Top Quotes: “The Book of Beautiful Questions” — Warren Berger

37 min readMar 19, 2021

Introduction

“When people ask, How does one become a better questioner?, I advise them to take a few lessons from a true ‘master questioner’ — the typical four-year-old child. Studies have shown that children at that age may ask anywhere from 100–300 questions a day. (Some research shows that the four-year-old girl asks even more questions than a boy of that age.)

Questioning at these early ages may seem like child’s play, but it’s a complex, high-order level of thinking. It requires enough awareness to know that one doesn’t know — and the ingenuity to begin to do something to remedy that. Young children discover early on that the information they seek can be easily extracted from other human beings, merely by using questions.

Neurological research shows that merely wondering about an interesting question activates regions of the brain linked to reward-processing. Curiosity — the act of wondering — feels good in and of itself, and thus, questions beget more questions. Think of curiosity as a condition — ‘like an itch.’ And that condition often leads to the action known as questioning, which is how we scratch the itch.

The four-year-old scratches away — until, at some point, she’s told to stop. But for a time, during her peak questioning years, she has no reluctance to ask about anything and everything — including the most fundamental questions, those basic ‘Why?’ queries that many of us are loathe to ask for fear of looking stupid. The questioning child isn’t weighed down by accumulated knowledge, biases, or assumptions about how the world works and why things are the way they are. Her mind is both open and expansive — an ideal condition for wondering, inquiring, and growing.

This seems to begin changing somewhere around age 5–6. The asking of questions (at least the ones verbalized at school) tends to subside steadily, year by year, according to research from the nonprofit Right Question Institute, which studies questioning and devises question-formulation exercises for schools. What was once a 100-per-day questioning habit dwindles down to a few questions — or none — by teens.”

“It’s convenient to blame this on our education system, which, for the most part, is test-driven and answers-based. And our schools could be doing much more to encourage questioning by students. But clearly, a number of additional forces and pressures work against questioning.

Foremost is 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 revealing what they don’t know and perhaps ought to know. It’s a near-paralyzing problem for young students and seems to get worse as they move into the peer-pressure-cooker environments of junior high and high school. Students fear they’ll ask the ‘wrong’ question — one that could be seen as off-topic or obvious — or that by asking any question, they’ll potentially be seen as uncool. As children become teens, coolness is generally associated with being in-the-know already — or acting as if you don’t care. To ask a question is an admission that 1) you don’t know, and 2) you do care — doubly uncool.”

“If fear is the first enemy of questioning, running a close second is knowledge. The more you know, the less you feel the need to ask. But the problem here is twofold. First, we can easily fall into the ‘trap of expertise,’ wherein knowledgeable people begin to rely too much on what they already know and fail to keep expanding upon and updating that knowledge. This is particularly perilous in times of rapid change. And there’s another problem with depending too much on our existing knowledge. To put it bluntly, we don’t know as much as we think we do.

This brings up the third and fourth enemies of questioning, which are related to each other: bias and hubris.”

Decision Making

“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?”

“The science simply doesn’t support the value of following your gut — in fact, it supports exactly the opposite approach to decision-making. If you make decisions based on instinct, your gut is going to be wrong more than it’s right.

When it comes to important decisions, we can put less trust in feelings and more in evidence. We can seek input from outside sources and differing perspectives — to try to see past our own biases and limited views. We can generate more options to choose from when making a decision (which experts say is a key element in arriving at better decisions). We can also factor in our limited tendencies to be overly cautious or too focused on short-term benefits, and strive to make decisions that are bolder and more forward-thinking.”

“Ask these 4 questions to check your biases and beliefs:

What am I inclined to believe on this particular issue? Start by trying to articulate your beliefs/biases.
Why do I believe what I believe? The ‘jugular question’ forces you to consider the basis of those beliefs.
What would I like to be true? A ‘desirability bias’ may lead you to think something is true because you want it to be.
What if the opposite is true? This question is inspired by ‘debiasing’ experts.”

“If none of the current options were available, what would I do? This forces you 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 answer — 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 who explain that, strange as it may seem, we give more sensible advice to others than we give ourselves.

Why would we do that? Research shows that ‘our advice to others tends to hinge on the single most important factor,’ as it should — but when we’re thinking about ourselves, we get caught up in too many large and small concerns.

Another odd but apparently effective self-distancing technique: Try asking yourself about a decision by using the third person — What should [your name] do in this situation? (instead of What should I do?). This can lead to cooler, more rational thinking because it allows us to see ourselves and the situation from an outside perspective.

To get even more distance from yourself, try asking about the decision from someone else’s perspective — as in, What would Warren Buffet do if faced with this decision? 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.”

“Most decisions should be made with somewhere around 70% of the information you wish you had. If you wait for 90%, in most cases, you’re probably being too slow.

But getting to 70% doesn’t happen in a blink. Decisions shouldn’t be rushed, for any number of reasons — not least of which is that people tend to make poor decisions under pressure. When faced with an important decision, it’s worth asking, Does this decision have to be made now? and Is this the right time to decide? It’s been shown that there’s times when we should avoid making decisions — when we’re tired, stressed, or just anxious to ‘get this thing over with!’ — because we’re more apt to decide based on emotion or impulse.

When you’ve decided to make a 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? and If I had to defend this decision at a later time, how would I do so?”

“Negativity bias can lead us to make choices that may not make sense or be in our best interest. It can be rooted in something that we experienced in the past that has a disproportionate influence on our current thinking and behavior; psychologists point to the case of people continuing to choose to drive instead of fly long after the 9/11 tragedy. (All that extra driving in an attempt to stay ‘safe’ led to an increase in car crashes.)”

Overcoming Fear

“It’s crucial to emphasize the Why? when trying to overcome fears — as in, Why would I want to do this thing or make this choice, even though it scares me? Rather than focusing on what you’re going to do (the thing inducing the fear), focus on the positive energy of the desired outcome. That outcome may be a personal benefit or it might involve having a positive impact on others. Either way, when the answer to Why am I doing this? is about making a difference, that inspires you and pulls you forward — and it becomes easier to move past the fear.”

“Courageous Questions to Overcome Fear or Shame:

What would I try if I knew I couldn’t fail? Identify bold possibilities.
What is the worst that could happen? This 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; this tells you what pitfalls to avoid.
…and how would I recover from that failure? Just thinking about how you’d 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’s ‘baby steps’ that could lead up to taking a leap.”

“Our natural aversion to change and risk sometimes steers us away from choices that could improve our lives. But what if we were encouraged to make bolder choices — would we then be happier? An economist conducted a study involving people in the midst of making a difficult decision. The subjects each agreed to abide by the results of a coin flip in making their choice — if the coin came up heads, they’d say yes to the job offer, marriage proposal, or whatever they were considering.

Six months later, he interviewed the subjects and found the heads (‘yes’) people were significantly happier than the tails (‘no’) people. What does it tell us? Left to our own devices (without a coin toss to guide us), we say ‘no’ too much when faced with an opportunity.

These days, risk-averse behavior is ‘everywhere, particularly among young people.’ Case in point: data shows that people under 30 today are far less likely than their counterparts in the past to relocate for their careers. In other words, when faced with the question Will you pursue this opportunity or would you rather stay put?, we’re apt to give in to the status quo bias.

But what if we reframed that question, enabling us to consider the same decision from a different perspective — seeing it from the future, looking back?

Examining a decision in this way can help us break free of the status quo. A friend was offered a job that would amount to a $70k pay increase but initially was reluctant to take the offer because it required that he move to a distant location. Then he changed his perspective by asking himself this question: What if I already had the job in that location and was offered a chance to move back closer to home — but with a $70k pay cut? Would I accept that?

Framed that way, his answer was no — which suggested to him that he should take the job (and he did). His initial reluctance to accept the offer was based on a common aversion to change. However, once he envisioned a future scenario in which he’d already made the move, he realized it was probably worth doing.

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 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. We need to vividly envision ourselves in a future scenario.

So if, for example, an opportunity comes your way and you’re trying to decide whether to take it, consider this question: If I look back years from now, will I wish I’d made a change when the opportunity was ripe? If you can imagine how ‘future you’ might feel about this, it can help guide you toward the better long-term decision.”

“In a famous IBM story an employee 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.’”

“Use a weighted question designed to push you a little more in one direction than the other: If I’m generally better off saying yes to bold decisions, why not say yes to this one? Framed this way, the question puts more of a burden on the ‘no’ side.

If you’re going to err on the side of ‘yes’ when making decisions, there’s a couple more questions to keep in mind, including: If I’m saying yes to this, what am I saying no to? This is intended to remind you of the ‘opportunity cost’ of any decision.”

“Try a ‘cancel-elation’ question. 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 cancelled? If you feel elation, you don’t want to do it. You’re doing it out of obligation or discomfort with saying no.

A final thought about deciding with the future in mind: Memorable experiences are worth a lot to ‘future you’ — perhaps more than cash bonuses which won’t last. The experiences you say yes to now will be the stories that are remembered and shared by ‘future you.’ Which brings us to one more crystal ball question: When I look back in five years, which of these options will make the better story? No one ever regrets taking the path that leads to the better story.”

Questions For Inspiration

“When you’re looking for an idea, you’re not really looking for just an idea, per se — you’re looking for a problem.

It’s the discovery and creation of problems that often sets the creative person apart. Social scientists have found in research that the most successful artists tended to take an existing situation and look for ways to rework it. They were less apt to try to solve problems in a straightforward way by following instructions. The ‘problem finder’ goes looking for trouble. The creative process can encompass both finding (and even making) the trouble, as well as fixing it with a creative solution.

Problem finding runs counter to the notion that creative people should be trying to think of ideas that emerge as fully formed solutions. It suggests that the ideas and solutions will come (hopefully) along the way, but the problem is the starting point. Problem finders look at the world around them, focus in on something in particular — a situation, an existing creation, a theme — and inquire deeply about it. What is lacking here? What is happening that doesn’t make sense? What is the story that isn’t being told? How might the whole thing be reinvented or turned upside down? And the most critical question: Why might I want to take on this problem and make it my own?

To find your big idea, ask these questions:

What stirs me? To find a ‘problem’ that’s worth devoting your creative efforts to solve, start with a high interest level — meaning it touches on something that matters to you.
What bugs me? Frustration is the starting point for many innovations and creative breakthroughs.
What’s missing? Whereas the previous question may focus on existing problems or inadequacies, this one focuses on the absence of something — a product that doesn’t exist but should, a need not addressed, a perspective that’s 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?”

“It’s not enough to just write down ideas and thoughts — you must also go back and review them regularly. At the end of each week, ask yourself What were my most creative ideas this week?

Or you can collect ideas in a notebook and transcribe them into a Word doc at the end of each week. Then, once a month, review all your idea notes. ‘It’s so telling when I’ve written down the same idea 2 or 3 times. If I was excited by it multiple times, that’s a really good sign.

Indeed, when an idea or thought keeps coming up in your life or work, it might be worth asking yourself: Is this a problem that is trying to find me? Sometimes a theme may follow you around without your being aware of it.”

“How do we become better at seeing potential creative opportunities that are all around? It’s a matter of looking at the world around us more closely. The goal is to see the familiar — which could include not only products we use but also the way we do our jobs, the people around us, or even the path we routinely travel to get to work — as if seeing it for the first time. Sit and quietly watch what happens in familiar places; you’ll invariably notice details you’d never been aware of before.

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 90-year-old?
What would a comedian 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.”

“Any business offering products or services should be asking What is missing? on a consistent, ongoing basis. And you shouldn’t necessarily ask by actually asking. It can be more effective to quietly observe people who are using a product or service in order to see where they may be having trouble. It’s a way to actually see what’s missing, in action.

But What is missing? also applies, in a different way, to artistic creations. Whereas the entrepreneur may be inquiring about what's missing (or lacking) in the existing world, the artist may be focused on what the world is ‘missing’ in terms of what we’re all failing to see — a perspective or a side of the story that the larger world is unaware of or misunderstands. If the artist can identify that gap, they’ve found a good problem.

Finally, there’s the question of potential impact. What is the upside if I do solve the problem? Will it make a difference? And is it a great business? One question focuses on the positive effect the product might have on people’s lives. The other tries to gauge whether the commercial need was big enough to support a substantial business.

Before committing to an idea, ask:

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

“Research feeds creativity. Before you generate new and original ideas, you have to develop your own expertise in one specific area so you can have a lot of material to draw upon.

It may seem that sudden ‘Eureka!’ insights have come out of the blue, but they don’t come into existence from nothing. Your ability to make new connections is limited — or empowered — by the amount of knowledge you have. So if your goal is to be struck by new ideas, you first have to do the relevant homework in whatever field you hope to be innovative.

While doing research, focus on ‘Why?’ questions to try to gain a better understanding of the problem or issue at hand. 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?”

“Flip the ratio of online vs. disconnected time. Instead of taking breaks from digital media, we should allow ourselves occasional breaks to indulge in it. In other words, get in the habit of asking the reframed question, When should I take a break to connect?

For those who can’t bring themselves to disconnect completely, ask the question If I must be connected, how can I at least reassert control? Create different and long passwords for each social media account and for your phone (the idea is to create a log-in barrier that at least slows you down); turn off all notifications; disable your Facebook newsfeed; batch your email inbox (so that email is delivered in bunches, say, three times a day).”

“Take advantage of the wonderful ‘twilight zone’ between sleep and the full waking state. Even before getting up from the bed, you can maximize that awakening period by summoning the ‘snooze muse.’ When your alarm goes off, hit the snooze button and instead of going back to sleep, use that ten minutes to think specifically about whatever creative project you’re working on.”

“If you’re having trouble getting started on a creative project, ask these six questions:

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

“Ask 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 be.
And what else? Also known as the ‘AWE’ question, it’s 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 For Bonding

“Aron studied ways in which his list of questions — tweaked and adapted for varying circumstances — might be able to create closeness among people in all kinds of situations and relationships. Could the questions be used to rekindle a spark among long-term couples who’d grown a little too used to each other? Yes, they could, Aron found (though he learned that, in this case, it worked better if a couple took the test with another couple, and they all shared questions round-robin style). Could the questions strengthen the relationship between people who might have less in common — and might even be adversarial in some cases? To test this, Aron had police officers share questions with citizens in their community. And he also ran the question experiment with pairs of people of different races.

In most cases, the experiments resulted in building a stronger bond — more warm feelings, greater respect — between the members of each pair. But they had an even greater impact, Aron learned: If he could get two people from different groups to like each other more, those feelings extended to the overall group. The person who shared questions with a police officer was then apt to respect all police more. Likewise for those who exchanged questions with someone from another race.”

“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, this 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.

Instead of Where are you from? try What’s the strangest/most interesting thing about where you grew up?

Think of this approach as the ‘open up and go deep’ questioning strategy. Take questions that are closed, meaning they call for simple factual yes or no answers (How long have you lived in Boise? Do you like it?) and make them more open-ended, calling for a more individualized answer (What brought you to Boise? What’s the most enjoyable thing about living there?) To make those open-ended questions even deeper, try crafting the question so that it’s asking for more of a feeling, an experience, a story. (What was it like when you first moved to Boise? What’s the single weirdest thing that ever happened to you there?)

There’s a tendency to think we shouldn’t ask ‘deeper’ questions of people we don’t know very well. Not so, says writer Tim Boomer, who believes we should be asking just such questions when we meet people on the job, at cocktail parties, even on a first date. Boomer noticed how awkward it was when people on dates tried to talk about superficial things like their commutes or the weather. This raised a couple of questions in his mind: ‘Why did being with a stranger so often mean we couldn’t immediately talk about meaningful things?’ and ‘Why can’t we replace small talk with big talk and ask each other profound questions right from the start?’

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 mom?
When did you last cry in front of another person? And by yourself?
What, if anything, is too serious to be joked about?”

“Eleanor Stanford compiled a list of questions designed to be asked by two people considering marriage. One particularly interesting question — Did your family throw plates? — is intended to find out about ‘conflict resolution patterns’ inherited from parents. Other questions on the list include: What do you admire about me?; Can you deal with my doing things without you?; and How do you see us ten years from now? (That last one can be made more specific by asking, What do you envision as our ideal future?)

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?”

“CEO Deb Harmon says that when she was growing up during family dinners, her dad would ask his children, What was the most difficult problem you had today? Next, he would ask them, How could you have handled this differently? ‘Through his questioning, he helped us become our own problem solvers.’”

“If you don’t want to keep asking the same question at family dinners, and find it difficult to come up with new ones on the fly, consider using a question jar. A few times a week, you and your children can take turns pulling out questions during dinner. Sample questions: If you were an inventor — what would you invent and why? What was your first thought when you woke up today? Who in your class seems lonely? What do you think is the biggest challenge facing our world today?

The questions are designed to unlock awareness on several levels, encouraging kids to think about themselves, other people, and the world at large. ‘Kids must become explorers of themselves first, and then their eyes open to other people in their lives,’ Doyle writes. ‘It’s a process, teaching curiosity, awareness, and compassion. This jar is a start.’”

Listening

“Rather than thinking about whether you agree or disagree with what someone’s telling you, the goal is to understand it, observes counselor Dianne Schilling. She recommends trying to ‘picture what the speaker is saying,’ so that it comes alive in your own mind. Even better than seeing it is to try to feel it. When someone’s telling you about an experience or a situation they’re dealing with, ask yourself: What must this feel like? At some point in the conversation, you may end up asking a version of this question directly to the other person — but first, start by using your imagination to try to empathize.”

“FBI analyst Robin Dreeke points out, ‘The second that I think about my response, I’m half listening to what you’re saying because I’m really waiting for the opportunity to tell you my story. Dreeke’s advice: ‘As soon as you hvae that story or thought you want to share, toss it.’ Return your attention to the speaker.’”

“She later came to realize that ‘I was interjecting my story of my own struggle, when it just needed to be about her.’ As Headlee puts it, ‘A conversational narcissist is the one that keeps taking the ball from the game of catch and not ever passing it back.’

Asking These Questions Will Make You a Better Listener:

Just to be clear, are you saying __? At key points, repeat back a paraphrase of what you’ve heard.
Can you explain what you mean by that? This is a classic ‘clarifying’ question used by interviewers to invite people to better explain themselves. (Tone is important: Go for curious, not puzzled or antagonistic.)
I imagine that made you feel ___, right? A variation of How did it make you feel? (which sounds too much like a psychiatrist’s question)
And what else? The ‘AWE’ question may be the best way to draw out deeper insights — and keep you in listening mode.”

“Paraphrasing and simple follow-ups such as the ‘AWE’ question are good for eliciting additional thoughts and greater clarification, but they may not get at deeper emotional feelings that people often have trouble expressing. To encourage the sharing of those feelings, Salit recommend using ‘empathetic listening.’ The idea is try to to identify the emotion a person is feeling and reflect it back in the form of a question.

She offers this example: ‘So, Bill, what I hear you saying is that you’re angry with me because I haven’t appreciated the lengths you’ve gone in trying to win over our Latin American customers. Those efforts have caused you a lot of sleepless nights, time away from the family, and marital problems. Is that right?’ Salit says, ‘This form of active listening is the hardest to undertake,’ but ‘if you’ve done it well, people will agree profoundly and powerfully with you.’

It can be effective for a listener to try to read and play back the emotions of the person speaking. Goulston recommends using a question such as: I’m trying to get a sense of what you’re feeling and I think it’s frustration. Is that correct? This goes beyond paraphrasing — and may seem as if it borders on putting words in someone’s mouth — but as long as you’re paying close attention to what the speaker is trying to express, your clarifying question is likely to be helpful.

As the questioner helps put emotions into words, follow-up questions can be used to further clarify: We’ve established you feel frustrated, but how frustrated were you? And what was the reason for that frustration? As Goulston notes, if you’re trying to work toward a solution, you may aim to arrive at: What needs to happen for that feeling to feel better?

Goulston refers to this as a form of listening and questioning that makes another person ‘feel felt’ — to show that ‘you understand and accept how the other person feels and that you’d feel the same’ if you were in that situation. ‘When people ‘feel felt,’ they feel less alone…less anxious and less defensive,’ Goulston writes, adding, ‘When you mirror what another person feels, the person is wired to mirror you in return…it’s an irresistible biological urge, and one that pulls the person toward you.’”

“Skip The Advice. Ask These 7 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 2–3x 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’s one step you could take to begin acting on this, right away?”

Criticism and Conflict

“Consider whether the criticism you intend to offer is truly actionable or useful (otherwise, why bother?). And be honest with yourself about whether there’s even a hint of enjoyment associated with offering the criticism. If so, you’re doing it for the wrong reasons.

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 out of saying this?
Am I deriving pleasure from criticizing?”

“Using a more appreciative approach, a questioner would avoid asking, What went wrong on this project? and instead might say, Take me through what happened on this project: What went well, what did you have problems with, and what can we learn from that going forward?

Positive questioning becomes even more important when the tension is already high. When family feuds, workplace conflict, or political polarization create a situation wherein attempts to criticize someone or ‘correct’ their views on an issue can make things worse, questioning can help — but it must be done carefully.”

“Rather than trying to attack to attack or disprove someone’s strongly held position, an alternative approach is to find nonthreatening ways to ask that person to take another look at their position. Here again, ‘counterfeit’ questions (criticism or judgment in the form of a question) don’t work: To ask someone, How in the world can you believe such a thing? is a verbal attack — and signals to the person you’re talking to that you’re not really interested in understanding their position.

A more effective approach is to start by allowing the other person to explain their position, and to try to show interest as they do. The FBI’s Robin Dreeke recommends saying something along the lines of ‘That’s fascinating — help me understand more about this.’ And as the person begins to explain their view more, it’s a good time to use some of the active listening techniques mentioned previously, such as paraphrasing and mirroring.

There’s nothing wrong with using ‘critical thinking’ types of questions to challenge someone to clarify or defend their views. Jay Heinrichs says it can be effective to show ‘aggressive interest’ by asking questions that seek definition and details from someone stating a case. In asking for definition, you might ask, When you say ‘freedom,’ how are you defining that term?

The point is to clarify the terms of the discussion, but it serves another purpose, too: When people are ‘asked to define the meaning of their terms,’ they ‘tend to come up with less extreme terms,’ says Heinrichs. Detail-seeking questions might include, What are the actual numbers of this epidemic you’re talking about? or What is the source of that info? These questions can be seen as a challenge to the speaker, so ask them calmly and politely, not in the tone of an interrogator. (Here again, phrases like ‘I’m curious,’ or ‘I was wondering,’ inserted at the beginning of the question, can work wonders in softening the tone.)

Having allowed the other person to state their case without judgment, ask for the same for yourself. (‘Can I briefly lay out for you what I think?) After you’re made your case, try to immediately shift the conversation to a common ground discussion, as opposed to ‘Let’s take turns demolishing each other’s arguments.’ Do this by using ‘bridge’ questions that encourage people to find positive aspects and shared values with opposing arguments.

Here are two good bridge questions: Can you find anything in your position that gives you pause? Is there anything in my position that you are attracted to or find interesting?

Be sure to answer both questions yourself as well. That way, both of you are encouraged to shift positions to draw closer to each other. You can use the same approach in talking about political candidates as opposed to issues:

You’ve done a nice job explaining why you support Candidate A — can you think of a couple things you dislike about her? And while you don’t support Candidate B, can you think of a couple of things about her you find worthwhile or interesting?

These types of questions encourage the other person to be more balanced in their thinking — to look for positives where they might be inclined to see only negatives, and vice versa. In cases where it seems difficult to coax someone to do this, you might try a questioning technique like this: On a scale of one to ten, how much of climate change do you think is true?

Use These ‘Bridge’ Questions To Try To Meet Halfway On A Divisive Issue:

What is it in your position that gives you pause?
What is it in my position that interests or attracts you?
On a scale of 1 to 10 (no value to 100% unassailable), how would you rate my position? And your own?
If you didn’t rate mine a 1 and yours a 10, why not?
Can we imagine a position that might at least partly satisfy both of us?”

“Questioning can also be used to encourage people to empathize with, or step into the shoes of, a person they may have strong feelings against. Using a hypothetical ‘What if?’ question such as, What if you were put in charge of Candidate B’s campaign tomorrow — how would you encourage her to try to reach out to people like you? Understanding that she’s not going to come all the way to your side, how do you think she could at least come partway? Be sure to do likewise on your end.

This can begin to move the conversation toward ‘common ground’ quetions like these:

Can we imagine a candidate who might make both of us happy? What would a hybrid of Candidates A & B look like? Or if you’re discussing an issue, Can we imagine a position on this issue that might at least partly satisfy both of us?”

Questions For Relationships

“Blogger Matt Fray shared a story with an irresistible title: ‘She Divorced Me Because I Left Dishes by the Sink.’ He wrote about how his marriage broke up for a number of reasons, not the least of which being that he had a habit of leaving an empty glass by the sink instead of moving it a few extra feet to put it in the dishwasher. To Fray, it was a trivial matter. But his wife saw it differently. As Fray eventually came to realize, it was about a personal lack of respect. She’d made it clear, again and again, that this simple act mattered to her, and he continually responded by showing that he didn’t care.

Fray wishes he’d asked himself a ‘crystal ball’ question: If I knew my marriage would end painfully as a result of something I’m doing or not doing, would I continue to make the same choice?

But as the problems in his marriage were unfolding, the questions on his mind were rhetorical ones: Who cares about a glass? and Why should it matter? Those actually wouldn’t have been bad questions if he’d considered them honestly. If he had, he might have figured out that the answers were 1) Someone important to him cared; and 2) Therefore it mattered.

Based on his experience, Fray offered this advice to others in a relationship: When you and your partner disagree, try to see if you can articulate each other’s feelings and perspective. Start by asking, Can I try to explain what I think your position is — and then you can do the same for me? ‘Because until we can accurately present one another’s arguments,’ Fray says, ‘it’s probably safe to conclude that neither of us understands what the other is actually saying.’

Fray’s questions could be summed up in one overarching question that might be asked regularly in all close relationships: What am I missing?”

“On a long drive with her best friend, writer Kaitlyn Wylde came up with a lengthy list of questions designed to deepen the relationship. Here’s 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?”

“Everyone in a close relationship should begin asking themselves on a regular basis: Am I missing a bid?

Another question to ask is, How should I be responding to the various bids coming from my partner? That’s nice; That’s interesting would fall into ‘minimal response’ (which is almost as bad as ignoring or ‘turning away’). Much better to engage with and draw out the bidder using questions. Yes, that’s a beautiful bird — do you know what kind it is? What do you find mos interesting about that story in the paper?

Some bids are more important than others. When someone tells you about something that’s bothering them, it’s worth listening closely and inquiring about how you might be able to help.”

“Instead of merely saying ‘Congrats’ or ‘That’s great,’ a questioner can draw out positive feelings associated with good news — which is a crucial ingredient in healthy relationships. An ‘active constructionist response’ can be expressed through questions such as, What was going through your mind when you heard the good news? You might speculate on those positive feelings as part of your question: You must have been so proud when you heard about this — what was that like? Another way to build on good news is to inquire about what led to it, as well as where it might lead: What new opportunities do you think this might create for you?”

“It may seem an apology is enough, but it’s much more effective to say the following three things in ten words, ending with a question mark. Start with a simple I’m sorry. Follow with an admission: I was wrong. End with a question: Will you please forgive me? It’s not easy to do, and the question at the end may be the toughest part — but also the most important. ‘By phrasing this as a question, we acknowledge that forgiveness isn’t an entitlement…That it’s a choice on the part of the other person.’ Given that choice, almost always the other person says ‘I forgive you.’’”

Questions For Work

“Questions Your Boss Will Love:

What would you do in my position?
What does your ideal employee look like?
What’s one thing that, if I did it differently, would make a difference to you?
What’s most important on your list to accomplish today — and is there any way I can help?
What’s the one thing if I did it differently would make a difference to you?”

“On truly important issues — such as how your business ops may be affecting the environment — consider applying a question based on an old Iroquois principle: What would the 7th generation think about what we’re doing? This principle, codified in the Iroquois Great Law of Peace, held that every decision should take into account its possible effects on descendants 7 generations into the future.”

Question Formulation

“1. Think of a ‘Question Focus.’ To begin, you need a premise or statement, in 2–3 words, that can provide a focal point for generating questions (e.g. Technological Change, 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 phrase.

2. Produce questions. Within a time limit (try 10 minutes), aim to generate and write down as many questions as you can think of pertaining to that focus. No answers, no debating which questions are best. Just keep inquiring from different angles.

3. Improve your questions. Begin to work on the questions you’ve written. Open the closed questions, and close the open ones. For example, Is a balanced life desirable? might be changed to 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.’

4. Prioritize the questions. Select 3 favorites. Look for those that stir interest and open up new ways of thinking about the issue.

5. 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?)

6. Reflect on what you’ve 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.”

“Six ways to build a better question:

Open it up. Instead of Have things changed since last year? ask How have things changed since last year?
Close it down. Look for faulty assumptions. Before wondering Why are we having this problem? 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 ecommerce 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. Instead of 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 that indicates the question is based on genuine interest, not criticism. Instead of Why are you doing it that way? ask I’m curious to know: why are you doing it that way?
Neutralize it. Make sure the question has no agenda, no attempt to lead someone toward a desired answer. 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?”

“After you’ve tried applying critical thinking to someone else’s claims, 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. Think of this as a way to use critical thinking and inquiry to combat stinkin’ thinkin’.

We’re all subject to the ‘negativity bias,’ a tendency to give too much weight in our thinking to negative events, perceptions, and possibilities. A setback at work can lead to thinking ‘I’m going to get fired.’ Listening to the news may convince you that ‘the world is going to hell in a handbasket.’

When you identify a feeling like that, write it down as a definitive statement, then challenge it with your critical thinking questions. What’s the evidence behind this claim? How reliable is it? What info is missing? Does the claim logically make sense? What’s the opposing side?”

“Focusing on a problem you’ve identified, start with as many ‘Why?’ questions as you can think of (Why does this problem exist? Why hasn’t someone solved it already?). Then use your imagination to brainstorm multiple ‘What if’ possibilities. 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.

You can also try the Why? What if? How? framework on a family issue or a problem at work. My family never seems to eat dinner together, or My department doesn’t get included enough.”

“When listening to a story, 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?).

People accustomed to being asked only rote questions by strangers at first may give you a look that suggests, You’re overstepping your bounds, stranger. If that happens, just say, ‘I like asking these types of questions because when I do, I often hear interesting stories.’ You’ve now explained that there’s a method to your madness, and the conversational ball is back in the court of the other person, who’s probably thinking, I must have an interesting story! I don’t want to be the person with no story!

Bonus tip: as the conversation shifts from questioning to sharing your own opinions and stories, remember to keep pausing to ask the other person: What do you think?”

“Let your family members know they’ll be playing the game of L.I.F.E. at dinner next Sunday, and they’ll start collecting and remembering moments to be shared at the next gathering.

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 capture children’s attention.
What piece of INFO did you learn this week? Sharing something that’s news to you or a piece of learning can entertain others and solidify the info in your own brain.
Is there anything you tried and FAILED at this week? 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.”

“1. In thinking of a questolution for yourself, phrase it as a ‘How might I?’ question (e.g. How might I get myself to drink more water?)

2. Write or print the question in bold type at the top of a sheet of paper and tape it to a wall.

3. Each time you think of an idea that might help you achieve the goal, phrase it as a ‘What if?’ question (What if I begin carrying a reusable bottle to work every day?) and jot it down under the overarching ‘How might I?’ question.

4. 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.”

“If you’re trying to encourage kids to question more it helps if you can convince them that questioning is cool. You might try pointing out that many things they probably love — the iPhone, Instagram, and many apps — started as questions. (If they demand specifics on that, you can find stories about cool stuff that started as questions on this book’s website.) And while you’re pointing this out to them, also point out that questioners are rebels and mavericks and rule breakers (from Elon Musk to Beyonce). And if that’s still not enough, you can point out that a lot of 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 friends ask. Write them down and tape them on the fridge or share them on social media.
When your kids come home from school, ask them if they asked a good question that day.
If you’re a manager or boss, ask for questions as if you really value them and want to hear them. Consider rewarding people who ask questions, especially first question askers.
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’s been given life.”