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

by Warren Berger

Adam Grant, we actually can be more persuasive, and therefore exert more power, when we act as “powerless communicators” who listen and ask questions.32 And as noted previously, people who listen and ask questions are showing interest—and “being interested makes you interesting,” says Goulston.

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?

Iain McGilchrist believes that the question “we should be asking ourselves is, what is it that my culture is preventing me from seeing?”49 He suggests we must strive to look past what is obvious and clear to us—forget about what everybody around us is “banging on about,” says McGilchrist—and try to see that which is obscured, and which perhaps runs counter to what you, and those around you, have been thinking all along.

The views people hold about various issues often become bound up with identity. When you attack those views, it can be perceived as a personal attack.

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?

Oprah Winfrey has written, “Proving I was right used to be a major character flaw.”65 She says it cost her precious time with friends and loved ones by prolonging fights and misunderstandings. She eventually changed her ways, and notes that “a single question got me started: Do you want to be right, or do you want peace?” It’s a good question for warring friends—and maybe warring countries, too—to keep in mind.

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?

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.)

pioneering business consultant Peter Drucker understood, long ago, that he could best serve clients by asking questions.74 Drucker said that many company leaders tended to come to him seeking answers to their business problems. However, Drucker’s reasoning was that these leaders actually knew far more than he did about their own businesses. They didn’t need an outsider with less knowledge of the business to tell them what to do. Instead, they needed someone who could bring an “outside view” to the challenges at hand, ask the questions that weren’t being asked (because the company insiders were too close to the problems and too steeped in their own expertise), and in so doing, help these business leaders to come up with their own answers.

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.

TO SHARPEN YOUR LEADERSHIP FOCUS, ASK THESE QUESTIONS What is the one thing I can do that would make everything else easier or unnecessary?38 Ask this “focusing” question at the start of any new challenge or project. (Gary Keller) What should we stop doing? Practice “systematic abandonment.” (Peter Drucker) What do I want to go big on? Ask this instead of “What am I giving up?” (Greg McKeown) Which stupid rule should we kill? Share this question with employees to see what they choose. (Lisa Bodell) At this moment, what is the highest, best use of my time? Use the “HBU” question to maximize personal productivity. (Angie Morgan)

RELEASE YOUR “INNER STEVE JOBS” BY ASKING “VISIONARY” QUESTIONS How can we become the company that would put us out of business? Start by envisioning a threat that doesn’t exist (yet). How can we brace ourselves for the third wave? It’s not the wave you’re on now or the one you can see breaking; it’s the big one yet to break. If an oracle could tell us about our business five years from now, what would we ask? Think of the most critical questions; then go to work on them (because you’re the oracle). What would the seventh generation think about what we’re doing? Take a lesson from the Iroquois about long-term planning. How might I make tomorrow visible? Inspire people by giving them a glimpse of a better future. What is our “vision question”? Forget the vision statement. Pursue the future with an open-ended query.

What’s the biggest challenge you’re facing? You can make the “challenge” question more specific (“on this project”) or more general (“in your job”). Are you making progress? If employees feel “stuck,” frustration sets in. Help me understand what led to … Instead of asking “Why?” about a problem, start the question this way—it’s wordier, but less accusatory. Is it clear what we’re doing and why? Ask employees this question with regard to company goals, directives, policy changes, and the vision for the future. How can I help? Per Doug Conant, the “ultimate leadership question.” But only ask it if you mean it.

TO ENCOURAGE A CULTURE OF INQUIRY, ASK THESE FOUR QUESTIONS How can we make it safe to question? Institute a strict “no judging” rule; all questions welcome, the more the merrier. How might we make questioning rewarding? Celebrate productive questions by verbal recognition. To go further, offer bonuses and other tangible incentives. How might we make questioning productive? Train people in how to question in ways that produce results. How can we make a culture of inquiry stick? Make questioning a central part of meetings and other regular activities.

Exercise: L.I.F.E. questions13 Questions can spark lively conversation when the family is together. The L.I.F.E. questions exercise can be done around the dinner table with kids once a week. The idea is to surface the little anecdotes and daily stories that create intimacy and shared memories. Go around the table and ask each person to share their four answers to the four L.I.F.E. questions. (Once your family members know they might be playing the game of L.I.F.E. at dinner next Sunday night, they’ll start collecting and remembering moments to be shared at the next gathering.) L. What weird LITTLE thing sticks out in your mind from this week? The little things that we choose to remember and share with others form the narrative threads of our lives, and focusing on the “weird” helps captures children’s attention. I. What piece of INFORMATION did you learn this week? Sharing something that’s news to you or a piece of learning can entertain others and solidify the information in your own brain. F. Is there anything you tried and FAILED at this week? Sara Blakely, the entrepreneur who founded Spanx apparel, was inspired by this question,14 asked often by her father at the dinner table. Acknowledging and discussing trial-and-error in a routine way helps us realize failing happens to all of us, is not something to be afraid of, and indeed helps us become better problem solvers. E. What memorable EXCHANGE did you have this week? This question reminds us to reach out once in a...

As discussed in the Leadership section, every leader of a company should make sure the organization has a strong backstory about its history and original purpose, a sense of what the company stands for, and a mission statement—or better yet, a mission question. What if the leaders of families did this?17 The author Bruce Feiler has explored this theme in his writing, and it was also covered recently in a New York Times column by Paul Sullivan. Based on these sources, here’s an exercise that uses questioning to develop a family story and an ongoing, inspiring family “mission question.” Exercise: Developing a family story and mission Begin with a focus on family heritage: Where were our ancestors born? When did they arrive in this country? What might our ancestors have had to overcome to get here? What are some traditions that have been passed down through our family? When and how did they get started? What are some family stories that you know? That I know? In particular, what difficulties did the family have to bounce back from? What were some of the greatest accomplishments by family members through the years? What do the stories mean to us today? What are some classic family jokes or songs? Then, transition to questions about meaning and purpose: What does it mean to be part of this family? Is how you feel about being part of this family different than how I feel? Of all the family members you have either known or heard stories about, who do you think lived the most inte...

A study at the University of Illinois found that when people were trying to motivate themselves to do something, they had better results asking (Will I do X? How can I do X?) as opposed to declaring (I will do X!) Why do questions motivate us more than resolutions? First of all, questions are more engaging than statements. They invite you (or even challenge you) to think about potential solutions. They get your brain working right away on a problem. For example, suppose instead of resolving that I will meet more interesting people this year! you were to ask yourself, How might I meet more interesting people this year? That question is likely to trigger speculative thought: Well, what if I were to do X? or What if I tried to do Y? Already, you are thinking of potential new ways to meet people. Questions are also less intimidating than resolutions. They put less pressure on you.

Here’s an exercise in which you can use questioning to try to change your own behavior by composing a resolution, with a twist. Call it a “questolution.” Exercise: Create your own “questolution” In thinking of a questolution for yourself, phrase it as “How might I?” question (e.g., How might I get myself to drink more water?). Write or print the question in bold type at the top of a sheet of paper and tape the sheet to the wall. Each time you think of an idea that might help you achieve the goal, phrase that idea as a “What if?” question (What if I begin carrying a reusable water bottle to work each day?) and jot it down under the overarching “How might I?” questolution. This very visible list of “What if?” questions you’re creating will cry out for action, and you’re likely to find yourself making step-by-step progress on your questolution.

In addition to the ones in this book, there are many more you can devise yourself. But I also believe that you should try to identify one particular question to pursue over time—call it your “big beautiful question” (BBQ). It should be bold and ambitious and actionable. My own BBQ started a decade ago as How might I encourage more questioning? Writing this book is just one of the ways I am still trying to explore that question.

As explained by Tim Brown, chief executive at the innovation firm IDEO, “How might” questions free you to do your best creative thinking.19 “The ‘how’ part assumes there are solutions out there—it provides creative confidence,” Brown says. “The word ‘might’ says we can put ideas out there that might work or might not—either way, it’s okay.”

(Go to amorebeautifulquestion.com/whats-your-beautiful-question). If you haven’t thought of your question yet, go to the site and check out some of the questions others are pursuing—it may spark an idea.