The Book of Beautiful Questions: The Powerful Questions That Will Help You Decide, Create, Connect, and Lead - by Warren Berger
Date read: 2020-01-25How strongly I recommend it: 9/10
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Most of us don't spend enough time asking questions, let alone the right questions. Great sample questions to help with decision-making, networking, leadership, and even with your family.
Contents:
My Notes
Elie Wiesel once observed: “People are united by questions. It is the answers that divide them.”
The five enemies of questioning are:
- Fear - Though many young children start out as fearless questioners, they gradually get the message—from teachers, parents, other kids—that asking a question carries risks, including the risk of revealing what they don’t know and perhaps ought to know.
- Knowledge - The more you know, the less you feel the need to ask.
- Bias - Some of them are hardwired in us; others may be based on our own limited experiences. But in either case, if we are predisposed to think something, we may be less open to considering questions that challenge that view.
- Hubris — Which can lead us to believe our biases are correct or are not biases at all. (“Everyone else is biased!”).
- Time (or the supposed lack of it) - We just don’t seem to make time for questioning—starting in school.
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?
Think of your innate questioning skills as a flashlight and the decision ahead of you as a dark room. Each question illuminates a new area (and the better the question, the more light it casts). As we confront the various unknowns surrounding a tough decision, each question—What am I really trying to decide here? What’s most important? What critical information do I have and not have?—enables us to see a little more clearly, and helps us to step forward in the face of uncertainty.
To take a more holistic view of your own assumptions about a particular issue you’re deciding on, break Penzias’s jugular question into three parts—the “What?,” the “Why?,” and the “What if?”
WHAT am I inclined to believe on this particular issue? What would I like to be true? A “desirability bias” may lead you to think something is true because you want it to be true.
WHY do I believe what I believe?
WHAT IF the opposite is true?
Galef suggests we ask ourselves this question: Am I a soldier or a scout? She explains that there is a very different mindset for a soldier as opposed to a scout. A soldier’s job is to protect and defend against the enemy, whereas the scout’s job is to seek out and understand. These two distinct attitudes can also be applied to the ways in which all of us process information and ideas in our daily lives. “Making good decisions is largely about which mindset you’re in,” Galef says.
Intellectual Humility - a state of openness to new ideas, a willingness to be receptive to new sources of evidence. These types of questions include:
- Do I tend to think more like a soldier or a scout? A soldier’s job is to defend, while a scout’s purpose is to explore and discover.
- Would I rather be right, or would I rather understand? If you place too much importance on being right, it can put you in “defense” mode and close off learning and understanding.
- Do I solicit and seek out opposing views? Don’t ask others if they agree with you—ask if they disagree and invite them to say why.
- Do I enjoy the “pleasant surprise” of discovering I’m mistaken? Finding out you were wrong about something needn’t be cause for shame; it’s a sign of intellectual openness and growth.
Five questions to detect B.S.:
- How strong is the evidence? Critical thinking starts with demanding that there be substance behind any claim. A subset of “evidence” questions might include, Does this evidence come from a solid source? Is there an agenda behind it?
- What are they not telling me? Sometimes the problem with information is not what is there, but what’s missing—whether it’s a news story with insufficient reporting or a sales pitch that leaves out important details.
- Does it logically follow? When people are trying to persuade you, they may use flawed reasoning that suggests you should believe A because of B.
- What is the opposing view? To avoid “weak-sense critical thinking,” be willing to seek out an opposing side of the issue you’re deciding on—and try to consider it with an open mind. Which of the conflicting views has more evidence behind it? Go with the side that has more weight.
If you can reframe that “yes or no” choice by changing it from a closed question to a more open-ended one, it can profoundly alter the decision you’re making. The closed question, Should I quit my job—yes or no?, becomes more open-ended by turning it into a “How?” or “What?” question, such as: How might I improve my situation at this job? What possibilities might exist between quitting or doing nothing?
Questions to open up possibilities:
- How can I “open up” the question to be decided? We have a tendency to make binary decisions (yes/no, either/or), which limits options. Trying using open-ended questions (What are the best ways …? How might I …?) to frame your decision.
- What is the great, the good, and the ugly? When making decisions, try to choose from at least three options. Do this by projecting three different potential outcomes or scenarios—one very positive, one moderate, and one negative.
- If none of the current options were available, what would I do? Imagine that the existing options you’re deciding between suddenly have vanished; this forces you to try to come up with additional possibilities. Upon returning to reality, you can weigh your newly-imagined options against the existing ones.
- What is the counterintuitive choice? Include one option that goes completely against the others; you probably won’t choose it, but it stimulates unconventional thinking.
- What would an outsider do? You can get an actual outsider to help answer this—or just try to look at the situation the way an outsider might.
One way to test the soundness of the decision is to consider these two questions:
- 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?
- Can the little person rise to the top? Seek the proof in the form of multiple stories of people who were able to make that climb.
- How does the organization react to mistakes? This will determine whether you can experiment and grow. (Another way of asking: Will I be punished for exploring?)
- Can I have influence in this organization? Find out whether people at all levels have a say.
- How have others here added to their skills? Another key determinant of whether you’ll be able to evolve.
- Does this place encourage camaraderie? The social aspect of work is more important than most think. Will I enjoy the “small pleasures” of my daily routine? Being happy in your job hinges on the little things you’ll be doing every day.
When someone invites you to do something, ask yourself: How would I feel if I accepted that invitation—and then found out it had been canceled? “If you feel elation, you don’t want to do it,” Ariely says. “You’re doing it out of obligation or discomfort with saying no.”
“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.”
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.
Gilbert now advises people to “follow your curiosity”—which may lead you to a passion (or many different ones).
The “assets-based” question is fairly simple and straightforward: It boils down to, What are my signature strengths?
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?
Six questions to help 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)
“Creativity is yoga for the brain.”
In the process, Kelley reassures students that whether they can draw well, for example, is not a measure of their creativity; that’s a specific skill, which can be developed over time. Creativity, on the other hand, is not a skill but a “mindset” or a way of looking at the world. And we all have the ability to look at something—a problem, a subject, a situation, a theme—and bring forth our own ideas and interpretations.
Ask these questions to help find your next big idea:
- 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.
- 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?
- 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?
Uset 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.
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.
- 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.
- 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?
- Just to be clear, are you saying ___? At key points, repeat back a paraphrase of what you’ve heard.
- Can you explain what you mean by that? This is a classic “clarifying” question used by interviewers to invite people to better explain themselves. (Tone is important: Go for curious, not puzzled or antagonistic.)
- I imagine that made you feel __ , right? A variation of How did it make you feel? (which sounds too much like a psychiatrist’s question).
- And what else? The “AWE” question may be the best way to draw out deeper insights—and keep you in listening mode.
- What 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?
- 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?
Bonus tip: As the conversation naturally shifts from questioning to sharing your own opinions and stories, remember to keep pausing to ask the other person, What do you think?
The instinct to criticize may be based on our own failings and frustrations. She recommends that before criticizing anyone, ask self-examining questions such as What’s motivating this critical urge? and How am I guilty of the thing I’m criticizing?
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?
- 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?
A “visionary helper” tends to exhibit a number of qualities we may not necessarily associate with leadership, including humility, curiosity, and open-mindedness.
One way to think about this new type of leader is as a “visionary helper”—a leader who not only charts a course for others to follow but also does whatever it takes (a nudge, a kind word, a supportive gesture) to get them moving in the right direction. A “visionary helper” tends to exhibit a number of qualities we may not necessarily associate with leadership, including humility, curiosity, and open-mindedness.
Conant says it’s common for aspiring leaders to be focused on what they hope to get from being a leader (status, glory, money) without thinking about what they’ll have to give up by committing to leading and helping others.
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.
- 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.
- 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.
- If we disappeared tomorrow, who would miss us? This speculative question helps clarify why you matter and to whom.
- What do we do that others can’t or won’t? This shifts the focus to an organization’s strengths and uniqueness.
- What are we against? It’s easy to say what you’re for. It’s more risky—and therefore carries more weight—for a company to oppose something.
- How might we be not just a company but a cause? Increasingly, organizations are expected to contribute something worthwhile—to employees, local communities, and the world.
- What is the one thing I can do that would make everything else easier or unnecessary 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)
- 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 question.
- 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.
- 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.
- How can we make it safe to question? Institute a strict “no judging” rule; all questions welcome, the more the merrier.
- How might we make questioning rewarding? Celebrate productive questions by verbal recognition. To go further, offer bonuses and other tangible incentives.
- How might we make questioning productive? Train people in how to question in ways that produce results.
- How can we make a culture of inquiry stick? Make questioning a central part of meetings and other regular activities.
Before joining a gathering and saying a word to anyone, ask yourself this question: What if I approached this party as if I were a journalist, looking for stories about the people in attendance?
Questions can spark lively conversation when the family is together. The L.I.F.E. questions exercise can be done around the dinner table with kids once a week.
L - What weird LITTLE thing sticks out in your mind from this week?
I - What piece of INFORMATION did you learn this week?
F - Is there anything you tried and FAILED at this week?
E - What memorable EXCHANGE did you have this week?
Exercise: Using questions instead of giving advice:
- 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?
Questions to ask your spouse instead of how was your day?:
- 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?