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

by Warren Berger

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. Thus, a critical thinker should always ask, What are they not telling me? when offered potential solutions that may neglect to mention side effects, hidden costs, and potential negative consequences.

USE THESE 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.

USE THESE FIVE 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.

A simple yet effective way to adopt a fresh perspective is by asking: If my friend had to make this decision, what advice would I give? The “advice” question is championed by many decision experts, including author and Duke University–based psychologist Dan Ariely, who explains that, strange as it might seem, we give more sensible advice to others than we give ourselves.33

To get even more distance from yourself, try asking about the decision from someone else’s perspective—as in, What would Warren Buffett do if faced with this decision? (Or for that matter, LeBron James?) The “outsider” whose perspective you adopt could be someone who has no connection to the issue you’re deciding on, or someone who might have only a slightly different perspective.

Having considered the many questions that can help inform a good decision, at some point you must stop asking questions and just decide. How does one know when that time has arrived? The venture capitalist Schroeder says: “In decision making, you’re always navigating between gathering enough information and gathering too much.” As to how much is enough, here’s an interesting formula from Amazon CEO Jeff Bezos: “Most decisions should probably be made with somewhere around 70% of the information you wish you had.38 If you wait for 90%, in most cases, you’re probably being slow.”

When you’ve decided to make the decision, try to make it twice—once, and then again a day or two later. People may be reluctant to second-guess themselves, but if a decision is a solid and considered one, it should hold up. One way to test the soundness of the decision is to consider these two questions: Is it possible to shoot holes in this decision?40 and 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 are you so afraid of?

an outsized fear of negative outcomes—also known as the “negativity bias”44—can lead us to make choices that may not make sense or be in our best interest. The negativity bias can be rooted in something that we experienced in the past that has a disproportionate influence on our current thinking and behavior;

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?

Why would I want to do this thing or make this choice, even though it scares me?

When you’re deciding on a possibility that makes you uneasy, focus on the positive feelings associated with taking a risk. Adam Hansen suggests clients ask themselves: Within this scary possibility, what excites me?

What is the worst that could happen?

“COURAGEOUS” QUESTIONS TO OVERCOME FEAR OF FAILURE What would I try if I knew I could not fail? Start with this favorite Silicon Valley question to help identify bold possibilities. What is the worst that could happen? This may seem negative, but the question forces you to confront hazy fears and consider them in a more specific way (which usually makes them less scary). If I did fail, what would be the likely causes? Do a “premortem” on a possible failure, listing some of the potential causes; this tells you what pitfalls to avoid. … and how would I recover from that failure? Just thinking about how you would pick up the pieces if you did fail tends to lessen the fear of that possibility. What if I succeed—what would that look like? Now shift from worst-case to best-case scenario. Visualizing success breeds confidence—and provides motivation for moving forward. How can I take one small step into the breach? Consider whether there are “baby steps” that could lead up to taking a leap.

The scientist and decision-making expert Gary Klein is a proponent of using “premortems”51 (doing a postmortem in advance) to envision what a potential failure might look like, so that you can then consider the possible reasons for that failure. To put the premortem into question form, you might ask: If I were to fail, what might be the reasons for that failure?

This is similar to “Premeditatio malorum”. A stoic philosophy that emphasise thinking about what are all the things that could go wrong and be prepared for it even before it happens. This doesn’t mean that you have to worry about it. This just means that you have to be prepared for it in a better way and prevent from getting attached to anything that is not in your control.

“What if I could not fail?”

“What would you do if you weren’t afraid?”

Will you pursue this opportunity or would you rather stay put?,

What if I already had the job in that location and was offered a chance to move back closer to home—but with a $70,000 pay cut? Would I accept that?

A question that enables us to envision a future scenario—in order to help with a present-day decision—could be thought of as a “crystal ball” question. Such questions are worth asking because we have a tendency to focus too much on the here and now. This inclination toward short-term thinking causes us to focus on immediate preferences while ignoring long-term aims and consequences. One way to counter it is to try to imagine how we might feel about something in the future. “Good decision-making is tied to our ability to anticipate future emotional states,”60 says Ed Batista, an executive coach who teaches at Stanford University. “We need to vividly envision ourselves in a future scenario.”

consider this question shared by writer Rob Walker: If I look back years from now, will I wish that I’d made a change when the opportunity was ripe?61 If you can imagine how “future you” might feel about this, it can help guide you toward the better long-term decision.

Which option will allow me to evolve and flourish?

Can I shape my destiny and have influence in this organization?

How will the boss react to mistakes?

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Grant references a famous IBM story involving an employee who made a mistake that cost the company $10 million. The employee figured IBM chief Tom Watson would fire him, but Watson’s response was: “Fire you? I just spent $10 million educating you.”

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QUESTIONS TO ASK BEFORE TAKING THAT JOB 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.

How have others at this company added new skills and expanded responsibilities?

How does the organization encourage “connectedness” between employees?

“Make sure you choose a career or project that you enjoy pursuing” and that offers the kind of “small pleasures in your daily routine” that often end up being a big part of what creates job satisfaction.

When making decisions for the long term, think of each important decision as a chapter within a larger story,66 advises Joseph Badaracco, a professor of business ethics at Harvard Business School. Then, ask yourself the following: How does that chapter fit with the larger narrative? Badaracco says that for a decision to make sense in that larger context, it should tie in with long-term goals and purposes. And when making such a decision, also be cognizant of obligations, relationships, and values, he adds. Badaracco recommends asking the question, What are my core obligations? (to an organization, customers, community, family), so that you can assess whether the decision serves those interests, too.

“Imagine yourself explaining your decision to a close friend or a mentor–someone you trust and respect deeply. Would you feel comfortable? How would that person react?”

Wish I knew these questions when I was in 12? I would have saved myself from doing a lot of mistakes. I would have been more cautious about my actions and I would have taken a lot of actions based on hardcore data in hand instead of just, what people stupidly call as ‘Gut’.

If I’m saying yes to this, what am I saying no to?67 This question, shared by the executive coach Michael Bungay Stanier, is intended to remind you of the “opportunity cost” of any decision.

psychologist Dan Ariely. He calls it the “cancel-elation” question.68 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.”

When I look back in five years, which of these options will make the better story?

Before looking at some of the questions designed to identify your true passion in life, it’s worth considering a contrarian question: 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 that ‘I’m going to find this thing I’m meant to do,’ ”71 says author 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.

Similarly, the author Elizabeth Gilbert says she has stopped advising people to “follow your passion”72 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”—which may lead you to a passion (or many different ones).

How does this help me in the pursuit of my tennis ball? There’s no simple formula for figuring out what your particular tennis ball is, but 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.

A dog chasing a tennis ball analogy.

How does this help me in the pursuit of my tennis ball? There’s no simple formula for figuring out what your particular tennis ball is, but 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.

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The “assets-based” question is fairly simple and straightforward: It boils down to, What are my signature strengths?

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What personal strengths did I display when I was at my best?74 Did I show creativity? Good judgment? Kindness?

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What are my superpowers?

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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.

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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?

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What did I enjoy doing at age ten?

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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?79 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)

What makes me forget to eat?

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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?

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What are my circumstances summoning me to do? What is my most useful social role?

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In what way do I wish the world were different?82 What problem can I help solve?

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