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

by Warren Berger

Another creativity-starter technique involves trying to think of “wrong ideas” at the outset of a project. The creative workshop leader Tom Monahan uses an approach called “180-degree thinking” in which “you start out making something wrong and then see if you can turn that bad thing into something good,”65 Monahan says. In the exercise, you might ask yourself, for example, What if I tried to create a car that is unable to move? Or an oven that can’t cook?

In his study of the creative process, Adam Grant describes five stages that tend to trigger different emotional responses in the creator.66 The energized, optimistic feeling at stage 1 (“This is awesome!”) is followed by a more realistic stage 2 (“This is tricky”). Then comes the dreaded stage 3 (“This is crap”), followed immediately by stage 4 (“I’m crap”). If the creator somehow crawls out of that pit, they work their way to stage 5 (“This might be okay.”), and finally arrive at completion, stage 6 (“This is awesome!”).

The key here is to make sure we don’t lose ourselves in the step 3 or step 4. We need to be strong and we can ask ourselves questions like if we have done this before?

In order to be able to ship often, you must be willing to ship early. Mark Zuckerberg of Facebook says, “We have the words ‘Done is better than perfect’ painted on our walls70 to remind ourselves to always keep shipping.” Zuckerberg refers to the “Hacker Way” of creating things, which involves “quickly releasing and learning from smaller iterations rather than trying to get everything right all at once.”

Even though I don’t see eye to eye with many of Mark Zuckerberg’s ideals, he is right about this one.

Just as important as being willing to accept failure is the willingness to accept feedback.

USE THESE QUESTIONS TO GET HONEST, USEFUL FEEDBACK ON YOUR WORK Am I coming across? Use feedback not to change your basic idea, but just to see if it’s being expressed clearly and understood. What do you like least about this? This question requires some courage to ask, but it’s important because it gives permission to offer honest criticism. It also focuses on where the biggest problem(s) may lie. And what else? Also known as the “AWE” question (more on this in part III). It is designed to extract additional criticisms and often yields deeper insights. What would you suggest I try? Good feedback usually tells you what’s wrong or missing but may not offer a solution. Use questioning to pull that out of the feedback giver.

Adam Grant points out, “The only way to improve is to get negative feedback—so if you decide not to seek out criticism you’re resigning yourself to stay at your current level of skill. Which to me is depressing.”

In trying to convince his students to be more open to feedback, Grant sometimes asks them: Is your goal to stay at your current level of skill, or to improve? When the question is framed that way, he says, almost everyone opts for improvement—and feedback.

In finding the right people to provide feedback on your work, seek out those whose opinions you respect and who are entirely on your side. Ask yourself, Who are my trusted advisors? When you’ve come up with a handful of candidates, “create your own advisory board,” Kelley says. The earlier you can get work to your “advisory board,” the better; their early input may help you avoid wasting time polishing and tweaking something that actually needs reworking.

This is your mentoring circle.

One of the most important feedback questions to ask is not, Is my idea good? (trust your own instincts on that), but simply, Am I coming across?

Feedback often is not prescriptive. According to Pixar executive Ed Catmull, “A good note says what’s wrong, what’s missing, what makes no sense.”77 It’s focused on the problems, not the solution. But if you are open to suggestions on specifically how to fix problems or make changes, ask for it: I was wondering about how to improve X or Y—what would you suggest I try?

To remain creative, you must think and behave like a novice, always discovering.

The author Elizabeth Gilbert, in a talk extolling the benefits of “the curiosity-driven life,”81 shares a wonderful analogy involving jackhammers and hummingbirds. According to Gilbert, people who behave like jackhammers focus obsessively on one thing, drilling deeper and deeper. Those who are more like hummingbirds follow their curiosity as they “move from tree to tree, from flower to flower … trying this, trying that.” So: Should a creative person be more like a hummingbird or a jackhammer? It probably depends what stage you’re at in your work. Curiosity can be a wonderful source of creative inspiration, constantly leading you to new ideas.

USE THESE QUESTIONS TO KEEP YOUR CREATIVE WORK FROM GETTING STALE How can I keep moving away from what I know? To avoid becoming a “comfortable expert” in your work, follow your curiosity. Is it time to be a jackhammer—or a hummingbird? The hummingbird keeps landing in new places; the jackhammer drills deep in one spot. What am I willing to abandon? To keep work fresh, you must give something up: reliable material, proven methods, familiar turf. How might I “go electric”? Like Dylan at Newport, a creative person should recognize that the times are a-changin’ and embrace new styles, tastes, forms, and technologies. Where is my petri dish? To experiment with your work, you may need to find a place where you can do so safely.

Questions show interest, create understanding, and build rapport. Those are three strong legs upon which a relationship can be built and supported.

Am I genuinely interested in the other person? Am I able to put my ego aside and suspend all judgment? Am I prepared to truly listen, as opposed to just acting as if I am listening? “If you don’t do all of these things, it can undermine the rapport you’re trying to build with your questions.”

To get better at asking the kinds of questions that do forge deeper connections with the people around us, we need to do a few things: endeavor to ask “authentic” questions rooted in curiosity; try to suspend judgment and withhold advice as we focus more on inquiry; take a small risk by being willing to ask open-ended, “deeper” questions (even of people we may not know very well); and be willing to listen carefully and follow up on what we’re hearing with questions that gently probe a little deeper.

People who have companionship are not only happier and healthier, but they also are likely to have a greater sense of “meaning”8 in their lives, according to the findings of The Power of Meaning author Emily Esfahani Smith.

When it comes to friendship, less may be more. A handful of intimate, deep relationships are worth more than five hundred “friends” on Facebook, at least in terms of producing the kinds of life-enriching benefits Esfahani Smith is talking about.

“When it comes time to exchange words with another human being, we find we’re all sort of empty-headed,” Colin says. But it can help if you come armed with the right questions. “A good way to get beyond small talk is to ask open-ended questions that invite people to tell stories, rather than give bland, one-word answers.” Colin adds: “Curiosity has to be at the heart of your heart when you talk to someone. The kind of curiosity that works best is a curiosity for stories.”

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.

Colin and Baedeker recommend putting a twist on more standard questions. Instead of How was your weekend, try What was the best part of your weekend? Instead of Where are you from?, try What’s the strangest/most interesting thing about where you grew up?

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?

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?

Doyle eventually began filling a jar of her own with questions at home. A few times a week, she and her children take turns pulling out a question during dinner. Sample questions: If you were an inventor—what would you invent, and why? What was your first thought when you woke up today? Who in your class seems lonely? What do you think is the biggest challenge facing our world today?

As the journalist Frank Sesno explains: “The simple act of asking, and of listening without comment or judgment” is powerful19 because it “invites a person to reflect and think aloud. It might even prompt a revelation.”

“Good listeners have a physical, mental, and emotional presence,22 and they know how to integrate all three,” says Judith Humphrey, founder of the communications firm the Humphrey Group. It’s worth noting that the Chinese symbol for listening incorporates the ear, the eyes, and the heart—a reminder that good listening really is a demanding activity.

Listening with an attentive mind and open heart is signaled partly through body language—eye contact, turning toward the speaker, nodding, keeping your arms unfolded—and partly by way of verbal responses.

As a reminder to talk less and listen more, try asking yourself the “WAIT question,”25 shared by psychologist Ronald Siegel. “WAIT stands for Why Am I Talking?,” Siegel explains, adding: “This simple question can help cultivate a reflective attitude” that restrains the impulse to interrupt and interject while listening to someone.

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.

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?

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.)

What does the world need from us?

The leader must be the one to look into the heart and soul of any type of organization or collective and ask, What is our mission and purpose? Why are we here?

“Who has influenced you most in your life?”1

When Lopez is not roaming the hallways or stopping in at classrooms, she is apt to steal a quiet moment away from the action to think about the larger goals and challenges for her school and its teachers and scholars. She has a vision of the school as a place that doesn’t just educate, but actually transforms the way underprivileged young people think about themselves, their circumstances, and the possibilities available to them. During those few quiet moments, Lopez grapples with big, difficult questions. What is the twenty-first century demanding of these kids, and how can the school provide that? How do you instill a sense of possibility in young people living amid poverty and hopelessness? How do you keep underpaid, overworked teachers from burning out?

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.

Ask yourself questions such as: When have I been at my best? What drove or inspired me at those times? What have I learned about working with other people (in doing so, when have I been effective, and what caused that?) When have I taken a principled stand? What have I gone out of my way to defend?

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.

former Trader Joe’s president Doug Rauch: If we disappeared tomorrow, who would miss us? And here’s another way of coming at it, as suggested by the Fast Company cofounder William C. Taylor: What do we do that other organizations can’t or won’t do?29

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.

Edgar Schein, a former MIT Sloan School organizational development expert and author of Humble Inquiry, has observed that a problem plaguing most organizations is poor upward communication—it’s “a major pathology,”51 he says. “Subordinates know lots of things that would make the place work better or safer that they for various reasons withhold.” When asked why they withhold much-needed information, employees typically answer that bosses and managers don’t want to hear about problems, or worse, are likely to “shoot the messenger.” The only way to change this, Schein says, is for the manager to go directly to subordinates and say, “I’m really interested and I’m listening.” If that doesn’t happen, he adds, we will “continue to have accidents and low quality products because the information isn’t surfacing.” More than ever before, leaders today must guard against what former General Electric chief Jack Welch refers to as “creeping insularity” that cuts the leader off from people and critical information. Welch notes that “Every day spent behind your closed door is a day you’re not out learning about your people,52 processes, and market realities.” He thinks every leader ought to have a sign facing them on their desk that reads, “Why are you still here?” Assuming we accept the premise that a leader should regularly leave the office and walk the floor asking questions—call it “ambulatory inquiry”—this raises the question: What should I ask all these people?

Am I seeking their thoughts, instead of just offering my own? Am I focused on their priorities, not mine? Am I offering them choices and options, instead of telling them what to do?

WHEN DOING “AMBULATORY INQUIRY,” A LEADER SHOULD NOT ASK … How’s it going? This is a rote question and elicits rote responses. Why did you ___? When you ask “why?” questions directly of employees, it shifts them into “justify” mode. Who screwed up here? Rather than focusing on a scapegoat, inquire about how best to address the issue and move forward. Haven’t we tried this already? Often uttered wearily by “Been there, done that” leaders. Say it enough times, and people will stop offering ideas altogether. AND SHOULD ASK … 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.