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

by Warren Berger

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

George Carlin: “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.”

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?

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?

author 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.

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.

keep an open mind: Would I rather be right or would I rather understand?21

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?

critical thinker should always ask, What are they not telling me?

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.

tricks that critical thinkers should always watch for, including arguments that rely on authority (I’m the president, so you should believe me), false dichotomies (You’re with us or against us), and “slippery slope” arguments (If we take this seemingly reasonable step, it will surely lead to something much worse).

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.

Rather than avoiding thinking about these, it’s generally better to come right out and ask: What is the worst that could happen?49

“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.

of failure, be sure to consider the opposite, as well, by asking: What if I succeed—what would that look like?52

QUESTIONS TO ASK BEFORE TAKING THAT JOB 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.

Newport’s advice: Pick a career that seems interesting (and leave passion out of it); then focus on becoming good at that thing, and eventually it may become your passion.

“follow your curiosity”—which may lead you to a passion (or many different ones).

What are my signature strengths?

What personal strengths did I display when I was at my best?74 Did I show creativity? Good judgment? Kindness?

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)

Is your goal to stay at your current level of skill, or to improve?

QUESTIONS TO ASK INSTEAD OF HOW ARE YOU? What’s the best thing that happened to you today? This can be adapted to ask about this week, the weekend, etc. What are you excited about in your life right now? What are you most looking forward to at this gathering? This one is good for conferences and other social events.

… AND INSTEAD OF WHAT DO YOU DO? What are you most passionate about? This is a great way to shift from a job (which may be boring) to interests. What problem do you wish you could solve? This shifts from present realities to larger goals and possibilities. What did you want to be when you were growing up? This question invites a story about growing up and the road that led to the present.

Instead of How was your weekend, try What was the best part of your weekend? Instead

QUESTIONS TO MAKE SOMEONE LIKE (OR EVEN LOVE) YOU What would constitute a perfect day for you? If you could change anything about the way you were raised, what would it be? What does friendship mean to you? How do you feel about your relationship with your mother? When did you last cry in front of another person? And by yourself? What, if anything, is too serious to be joked about? From Arthur Aron’s thirty-six questions experiment. For the full list, visit www.amorebeautifulquestion.com/36-questions.

QUESTIONS TO ASK YOUR SPOUSE INSTEAD OF HOW WAS YOUR DAY?14 Sara Goldstein of Mother.ly came up with twenty-one questions; here are six of them. When did you feel appreciated today? Will you remember any specific part of today a year from now? How can I make your day easier in five minutes? If we were leaving for vacation tonight, where do you wish we were heading? What made you laugh today? What do you wish you did more of today?

ASKING THESE QUESTIONS WILL MAKE YOU A BETTER LISTENER Just to be clear, are you saying ___? At key points, repeat back a paraphrase of what you’ve heard. Can you explain what you mean by that? This is a classic “clarifying” question used by interviewers to invite people to better explain themselves. (Tone is important: Go for curious, not puzzled or antagonistic.) I imagine that made you feel __ , right? A variation of How did it make you feel? (which sounds too much like a psychiatrist’s question). And what else? The “AWE” question may be the best way to draw out deeper insights—and keep you in listening mode.

What could we try in order to solve this problem … and what else? or What issues should our company be thinking about … and what else?

SKIP THE ADVICE. ASK THESE SEVEN QUESTIONS TO HELP SOMEONE FIGURE IT OUT FOR THEMSELVES What is the challenge that you’re facing? What have you tried already? If you could try anything to solve this, what would you try? And what else? (Repeat this two or three times, as needed, to surface additional ideas.) Which of these options interests you most? What might stand in the way of this idea, and what could be done about that? What is one step you could take to begin acting on this, right away?

BEFORE YOU CRITICIZE SOMEONE, ASK YOURSELF THESE QUESTIONS What’s motivating this critical urge? How am I guilty of the thing I’m criticizing? How would I react if someone said something similar to me? What positive result do I hope will come of saying this? Am I deriving pleasure from criticizing?

USE THESE “BRIDGE” QUESTIONS TO TRY TO MEET HALFWAY ON A DIVISIVE ISSUE What is it in your position that gives you pause? What is it in my position that interests or attracts you? On a scale of one to ten (one having no value at all, ten being 100 percent right and unassailable), how would you rate my position? And your own? If you didn’t rate mine a one and yours a ten, why not? Can we imagine a position that might at least partly satisfy both of us?

QUESTIONS TO ASK YOUR BEST BUD59 On a long drive with her best friend, the writer Kaitlyn Wylde came up with a lengthy list of questions designed to deepen the relationship. Here are five of them. What do you struggle with on a day-to-day basis? What have you always wanted to try? If you could start your own nonprofit, what would it be? What would be the title of your autobiography? If you had to live in another country for a year, where would that be?

Start with the simple apology: I’m sorry. Follow with an admission: I was wrong. End with the question: Will you please forgive me? For maximum effectiveness, say all ten words.

QUESTIONS THAT YOUR BOSS WILL LOVE What would you do in my position? What does your ideal employee look like? What’s the one thing that, if I did it differently, would make a difference to you? What is most important on your list to accomplish today—and is there any way I can help?

Are you satisfied with your own performance? and What do you think is working well, and what is not?,

What do you not have time to work on, that you’d like to be working on?,

One of the most important questions any manager can ask their employees is: What questions do you have for me? If

What’s the coolest thing you’ll be working on this week? What are you excited about in your job right now?

QUESTIONS TO ASK ABOUT A CO-WORKER YOU REALLY CAN’T STAND Is it possible I’m overreacting? (Get an “outside view” by describing the situation to a trusted co-worker.) Drill down: Which of this person’s specific behaviors most bother me? Of those, which actually interfere with my ability to do my job? Of those, which are changeable? Is there a way to politely ask this person to make one change? Who could mediate? (Ideally someone who is known and trusted by both parties.) How might I create distance? (If possible, move to another desk; if not, consider headphones.)

BEFORE TAKING ON A LEADERSHIP CHALLENGE, ASK Why do I want to lead this endeavor? Why would others want me to lead them? Does the answer to the first question also work as an answer to the second? If not, your reasons for wanting to lead may be too self-serving.

TO DETERMINE IF YOU’RE READY TO BE A TWENTY-FIRST-CENTURY LEADER, ASK Am I willing to step back in order to help others move forward? Many aspiring leaders are rising stars and high performers, but success as a leader will depend more on helping others achieve success. Do I have the confidence to be humble? The balance is to be humble enough to admit you don’t have all the answers—while being confident that you can help the organization to figure them out. Can I learn to keep learning? Rising uncertainty means today’s leaders cannot rely on their own expertise. They must be restless learners. Do I seek to create an organization in my own image? Too many leaders surround themselves with similar people, depriving the organization of the diverse thinking needed to be successful today. Overconfidence

“I must be willing to admit I may not have the answer … but at the same time be confident I can help all of us to find the answers.” Which can be boiled down to a second question that every aspiring leader should ask: Do I have the confidence to be a humble leader? A third question for aspiring leaders involves the U in VUCA:

What is my code? As he defines it, the code is a set of principles and behaviors that can guide you as a leader. In

USE THESE QUESTIONS TO “CRACK YOUR CODE” AS A LEADER Who are my formative influencers? Leadership values are instilled early, often from relatives or teachers; revisit those lessons. When have I been at my best? Study your past successes to assess strengths and productive behaviors. When have I come up short—and why? Failures usually contain lessons that may be useful in developing guiding principles. What have I taken a stand for (and against)? This question can help clarify what matters most to you—which should shape your leadership code. What is my logline? Share your values by way of a story—and boil it down to a line or two that sums up what you’re “about” as a leader.

ASK THESE “MISSION” QUESTIONS TO CLARIFY WHY YOUR COMPANY MATTERS If we disappeared tomorrow, who would miss us?28 This speculative question helps clarify why you matter and to whom. What do we do that others can’t or won’t? This shifts the focus to an organization’s strengths and uniqueness. What are we against? It’s easy to say what you’re for. It’s more risky—and therefore carries more weight—for a company to oppose something. How might we be not just a company but a cause? Increasingly, organizations are expected to contribute something worthwhile—to employees, local communities, and the world.

What if we stopped celebrating being busy as a measure of importance?