How much do I want to read more? 7/10
I never thought so many questions could be so inspiring.
This book is an invitation to think by ourselves. To ask the right questions at the right time, and reflect on it.
“A fascinating look at the power of questioning to ignite change—in our companies, schools, careers, and in our daily lives.”
[quote, Dorie Clark]
“The Book of Beautiful Questions gives us the power to re-imagine our lives.
Introduction - Why Question?
To me, any question that causes people to shift their thinking is a beautiful one.
The simplest and most powerful thing that happens when we ask ourselves questions is that it forces us to think.
What can we learn from a four-year-old girl?
the four-year-old girl asks even more questions than a boy of that age. She is the ultimate questioning machine.
Can questions bridge the gap between us?
[quote, Elie Wiesel]
“People are united by questions. It is the answers that divide them.”
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?
PART I - Questions for Better DECISION-MAKING
Why should I question my own decisions?
What is my tennis ball?
the greatest challenges we all face—identifying or clarifying a sense of purpose in our lives?
Should I even be asking, “What’s my passion?” Some feel that the “passion” question can do more harm than good. “Young people get paralyzed by the idea.
Cal Newport. “Passion is not something you follow. It’s something that will follow you as you put in the hard work to become valuable to the world.” 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.
Elizabeth Gilbert says she has stopped advising people to “follow your passion” because it creates pressure for those who may have no idea what their one true calling might be—if there even is one. Gilbert now advises people to “follow your curiosity”
the most successful people “are obsessed with solving an important problem, something that matters to them. They remind me of a dog chasing a tennis ball.”
To increase your chances of happiness and success, Houston advises, you must find your tennis ball—“the thing that pulls you.”
Identifying what that “tennis ball” is can have a clarifying effect on many other decisions and choices that come along—because you can now ask, in effect, How does this help me in the pursuit of my tennis ball?
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.
What are my signature strengths?
Martin Seligman says you can identify these qualities by thinking and even writing about specific times when you’ve been at your best, then inquiring more deeply about those successful episodes: What personal strengths did I display when I was at my best?74 Did I show creativity? Good judgment? Kindness? Seligman says that as you begin to figure out what you’re good at, the next challenge is to figure out how to deploy those strengths.
What are my superpowers?
“unpack the combination of personality traits and aptitudes you bring effortlessly to any situation.”
Having identified your strengths, you’ll be in a better position to make the most of what you already have going for you.
Once you’ve inquired about what you’re good at, ask yourself what you’re naturally interested in—the two may overlap, but not necessarily.
The idea is to become “an anthropologist of your own life.
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?
What did I enjoy doing at age ten?
After drawing up a list of favorite childhood activities, “see what still resonates with you today. And then it’s a process of updating those loves. You may have loved something that doesn’t even exist now, or doesn’t make sense in your life now—but you may be able to find a new version of that.”
What makes me forget to eat?
Manson shares that in younger days, he would forget to eat while playing video games—then he later found that he experienced that same level of immersion when writing.
For other people, that feeling may come when teaching, solving problems, or organizing things. “Whatever it is, don’t just look at the activities that keep you up all night,” Manson says, “but look at the cognitive principles behind those activities … They can easily be applied elsewhere.”
Looking beyond skills and natural interests—and beyond yourself—one can study the larger world and ask the question: What is needed and how might I help?
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?
Angela Duckworth, who advised readers not only to “move toward what interests you” but also to “seek purpose.” So rather than just asking what you want to do with your life, Duckworth recommends asking: In what way do I wish the world were different?
What problem can I help solve? She adds: “This puts the focus where it should be—on how you can serve other people.”
The goal of improving people’s lives may seem rather grand, but as the author Daniel Pink points out, it can manifest itself in more modest ways. “You can think of Purpose with a capital P, says Pink, which might involve feeding the hungry or solving the climate crisis.
“I also think there is another kind of purpose with a small p,” he adds. It can be measured by asking, for instance, “If I didn’t come into work today, would things be worse?”
You can use the following two questions to distinguish between the two different types of purpose: With “capital P” Purpose the question is, Am I making a difference? With “small p” purpose the question is, Am I making a contribution? Pink notes that both types of purpose are worthwhile and meaningful; the latter may be more attainable than the former.
Whether you’re trying to find a new business opportunity or identify a possible lifelong pursuit, if you want to tackle a truly ambitious beautiful question—one designed to help you find the ultimate tennis ball—consider this one: 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.
The tennis ball won’t always taste good. Newport observes that people tend to think once they find a pursuit that fits their idea of a calling or passion, it’s going to be easy after that. But he has seen some of his students quickly give up on interests and potential careers as they discover that it’s hard to master anything. “They find that ‘I’m not automatically good at it, so it must not be my passion.’ ”
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?”
If you’ve tried asking all of the preceding questions and still have not found your tennis ball, 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?
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.
In trying to figure out your sentence—which could also be thought of as a personal mission statement—try asking, How would I like to be remembered? What matters most to me? What change would I like to create?
For many people, finding purpose—chasing the tennis ball—is tied to creativity, which is the focus of the next section. If you’ve decided to pursue a more creative life, there are many penetrating questions that can help with the challenges of figuring out what to create, how to motivate yourself to get started or keep going, how to determine if your work is good and how it can be improved, and how to keep evolving and staying fresh in your ongoing creative pursuits.
These questions apply to the individual working in solitude or to the group trying to create and innovate together. They pertain to works of art that aspire to express an original thought, as well as inventive products that aim to change a business or the way people live. And they are relevant whether you tend to think of yourself as “creative” or not.
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? 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)
Chapter one, All Questions
- Why should I question my own decisions?
- What am I really trying to decide here? What’s most important? What critical information do I have and not have?
- Why are we making decisions as if we’re still in the jungle?
- Should I rely on my gut instinct when making decisions?
- How can I override those gut instincts?
- What if we could open up a wider view—using our questioning flashlight to do so?
- Why do I believe what I believe?
- What am I inclined to believe about this particular issue?
- What did I once believe that is no longer true?
- What would I like to be true?
- What if my beliefs or assumptions on this issue are just plain wrong?
- What are some reasons that my initial judgment might be wrong?
- Am I thinking like a soldier or a scout?
- Would I rather be right, or would I rather understand?
- Do I solicit and seek out opposing views?
- Do I enjoy the “pleasant surprise” of discovering I’m mistaken?
- Is this someone who would rather be right or would rather be successful?
- What do you most yearn for—to defend your own beliefs or to see the world as clearly as you can?
- Why should I accept what I’m told?
- (Critical Thinking Questions): What is the evidence behind this claim and how strong is it?; Does this evidence come from a solid source? Is there an agenda behind it?; Cui bono?—Latin for “Who benefits?”; What are they not telling me?; Does it logically follow?; What’s the other side of this issue? Is there actually another side?; Which of the conflicting views has more evidence behind it?; Does my critical thinking have an agenda?
- What if this isn’t a “yes or no” decision?
- How do I open up more options?
- What is the great, the good, and the ugly?
- What is the counterintuitive option?
- How can I “open up” the question to be decided?
- If none of the current options were available, what would I do?
- What would an outsider do?
- If my friend had to make this decision, what advice would I give?
- What should [my name] do in this situation? (instead of what should I do?)
- What would Warren Buffett do if faced with this decision? (Or for that matter, LeBron James?)
- If we got kicked out and the board brought in a new CEO, what do you think he would do?
- Does this decision have to be made now? Is this the right time to decide?
- Is it possible to shoot holes in this decision?
- If I had to defend this decision at a later time, how would I do so?
- Where in my life right now am I living under the fog of indecisiveness?
- What would I try if I knew I could not fail?
- What are you so afraid of?
- How can questioning help with something as primal and powerful as fear?
- What is your earliest memory of this fear? How do you react to it? What has it kept you from doing? How might things change if you were able to overcome this fear?
- (Courageous Questions): Why would I want to do this thing or make this choice, even though it scares me?; Within this scary possibility, what excites me?; What is the worst that could happen?; And how would I recover from that?; If I did fail, what would be the likely causes?; What if I succeed—what would that look like?; How can I take one small step into the breach?
- How can we generate more ideas?
- How can we quickly and inexpensively test those ideas?
- What if cost were not an issue?
- What would you do if you weren’t afraid?
- What would “future me” decide?
- What if we were encouraged to make bolder choices—would we then be happier?
- Will you pursue this opportunity or would you rather stay put?
- If I look back years from now, will I wish that I’d made a change when the opportunity was ripe?
- Which option will allow me to evolve and flourish?
- (Questions on Whether to Take a Job): Can the little person rise to the top? Can I shape my destiny and have influence in this organization?; How will the boss react to mistakes?; How have others at this company added new skills and expanded responsibilities?; How does the organization encourage “connectedness” between employees?; How does the organization react to mistakes?; Will I be punished for exploring?; Will I enjoy the “small pleasures” of my daily routine?
- Why are people fully aware that present benefits are important in their current job, and yet expect not to care about those benefits in the future?
- How would I later explain this decision to others?
- What are my core obligations?
- Imagine yourself explaining your decision to a close friend or a mentor–would you feel comfortable? How would that person react?
- If I’m generally better off saying yes to bold decisions, why not say yes to this one?
- If I’m saying yes to this, what am I saying no to?
- How would I feel if I accepted this invitation—and then found out it had been canceled?
- What if putting experience first makes us happier, more fulfilled, more creative and more memorable people?
- When I look back in five years, which of these options will make the better story?
- (Passion Questions): What is my tennis ball?; How does this help me in the pursuit of my tennis ball?; Should I even be asking “What’s my passion?”; What are my signature strengths? What personal strengths did I display when I was at my best?; What are my superpowers?; When was I truly happy and why?; What activity or theme do I keep coming back to?; When do I seem most like myself?, What did I enjoy doing at age ten?; What makes me forget to eat?; In what way do I wish the world were different?; What is my sentence?
- What is needed and how might I help?
- What are my circumstances summoning me to do? What is my most useful social role?
- If I didn’t come into work today, would things be worse?
- Am I making a difference? Am I making a contribution?
- How might I apply my signature strengths to a pursuit that is of natural interest to me and helps others?
- What is your favorite flavor of shit sandwich? What struggle or sacrifice are you willing to tolerate?
- How would I like to be remembered? What matters most to me? What change would I like to create?
PART II - Questions for Sparking CREATIVITY
David told Tom that he was grappling with a large question: What was I put on this earth to do?
He’d already built a great business, had a loving family, a beautiful house. But when he thought about some additional way that he might leave a lasting impact, Kelley arrived at this beautiful question: How can I help as many people as possible rediscover their creative confidence?
philosophy about creativity (Tom and David Kelley):
- 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 appears and tells you what to do,” as David puts it. The Kelleys use the term “design thinking” to describe the IDEO approach to generating creative ideas and bringing them to life. I think of it as “applied questioning”—because much of it revolves around asking specific types of questions at each stage of the creative process.
These three ideas—that creativity matters to all of us; that we’re all capable of being more creative in our work (and our lives); and that there are basic steps we can take to stimulate our creativity and guide it toward productive results.
While most of the questions to follow will address the “how” of creating, I tend to think it’s wise to begin with “why.” Making the commitment to be creative is a major undertaking. Why be creative? There is an abundance of great creative work out there already. Why add to the pile? There’s no way of knowing if your creative work will be financially rewarding, or even whether it will be liked by anyone, including yourself. Why take the risk?
The 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?
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 lab comes closest to the ideal we all hope to get from life—and so rarely do.”
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.
TO 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.
ASKING 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?
- Why create?
- What was I put on this earth to do?
- How can I help as many people as possible rediscover their creative confidence?
- Why be creative? Why add to the pile? Why take the risk?
- Am I willing to decide in favor of creativity? And if so, why?
- Given the benefits, why would anyone not decide in favor of creativity?
- Where did my creativity go?
- (Questions Not to Ask About Creativity): Am I creative?; How creative am I?; Where will I ever find an original idea? Hasn’t everything been thought of already?; Where will I find the time to create?; How can I come up with an idea that will make money?
- What if I knew at the outset that there was no possibility of fame or fortune from this work—would I still want to do it?
- What if I go looking for problems?
- In an era of sleek smartphones, why are thermostats still so dumb?
- Why is it that some of the raw materials we encounter inspire us, and others don’t? And can we seek out the ones that do?
- (Problem-Finding Questions): 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?; Why might I want to take on this problem and make it my own?; What stirs me?; What bugs me?; What’s missing?; What do I keep coming back to?; What is ripe for reinvention?
- What’s wrong with this product? Why doesn’t [a better] product exist?
- What were my most creative ideas this week?
- Is this a problem that is trying to find me?
- (Questions to Help You See More): What might I notice if I were encountering this for the first time?; What if I stand on the desk? (to get a different view); What is in the background?; What here would fascinate a five-year-old?; What would Seinfeld be amused by?; What would Steve Jobs be frustrated by?; How would a traveler see this?
- When am I most resonant? What are people responding to in my work?
- Why should this be my problem?
- Do I look forward to thinking about this topic?
- Will I want to commit to this six months or a year down the road?
- Will I still love this problem tomorrow?
- Can I make a unique contribution here?
- What am I adding that somebody else couldn’t?
- Is this a challenge that I can apply my skills to?
- If others are pursuing the same idea, what’s my twist? How might my approach differ from others?
- What is the upside if I do solve the problem?
- Can I own this problem?
- How might I create a thermostat as appealing an iPhone?
- (The Four Whys): Why does this problem matter? Why does it exist in the first place? Why hasn’t someone solved it already? Why might that change now?
- Where is my tortoise shell?
- Where will I actually be able to create?
- When should I take a break to digitally connect?
- If I must be connected, how can I at least reassert control?
- What if we saw attention in the same way that we saw air or water, as a valuable resource that we hold in common?
- 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”?
- Am I pruning the vine?
- What if I trade the morning news for the “morning muse”?
- Instead of taking breaks from social media, what if I reverse that?
- When is my creative prime time?
- How can we resist the urge to fill in the blank spaces on the calendar?
- Am I a lark or an owl?
- How can I fight through that initial period and not give up?
- How can I put myself in creator’s jail?
- What is my early release time? Shall I offer myself a brief furlough?
- What activities distract me a little but not too much?
- Am I willing to kill the butterfly?
- Can I live with this discrepancy between imagination and reality? If I can’t create the thing I dream of, can I at least create the thing I’m capable of making?
- Do I have what it takes to make the idea actually happen?
- Who will hold me accountable?
- Am I chasing butterflies?
- Am I rearranging the bookshelves?
- (Questions for Getting Started): How can I lower the bar?; What if I begin anywhere?; Can I make a prototype?; What can I do with what I already have?; What small first step can I take to give form to my idea?
- How do I get “unstuck?”
- Who would look at this problem from a different angle?
- What would Lincoln think in a situation like this?
- If I were to imagine future me, ten or twenty years ahead, how do I imagine I’d look at this problem differently?
- What if I tried to create a car that is unable to move? Or an oven that can’t cook?
- Have I ever solved a problem like this before?
- Have other people with my motivation and ability been able to accomplish something remotely similar?
- Am I ready to “go public”?
- Do I want to be done or do I want to improve?
- (Feedback Questions): Am I coming across?; What do you like least about this?; What would you suggest I try?; Is my goal to stay at my current level of skill, or to improve?; Why am I resistant to simply accepting this gift? (of feedback); Who are my trusted advisors?; How do you figure out when to listen to other people—and when to listen to yourself?; Is the feedback suggesting that I alter my vision or merely improve upon the execution?; I was wondering about how to improve X or Y—what would you suggest I try?; How well did I take that feedback?
- How do I stay “en route”?
- How can you keep moving away from what you know?
- Should a creative person be more like a hummingbird or a jackhammer?
- What am I willing to abandon?
- How might I “go electric”?
- Where is my petri dish?
PART III - Questions to Help CONNECT WITH OTHERS
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?
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.
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?
QUESTIONS TO ASK YOUR BEST BUD
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?
PART IV - Questions for Stronger LEADERSHIP
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.
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.
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.
CONCLUSION - The Inquiring Life
questioning plus action can lead to change (Q + A = C), whereas questioning minus action equals philosophy (Q − A = P).
Think of a surgeon or airline pilot, for example, who refers to a printed checklist of important reminders1 (Don’t forget to do X, Y, and Z before takeoff);
These three themes—challenging assumptions, shifting perspectives, considering opposites—are worth keeping in mind as you think of new questions to add to your list.
So here is a suggestion: Try to ask at least one naïve question before noon tomorrow. It can start as a question you ask yourself. (Why coffee? Why do I drink coffee each morning? How did this whole coffee thing get started? What’s the history of coffee? When did they invent these K-cup machines? I wonder, did that invention start with a question? Okay, Google, get ready because I have some questions for you …)
If you really want to be ambitious, follow the Arno Penzias daily “jugular” question approach. Every day, ask yourself, Why do I believe what I believe?
find just a few moments during your daily commute to think about questions—perhaps more immediate ones, involving the challenge of the day. A few minutes may not seem like much, but it adds up.
Exercise: The Question Formulation Technique
- Think of a “Question Focus.” To begin, you need a premise or statement, in two or three words, that can provide a focal point for generating questions. (e.g., “Technological change” or “Encouraging curiosity” or “A balanced life”). Don’t use a question as a starting point—it’s easier to form questions around a statement or a phrase.
- Produce questions. Within a time limit (try ten minutes), aim to generate and write down as many questions as you can think of, pertaining to that QFocus. Only questions are welcome—no opinions or answers, and no debating which questions are best. The idea at this point is to just keep inquiring about the subject from different angles.
- Improve your questions. Begin to work on the questions you’ve written down. Open the closed questions, and close the open ones. For example, a closed question that began as Is a balanced life desirable? might be changed to an open one: Why is a balanced life desirable? In doing this, you’ll see that a question can be narrowed down in some cases, expanded in others—and you begin to see that “the way you ask a question yields different results and can lead you in different directions,” says Dan Rothstein of the Right Question Institute.
- Prioritize the questions. Select three favorites. Look for those that stir interest and open up new ways of thinking about the issue.
- Decide on next steps. This includes whether and how you might want to act on the prioritized questions. (Might you want to share these chosen questions with others? Undertake research in order to answer them?)
- Reflect on what you have learned. Spend a few moments thinking about what it felt like to “think in questions,” and what you learned about the process of formulating questions. (Did it get easier as you went along? Did you discover any tricks for improving questions or for using one question to develop another?) This helps solidify the learning and will help you get better at doing it next time.
Exercise: Six ways to build a better question
- Open it up. If you want something more than a “yes or no” answer, take a closed question and open it up by starting the question with words like “What?,” “Why?,” or “How?” So instead of asking, Have things changed since last year?, it’s better to ask: How have things changed since last year?
- Close it down. There are times, however, when closing a question (so that it elicits a simple “yes or no” answer) can help you identify a built-in faulty assumption. Before spending too much time wondering, Why are we having this problem?, you may want to ask: Is it a problem?
- Sharpen it. Precise questions will tend to yield better answers. Instead of How will current changes in the market affect us?, it’s better to ask, How will the rise of e-commerce in the market affect us?
- Add a “Why?” to it. I’m a big believer in getting to the “question behind the question,” and that can often be done by adding “Why?” to the end of a question. So instead of just asking, What trend are you most concerned about?, ask What trend are you most concerned about—and why?
- Soften it. Questions can be confrontational. It can help to add a softening phrase at the beginning, one that indicates the question is based on genuine interest, not criticism. So instead of, Why are you doing it that way?, ask I’m curious to know: Why are you taking that approach?
- Neutralize it. Make sure the question is neutral with no agenda, no attempt to lead someone to a desired answer. Leading questions may work for prosecutors and interrogators, but generally should be avoided. Terrible leading question: Wasn’t that movie awful? Slightly better: Do you think that movie lived up to the hype? Better still: What did you think of that movie?
Exercise: Critical thinking workout
Read over an opinion column or essay from a newspaper or blog and then run through these five questions:
- How strong is the evidence? Try to list how many points are presented to make the case. Then consider the evidence behind each point: Does this evidence come from a solid source? Can I identify a possible agenda behind it?
- What are they not telling me? Look for what is missing from the article—insufficient reporting, lack of important details, or of opposing viewpoints.
- Does it logically follow? Be on the lookout for flawed reasoning that suggests you should believe A because of B—when in fact there may be a tenuous connection between A and B.
- What is the opposing view? If it hasn’t been clearly presented, try to think of what someone in opposition would say. If possible think of several opposing points.
- Finish the exercise by asking yourself the hardest question: Which side has more evidence behind it? Having thought about opposing viewpoints, are they stronger than the original argument? Or is the author’s point (even if imperfect) still valid? An important part of critical thinking is being able to make a reasoned judgment call, even when there is something to be said for and against both sides of an argument.
Exercises: Combating stinkin’ thinkin’
see what happens when you use the same kind of thinking on one of your own beliefs—in particular, try to identify something you hold a negative view about. Then use questions to challenge the validity of that negative view, while considering the positive side.
We all are subject to the “negativity bias,” a tendency to give too much weight in our thinking to negative events, perceptions, and possibilities.
the news may convince you that “the world is going to hell in a handbasket.”
What is the evidence behind this claim? How reliable is it? What information is missing from this claim? Does the claim logically make sense? What is the opposing side?
Is this bad feeling I have really true?8 Is there another way of viewing this situation?
If my best friend were to say this same negative thing about himself, what would I say to him?
What went well today?
What if I looked at the world around me with a fresh eye?
How can you get yourself to look at your familiar everyday world with a fresh eye?
As explained by Robin Williams’s character in the film, when you stand on your desk “the world looks very different from up here.”
Exercise: Seeing things in a fresh way
- Take a photo, using your phone camera, of something you see every day. It could be a close-up photo of your breakfast or your workplace, your coffee shop or your health club lobby.
- Take a close look at what’s going on in the photo. Try shifting your focus from the object or patterns in the foreground to those in the background. Zoom in for details; zoom out for context.
- Try to find three things you notice in the picture that you’ve never noticed before—small details, juxtapositions, patterns.
- Turn each of those three things you noticed into a question—then see if you can add another question to the original question. (Why is one side of my desk so cluttered and the other side so clean? What does that say about the way I work?)
Exercise: Problem finding
this time, instead of taking a random photo, write down things that “bug” you: You can’t find time to read the news; the front door of the building is hard to open; the line waiting for coffee is too long, etc.
Next, subject one of your daily irritations to a “Why?,” “What if?,” “How?” cycle of questioning. Innovators and inventors often tackle problems by asking “Why?,” “What if?,” and “How?” questions — in that order.
“Why?” questions help us to understand a problem; “What if?” questions help us imagine possible alternatives; “How?” questions, which tend to be more practical and action-oriented, lead us toward a solution.
Focusing on one of the problems you’ve identified, start with as many “Why?” questions as you can think of (Why does this problem exist in the first place? And why hasn’t someone solved it already?). Then use your imagination to brainstorm multiple ‘What If’ possibilities (What if we tried X? What if we tried Y?). Next, pick the “What if?” question you like best and reframe it as a “How?” question—as in, How might I take this crazy “what if?” idea and actually own it as a project? How would I take the first step? Whether or not you keep pursuing this question beyond this exercise, you’ve probably already identified ways to minimize your daily irritation.
Exercise: Connective inquiry
What if I put this together with that?
example: the iPhone or the book "Abraham Lincoln: Vampire Hunter"
What if Attila the Hun was plopped down in Silicon Valley? What if a potato peeler were combined with gloves?
What’s interesting about it, and what doesn’t work? Is there a similar but different combination that might be more interesting?
How (and with whom) shall I break the ice?
The challenge is to break the habit of asking rote introductory questions (How are you? What do you do?), and try diving in at the deep end of the questioning pool.
Exercise: “Conversation starting” questions
What if I approached this party as if I were a journalist, looking for stories about the people in attendance?
What are some favorite stories you like to share about yourself? Working backwards from that, what kind of questions could someone ask to elicit those stories from you? This will provide a general sense of the kinds of questions you should be asking.
What are you working on that you’re really excited about these days? What’s the most interesting thing you’ve done/learned in the past week? If you could pick anyone, who would you like to spend an afternoon with?
Once you’ve initiated a conversation, use tools of active listening, such as paraphrasing or echoing, for clarification and to show you’re paying attention (You actually climbed to the top?). And use follow-up questions to draw out emotion (How did it feel when you were up there?).
What do you think?
That is a favorite question of the Harvard University–based questionologist James Ryan, who says “It’s a question that’s not only useful to ask, but is a good reminder to make sure that you are soliciting the views of other people in a room. If you don’t consciously invite people to participate, they might remain silent and the conversation typically suffers because of that.”
Exercise: L.I.F.E. questions
The idea is to surface the little anecdotes and daily stories that create intimacy and shared memories.
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.
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.
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.
What memorable EXCHANGE did you have this week?
This question reminds us to reach out once in a while beyond How you doing?, and show our curiosity about what others think and feel.
Exercise: Using questions instead of giving advice
Try this exercise one-on-one with a spouse, friend, or colleague at work. The first step is to ask this person: Do you have a problem or challenge you’d like advice on? Then, when they share their problem, don’t tell them your brilliant idea of what they should do. Instead use questions to help them figure it out for themselves.
- What’s going on? (Tell me about the challenge 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 question several 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?
What if I interview myself?
As you use questioning to draw out stories of others, why not do the same to yourself? The self-interview can help you clarify your own personal story. Then you’ll be sure you have a good narrative to tell about yourself in a job interview, at a networking function, on an elevator with your boss, or any time you need a strong answer to the question, So what’s your story?
Exercise: Creating your best story
You want a story that best reflects who you are, what you’ve accomplished, what matters to you, and where you’re headed. These kinds of things are also what people get asked at an in-depth job interview where the interviewer is trying to determine your strengths, ambitions, your awareness of flaws and what you’re doing about it. So it makes sense to use job interview questions to help you develop your best story.
- Would you rather be respected or feared?
- What is your biggest dream in life?
- When you were a child, who or what did you want to be?
- When you have failed, how did you respond?
- If people were asked how you treat them, what do you think they’d say?
- What is your sentence? (Meaning, if you had to summarize your life in one sentence, what would that sentence be?)
- What is your tennis ball? (What is the thing that you chase as intently as a dog chases a tennis ball?)
- What are you trying to get better at?
think about how to weave those answers together to form a narrative. As in: I am someone who
Keep working on the story until it fits together well and flows, with a beginning, middle, and end. And have it available in your head to use on short notice, as a whole or in parts.
Can questioning help bring my family closer together?
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?
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 interesting life? Why?
End with questions exploring a sense of shared mission:
- What are our family values?
- What is this family trying to do beyond daily living? What’s the greater purpose of our family?
- How might we create a “How might we …” mission question for the family?
- How might I contribute to the mission?
What if I trade my resolutions for “questolutions”?
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.
"I will meet more interesting people this year!" versus "How might I meet more interesting people this year?"
Well, what if I were to do X? or What if I tried to do Y?
Questions are also less intimidating than resolutions. They put less pressure on you.
No one really wants to hear your declarations of the wonderful things you’re promising to do. But when you share a question with others (I wonder how I could do a better job of X, or How might I improve Y?), it invites people to think about that question themselves.
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.
How can I encourage others to question more?
Exercises: Making questioning fun and appealing to others
- At home, make one night a week “question night,” during which family members can only communicate with one another by questions. Try to think of songs with a question for the title. (I’ve got a running list going at www.amorebeautifulquestion.com/50-question-songs). Do a question-storming or another question-related activity; some examples can be found here www.questionweek.com/exercises-to-build-your-questioning-muscles.
- If you’re trying to encourage kids to question more, it helps if you can convince them that questioning is cool. This is difficult because many young people over a certain age think questioning is decidedly “uncool.” also point out that questioners are rebels and mavericks and rule breakers (from Elon Musk to Beyoncé). questioners, particularly in Silicon Valley, have become some of the most successful people in the world because of their questions.
- Celebrate good questions that your kids or your friends ask. Write the question down and tape it on the refrigerator or share it on social media.
- When your kids come home from school, ask them if they asked a good question that day. This tip is inspired by a quote from the Nobel Laureate scientist Isidor Isaac Rabi, who said that when he was growing up in Brooklyn, all the other mothers asked their kids, “So did you learn anything today?” But Rabi’s mother would ask him, “Izzy, did you ask a good question today?” Rabi believes his mother’s question about questions had a profound influence that contributed to him becoming a scientist.
- If you are a manager or boss, ask for questions as if you really value them and want to hear them. Consider giving rewards to people for asking a question. When I do a talk, I often give a free book to the first person in the audience to ask a question. “First question” askers are courageous, and they make it safe for everyone else to ask questions.
- When someone asks a good question, don’t say simply, “That’s a good question.” Tell them why you think it’s a fascinating or important question—and ask them what they might like to do with that question, now that it has been given life.
What is my one “big beautiful question”?
How might I encourage more questioning?
Start by looking to where your interests and passions lie. Ask yourself some questions about what moves you, what you care deeply about, what you feel you were meant to do.
keep your eyes open for the right “problem”—one that stirs you, and that you might be able to “own” in your own way.
It might turn out to be a problem right in front of you—but you may need to step back to see it fresh.
if you haven’t put it into question form, give it a try.
this will help get your mind thinking about the challenge in a new way.
think about phrasing it in the “How might I” format.
it enables one to construct a question that is open and expansive, yet still action oriented.
in its full form it now reads: How might I encourage more questioning, through writing and in-person contact, at businesses as well as nonprofit organizations, but with a primary focus on education?
The reason to expand your question in this way is to remind yourself of key things you should be focused on within the overall challenge.
the sweet spot of questioning as “a question that is hard (and interesting) enough that it is worth answering—and easy enough to actually answer it.
an array of beautiful questions sent in by readers. (Go to amorebeautifulquestion.com/whats-your-beautiful-question).
Most important, stay with your question. In the age of Google, we have come to expect instant answers to our questions. But the best questions, the beautiful ones, cannot be answered by Google. They require a different kind of “search.” Be willing to go on that journey of inquiry—and try to enjoy working on your question, grappling with it, sleeping with it, and just being in its engaging company.
- How might I begin to act on my questions?
- Can we simply advise ourselves to “question more” and then expect that shift into questioning mode will happen when needed?
- Did you ask the important questions you’re supposed to ask?
- How might I reward myself for questioning?
- How can I warm up my questioning muscles?
- Can I build a better question?
- How might I test my built-in baloney detector?
- Is this bad feeling I have really true? Is there another way of viewing this situation?
- What if I looked at the world around me with a fresh eye?
- What if Attila the Hun was plopped down in Silicon Valley? What if a potato peeler were combined with gloves?
- What’s interesting about it, and what doesn’t work? Is there a similar but different combination that might be more interesting?
- How (and with whom) shall I break the ice?
- What if I approached this party as if I were a journalist, looking for stories about the people in attendance?
- (L.I.F.E. Exercise Questions): What weird LITTLE thing sticks out in your mind from this week? What piece of INFORMATION did you learn this week? Is there anything you tried and FAILED at this week? What memorable EXCHANGE did you have this week?
- (Self-Interview Questions): What is your biggest dream in life?; When you were a child, who or what did you want to be?; When you have failed, how did you respond?; If people were asked how you treat them, what do you think they’d say?; What is your sentence? (Meaning, if you had to summarize your life in one sentence, what would that sentence be?); What is your tennis ball? (What is the thing that you chase as intently as a dog chases a tennis ball?); What are you trying to get better at?
- Can questioning help bring my family closer together?
- (Family Heritage Questions): 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?
- (Family Purpose/Mission Questions): 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 interesting life? Why?; What are our family values?; What is this family trying to do beyond daily living? What’s the greater purpose of our family?; How might we create a “How might we” mission question for the family?; How might I contribute to the mission?
- What if I trade my resolutions for “questolutions”?
- How might I meet more interesting people this year? How might I get myself to drink more water?
- How might I encourage others to question more?
- Izzy, did you ask a good question today?
- What is my one “big beautiful question”?
- Where and how might you find your big beautiful question?