETECT B.S. How strong is the evidence? Critical thinking starts with demanding that there be substance behind any claim. A subset of “evidence” questions might include, Does this evidence come from a solid source? Is there an agenda behind it? What are they not telling me? Sometimes the problem with information is not what is there, but what’s missing—whether it’s a news story with insufficient reporting or a sales pitch that leaves out important details. Does it logically follow? When people are trying to persuade you, they may use flawed reasoning that suggests you should believe A because of B. What is the opposing view? To avoid “weak-sense critical thinking,” be willing to seek out an opposing side of the issue you’re deciding on—and try to consider it with an open mind. Which of the conflicting views has more evidence behind it? Go with the side that has more weight.

Dan Heath, authors of the book Decisive, concur that “the first villain of decision making—‘narrow framing’29—is the tendency to define our choices too narrowly, in binary terms.” So then: How do you open up more options? Simple: Ask yourself to do so.

USE THESE FIVE QUESTIONS TO OPEN UP POSSIBILITIES How can I “open up” the question to be decided? We have a tendency to make binary decisions (yes/no, either/or), which limits options. Trying using open-ended questions (What are the best ways …? How might I …?) to frame your decision.

What is the great, the good, and the ugly? When making decisions, try to choose from at least three options. Do this by projecting three different potential outcomes or scenarios—one very positive, one moderate, and one negative. If none of the current options were available, what would I do? Imagine that the existing options you’re deciding between suddenly have vanished; this forces you to try to come up with additional possibilities. Upon returning to reality, you can weigh your newly-imagined options against the existing ones. What is the counterintuitive choice? Include one option that goes completely against the others; you probably won’t choose it, but it stimulates unconventional thinking. What would an outsider do? You can get an actual outsider to help answer this—or just try to look at the situation the way an outsider might.

The Heath Brothers point to research showing that “our advice to others tends to hinge on the single most important factor,” as it should—but when we’re thinking about ourselves, we get caught up in too many large and small concerns. Or as the Heaths put it: “When we think of our friends we see the forest. When we think of ourselves, we get stuck in the trees.”34

“COURAGEOUS” QUESTIONS TO OVERCOME FEAR OF FAILURE What would I try if I knew I could not fail? Start with this favorite Silicon Valley question to help identify bold possibilities. What is the worst that could happen? This may seem negative, but the question forces you to confront hazy fears and consider them in a more specific way (which usually makes them less scary). If I did fail, what would be the likely causes? Do a “premortem” on a possible failure, listing some of the potential causes; this tells you what pitfalls to avoid. … and how would I recover from that failure? Just thinking about how you would pick up the pieces if you did fail tends to lessen the fear of that possibility.

What if I succeed—what would that look like? Now shift from worst-case to best-case scenario. Visualizing success breeds confidence—and provides motivation for moving forward. How can I take one small step into the breach? Consider whether there are “baby steps” that could lead up to taking a leap.

The scientist and decision-making expert Gary Klein is a proponent of using “premortems”51 (doing a postmortem in advance) to envision what a potential failure might look like, so that you can then consider the possible reasons for that failure. To put the premortem into question form, you might ask: If I were to fail, what might be the reasons for that failure? Decision researchers say using premortems can temper excessive optimism and encourage a more realistic assessment of risk.

While you’re envisioning the possibility of failure, be sure to consider the opposite, as well, by asking: What if I succeed—what would that look like?52 Jonathan Fields points out that this question

is important because it can help counter the negativity bias. Fields recommends visualizing, in detail, what would be likely to happen in a best-case scenario. The reality may not live up to that, but that vision can provide an incentive strong enough to encourage taking a risk.

This inclination toward short-term thinking causes us to focus on immediate preferences while ignoring long-term aims and consequences. One way to counter it is to try to imagine how we might feel about something in the future. “Good decision-making is tied to our ability to anticipate future emotional states,”60 says Ed Batista, an executive coach who teaches at Stanford University. “We need to vividly envision ourselves in a future scenario.” So if, for example, an opportunity comes your way and you’re trying to decide whether to take it, consider this question shared by writer Rob Walker: If I look back years from now, will I wish that I’d made a change when the opportunity was ripe?61 If you can imagine how “future you” might feel about this, it can help guide you toward the better long-term decision.

Can the little person rise to the top? Seek the proof in the form of multiple stories of people who were able to make that climb. How does the organization react to mistakes? This will determine whether you can experiment and grow. (Another way of asking: Will I be punished for exploring?) Can I have influence in this organization? Find out whether people at all levels have a say. How have others here added to their skills? Another key determinant of whether you’ll be able to evolve. Does this place encourage camaraderie? The social aspect of work is more important than most think. Will I enjoy the “small pleasures” of my daily routine? Being happy in your job hinges on the little things you’ll be doing every day.

there are three categories of questions you can ask: about your own strengths or assets; about your natural interests; and about the ways in which you might contribute to something larger than yourself.

become “an anthropologist of your own life,”77 says coach and Essentialism author Greg McKeown, who recommends asking yourself: When was I truly happy and why? What activity or theme do I keep coming back to? and When do I seem most like myself? This can include not only present activities, but past ones as well—going back to childhood. The psychologist Eric Maisel recommends asking, What did I enjoy doing at age ten?78 After drawing up a list of favorite childhood activities,

SIX QUESTIONS TO HELP YOU FIND YOUR PASSION What is my tennis ball? Identify “the thing that pulls you” … that holds the potential to engage you as single-mindedly as a dog chasing a tennis ball. (Drew Houston) What makes me forget to eat?79 If it matters to you more than food, that says a lot. (Mark Manson) What did I enjoy doing at age ten? By looking back into the past, you may get a glimpse of what you should do going forward. (Eric Maisel) What are my superpowers? Take inventory of “the combination of personality traits and aptitudes you bring effortlessly to any situation.” (Keith Yamashita) In what way do I wish the world were different? This question “puts the focus where it should be—on how you can serve other people.” (Angela Duckworth)

What is my sentence? This question helps you distill purpose to its essence by formulating a single sentence that sums up who you are and what, above all, you aim to achieve. (Daniel Pink)

What makes me forget to eat? Forbes columnist Mark Manson has picked up on this idea, which derives from the work of psychologist Mihaly Csikszentmahalyi on “flow”80 (people who enter a state of creative flow while working tend to lose track of time and everything else not related to the work they’re doing at that moment).

ask the question: What is needed and how might I help? The journalist David Brooks writes about the difference between people who pursue the “Well-Planned Life,”81 which emphasizes individual agency, and those leading the Summoned Life, who are inclined to ask, What are my circumstances summoning me to do? What is my most useful social role? This theme was addressed in an essay written for college graduates by the psychologist and Grit author Angela Duckworth, who advised readers not only to “move toward what interests you” but also to “seek purpose.”

How might I apply my signature strengths to a pursuit that is of natural interest to me and helps others? By addressing all three “passion” elements—strengths, interests, purpose—it can help guide you to something that both engages you and enables you to use your gifts to make a difference.

Considering how hard it is to do anything worthwhile, perhaps a good question to keep in mind is this off-color one,85 shared by Mark Manson: What is your favorite flavor of shit sandwich? As Manson explains, “Everything sucks, some of the time … So the question becomes: What struggle or sacrifice are you willing to tolerate?”

perhaps what’s needed is not another question but rather a definitive statement—one that sums up who you are and what you mean to achieve in this life. If that seems like something that would be difficult to produce, it’s actually not—you just have to ask yourself, What is my sentence?86 This question was once posed by journalist and Congresswoman Clare Booth Luce to President John F. Kennedy. Luce told Kennedy “a great man is a sentence”—meaning that a leader with a clear and strong purpose could be summed up in a single line (e.g., “Abraham Lincoln preserved the union and freed the slaves”). Daniel Pink, an admirer of Luce’s question, points out that it can be useful to anyone, not just presidents.

Through teaching, coauthoring the book Creative Confidence, delivering a TED Talk, and creating online courses, they began to put forth a philosophy about creativity that had three core principles behind it: That creativity is essential to business and career success—and that, in Tom’s words, “creativity has a way of spilling over into your whole life,” making it more fulfilling and productive. That each of us is creative—though many of us have been conditioned, in the years since childhood, to believe we’re not. During their years teaching university courses and working with employees and clients at their firm, IDEO, the Kelleys had seen, firsthand, that if you could instill in someone a sense of “creative confidence”—a belief in one’s own ability to generate creative ideas and bring them to life—you could unlock that person’s creative potential. That there are ways to surface creative ideas and develop them by following certain steps and behaviors. By following this process, creativity could be summoned as needed, and hence one didn’t have to wait until “an angel of the Lord appears2 and tells you what to do,” as David puts it. The Kelleys use the term “design thinking” to describe the IDEO approach

questioning can help with many of the challenges associated with creativity, including: finding an original idea; overcoming creative blocks; figuring out when and where your creativity can flourish (even in the midst of abundant distractions); knowing how to improve, finish, and “ship” creative work; and finding ways to continually evolve so that your creative work doesn’t grow stale.

psychologist Robert Sternberg studied successful creative people3 and found that, at some point, they’d made a conscious decision in favor of being creative. Sternberg concluded that, “without the decision, creativity will not emerge.” In light of Sternberg’s findings, perhaps the first question any of us should ask about creativity is: Am I willing to decide in favor of it? And if so, why? There are many potential answers, but here is a good one to start with: Even if your creative work never goes beyond the room where you labor over it, it can have a highly positive impact—on you. Research has shown that just doing one creative task, no matter how small,4 can add to your happiness and increase your sense of well-being. As the productivity author Phyllis Korkki puts it, “Creativity is yoga for the brain.”

when people become fully engaged in a project that pushes them to the limits of their imagination and capability, it’s a one-of-a-kind feeling. Csikszentmihalyi observed: “The excitement of the artist at the easel or scientist in the lab6 comes closest to the ideal we all hope to get from life—and so rarely do.”

The author Brené Brown found about a third of those she interviewed could recall a “creativity scar”11 from when they were younger—a time when they were told their creative work wasn’t good enough. The discouragement may even come from friends and family members

IF YOU WANT TO BE MORE CREATIVE, STOP ASKING THESE 6 QUESTIONS These are wrong questions that people often ask about creativity. Read the answers below—then stop asking them. Am I creative? If you’re human, you are creative. There is no “creativity gene” that some have and others lack. It’s a gift that is available to everyone. How creative am I? It’s difficult to measure or answer this (and besides, it’s not a competition). Better to rearrange the question and ask: How am I creative? You will likely find many answers to that question. Where will I ever find an original idea? (Hasn’t everything been thought of already?) You don’t have to create from whole cloth; almost every new idea consists of fragments of existing ideas. And the fragments are everywhere. Where will I find the time to create? Start by turning off your iPhone (unless you use it to create). How can I come up with an idea that will make money? Don’t begin with the outcome in mind. Find and develop a worthy idea; the money will follow (maybe).