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

by Warren Berger

most successful artists tended to take an existing situation and look for ways to rework it. They were less apt to try to solve problems in a straightforward way by following instructions. The “problem finder” goes looking for trouble. The creative process can encompass both finding (and even making) the trouble, as well as fixing it with a creative solution. Problem finding runs counter to the notion that creative people should be trying to think of ideas that emerge as fully formed solutions. It suggests the ideas and solutions will come (hopefully) along the way, but the problem is the starting point. Problem finders look at the world around them, focus in on something in particular—a situation, an existing creation, a theme—and inquire deeply about it: What is lacking here? What is happening that doesn’t make sense? What is the story that is not being told? How might the whole thing be reinvented or turned upside down? And the most critical question: Why might I want to take on this problem and make it my own?

TO FIND YOUR BIG IDEA, ASK THESE QUESTIONS What stirs me? To find a “problem” that’s worth devoting your creative efforts to solve, start with a high interest level—meaning it touches on something that matters to you. What bugs me? Frustration is the starting point for many innovations and creative breakthroughs. What’s missing? Whereas the previous question may focus on existing problems or inadequacies, this one focuses on the absence of something—a product that doesn’t exist but should, a need not addressed, a perspective that is underrepresented. What do I keep coming back to? Pay attention to recurring themes that keep coming up in your work or even in your conversation. It may be a sign that your big idea is trying to find you.

What is ripe for reinvention? It could be a product but also a classic story, a theme, or a genre.

IDEO’s Tom Kelley says frustration is such a rich source of creativity and innovation that all of us should try to tap into it by creating our own “bug lists”—documenting all the things encountered in everyday life that seem in desperate need of improvement—and then referring to that list regularly as we’re searching for creative endeavors to tackle.

Kelley brothers recommend “capturing ideas systematically.” David Kelley keeps a whiteboard and marker in the shower. Tom never goes anywhere without his trusty notebook. But it’s not enough to just write down ideas and thoughts—you also must go back and review them, regularly. At the end of each week, Tom asks, What were my most creative ideas this week? The answers are there in his notebook.

SEE THE WORLD DIFFERENTLY, ASK What might I notice if I were encountering this for the first time? Apply this “fresh eye” approach to your job, the people around you, your everyday path to work. What if I stand on the desk? Not necessarily to be taken literally, but try changing the angle from which you view things. What is in the background? Try to focus on that which is usually obscured or ignored. What here would fascinate a five-year-old? Or a ninety-year-old? What would Seinfeld be amused by? Use a comic observer’s eye to look for inconsistencies. What would Steve Jobs be frustrated by? Use an innovator’s eye to notice inadequacies.

Whereas the entrepreneur may be inquiring about what is missing (or lacking) in the existing world, the artist may be focused on what the world is “missing” in terms of what we’re all failing to see—a perspective or a side of the story that the larger world is unaware of or misunderstands. If the artist can identify that gap, she has found a good problem.

BEFORE COMMITTING TO AN IDEA, ASK Can I own this problem? The best kind of problem is the one that you, alone, have noticed. But if others are pursuing it, then the question becomes: What is my special twist? What can I bring to this that others can’t? This is not so much about the approach you have in mind (that’s your special twist), but more about your talent, perspective, expertise—and how all of that can enable you to make a unique contribution to this creative challenge. Will I still love this problem tomorrow? This is a “crystal ball” question: It requires you to try to envision how well the subject, and the work itself, is apt to keep you engaged and enthused over time. What is the potential upside? Not to be confused with trying to predict hard outcomes (Will I make a million bucks on this idea?), but rather trying to envision the positive impact this project could have in a best-case scenario.

author Amy Tan has said that when she can frame the idea she’s working on as a question, it provides “a focus”29 that can guide her through the creative process.

Research feeds creativity,31 says Kyung Hee (KH) Kim, an education professor at William & Mary who has been researching creativity for the past twenty-five years.

use a similar “Four Whys” approach to dig into the motivations of a fictional character, for instance: Why does this character matter? Why is he frustrated? Why hasn’t he done something about that? Why might he be ready to do something about it now? The actress Laura Linney has said that when she first gets a role, “I read the script and ask, ‘Why?’ until there’s no more ‘Why?’ to ask.”33

THESE “FOUR WHYS” WILL HELP YOU UNDERSTAND ANY PROBLEM Why does this problem matter? Use research to clarify what is at stake by digging deeper into who is affected and how. Consider the significance of that, in terms of overall effect and future ramifications. Why does the problem exist? Try to get to the root causes that put this problem into motion. (This may necessitate additional “whys” to get all the way down to the root.) Why hasn’t it been solved already? This will make clear the obstacles you are up against (and may uncover past efforts that hold lessons).

Why might that change now? What are the conditions and dynamics that might bring about a desired change? Having asked the “Why?” questions

34 I was struck by his insistence that any creative person who wants to actually create must regularly escape to what Cleese called a “tortoise enclosure”—a quiet, secure place where one can be alone with one’s imagination.

may seem that the place where you create is incidental and that creativity can happen anytime, in any place. But creativity generally requires the creator’s focused attention—and that is under siege today by forces that endlessly distract. There has never been a greater need for a shell, a cave, or some other form of refuge. So after asking, Why do I want to create? and What might I want to create?, be sure to ask: Where will I actually be able to create?

the place where you create must allow for focus. “Focus is the new IQ,”36 says Cal Newport, author of the book Deep Work. As Newport notes, the enemy of focus is distraction—and it has reached epidemic proportions. Newport and others have observed that distraction is built into social media technology—with much of it designed to “hijack the executive attention network in the brain,”

Constant interruptions can keep you from concentrating—which is, of course, a necessary part of creating. And the steady influx of messages, emails, and tweets provide a tempting alternative to actually doing creative work. The truth is, most of us would much rather answer another email than face the blank page. We want to be distracted. As the designer Stefan Sagmeister puts it, “It is easier to react than to create.”38

What if we saw attention in the same way that we saw air or water, as a valuable resource that we hold in common?39 This then leads to a second question, How might I begin to protect this precious resource?

IF YOU CAN’T FIND THE TIME TO BE CREATIVE, ASK YOURSELF THESE FIVE QUESTIONS If I began to see my attention as a precious resource, how might I better protect it? How can I shift from a “manager’s schedule” to a “maker’s schedule”? The former tries to fill every hour with appointments; the latter is designed with multi-hour, uninterrupted blocks. Am I pruning the vine? If you’re juggling many projects and pastimes, consider cutting back lesser ones to provide more time for the primary ones. What if I trade the morning news for the “morning muse”? The morning can be a prime time for creative thinking, so skip the morning news and march straight from the bed to the tortoise shell. Instead of taking breaks from social media, what if I reverse that? Spend more time disconnected and think in terms of taking breaks to social media.

Recent studies have shown that bored people tend to come up with more ideas.42 Boredom leads to daydreaming, which is associated with creative epiphanies. We actually don’t do enough daydreaming these days, the psychologist Sandi Mann says, because “we try to

For the creative person to be truly productive, he says, you must create “barriers of space and time.” Significant blocks of time are needed for deep creative work. How much time depends on the individual;

makers are creating, while managers are reacting. One takes more time than the other. If you aspire to do more “making” (creating), consider the question, How can I shift from a manager’s schedule to a maker’s schedule?

blank spaces are the spaces where you’re supposed to do the most meaningful work.” It’s all those other things filling up the calendar that should be seen as expendable. So the challenge is: How can we resist the urge to fill in the blank spaces?

make a conscious effort to “prune the vine,”46 says creativity coach Todd Henry. He notes that just as a winemaker must prune some good fruit so that better fruit can get the needed resources, creative professionals must cut back on activities and new projects that may interfere with deep work on primary projects. “If we’re squeezing all the white space out of our lives by filling it with activity, if we’re not pruning and saying no to things on occasion, then we’re not going to have the space we need to innovate or think,”

in the 1930s, the writing teacher Dorothea Brande wrote a persuasive argument for doing creative work in the mornings, when we’re in the midst of the “waking dream.” As Brande put it: “To have the full benefit of the richness of the unconscious”49 you must begin your creative work “when the unconscious is in the ascendant.” In the mornings, Brande advised, get up a half hour earlier than usual and—“without talking, without reading the morning’s paper”—begin to write. This advice can be extended beyond writing to any creative endeavor: Get up, go someplace quiet, and start thinking and capturing ideas. Try to take advantage of what Brande calls the wonderful “twilight zone between sleep and the full waking state.”

Kelley calls the “snooze muse.” When your alarm clock goes off, hit the snooze button and instead of going back to sleep, use that ten minutes to think specifically about whatever creative project you’re working on.

The actual, tangible creation rarely measures up to the vision. The disparity can be especially great in the first stages of trying to give form to an idea, when efforts to produce something may be clumsy and misguided. It can be dispiriting—so much so that Patchett believes it’s the reason why many people never are able to write the “great novel” that is in their heads. “Only a few of us are going to be able to break our own hearts by trading in the living beauty of the imagination for the stark disappointment of words,” she writes. So the question that must be asked upon beginning work on an idea is: Can I live with this discrepancy between imagination and reality? Or, to paraphrase Patchett, If I can’t create the thing I dream of, can I at least create the thing I’m capable of making?

“The tendency to jump from idea to idea spreads your energy horizontally instead of vertically.” In order to stop hopping, Belsky says, you must chart a clear course of action for each of your ideas—one that forces you to stay focused and keep taking next steps. Creative people tend to have a built-in resistance to organizational processes; we’d rather be dreaming up the next idea, which is why so many ideas never get past the dreaming stage to the “doing” stage.

Staying with ideas takes discipline. There will be times when you get “stuck” and have trouble moving forward with an idea and times when you just feel sick of it. At these difficult stages of idea development, it’s tempting to revert back to the more fun stage of idea generation. But as Belsky points out, anyone can come up with ideas.

YOU’RE HAVING TROUBLE GETTING STARTED ON A CREATIVE PROJECT, ASK THESE SIX QUESTIONS Am I chasing butterflies? Meaning you keep thinking of new ideas instead of moving forward with an existing project. To develop an idea, you must pick one butterfly and pin it down. Who will hold me accountable? Share your idea with someone–and schedule a series of small deliverables. Am I rearranging the bookshelves? This refers to the act of “preparing to create.” It may involve setting up a workspace, taking lessons, or doing research—each of which is fine until the point it becomes a stall tactic. How can I lower the bar? Instead of trying to begin with greatness, be willing to start off with something merely okay or even bad. What if I begin anywhere? If you’re stuck trying to think of a beginning, start in the middle, at the end, or somewhere in between. Can I make a prototype? Find some way to give rudimentary form to your idea (outline, rough sketch, collage, beta website).

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!”).

You think about all the people you know who are managing to do things with similar difficulty or scope—and if they can do it, I can probably pull this off, too.” If you can work your way through the difficult middle stages of creativity, confidence and enthusiasm tends to return as you draw close to completion. Indeed, finishing up a project—and adding those final tweaks and polishes—can be so satisfying that you might not want it to end.

“Every time you raise your hand, send an email, launch a product or make a suggestion, you’re exposing yourself to criticism.” If you ship, Godin adds, “you might fail. If you ship, we might laugh at you.” But it’s the chance you must take as a creative person because, as Godin puts it, “Real artists ship.” And the most successful ones tend to ship often. In today’s intensely competitive marketplace, the more ideas and creations you put out there, the better your chances of breaking through. Creativity researcher Dean Keith Simonton, who has conducted studies on successful creative people, says, “Creativity is a consequence of sheer productivity.69

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.”

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.

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. Be honest when asking for feedback. “If you know that feedback will meet resistance or dismissal from you,73 then ask only for positive thoughts,” says the writer Kwame Dawes. It may be that all you want “is encouragement to continue—if so, then say that.”

Mike Birbiglia, a veteran stand-up comedian and director of the film Don’t Think Twice, writes that when he sought out feedback on his own film, “I’d get my friends all drunk on pizza and then ask them hard questions like: What do you like least about the script?”74

Is the feedback suggesting that I alter my vision or merely improve upon the execution? Be wary of the former and more receptive to the latter.

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 return to Kelley’s earlier point, you don’t have to follow feedback suggestions, so there’s little downside in getting as much input as possible from trusted sources.

After you’ve found a problem worth pursuing, retreated to your shell, managed to begin anywhere, survived the middle “suck stages” of creativity, responded to feedback, and, finally, “shipped” your completed work out into the world, what ultimately happens next to that work may be out of your hands. But whatever comes of it, no matter—a new problem is out there waiting to be found, as the creative cycle begins all over again.

Carlin explained that “an artist has an obligation to be en route—to be going somewhere. There’s a journey involved here and you don’t know where it is going—and that’s the fun. So you’re always going to be looking and seeking and trying to challenge yourself. It keeps you trying to be fresh, trying to be new.”

To remain creative, you must think and behave like a novice, always discovering. A creative person who remains “en route” is exposed to more diverse ideas and more varied influences—which can end up providing richer source material for those mental connections and “smart recombinations” that form new ideas. How can you keep moving away from what you know? The easiest way is to follow your curiosity. 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.”

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.

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.

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.

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?

“A conversational narcissist is the one that keeps taking the ball from the game of catch and not ever passing it back.” 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.

One of the most effective follow-up questions consists of three simple words: And what else? Michael Bungay Stanier, a renowned executive coach (and another person I would categorize as a fellow questionologist), calls And what else? the “AWE” question,30 and considers it to be “the best coaching question in the world.”