Self Help

The Book of Beautiful Questions - Warren Berger

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Matheus Puppe

· 87 min read

Here is a summary of the praise and reviews for The Book of Beautiful Questions:

The Book of Beautiful Questions has received widespread praise from experts, authors, and media. Reviewers call the book “a vital read,” “a transformational resource,” and “a potential game-changer.” They say it provides “hundreds of questions that can help you be a better thinker, partner, problem-solver, and leader.” The book shows “the power of questioning to ignite change” and helps readers “identify where opportunities lie and how to seize them.”

Warren Berger’s previous book, A More Beautiful Question, also received very positive reviews. Reviewers called it “a fascinating look at the power of questioning,” “profound and eye-opening,” and said “it demonstrates just how far an inquisitive mind can take you.” The book helps readers “understand the power of questions to change the world.”

In summary, Warren Berger and his books on questioning and inquiry have been widely praised for showing how to use questioning to improve thinking, decision making, creativity, relationships, and leadership. Reviewers say his books provide practical and thought-provoking questions that can help transform how people approach challenges and opportunities in work and life.

• The book provides a collection of useful questions and questioning strategies that can be applied to various everyday situations. The questions come from a variety of sources, including entrepreneurs, teachers, therapists, executives, and scientists.

• Questioning helps in four key areas: decision-making, creativity, connecting with others, and leadership. For decision-making, questioning prompts critical thinking to avoid common mistakes. For creativity, questioning fires the imagination and helps advance ideas. For relationships, questioning builds connections and understanding. For leadership, questioning helps set vision and address challenges.

• The simplest benefit of questioning is that it forces us to think deeply or slowly, considering multiple perspectives. This leads to better choices and outcomes. While this book provides questions, the goal is to build a habit of developing your own questions. Questioning is a skill that must be strengthened with practice.

• We can learn from the questioning of four-year-old children, who ask 100-300 questions per day. Their questioning shows an awareness of what they don’t know and a drive to find answers from others. Neurologically, the act of wondering about interesting questions activates the brain’s reward system.

• Questioning has obstacles, including a general reluctance to ask questions due to fear of looking ignorant or the assumption that questions mean you have weak knowledge or judgment. But questioning leads to learning, creativity, innovation, and progress. Leaders and experts in any field continue questioning throughout their lives.

• Two examples of master questioners worth emulating are philosopher Socrates and physicist Richard Feynman. They show how questioning with a sincere desire to understand, not prove a point, can yield insights and breakthroughs. Questioning the status quo or conventional wisdom moves us forward.

That covers the key highlights and main themes around questioning from the book summary. Please let me know if you would like me to explain or expand on any part of the summary.

The five enemies of questioning are:

  1. Fear: Fear of looking stupid, annoying others, revealing what we don’t know. This fear starts in childhood and continues into adulthood, especially in workplaces.

  2. Knowledge: The more we know, the less we feel the need to ask questions. But we can fall into the “trap of expertise” where we rely too much on what we know and stop learning. We also don’t know as much as we think we do.

  3. Bias: We may be predisposed to think in certain ways and less open to questions that challenge those views. We need to question our own biases and assumptions.

  4. Hubris: Lack of humility can lead us to believe our biases are correct or that we have little to learn from questioning.

  5. Time: There seems to be little time for questioning, contemplation or critical thinking. We feel pressure to make quick decisions and take action without asking why. But taking time to question can lead to better decisions and outcomes.

To foster a questioning habit:

• Overcome the fear of asking questions by doing it, one question at a time. Group exercises can help. Asking “naïve” questions can produce insights.

• Make questioning a habit and part of your routine. Do it on the way to work, at work, and in everyday interactions. Release your “inner four-year-old.”

• See situations as a curious four-year-old would. Ask yourself how a four-year-old might see it. Question assumptions and ask “Why?”

• Successful, productive leaders make time for thoughtful questioning, especially when facing new challenges or starting new endeavors. We can follow their lead.

•Encourage questioning in others through our own example and by promoting an environment where people feel comfortable asking questions without fear of embarrassment or judgment. Lead by questioning.

Questioning is an essential skill, especially in today’s fast-changing world. It helps in learning, adapting to change, creativity, decision making, relationships, and leadership.

Some key points:

  • Questioning helps individuals and organizations survive and prosper in times of rapid change. It allows us to keep learning, updating what we know, and reinventing ourselves.

  • Questioning fuels creativity. It can help overcome lack of inspiration or feeling stuck. It guides analysis and feedback. Creativity is key to careers, happiness, and solving world problems.

  • Questions help build connections between people. They show interest in others and invite sharing and empathy. Asking questions can transform relationships and help address societal divides. Questioning is a key leadership skill for visionary leaders.

  • Questioning is important for identifying good leaders and information sources. It helps in making sensible choices in a confusing world.

  • Questioning is essential for democracy. It allows us to challenge assumptions, be skeptical of authority and charlatans, and make informed decisions. If we lose the ability to question, we are vulnerable to manipulation.

  • The future depends on developing questioning individuals and a questioning society. Questioning helps ensure progress.

In summary, questioning has significant benefits at both the individual and societal level. It is a skill that deserves far more attention and nurturing. The future depends on it.

Here are the key points:

  1. Carl Sagan emphasized the importance of asking interrogatory or probing questions that challenge assumptions and accepted views. For critical thinking, we must be willing to ask such questions and consider answers that may contradict our existing beliefs.

  2. According to psychologist Daniel Levitin, we live in an era of information overload that strains our ability to think critically. As a result, we often make decisions based on emotions rather than evidence and logic.

  3. To improve decision making, Levitin recommends asking critical questions, such as:

  • 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?
  1. We should apply critical thinking and questioning not just to political and consumer choices but to important life decisions as well. Questioning helps us overcome cognitive biases and irrational fears to make balanced, courageous decisions aligned with our key priorities and passions.

  2. People tend to favor quick, instinctive decision making, but research shows that following your gut often leads to poor outcomes. Our instincts evolved for simpler times and environments, and they are prone to errors and biases.

  3. Asking questions is an effective way to counter our tendency toward fast, intuitive decision making. Questions help us slow down, gather more information, see multiple perspectives, and make choices based on evidence rather than emotions. They make the hard work of difficult decision making easier and more engaging.

  4. Not every small decision requires deep analysis and questioning. But for important life choices, taking the time to ask probing questions leads to better outcomes. Questions illuminate uncertainties and unknowns, enabling us to make progress in the face of ambiguity or complexity.

So in summary, for better thinking and decision making, we must cultivate the habit of asking interrogatory questions, consider a diversity of perspectives, and make evidence-based choices—especially for meaningful life decisions. Questions are powerful tools for overcoming biases, avoiding snap judgments, and gaining clarity on what really matters.

• We are prone to making poor decisions due to cognitive biases and mental shortcuts. Some key decision-making traps include:

  • Fear of the unknown: We prefer the status quo and shy away from change.

  • Focusing on the wrong information: We give too much weight to recent or emotionally-charged information.

  • Overconfidence in our predictions: We think we know more than we actually do.

  • Confirmation bias: We favor information that confirms what we already believe.

• These tendencies can negatively impact decisions by giving us an illusion of knowledge and expertise. We form a limited, distorted view of a situation but believe it is complete. This is known as “What you see is all there is” or WYSIATI.

• To make better decisions, we must question ourselves to overcome these tendencies. Some key questions to ask include:

  • Why do I believe what I believe? Question the basis for your assumptions and beliefs.

  • What would I like to be true? Identify your desirability bias - what you want to believe may not be the truth.

  • What if the opposite is true? Consider alternative perspectives that contradict your beliefs. This “consider the opposite” approach combats biases.

  • Am I thinking like a soldier or a scout? Be open-minded like a scout, not close-minded like a soldier. Admit what you don’t know and be willing to accept you might be wrong.

• Questioning yourself in this way helps you gain a wider, more holistic perspective. You open up to possibilities beyond your first impulse or inclination. The choice that emerges may be your first instinct, the opposite, or something in between. But through questioning, you gain insight and make a more informed decision.

• In summary, not questioning your beliefs and assumptions is itself a poor decision. Rigorous self-questioning and seeking alternative perspectives are keys to overcoming biases and gaining the insight needed for good decisions. Constantly examine why you think what you think.

  • To make good decisions, adopt a “scout mindset” rather than a “soldier mindset.” A scout explores and seeks to understand, while a soldier defends against perceived threats.

  • Develop “intellectual humility” by decoupling your beliefs from your ego. Be willing to accept new evidence and admit when you’re wrong. Ask yourself: “Would I rather be right or would I rather understand?”

  • Question information and claims critically. Ask about the evidence behind them and consider what may be missing or left out. Some key critical thinking questions include:

  1. What is the evidence? How strong is it? From what sources?

  2. What are they not telling me? What’s missing from the information?

  3. Does it logically follow? Do the arguments or reasons actually support the conclusion?

  4. Are there alternative explanations or perspectives? Look for other ways of interpreting the information or issue.

  5. What are the consequences or implications? Think through the impact and outcomes that may result.

  • Critical thinking requires effort but can be developed by habitually employing incisive questions to evaluate information and claims before accepting or acting on them. While it may feel good to assume you’re right, critical thinking helps lead to better decisions and understanding.

  • Learn to feel intrigued rather than defensive when encountering opposing views or information that contradicts your own beliefs. An open and curious mindset will serve you well.

  • To avoid weak-sense critical thinking, seek out opposing views and consider them with an open mind. Choose the side with more evidence.

  • Watch out for logical fallacies like appeals to authority, false dichotomies, and slippery slope arguments. Consider whether there actually are two sides to an issue.

  • Consider whether your critical thinking has an agenda or is skewed to favor your preexisting views. To be a strong critical thinker, you must be willing to question all aspects of an issue, including your own inclinations.

  • Don’t frame decisions as binary “yes or no” choices. Ask open-ended questions to generate more options. Aim for at least three options: best-case, moderate, and worst-case scenarios. Consider counterintuitive options as well.

  • If existing options were unavailable, what would you do? This helps stimulate new possibilities.

  • Consider an outsider’s perspective. Get input from actual outsiders or try to adopt an outsider’s view yourself. This can provide a fresh look at the situation.

  • In summary, critical thinking requires considering multiple sides, questioning your own views, generating more options, and taking new perspectives. The more you practice these skills, the better your decisions can be.

Does this summary accurately reflect the key points about critical thinking and decision making from the opposing view section? Let me know if you would like me to clarify or expand on any part of the summary.

  • We often have a “limited view” of decisions because we’re too close to the issue. It helps to gain perspective by considering how others might view the situation.

  • Asking “what advice would I give a friend?” or considering “what would a new CEO do?” can provide distance and a fresh perspective.

  • Speaking about yourself in the third person, e.g. “what should Warren do?” can also help you gain objectivity.

  • Getting input from outsiders, like advisors or consultants, provides an external perspective. Their outside view may completely reframe the decision.

  • Most decisions should be made when you have about 70% of the information you want. Waiting too long leads to making rushed, poor quality decisions.

  • It’s best to avoid deciding when tired, stressed or anxious. Revisit important decisions a couple days later to confirm them. Ask if the decision could be criticized or how you’d defend it.

  • Indecision due to uncertainty keeps people from moving forward. Ask “where in my life am I avoiding decisions?” and “what would I try if I knew I could not fail?”

  • Fear of negative outcomes, like ending up “dead and broke,” often drives poor decision making. Our “jungle instincts” for risk avoidance don’t serve us well in modern life. We must overcome negativity bias and unrealistic fears.

  • Summary: Gaining perspective, managing fear and negativity, deciding with imperfect information, and reconfirming choices leads to better decisions and less indecision. Overcoming unrealistic risk avoidance helps people move forward.

•Questioning can help identify underlying fears influencing decisions and behaviors. Verbalizing fears helps in coming to grips with them.

•Asking questions about one’s fears, like earliest memory of the fear or what the fear has prevented one from doing, helps in analyzing them. This helps see the irrationality of fears and distinguish real vs imagined risks.

•Focusing on the positive benefits of overcoming a fear, the ‘why’ behind facing the fear, helps provide motivation and inspiration to move past the fear.

•Examining both positive (what excites about the possibility) and negative (worst that could happen, how to recover) aspects of a risky choice helps gain a balanced perspective. This can lessen fears and build confidence in the choice.

•Thinking about failure in a vague, exaggerated way increases fear. Envisioning what actual failure may look like, including causes and how to recover, helps see that failure is rarely absolute and lessens fear. This ‘premortem’ technique provides a realistic view of risks.

•Also envisioning what success may look like provides motivation and counters negativity bias.

•Taking small steps into a risky situation or slowly building up exposure to the fear in a gradual way helps in overcoming fear and building courage.

•Asking ‘what if’ questions that shift reality, like ‘what would I try if I could not fail’, opens up imagination and allows consideration of bolder options. Though constraints exist in reality, this technique broadens thinking.

•A related question ‘what would you do if you weren’t afraid’ can prompt re-examination of a situation to ensure one is not taking the easy or comfortable path out of fear. It encourages pursuing the right path, not the path of least resistance.

•In summary, questioning techniques like identification of underlying fears, premortems, envisioning success, reality-shifting what-ifs, and consideration of small initial steps can help build courage and overcome the fear of facing risky possibilities. A balanced and realistic perspective on risks and benefits is key.

  • The story describes a man who was offered two job opportunities: one risky in San Francisco, and one “safe” in Houston. He chose the risky option and says he’s now thriving. The “safe” Houston company ended up going bankrupt.

  • Studies show we have a tendency to choose the safer, status quo option, even when bolder choices could lead to greater happiness and fulfillment. A study found people who made bolder choices based on a coin flip were happier 6 months later.

  • To counter this tendency, it helps to reframe decisions by envisioning how you might view them in the future. A question like “What would ‘future me’ decide?” can help shift your perspective.

  • When considering opportunities with long-term implications, ask “Which option will allow me to evolve and flourish?“. Consider growth opportunities, ability to progress in your career, learn new skills, have influence, opportunities for camaraderie, and enjoying your daily work.

  • Think of important decisions as part of your life’s larger narrative. Consider how each decision would fit with and serve your core obligations, relationships, values and long-term goals.

  • Imagine explaining your decision to someone you respect. If you’d feel uncomfortable, that may indicate it’s not the right choice. While avoiding regrets, don’t be overly cautious, as the biggest regrets are often from not taking opportunities.

  • Rather than a random coin flip, consider questions like “What would ‘future me’ decide?” to help determine the choice most aligned with your future growth and fulfillment. The right choice should allow you to become a better version of yourself over time.

That covers the key highlights and takeaways from the passage on making bold and fulfilling life decisions. Please let me know if you would like me to explain or expand on any part of the summary.

  • Weighted questions can subtly push you toward a particular answer by putting more burden on one side. For example, “If I’m generally better off saying yes to bold decisions, why not say yes to this one?” The question implies you should say yes unless you have a strong reason not to.

  • When making decisions, also ask: “If I’m saying yes to this, what am I saying no to?” This question reminds you of opportunity costs—what you may miss out on by choosing one option. Don’t say yes to things just to fill time unless they’re worthwhile.

  • Don’t say yes just out of politeness. Ask: “How would I feel if I accepted this invitation—and then found out it was canceled?” If you’d feel relief, you don’t really want to do it.

  • Memorable experiences are valuable to your future self. Ask: “What if putting experience first makes us happier and more fulfilled?” Research suggests it does. Also ask: “When I look back in five years, which option will make the better story?” You’re unlikely to regret the choice that leads to the better story.

  • Finding purpose or “your tennis ball”—the thing that motivates you—can be challenging. Don’t get paralyzed looking for your “passion.” Instead, pick an interesting path and work to become valuable. Your passion may follow. Also follow your curiosity, not just your passion.

  • Ask about your strengths, interests, and ways to contribute. For strengths, ask: “What are my signature strengths?” or “What are my superpowers?” Identify strengths you display when at your best. For interests, ask: “When was I truly happy and why?” “What activity do I keep coming back to?” “What did I enjoy at age 10?” See what still resonates.

  • Other questions: “What makes me forget to eat?” If it matters more than food, that’s meaningful. “In what way do I wish the world were different?” Focus on how you can serve others. “What is my sentence?” Distill your purpose into one sentence summing up who you are and what you aim to achieve.

The key is to ask the right questions to gain insight into yourself, determine what motivates and fulfills you, and find your purpose or “tennis ball” in life. Thoughtful questions can help uncover hidden truths and open up new possibilities.

  • People can pursue either a “Well-Planned Life” that emphasizes individual agency or a “Summoned Life” where they ask what circumstances are calling them to do and how they can best contribute. Psychologist Angela Duckworth recommends seeking purpose by considering how you can help solve a problem or serve others.

  • Purpose can be either capital-P, focused on major issues like hunger or climate change, or small-p, measured by whether your absence would make things worse. Both provide meaning but the latter may be more achievable.

  • To find purpose, ask how your strengths and interests can help others. But know that any pursuit will have hardships. A good question is “What struggle are you willing to tolerate?”

  • If you can’t find purpose, ask “What is my sentence?” - how would you like to be remembered? This can reveal your mission.

  • Creativity is key to purpose and life success but many believe they lack it. However, everyone is creative, and it can be developed by following a process like design thinking which uses questions.

  • Questioning addresses why creativity matters; how everyone can be more creative; and how to stimulate creativity, overcome blocks, improve work, and stay fresh. Questions help see opportunities and navigate challenges.

  • Ask why be creative given the abundance of work and risks. Deciding to be creative can unlock potential. Studies show successful creative people choose to be creative.

  • The Kelley brothers worked to help others rediscover creative confidence through teaching that creativity spills into life; everyone is creative but needs to overcome belief otherwise; and design thinking elicits creativity.

  • Creativity questions shift perspective, inspire, navigate ups and downs, and boost confidence to see challenges as opportunities. They address finding ideas, overcoming blocks, maximizing creativity, improving work, and evolving.

• Creativity has benefits beyond just personal satisfaction. It can make you happier and improve your well-being. Engaging in creative work leads to a state of flow that provides enjoyment and a sense of purpose.

• The end result of the creative process can be shared with others, which provides meaning for the creator and value for the audience. Sharing creative work is a kind of gift.

• Creativity is a key skill for success in business and leadership. Companies value the ability to generate new ideas, products, and solutions. Creativity will only become more important as technology replaces many jobs. Those who can create will have more opportunities.

• Everyone has the capacity for creativity. The belief that only some people are creative is a myth. Creativity is a mindset available to all. While childhood creativity seems to decline for many, it can be rediscovered and nurtured.

• Avoid asking the wrong questions about creativity, like “Am I creative?” or “Where will I find an original idea?” These questions stem from mistaken assumptions and will inhibit creativity.

• Don’t focus on the outcome or whether your creative efforts will be successful. No one can predict outcomes with much accuracy. Successful creators forge ahead despite the uncertainty. Some successes will come through sheer productivity.

• Start creating, even with small steps. You don’t need the perfect idea or starting point. Take one small action to begin tapping into your creativity. Build from there.

• Turn off distractions like your phone to make time and space for creativity. You don’t necessarily need to find extra time—just use the time you have more purposefully.

The key message is that anyone can choose to nurture their creativity. While obstacles and doubts may arise, avoid questioning your creativity or ability. Focus on the work, not the outcome. Start anywhere and build momentum. Creativity will enrich your life and open up opportunities. Make the decision in favor of creativity.

To increase your creativity, look for problems to solve rather than ideas to generate from scratch. Problems provide raw material to work with. The key is finding problems that stir your interest or frustrate you in some way. Some questions to ask yourself to uncover problems worth solving:

•What stirs me? Focus on topics or issues you care deeply about.

•What bugs me? Look for existing frustrations, inadequacies or situations that bother you.

•What’s missing? Identify unmet needs or gaps waiting to be filled.

•What do I keep coming back to? Pay attention to recurring themes in your interests or conversations. They could point to a problem you want to tackle.

•What is ripe for reinvention? Consider updating or reimagining existing products, stories, genres or other elements.

Creativity often comes from combining existing ideas or elements in new ways. Look for inspiration all around you, not just from overtly “creative” sources. With the right mindset, raw material for new ideas can be found anywhere.

The key is to start with a problem, not an idea. The problem provides a focal point to work around and a purpose. Ideas and solutions will emerge as you dive into solving the problem.

Some examples of creatives who found problems to solve:

•Tony Fadell (Nest thermostat) was frustrated with ugly, unintuitive thermostats and saw an opportunity to reinvent them using modern design and technology.

•Lin-Manuel Miranda (Hamilton musical) was stirred by the story of Alexander Hamilton’s life but wanted to tell it in a wholly new way—through hip hop and rap. He saw that as a problem worth solving.

•Steve Jobs (iPhone) combined elements of existing products (cell phone, Blackberry, iPod, camera) to solve the problem of having so many separate devices. He created an entirely new product.

In short, to boost your creativity, become a problem finder rather than an idea generator. Look for the problems, frustrations and unmet needs around you, and your ideas will follow.

The key to finding creative problems worth solving lies in seeing the familiar in unfamiliar ways. This involves paying closer attention to details in our everyday environments, listening for expressions of dissatisfaction from “customers,” and asking questions that shift our perspective.

Some questions that can help uncover problems include:

  • What might I notice if I were encountering this for the first time?
  • What is in the background?
  • What here would fascinate a five-year-old? Or a ninety-year-old?
  • What would Seinfeld be amused by?
  • What would Steve Jobs be frustrated by?
  • What is missing?

Once a problem has been identified, it’s important to determine if it’s the right problem for you to pursue. Questions to ask include:

  • Will I still love this problem tomorrow?
  • Can I make a unique contribution here?
  • Is this a challenge I can apply my skills to?
  • Can I own this problem? If others are pursuing the same idea, what’s my twist?
  • What is the potential impact if I solve this problem?

The story of Tony Fadell and the Nest thermostat illustrates how frustration with an everyday problem (in this case, a poorly designed thermostat) can lead to a creative solution, if the right person applies themselves to reimagining what’s possible. The lessons here point to the value of cultivating our “problem-finding” skills through closer observation of the world around us, and learning to see the familiar in unfamiliar ways.

Tony Fadell, co-creator of the Nest Learning Thermostat, asked himself two important questions before pursuing the idea:

  1. Will it make a difference? - Focusing on the potential positive impact.

  2. Is it a great business? - Evaluating the commercial viability.

Fadell researched the thermostat market to determine the potential business opportunity and impact. Though the outcomes were uncertain, the potential upside seemed considerable if executed well.

Rather than focus on potential financial outcomes, Fadell considered the creation’s possible impact and effects. Phrasing the challenge as a question, like “How might I create a thermostat as appealing as an iPhone?” can help spark ideas.

To foster creativity, immerse yourself in research to provide raw materials for new ideas. Ask “why” questions to gain insight, like:

  1. Why does this problem matter?
  2. Why does it exist?
  3. Why hasn’t it been solved?
  4. Why might that change now?

Research and questions lead to an incubation period where ideas form. This requires deep focus in an environment conducive to creative work, free of distractions. John Cleese calls this a “tortoise enclosure” - a place to be alone with your thoughts for a set time.

Find your productive space, whether a “cave” like the author’s or a coffee shop like Scott Adams’. Protect your ability to focus, which fuels creativity. Ask:

  1. Where will I actually be able to create?
  2. What if we saw attention like air or water, a valuable resource we hold in common?
  3. How might I begin to protect this precious resource?

Limit distractions and make time to focus. Creativity requires concentration, while constant interruptions and the pull of digital media make it hard to focus. It’s easier to react than create, so protect opportunities to think.

Connected time refers to being constantly plugged into technology and digital media. This constant stimulation and distraction reduces our ability to focus and be creative. Disconnected time refers to taking breaks from technology to allow for creative thinking and productivity.

Some tips for balancing connected and disconnected time:

•Ask yourself: When should I take a break to connect? This reframes technology use as the indulgence, rather than disconnected time.

•For those who struggle to disconnect, ask: If I must be connected, how can I reassert control? Tips include using long, complex passwords; turning off notifications; disabling social media feeds; batching email; using grayscale phone screens. These make technology less addictive and distracting.

•Ask yourself questions to help balance connection and disconnection:

›How can I protect my attention? Treat it as a precious resource.

›How can I shift to a “maker’s schedule” with long blocks of uninterrupted time? Rather than a “manager’s schedule” with frequent short blocks of time.

›Am I pruning the vine? Cutting out distractions and lesser priorities to focus on what really matters.

›What if I trade the morning news for the “morning muse”? Use prime creative time for thinking, not consuming news.

›Instead of breaks from social media, what about breaks to use social media? Spend more time disconnected.

•Determine your prime creative time. Do a “flow test” to find when you feel most productive and creative. Restructure your schedule to maximize these periods. Mornings are often most creative for many.

•Use the “snooze muse”—the 10 minutes after your alarm goes off—to think about your creative projects. Tap into your unconscious mind.

•To overcome the urge to abandon creative work when struggling, ask: How can I put myself in “creator’s jail”? Use timers, locks, accountability partners to force yourself to persist. But also schedule “furloughs”—brief breaks to recharge. Starting with 45-90 minutes of focus at a time is helpful.

•Letting your mind wander during breaks can spark creativity. If stuck, a change of scenery or shift in mental state may help new ideas emerge.

  • It can be easier to gain an insight or idea when you’re distracted or your mind is wandering instead of when you’re intensely focused on a task. Taking a walk, showering, doing mindless chores are good ways to stimulate creativity.

  • However, be careful not to get too distracted. Creatively stimulating activities like going to a museum are good, but highly distracting activities like watching a movie may hamper your own creative thinking.

  • Developing an idea often requires “killing the butterfly”—taking an idea from your imagination and pinning it down in concrete form, which is difficult and can be disappointing. But learning to live with the gap between your imagination and what you can actually execute is key to creativity.

  • To develop an idea, stay focused on it rather than jumping to new ideas. Map out concrete steps to keep yourself accountable. Build a community of support around your idea.

  • Be wary of excessive preparation and “rearranging the bookshelves” as a stalling tactic. While some preparation is good, constantly preparing and never creating is problematic. Ask what you can do now with what you have.

  • Don’t get stuck trying to figure out the perfect place to start. Just start anywhere, even if what you create at first is imperfect. You can always revise and improve later. The key is just beginning.

  • Making a quick prototype or draft can be a good way to overcome the fear of the blank page and give rough form to an idea. Then you have something to work with and build upon.

  • It’s often best to begin a creative project anywhere—with a fragment of an idea, a flawed prototype, or in the middle of a story. Ask yourself “What if I allow myself to begin anywhere?”Beginning badly or imperfectly can be better than not beginning at all. You can always revise or scrap your initial efforts.

  • To get unstuck in the creative process, use questioning to access new perspectives, such as by imagining how admired thinkers might view your problem or by shifting your own perspective to the past or future. Trying to generate “wrong” ideas can also spark insights.

  • The middle stages of a project can be the hardest, when initial enthusiasm fades but the end remains distant. Use self-questioning here to challenge negative feelings and remind yourself of your abilities and past successes. Looking at what others have accomplished can also motivate you.

-Once your work is finished or nearly so, share it with others. Keeping ideas locked away out of fear that someone might steal or criticize them is counterproductive. Putting ideas on open display, as at creative companies like TBWA\Chiat\Day, leads to a free exchange that benefits the originator.

-Successful creators “ship”—they share their work, launch their products, and expose themselves to criticism. While risky, shipping frequently leads to more successes. “Done is better than perfect.” Releasing smaller iterations, as in the “hacker way,” allows you to get feedback and make improvements. Waiting for ideal circumstances means lost opportunities.

-You must decide whether you want a project to be done or want to keep improving it endlessly. Steve Jobs said, “Real artists ship,” but also that “creativity is connecting things”—and connections often happen in the extra time spent polishing and revising. Determine what level of imperfection you can tolerate, then move on to the next creation.

The key to staying creative over the long run is to remain “en route”—to keep moving, exploring new ideas, and reinventing oneself. This means:

•Follow your curiosity. Curiosity leads to new ideas and inspiration. While unfocused curiosity can lead to distraction, focused curiosity helps drive you to dig deeper into a topic or project.

•Think like a novice. Experts tend to get trapped in their expertise and have trouble seeing new possibilities. Approaching your work with a beginner’s mindset helps you discover new ideas.

•Be willing to start over. Throw out old work and old ways of thinking. Starting from scratch, even when it’s scary, is how creative people stay fresh and relevant.

•Expose yourself to diverse influences. The more inputs and ideas you’re exposed to, the more possibilities for new combinations and connections. Actively seek out new areas of interest and new sources of inspiration.

•Trust the process. Even when you have to let go of past successes, trust that the mindset and methods that led to previous creative breakthroughs will help you find the next one. The creative journey is one of perpetual novelty and reinvention.

• Evaluate how well you accept feedback. Receiving feedback is a gift, even if it’s critical. Look for feedback that helps you improve the execution and clarity of your vision, not feedback that tries to alter your vision entirely. Accept all feedback with an open and grateful mindset.

In summary, staying en route as a creative person means embracing continual change, following your curiosity into unexplored territory, and trusting in the ongoing process of creative reinvention. While it may feel uncomfortable or even scary at times, it’s the only way to ensure your work stays vital, fresh, and inspired.

  • In the 1960s, Arthur Aron conducted research on ways to create instant intimacy between strangers. He found that asking a series of personal questions, increasing in depth and vulnerability, was an effective way to build connection.

  • Aron developed a list of 36 questions that could be used to create closeness between strangers. When people asked each other these questions, they often formed highly positive feelings and in some cases even fell in love.

  • Aron’s question strategy went viral in 2015 when a New York Times article described how two acquaintances fell in love after asking each other Aron’s 36 questions. Aron has continued to study how variations of these questions can strengthen relationships in many contexts.

  • Questions show you care, encourage others to reveal personal details, and allow you to respond in a way that builds rapport and understanding. This is why questions are such a powerful way to form connections.

  • If two people from different groups connect through questions, their positive feelings often extend to the groups themselves. So facilitating connections between groups through questions and sharing can help build broader intergroup understanding.

  • In summary, questions have the power to create intimacy, strengthen relationships, build intergroup bonds, and spread positive feelings. Thoughtfully using questions to connect with others can have significant and far-reaching impacts.

  • Professionals, like former FBI agents, are trained to ask open-ended questions that encourage people to reveal information. The wording and attitude matter. Genuine interest and suspending judgment are key.

  • As children, we intuitively asked questions to connect with others. As adults, we often misuse questions, asking rote, judgmental, or advice-giving questions instead of authentic, curious ones.

  • To build connections, ask authentic questions rooted in curiosity, suspend judgment, take risks by asking deeper questions, and listen carefully.

-Technology has enabled superficial “connections.” But research shows that close companionship—not lots of superficial contacts—is key to happiness, health, and meaning.

  • Rote questions like “How are you?” often lead to rote answers and conversation stoppers. Better options probe for stories and feelings, like “What’s the best thing that happened today?” or “What are you passionate about?”

  • Put a twist on standard questions. Instead of “How was your weekend?” ask “What was the best part of your weekend?” Instead of “Where are you from?” ask “What’s the strangest thing about where you grew up?”

  • Don’t avoid “deeper” questions with new people. Replace small talk with “big talk.” Ask profound questions to make a connection. For example, “What would be a perfect day for you?”

-The key is to be genuinely interested in learning about the other person. Curiosity and suspending judgment are key. The questions should invite stories, feelings, and experiences, not just facts.

If you could change anything about the way you were raised, what would it be? He would focus more on developing independence and self-sufficiency.

What does friendship mean to you? Friendship is about mutual understanding, trust and support.

How do you feel about your relationship with your mother? The relationship could be improved. There is a lack of emotional connection and understanding.

When did you last cry in front of another person? And by yourself? He rarely cries in front of others. He last cried alone a few months ago during a low moment.

What, if anything, is too serious to be joked about? Some topics that are too serious to joke about include death, terminal illness, and violence.

To listen with your whole body:

•Ask yourself if you are ready and able to listen fully before engaging in an important conversation. Make sure you are in the right mindset and place to focus.

•Listening is more than just hearing - it requires physical, mental and emotional presence. Give the speaker your full attention using your eyes, ears and heart.

•Pay attention to body language and tone as well as the actual words being said. Look for the emotional meaning and context behind what is being communicated.

•Don’t just passively nod along. React and respond to show you understand and encourage the speaker to share more. Ask follow up questions.

•Withhold judgment and advice. The goal is to understand the other person, not evaluate or try to “fix” them. Listen without trying to solve the problem.

•If needed, reflect back what the speaker has said to confirm understanding. Paraphrase their main thoughts and feelings.

•Give the speaker your time and patience. Often people need to think out loud, and the most meaningful insights may come at the end of the conversation. Be willing to sit in silence.

•Respond with empathy, compassion and care. Make eye contact, soften your tone of voice and reflect the emotional experience of the speaker. Mirror their energy and mood.

•Focus on listening to understand rather than just reply. Try to see the issue from their perspective. The more you understand them, the better you can support them.

• An attentive, open mind is key to good listening. Rather than judging what someone says, try to understand and empathize with their perspective. Use your imagination to “feel” what they feel.

• Body language and verbal responses signal you are listening. Make eye contact, nod, and say things like “just to be clear…” But also remain quiet and avoid interrupting.

• Avoid “conversational narcissism” where you make the conversation about yourself. Don’t share your own stories or opinions, focus on the other person.

• Ask clarifying questions to make sure you understand, like: “Just to be clear, are you saying…?” or “Can you explain what you mean by that?”

• Use “echo” or “mirroring” questions, where you repeat key words as a question, e.g. “Nobody cares?” This encourages the speaker to explain further and feels heard.

• The “AWE” question, “And what else?”, is very effective for eliciting more insights and ideas. Ask with genuine interest and up to 3 times. It allows you to remain in a supportive role.

• Use “empathetic listening” to reflect the emotions you think the speaker feels, e.g. “It sounds like you felt frustrated. Is that right?” This can encourage sharing of deeper feelings. Follow up to clarify the level and source of emotion.

• Overall, the goal is to discover the root issue or feeling, so you can then work towards solutions. Keep asking clarifying questions until you get to the heart of the matter.

• Listening well requires effort but can have meaningful benefits. It builds trust, fosters better understanding, and leads to more productive outcomes. With practice, these techniques can become second nature.

• Asking questions is a better approach than giving advice. Asking questions helps the other person feel understood and less defensive, and it guides them to find their own solutions rather than imposing your solutions on them.

• We tend to give advice because it makes us feel in control and high status. But advice is often not as good as we think and can damage relationships. It’s better to ask questions to help the other person gain insights and clarity.

• Ask open-ended questions to help the other person surface multiple options and ideas. Then ask which options interest them most to discuss further. Ask practical questions to help them develop a concrete plan of action.

• Before criticizing someone, ask yourself questions to examine your own motivations and possible hypocrisy. Consider whether the criticism will be constructive and useful. And be honest about whether you’re deriving pleasure from it. Criticism often does more harm than good.

• “Counterfeit questions” that are really veiled criticism are just as harmful. In the workplace, ask questions to provide constructive feedback aimed at helping someone improve, rather than just criticizing.

• The key is to advise less by giving solutions, and inquire more by asking insightful questions. This helps empower the other person and leads to better outcomes. But advice and criticism still have their place at times. Use good judgment.

The overall message is that asking good questions is a powerful way to help and guide others, as opposed to the more common habits of giving advice and criticism. But advice and criticism are not always bad; they depend on the context and your motivations and approach. The key is learning to distinguish when each approach—questioning, advising, criticizing—is most appropriate and potentially helpful.

The key points made in this essay are:

  1. Appreciative Inquiry is an approach that emphasizes focusing on strengths and solutions rather than weaknesses and problems. It involves asking positive questions that encourage a constructive conversation, rather than judgmental questioning that can create tensions.

  2. Playwright Lynn Nottage used an approach of “replacing judgment with curiosity” when interviewing people in Reading, PA for her play Sweat. By listening without judgment to people with very different backgrounds and beliefs than her own, she gained insight and understanding that she was then able to convey to audiences. This approach of open-minded, empathetic questioning can help bridge divides.

  3. Questioning ourselves and our own views and biases is important before questioning others in a confrontational situation. We should examine our own motivations and consider how we can be open-minded in the conversation. Curiosity about other perspectives signals a willingness to learn.

  4. Considering both sides of an issue, even if we still disagree with one side, is an important part of critical thinking. We should avoid “weak-sense critical thinking” where we only consider ideas that confirm what we already think. Evaluating other perspectives fairly can strengthen our own positions.

  5. To consider other sides openly, we must recognize and account for our own biases and preconceptions. Asking ourselves questions like “Why do I believe what I believe?” and “How might I own my own biases?” can help achieve a more open and curious frame of mind.

  6. The approaches suggested here are aimed at defusing arguments and encouraging productive conversation, not “winning” or persuading. They involve a willingness to listen, share, and find common ground.

The overall message is that approaching ideological divides and difficult conversations with an open and inquisitive mindset can help repair relationships and promote understanding. This begins by questioning ourselves and our preconceptions, then extending open-mindedness and empathy toward others through appreciative questioning and listening.

• Self-interrogation or questioning your own views and beliefs is useful because your positions may have been formed long ago and may no longer reflect your current thinking. You may not even fully understand why you hold certain views.

• Questioning yourself can help reveal biases you may hold. The first step is acknowledging you have biases. Then you can try to account for them when evaluating new information. Ask yourself how your biases might be influencing your judgment.

• Your views are often shaped by the surrounding culture and people around you. Question what your culture may be preventing you from seeing— try looking past conventional wisdom.

• When discussing divisive issues with others, avoid trying to persuade them or prove them wrong. This usually does not work and can seem like a personal attack.

• Allow the other person to explain their view, show interest, and use active listening. You can then explain your view. Shift the discussion to finding common ground and shared values.

• Use “bridge” questions to encourage balanced thinking, like: “Can you find anything in your position that gives you pause?” “Is there anything in my position you find interesting?” Ask people to rate aspects they disagree with to get them thinking about the other side.

• Questioning can encourage empathy by asking people to imagine the other perspective. For example, ask “What if you had to advise the opposing candidate? What would you suggest to reach people like you?”

• Move toward “common ground” by imagining a compromise candidate or solution. Look for shared principles and interests. Question how to satisfy both sides.

• The goal is to meet each other halfway, not persuade. Look past differences to find common ground and a mutually agreeable solution. Questioning in a spirit of openness and understanding can help make progress.

The key is to find common ground and work together. Some suggestions:

  • Ask open-ended questions to understand the other perspective, e.g. “Can I try to explain what I think your position is?” Then you can articulate each other’s views and find areas of agreement.

  • Focus on the relationship, not who’s right. Ask yourself, “Do I want to be right or do I want peace?” It may be better to compromise.

  • Pay attention to the other person’s “bids” for connection and respond actively and constructively. Ask follow up questions and show you’re listening. This builds closeness.

  • Before ending a relationship, ask exploratory questions to see if it can be saved, e.g. “How might we begin to save this marriage?” Make a list of what each person can do.

  • If you’re at fault, apologize sincerely using 10 words: “I’m sorry. I was wrong. Will you please forgive me?” Asking for forgiveness is key.

  • Look for small areas of agreement and build on those. Compromise where you can. Treat the other person with patience, empathy and respect.

  • Accept that change can take time. Rather than attacking the other’s views, say “We’re all in this together—let’s learn about this together.” Look for common ground and a “shared quest for truth.”

To strengthen partnerships:

  • Ask questions regularly to avoid taking each other for granted, e.g. “What am I missing?” Try to see from the other’s perspective.

  • Share struggles, dreams, and good news. Respond supportively with follow up questions. This builds closeness.

  • Do small things to show you care, even if they seem trivial. It’s often the little gestures that matter most.

  • Make time for meaningful conversations. Ask thought-provoking questions about life goals, values and the relationship.

  • Compromise when possible. Focus on mutually agreeable solutions rather than who’s right. Treat each other with patience, empathy and respect.

Does this help summarize some suggestions for finding common ground and strengthening relationships? Let me know if you have any other questions!

• Asking questions is important for building trust and collaboration in the workplace. However, people are often hesitant to ask questions at work due to hierarchical structures and the perception that questions may challenge authority.

• It is important for employees to continually ask questions to better understand their jobs and improve their performance. Experienced employees in particular may be reluctant to ask questions, but managers today generally appreciate employees who question the status quo. When “questioning up,” frame questions respectfully and do some homework first. Asking for advice is a good way to show respect and get useful information.

• Managers can benefit from learning to “question down”—asking interested, authentic questions of subordinates. However, many managers are accustomed to telling rather than asking. Questioning helps build rapport, figure out how to manage better, and address problems in a constructive way. Questions can help determine if employees are engaged and identify obstacles to their best work.

• Important questions for managers to ask employees include:

  • Are you satisfied with your own performance?
  • What do you think is working well, and what is not?
  • What do you not have time to work on, that you’d like to be working on?
  • What questions do you have for me?

• In summary, questioning—in both directions—helps to build understanding, identify and solve problems, determine priorities, and increase engagement and collaboration in the workplace. But people must overcome the tendency to avoid questions, especially in hierarchical environments. With practice, the benefits of questioning can outweigh the risks.

• Managers should be receptive to questions from employees and take them seriously. It’s okay not to have an immediate answer; just commit to giving the question thought and following up.

• The best questions are rooted in curiosity. Questions that convey a sense of curiosity about employees and their work can help build connection and show you care. For example, ask “open and deep” questions like: What’s the coolest thing you’ll work on this week? What excites you about your job now?

• Questions can also improve relations between co-workers by showing an interest in what colleagues care about. But use judgment in how personal your questions get. Ask relationship-building questions, but be aware of appropriate boundaries.

• For difficult co-workers, questions may help find common ground. But also ask yourself questions to determine the best way to adapt, like: Am I overreacting? Which of this person’s behaviors actually interfere with my work? What can I politely ask them to change? Who could mediate? How can I create distance?

• Companies should regularly ask: What does the world need from us? People on the frontlines—like sales reps, customer service staff, and field researchers—are well positioned to ask questions that provide this insight.

• Salespeople, in particular, should adopt a “question pitch” instead of a sales pitch. Asking questions encourages customers to think of their own reasons to buy from you. It helps build rapport and shows you want to solve their problems, not just make a sale. The goal becomes building long-term relationships, not just short-term sales.

• Consultants, too, should “ask, don’t tell.” Like salespeople, ask questions to understand the client’s problems fully and help them come to their own solutions. Provide an outside view to ask questions insiders may miss.

• Within an organization, questions should flow in all directions: employees up, managers down, and outward to customers and stakeholders. But leaders must also look inward and ask: What is our mission and purpose? Why are we here?

• A new model of leadership is emerging focused on leading through questioning. Leaders must ask the powerful questions that help bring people together around a shared purpose.

  • Nadia Lopez, principal of Mott Hall Bridges Academy, has influenced her students through personal interactions and teaching them critical thinking skills. She regularly questions them to help uncover problems, set them on the path to solutions, and encourage them to achieve their potential.

  • Lopez exemplifies a new kind of visionary leadership focused on serving and supporting others. These “visionary helpers” lead through humility, curiosity, open-mindedness, and by asking thoughtful questions. They aim to inspire and empower their teams and organizations.

  • This leadership style is well-suited for today’s fast-changing, uncertain world. It requires flexible thinking, the ability to anticipate change, strong communication, and understanding different perspectives.

  • However, there is currently a leadership crisis as many leaders fail to demonstrate these qualities. Despite a wealth of advice, leadership today often falls short.

  • Becoming a better leader requires self-reflection and a willingness to question one’s own assumptions and instincts. Developing the right mindset and judgment is an “inside-out” process. Visionary leaders nurture their capacity for understanding, caring for others, and moral reasoning.

  • Questions are a key tool for visionary leaders to build understanding, guide others to solutions, and create a culture where people feel heard and able to achieve their potential. Asking the right questions, listening, and acting with compassion and integrity are leadership skills that can be strengthened over time.

  • Visionary leadership starts with leaders who aim to serve, empower, and lift people up. By focusing on continuous self-improvement and understanding others, leaders can have a profound, positive impact. Building a better future will require this kind of enlightened leadership.

• Leaders often rise to leadership positions without doing the necessary intellectual work to determine why they want to lead and what kind of leader they want to be. As a result, they end up practicing “seat of the pants” leadership that relies too much on external advice and not enough on inner reflection.

• To avoid this trap, aspiring leaders should ask themselves some fundamental questions to clarify their thinking, such as:

  • Why do I choose to lead? The answer should be more than personal ambition or status. It should relate to a sense of purpose and a desire to help others.

  • Why would others want me to lead them? The answer to this should align with the answer to the first question. If the reasons are too self-serving, they likely won’t motivate followers.

  • Do I have the confidence to be humble? Leadership today requires qualities like humility, the ability to help others succeed, and a willingness to delegate and share the spotlight. Overachievers often struggle with this transition.

  • Am I willing to step back from personal achievement in order to help others move forward? Leadership is about enabling others, not starring as the top performer. Leaders must be willing to shift from “doing” to helping others “do.”

• The philosophy of “servant leadership” suggests leaders should put other people’s needs first and focus on helping them to succeed and become leaders themselves. This approach has roots in the military, where leaders must prepare others to step up and take over at any time. Adopting this mindset in business requires leaders to embrace more relational skills like coaching, communicating, and building trust.

• In summary, leadership today demands qualities that run counter to the ambitious, achievement-oriented tendencies of many aspiring leaders. Successful leaders are able to make the mental shift to focusing on enabling and empowering others. But that transition starts with asking the right questions of oneself. Doing the internal work to clarify one’s purpose and approach before taking on a leadership role.

The organizational psychologist Tomas Chamorro-Premuzic observes that we “commonly misinterpret displays of confidence as a sign of competence.” This overconfidence can breed hubris in leaders, which then spreads to the organization’s culture. Hubristic behaviors like micromanaging, blaming others, and self-glorification are detrimental today. Leaders must balance confidence and humility.

To determine if you’re ready to lead today, ask yourself:

  1. Am I willing to step back to help others move forward? Effective leaders empower others rather than seeking the spotlight.

  2. Do I have the confidence to be humble? Leaders must be confident to inspire others but humble enough to accept that they don’t have all the answers.

  3. Can I learn to keep learning? Today’s rapid change means leaders must constantly adapt. They can’t rely on past expertise and must indulge their curiosity.

  4. Do I seek to create an organization in my own image? Leaders must foster diversity to get a range of viewpoints and anticipate change. Homogeneous “old boys’ clubs” limit an organization.

Effective twenty-first century leaders must make time for reflection to gain insight into strategy and see the big picture. Reflection prepares leaders to respond well to challenges and “lead on demand.” Leaders must discipline themselves to schedule and protect time for thinking.

Why must leaders retreat in order to lead?

•Reflection leads to better insight and vision. It allows the mind to connect ideas, search for meaning, and envision the future.

•Reflection anchors leaders in their principles so they can respond confidently to change instead of reacting hastily.

•Thinking in advance prepares leaders to “lead on demand” when challenges arise.

•Finding time requires discipline. Leaders must schedule time for reflection and protect it from being overridden by urgent demands. Early mornings or late days often work.

•An hour of uninterrupted time is ideal for deep thinking and capturing thoughts in writing. But any time is better than none.

•Reflection is a key habit of effective leadership. As Doug Conant said, “When leaders say they don’t have time to think, that’s BS.” Leaders must make the time.

Reflection is a critical activity for effective leadership. It involves taking time to examine your core values, priorities, and vision. Reflection should start as a solo activity where you deeply explore questions about your leadership principles and purpose. You can then get input from a trusted partner.

To reflect on your core values, ask yourself questions like: What is my code? What are my formative influences? When have I been at my best or come up short? What have I taken a stand for? Share your values through a story or “logline.” The “Galatea Effect” shows that articulating your values shapes your behavior. Communicate your values through words and consistent action.

Regularly assess if you’re living according to your values. Ask: Did I live up to my code? How can I improve? An organization should also have a clear code and purpose. To uncover this, ask: Why are we here? When have we been at our best? Who would miss us if we disappeared? What makes us unique? What do we stand against? How can we be a cause, not just a company?

The leader must reinforce the organization’s essential purpose and see if it still holds true. Asking provocative questions can reframe perspective, like: If we disappeared tomorrow, who would miss us? What do we do that others can’t or won’t? In today’s world, organizations and leaders must take a stand on ethical issues. Articulate what you stand for and against.

In summary, reflection at an individual and organizational level is key to leadership. It involves examining your core principles and purpose, sharing them with others, and ensuring your actions align with your values. Reflection is an ongoing process that requires continually asking difficult questions.

  • Leaders today must consider social justice issues and company purpose. Merely donating to causes is not enough. Leaders must determine their organization’s “higher calling” and commit to it through consistent policies and actions.

  • Leaders often feel pressure to do more and chase every new opportunity. But this leads to lack of focus and diminished productivity. Leaders must learn to do less by changing their attitudes (stop equating being busy with importance) and behaviors (choose between options instead of trying to do both).

  • To sharpen focus, leaders should ask questions like: Is this necessary? What do we stand to lose? What do I want to go big on? What stupid rule should we kill? What is the highest, best use of my time?

  • Another important question is: What truly matters now? Leaders must determine current priorities and devote resources to them. Asking what matters at the start of each meeting helps determine if the meeting itself should even happen.

  • The “focusing question” is: What is the one thing I can do that would make everything else easier or unnecessary? This helps identify a single priority to focus on immediately.

  • Leaders must anticipate changes far into the future, not just what’s on the horizon. They need to spot “the third wave” - changes that will significantly impact their organization someday. Asking “How can we become the company that would put us out of business?” encourages radical thinking about how your company’s competitive advantage could be disrupted. Preparing for multiple possible futures is key.

  • Other tips for anticipating the future: Question assumptions and beliefs, encourage dissent, explore the fringe, and make incremental bets on new possibilities. Consider new partnerships and keep an open and curious mindset. The future belongs to those with the most imagination and courage.

• Leaders must look ahead to anticipate future challenges and opportunities. This requires asking “visionary” questions that explore future possibilities.

• It’s hard for leaders to look into the future due to immediate pressures and a bias toward the present. A consultant recommends “shifting temporal references” by thinking about current issues from the perspective of 1, 2 and 5 years ahead.

• One technique is to ask “oracle questions” that imagine what you’d want to know about the future if you had access to an oracle. Though there’s no real oracle, it spurs future-focused thinking.

• Speculative questions can envision future threats, like “How can we become the company that would put us out of business?” They can also explore opportunities, like “What if we could do what we do now much faster—what might we achieve?”

• Reading “weather reports” from futurists and forecasters and observing trends in your own interactions can help identify the “third wave”—future changes—coming your way. Look ahead in stages, from 1 to 2 to 5 to 7 years.

• Share your vision by “making tomorrow visible” through experiences that let others glimpse the future. Turn vision statements into open-ended “vision questions.”

• Leaders must also look outward, asking “How can I help?” to understand external challenges and support others. Doug Conant turned around Campbell Soup by first improving morale through this outward focus. He learned it early in his career from an executive coach who asked “How can I help?”

• Looking ahead and looking outward require different types of questions but are both key to visionary leadership. Together they shape a “visionary helper” approach.

  • Doug Conant turned around Campbell Soup Company as CEO between 2001 to 2011 by engaging with employees through questioning. He asked questions like “What’s going well?” and “How can I help?” to build rapport and trust.

  • Asking good questions requires humility, a desire to help, and a willingness to act on the responses. Conant walked around the company, handwrote praise notes, and engaged with many employees.

  • Studies show many employees today feel disengaged at work. Questioning leaders can identify problems, provide support, build trust, and get critical information to improve the organization.

  • Employees often withhold information from bosses because they fear retaliation or don’t think the bosses care. The only way to change this is for leaders to directly ask questions with genuine interest.

  • Leaders should ask open-ended questions to draw out meaningful responses, avoid leading or rhetorical questions, and focus on strengths and solutions rather than problems and blame.

  • Case Western Professor David Cooperrider advocates “Appreciative Inquiry” where leaders focus on what’s working rather than problems. Ask positive questions, then inquire optimistically about growth and improvement.

  • Avoid asking “Why?” questions directly to employees as it can make them defensive. Focus on collaborative solutions. Ask “How can I help?”

  • FBI agent Robin Dreeke recommends leaders ask themselves “How can I make the conversation about them?” Focus on the other person’s needs, priorities, options rather than your own. Remove judgment and ego.

  • Don’t ask rote questions like “How’s it going?”. Do ask questions like “What’s the biggest challenge?” or “Are you making progress?”. Say “Help me understand what led to…” rather than “Why did you…?”. Ask if goals and vision are clear.

  • Dreeke likes using “challenge questions” to build rapport as people want to discuss their priorities and concerns, allowing you to offer help.

• Leaders can encourage a culture of curiosity and questioning by modeling that behavior themselves. They should openly discuss what they’re curious about and how they think through problems.

• A culture of inquiry provides benefits like tapping into collective intelligence, encouraging learning and adaptation to change. However, leaders must be prepared to actually address the questions and concerns that arise. Saying “don’t bring me problems, bring me solutions” defeats the purpose.

• Leaders should ask themselves if they’re truly ready to foster a questioning culture. It requires tolerance for debate and independent thinking. Leaders must embrace questions and experiments, not just solutions.

• To start building a culture of curiosity, leaders can announce they want to hear about the problems people have noticed. They can encourage inquiry through modeling and by valuing questions and the learning process.

• A culture of questioning helps companies innovate, tap collective wisdom, and support learning. It leads to a more engaged, fulfilled workforce. But leaders must be willing to thoughtfully address the questions that arise.

• If leaders want new ideas and innovation, they need input and questions from throughout the organization. But they must ensure those questions don’t go ignored. Leaders should consider how they’ll respond before launching an initiative to increase questioning.

• Leaders can begin by asking themselves whether they have the patience and willingness to foster a truly curious culture. Do they embrace messy learning processes, not just solutions? Are they open to input that challenges the status quo? If not, a questioning culture may backfire.

That covers some of the key highlights around developing a culture of curiosity and the role of leaders in encouraging more questioning. Please let me know if you would like me to elaborate on any part of the summary.

To build a culture of inquiry, leaders should model questioning behavior and create conditions that encourage curiosity and learning. Four key questions can help in this effort:

  1. How can we make questioning safe? Establish a “no judging” rule and create anonymous ways for people to ask questions. This reduces fear of speaking up.

  2. How might we make questioning rewarding? Recognize and celebrate good questions. Consider offering bonuses and incentives for questions that lead to improvements.

  3. How might we make questioning productive? Train people in effective questioning techniques and methods. Teach them to use questions to achieve results, not just wonder aimlessly.

  4. How can we make a culture of inquiry stick? Make questioning a habit by incorporating it into regular meetings and activities. For example, start each meeting with a question or hold “question days.” Challenge people to ask one ambitious question per week.

To encourage productive questioning, teach people how to turn questions into solutions and results. Questioning should be aimed at driving real change, not just speculation. Employees need to understand how to use questioning methods to progress from identifying a possibility to figuring out how to realize it.

Making a culture of inquiry stick requires making questioning a habit through regular exercises and rewards. The more questioning becomes embedded in standard business practice, the more instinctive it will feel for people to challenge assumptions and the status quo. Overall, the goal is to move from declaring the importance of a culture of inquiry to actively creating the conditions that will bring it about. Leaders must model the change they want to see.

To cultivate an inquiring life, people and organizations need to take action on questions. Some suggestions for doing this include:

•Using “external cues” as reminders to slow down and question more in important situations. This could include checklists, reminders from a “trusted other,” or “Q-cards”—pre-prepared questions to have on hand for various situations.

•Developing your own customized questions over time based on three main themes: 1) challenging assumptions, 2) shifting perspectives, and 3) considering counterintuitive possibilities.

•Overcoming the “enemies of questioning”—fear, knowledge, bias, hubris, and lack of time—through action. For example, try asking at least one naive question each day to build up your questioning courage. Start by asking fundamental questions of yourself, then take your questions public.

•Recognizing that while changing habitual patterns of thinking and behavior is difficult, it is possible for people to become more thoughtful and questioning, especially with practice and outside support. But some level of automatic thinking is also useful at times. The key is learning when to shift into a more deliberate, questioning mode.

•Using the many questions provided in this book as a starter kit, and adding your own questions over time as you develop a sense of which are most effective and customized to your needs. The questions can be a way to achieve more meaningful results in work, relationships, and life in general. But questions without action tend to lead to philosophy rather than change.

So the concluding advice is: keep questioning, take action on your questions, and make inquiry a habit through constant practice and refinement. An inquiring life is a more thoughtful, impactful, and beautiful life. But it requires effort and courage to achieve. Asking the questions is the first important step.

To strengthen your questioning habits and critical thinking skills, try these exercises:

•Question formulation technique: Come up with a short phrase as a “question focus.” Then generate as many questions as possible about that focus in a set time. Improve and prioritize the questions. Identify next steps and reflect on what you learned. This helps build the skill of rapid, effective questioning.

•Six ways to build a better question: Open up closed questions and close open questions. Sharpen vague questions. Add “why” to questions. Soften confrontational questions. Make sure questions are neutral, with no agenda.

•Critical thinking workout: When reading an opinion piece, evaluate the evidence, look for what’s missing, check if the reasoning logically follows, consider opposing views, and determine which side has more evidence. Asking these questions helps tune up your “baloney detector.”

•Start with small steps. Forming new habits takes time. Start by allocating just a few minutes a day to active questioning and reflection. Build in rewards and accountability. Cut back on time wasters like social media to free up more time for thinking.

•Find your “questioning place.” Establish a regular time and place free of distractions where you can reflect on important questions. It could be early morning, during your commute, or before bed. Over time, these short periods of focused questioning can lead to valuable insights.

The key is making a habit of questioning in action and in reflection. Questioning in action means slowing down to ask questions while working and communicating. Reflective questioning means setting aside dedicated time to ponder deeper questions about your direction, goals, and assumptions. Together, these types of questioning strengthen your ability to think critically and creatively.

Here is a summary of the main points:

  • Critical thinking involves making reasoned judgments, even when arguments have both strengths and weaknesses. It’s important to consider both sides.

  • We can apply critical thinking to combat “stinkin’ thinkin’” - negative thoughts and biases. This involves questioning the evidence and logic behind such thoughts, considering alternative perspectives, and identifying what information may be missing or unreliable.

  • Exercises for applying critical thinking and developing a “fresh eye” include:

  1. Take a photo of something familiar and look for new details or patterns. Turn what you notice into questions.

  2. Identify small problems or irritations in your daily life. Then apply “Why?,” “What if?,” and “How?” questions to explore the problem and imagine solutions. This helps with problem finding and solving.

  3. Combine two unrelated things or ideas and explore the possibilities. Ask “What if?” to imagine interesting hybrids and connections. This boosts creative thinking.

  4. Prepare open-ended “conversation starting” questions before joining a social gathering. Try approaching it with a journalist’s mindset to elicit stories from people. Listen and ask follow up questions. This can help establish meaningful connections.

In summary, the author recommends applying critical thinking through purposeful questioning. This can combat negative biases, foster creativity, build connections, and lead to new insights or solutions. While arguments may have some weaknesses, the overall point about the value of critical thinking and deep questioning seems valid. The suggested exercises provide useful tools for practicing and strengthening this skill.

Does this summary accurately reflect the main takeaways and arguments presented in the passages? Let me know if you have any other questions!

Here is a summary of the advice, without the accompanying stories:

Use questions to spark lively conversation when together with family. The L.I.F.E. questions exercise can surface little anecdotes and stories that create intimacy.

Try using questions instead of giving advice. Ask the person to share their problem, then use guiding questions to help them figure it out themselves. Questions like: What have you tried already? What might work? What’s holding you back? What’s one step you could take?

Interview yourself to clarify your own story. Ask yourself questions like: What’s your sentence? What’s your tennis ball? What are you trying to get better at? Develop a narrative from your answers.

Develop a family story and mission using questions. Ask about family history, values, purpose. Create a “How might we” mission question.

Try “questolutions” instead of resolutions. Phrase goals as engaging questions, like “How might I meet interesting people this year?”. Questions motivate us more, put less pressure, invite input, and trigger solutions. Note ideas as follow-up “What if?” questions.

  • Encouraging a “culture of inquiry” means fostering an environment where questioning is valued and encouraged. This can be done at work, school, home, or in your community. Some exercises to help build a culture of questioning include:

  • Designating one night a week as “question night” for families where you can only communicate through questions.

  • Coming up with songs that have questions in the title to show how common questioning is.

  • Doing question-storming activities with groups.

  • Pointing out to kids that many inventions they love came from questions and that questioners are often successful, rebellious people.

  • Celebrating good questions by writing them down or sharing them on social media.

  • Asking kids if they asked any good questions in school that day.

  • As a manager, reward employees for asking good questions. Give the first person to ask a question a reward to encourage others.

  • Find your “big beautiful question”—an ambitious yet actionable question you want to pursue. Look at your interests and passions for inspiration. Phrase it as a “How might I” or “How might we” question. Make it challenging but answerable. Don’t be afraid of a multi-part question. Share your question with others. Stay with your question even if you can’t get an instant answer.

  • Leaders should find a “big beautiful question” to rally their organization around a shared vision.

  • Thank editors George Gibson and Ben Hyman as well as literary agent Jim Levine for making the book happen. Thank researchers David Cleary, Lauren Dial, Marshall Saenz, and Emeka Patrick for their help. Thank interviewees for their generosity including Adam Grant, Nadia Lopez, Douglas Conant, Arthur Aron, Angie Morgan, Daniel J. Levitan, Katherine Milkman, Neil Browne, Ed Hess, David Burkus, Adam Hansen, Robin Dreeke, Don Derosby, and Michael Bungay.

Here’s a summary of the key people and sources mentioned in the introduction:

  • Questionologist: A term the author coined to describe someone focused on the art and science of questioning.

  • Daniel Kahneman and his book Thinking, Fast and Slow: Kahneman’s work explores how our minds operate in two modes: fast (intuitive) and slow (deliberate) thinking. Asking questions engages our slow, deliberate mode.

  • Studies showing children ask many questions, up to 300 a day: Research indicates kids have an innate drive to ask questions to gain information from others. This tendency diminishes over time due to social conditioning.

  • Neuroscience research on curiosity and question-asking: Studies show questioning stimulates our brains in ways that make us perceive information as more interesting and memorable. The act of wondering about questions produces pleasure chemicals in our brains.

  • The “expertise trap”: As we gain knowledge in a field, we may stop questioning and become overconfident in what we know. Questioning helps combat this tendency.

  • Steve Jobs and George Carlin as examples of relentless questioners: Both were known for constantly challenging the status quo and asking “why” about things.

  • Studies on human connection and happiness: Research shows developing meaningful connections with others is key to well-being and happiness. Asking questions is an effective way to build connections.

  • The importance of asking skeptical and critical questions: Thinkers like Elie Wiesel, Carl Sagan, and Daniel Levitin emphasize the need to ask tough, probing questions—especially in the Internet era, where misinformation abounds. Skeptical questioning helps with “baloney detection” and critical thinking.

  • The potential downside of combative questions: While critical questions are important, overly antagonistic questions can be counterproductive, shutting down discussion rather than stimulating it.

That covers the essence of the key ideas, examples, and research findings discussed in the introduction regarding why questioning is so important. Please let me know if you would like me to explain or expand on any part of the summary.

Here’s a summary of the key points around decision making:

• Don’t rely on your gut instincts alone. They can be prone to biases and errors. Ask questions to clarify your thinking.

• Consider alternatives and don’t frame options too narrowly. Look for at least 3 options. The “vanishing options” question can help open up new choices.

• Get perspective. Try seeing the decision through the eyes of someone else. Ask what a new CEO might do. Or think about the decision in the third person.

• Don’t wait for perfect information. Most decisions can be made with around 70% of the desired info. Some info will always be unavailable or uncertain.

• Avoid deciding when tired or stressed. Our judgment is impaired in those states. Put the decision off if possible until you’re able to think clearly.

• Look for ways your decision could be wrong. Try to shoot holes in your reasoning and identify weak spots. Consider the opposite choice.

• Where are you stuck in “the fog of indecisiveness”? Name the areas of your life where you’re struggling to choose a path forward. Then take steps to gain clarity.

• We have a “negativity bias” that makes us weigh negative info more heavily. But risks are often less likely than we perceive. Look at probabilities objectively.

• Inertia and loss aversion lead us to stick with default options longer than we should. We’re prone to “sunk cost fallacy” - holding onto past choices due to investment made.

• Consider context and trust your values and priorities to guide you. Don’t get distracted by seemingly urgent demands. Take time to reflect on what really matters.

• Have the courage to act in the face of uncertainty and imperfections. Some risk and discomfort is inevitable. But staying stagnant is also a choice that brings regret.

• Review how your decisions turned out and learn from them. We often don’t get the chance to see the consequences of our choices. Look for ways to improve your judgment and decision process.

  • Recent research found that miles driven in the U.S. declined for the first time since 1995, and driver mortality rates declined too.
  • Researchers investigated the reasons for the declining road deaths and miles driven. They found that young adults are learning to drive and obtaining licenses at a lower rate. People are also relying more on alternative transportation like walking, biking, and public transportation.
  • The decline in driving may be due to a combination of economic factors as well as a desire for more sustainable and active lifestyles. Young people today also value connectivity and access over vehicle ownership.
  • The researchers expect the trends to continue as companies invest in autonomous vehicles and ride-sharing, and cities improve infrastructure for alternative transportation. Overall, reduced driving could have public health benefits and reduce costs from traffic fatalities and injuries.

Here’s a summary of key points from the sources:

• Creativity is a skill that can be developed. Research shows even doing small creative acts can strengthen your creative abilities. Creative work also provides a sense of control and flow that can be rewarding.

• There are some common myths about creativity, including the notion that some people are just born creative. In reality, creativity arises from a mix of nature and nurture, environment and experiences, work and play. Everyone has the capacity for creativity.

• Paying close attention to the world around you and making unexpected connections are hallmarks of creative thinking. Many ideas come from combining unrelated concepts or insights in new ways. Lin-Manuel Miranda’s Hamilton was born of a flash of insight connecting the story of Alexander Hamilton to modern musical forms.

• Creative ideas often arise from problems, frustrations, questions, and the desire for something new or better. Tony Fadell created the iPod out of frustration with existing MP3 players. Focusing on the right problems or questions fuels creativity.

• Research and immersing yourself in a topic feeds creativity. Lin-Manuel Miranda researched Hamilton’s life and times to write his musical. Creativity depends on existing knowledge that can be recombined in new ways.

• Attention and focus are essential but increasingly scarce resources for creativity. You need idle time for ideas to emerge and focus to develop them. Some tips for managing attention and focus:

› Take regular breaks from distractions like social media and devices.

› alternate between open-ended thinking and more focused working. John Cleese talks about creating “tortoise enclosures” for open mode and “hare enclosures” for closed mode.

› Try to maintain pockets of “unscheduled” time in your schedule. Creativity arises from boredom and aimless moments, not just structured creative work.

› Do your most creative work during your peak hours when your mind is most agile. For many, mornings are optimal. Find your best time and protect it.

› Prune unnecessary commitments and distractions. Say no so you can create the space for your best work.

› Give yourself constraints to focus your thinking, like framing the problem as a question. Constraints spur creative solutions.

• Persistence and resilience are also vital. Creativity is work, and work inevitably involves some failure and rejection before success. But giving up too easily will ensure failure. Stick-with-it-ness is key.

That covers some of the major highlights on developing and strengthening your creative abilities according to the sources. Let me know if you would like me to elaborate on any part of the summary.

• Unconscious mind can be a source of rich insights and ideas. Tapping into it through activities like mind-wandering, tending a garden, composing in your head can fuel creativity.

• Having constraints, deadlines and accountability to others helps in completing creative work. Keeping projects quiet makes them easier to abandon. Share your work to get useful feedback.

• There are ways to solicit good feedback: Ask open-ended questions, find people who will be constructively critical, consider feedback that points out what’s not working. But don’t feel obliged to implement every suggestion. Listen to yourself too.

• Continually reinventing and evolving your craft or work can keep it fresh and relevant. This may mean abandoning what you’re known for to try something new. Curiosity fuels reinvention.

• Meaningful relationships and social connections are vital for happiness, health and longevity. Simple questions can help build new connections or strengthen existing ones.

• At work, having friends leads to greater happiness, health and sense of purpose. Pointless questions can be a way to start a conversation and make a connection.

• Constraints like limited time can spur more meaningful conversations. More profound questions on hopes, values and life’s meaning can build closeness. But begin with casual questions before diving deep.

• An FBI behavior expert recommends using open-ended questions, active listening, finding common interests, validating others and being genuinely enthusiastic as ways to build rapport and trust.

• The article suggests asking open-ended questions that start a genuine conversation, rather than superficial questions like “What do you do?” Some examples:

  • Did your family throw plates?
  • What would marriage offer us that we don’t already have?
  • What was the most difficult problem you had today?
  • What have you failed at this week?

•The article recommends using a “question jar” with thought- provoking questions to ask your spouse or partner instead of “How was your day?” For example:

  • What are you most grateful for today?
  • What made you smile today?
  • How can I support you right now?

• Good listening involves preparing your mind, paying close attention with your body and mind, avoiding distractions, not thinking about your response, and paraphrasing. Some tips for better listening:

  • Picture what the speaker is saying.
  • Ask the “WAIT” question: Why Am I Talking?
  • Use “mirroring” by paraphrasing what the speaker said.
  • Use “empathetic listening” by listening for the emotional meaning.

• The article suggests avoiding criticism of friends and family. Instead, approach them with curiosity and empathy. For difficult conversations, ask bridge questions to build connection, like: “What do we understand in common?” or “Where do we agree?”

• Curiosity exists in the gap between what we know and don’t know. To gain insight into your own close-mindedness, find a “trusted other” to ask you thought-provoking questions. Questions like “What is my culture preventing me from seeing?” can lead to discoveries.

• When talking to someone with whom you disagree, show “aggressive interest” in their perspective by asking open and curious questions. Build patience and find common ground. As Bill Nye says, “You have to listen to people and understand where they’re coming from.”

• The article suggests letting go of the “sense that we have a monopoly on the truth.” Curiosity and openness are more constructive approaches.

Here is a summary of the key ideas:

  • Close relationships can suffer if we fail to pay attention to what’s in front of us. Psychologist John Gottman says kindness is key to healthy relationships.

  • Asking questions is important to improving relationships. Relationship coach Michael Hyatt suggests apologizing sincerely when you’re wrong. Letting go of the need to prove you’re right can help resolve conflicts.

  • To be a good leader, focus on influence rather than control. The leadership environment today is fast-changing and complex (“VUCA”). Flexible, adaptive thinking is key.

  • Leadership comes from within. The best leaders have a purpose greater than themselves and serve the needs of others first. Overconfidence and hubris are toxic to leadership.

  • The most effective modern leaders demonstrate courage, curiosity, and the ability to bring together diverse perspectives. They surround themselves with people who think differently and challenge them.

  • Good leaders ask questions to diagnose problems, determine priorities, and understand their followers’ needs. They listen to build trust and gain input and buy-in.

  • Leaders should reflect regularly on questions like: Who has most influenced me? What can I do to address key problems? Do I have the courage to move beyond the status quo? Am I open to different views that contrast with my own?

The summary outlines key questions and advice around relationships, leadership, and self-reflection from various experts and resources. The major themes center around learning to listen, let go of ego, think openly and adaptively, and serve others with compassion. Regular self-reflection and soliciting input from diverse sources are also emphasized as important leadership practices.

• Great leaders embrace diversity and encourage dissenting views. Diverse teams correlate with higher performance.

• Great leaders make time for reflection and thinking. Reflection leads to better insights and strategy.

• Great leaders know themselves and their core values. They act with integrity and speak the truth, even if uncomfortable. They have a clear vision and purpose.

• Great leaders focus on the important and essential, not trivial distractions. They say no and make tough choices. They systematically abandon low-impact activities.

• Great leaders look to the horizon and the future, not just immediate problems. They consider how decisions will impact the future.

• Great leaders create a shared vision and purpose. They obsess about company culture and employee engagement. They communicate well and listen through humble inquiry.

• Great leaders ask good questions, like: What truly matters? What’s working and not working? What are we missing? How can we put ourselves out of business?

• Great leaders make progress on meaningful work. They understand obstacles as can’t do it, won’t do it, or don’t know how. They coach employees and support growth.

• Great leaders surround themselves with people smarter and more talented than themselves. They know that groups are smarter than individuals.

• Great leaders foster learning and curiosity. They create an environment where curiosity, questioning, and growth are encouraged. Talented employees stay and thrive.

• In summary, great leaders reflect, focus, see the future, build vision and culture, ask great questions, drive progress, develop talent, and cultivate learning. This is the journey to leadership excellence.

Here is a summary of the key questions from the introduction:

Why question? Isn’t the study of questions as worthy of classification as the study of ticks and mites? What if I just declared myself a questionologist? Why does this problem or situation exist? What are the underlying forces, the larger issues at play? What might be an interesting new way to come at this challenge? How can questioning help us decide, create, connect, and lead? What am I really trying to achieve here? What can we learn from a four-year-old girl? How does one become a better questioner? What are the five enemies of questioning? Will asking questions make it seem as if I don’t know how to do my job? Will it annoy my colleagues and supervisors?
How might a four-year-old see this situation? Am I willing to be seen as naïve? Am I comfortable raising questions with no immediate answers?
Am I willing to move away from what I know? Am I open to admitting I might be wrong? Am I willing to slow down and consider? What if I find that I have no ready answer for the serious questions I ask myself? Is it really worth taking the time to question? Why is questioning now more important than ever? Can questions bridge the gap between us? Can a leader empower others through questioning?

The key themes around these questions are: Developing a questioning mindset and habit, overcoming barriers to questioning, using questioning to gain new perspectives, empowering others through questioning, and the importance of questioning in today’s world.

Questions to embrace uncertainty, be vulnerable yet confident:

  • Why should I question my own decisions?
  • What am I really trying to decide here? What’s most important?
  • Why are we making decisions as if we’re still in the jungle?
  • Should I rely on my gut instinct when making decisions?
  • How can I override those gut instincts?
  • What if we could open up a wider view—using our questioning flashlight to do so?
  • Why do I believe what I believe?
  • Am I thinking like a soldier or a scout?
  • Would I rather be right, or would I rather understand?
  • Do I solicit and seek out opposing views?
  • Do I enjoy the “pleasant surprise” of discovering I’m mistaken?
  • Is this someone who would rather be right or would rather be successful?
  • What do you most yearn for—to defend your own beliefs or to see the world as clearly as you can?

Questions for better decision making:

  • Why should I accept what I’m told? (list of critical thinking questions)
  • What if this isn’t a “yes or no” decision?
  • How do I open up more options?
  • What is the great, the good, and the ugly?
  • What is the counterintuitive option?
  • How can I “open up” the question to be decided?
  • If none of the current options were available, what would I do?
  • What would an outsider do?
  • Does this decision have to be made now? Is this the right time to decide?
  • Is it possible to shoot holes in this decision?
  • If I had to defend this decision at a later time, how would I do so?
  • Where in my life right now am I living under the fog of indecisiveness?
  • What if putting experience first makes us happier, more fulfilled, more creative and more memorable people?
  • When I look back years from now, will I wish that I’d made a change when the opportunity was ripe?
  • Which option will allow me to evolve and flourish?

Questions to spark creativity:

  • Why create?
  • What was I put on this earth to do?
  • Why be creative? Why add to the pile? Why take the risk?
  • Am I willing to decide in favor of creativity? And if so, why?
  • Given the benefits, why would anyone not decide in favor of creativity?
  • Where did my creativity go?
  • What if I knew at the outset that there was no possibility of fame or fortune from this work—would I still want to do it?
  • What if I go looking for problems?
  • In an era of sleek smartphones, why are thermostats still so dumb?
  • How might I create a thermostat as appealing an iPhone?
  • The Four Whys questions
  • Where is my tortoise shell?
  • Where will I actually be able to create?

Here is a summary of the questions:

Viewing attention as a valuable resource:

  • How can I better protect my attention?
  • How can I shift from a “manager’s schedule” to a “maker’s schedule”?
  • Am I pruning the vine?
  • What if I trade the morning news for the “morning muse”?

Creating time and space:

  • Instead of taking breaks from social media, what if I reverse that?
  • When is my creative prime time?
  • How can we resist filling in blank spaces on the calendar?
  • Am I a lark or an owl?

Fighting through obstacles:

  • How can I fight through the initial period and not give up?
  • How can I put myself in “creator’s jail”?
  • What is my early release time? Shall I offer myself a brief furlough?

Distraction and focus:

  • What activities distract me a little but not too much?
  • Am I willing to kill the butterfly?

Dealing with imperfection:

  • Can I live with the discrepancy between imagination and reality?
  • If I can’t create the thing I dream of, can I at least create the thing I’m capable of making?

Accountability and motivation:

  • Do I have what it takes to make the idea actually happen?
  • Who will hold me accountable?

Escaping productivity theater:

  • Am I chasing butterflies?
  • Am I rearranging the bookshelves?

Getting started:

  • How can I lower the bar?
  • What if I begin anywhere?
  • Can I make a prototype?
  • What can I do with what I already have?
  • What small first step can I take to give form to my idea?

Getting unstuck:

  • How do I get “unstuck”?
  • Who would look at this problem from a different angle?
  • What would Lincoln think in a situation like this?
  • If I were to imagine future me, how would I look at this problem differently?
  • Have I ever solved a problem like this before?
  • Have other people with my motivation and ability been able to accomplish something remotely similar?

Going public and receiving feedback:

  • Am I ready to “go public”?
  • Do I want to be done or do I want to improve?
  • Am I coming across?
  • What do you like least about this?
  • What would you suggest I try?
  • Is my goal to stay at my current level of skill, or to improve?

Staying creative:

  • How do I stay “en route”?
  • How can I keep moving away from what I know?
  • Should a creative person be more like a hummingbird or a jackhammer?
  • What am I willing to abandon?
  • How might I “go electric”?
  • Where is my petri dish?

Connecting with others:

  • Why connect?
  • Why not do a study on romantic love?
  • How might we create instant intimacy between strangers?
  • Could questions be used to rekindle a spark in long-term couples?
  • Could questions strengthen relationships between adversarial people?
  • Am I genuinely interested in the other person? Can I suspend judgment and truly listen?

Here is a summary of the questions:

Questions for Saving a Marriage: I’m sorry. Will you please forgive me?

Questions for Connecting at Work: Can questioning help us connect in the workplace?; How can I ask questions of coworkers without overstepping bounds or putting them on the defensive?; What is my job?; How might I do it better?; Given all the changes yesterday, what is my job today?; Why are certain procedures and practices in place? Why is that old equipment still in use? What might be the benefits and costs of making a change (to policies or equipment) and how difficult would it be to do that?; I have noticed that our competitors are using new software that enables them to move much more quickly. I’m wondering how we might adapt to this—and whether there’s anything specific that I can do differently in my role?; (Questions for Your Boss): What would you do in my position?; What does your ideal employee look like?; What’s the one thing 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?; Why is it hard for managers to “question down”?; Are you satisfied with your own performance?; What do you think is working well, and what is not?; What do you not have time to work on, that you’d like to be working on?; What questions do you have for me?; Anything you’d like to know about the new policy we’re implementing? Or about where we envision this company or this division five years from now?; I’m curious, why did you choose to do it this way?; What’s the coolest thing you’ll be working on this week? What are you excited about in your job right now?; (Questions about a Difficult Co-Worker): Is it possible I’m overreacting?; Which of this person’s specific behaviors most bother me?; Of those, which actually interfere with my ability to do my job?; Is there a way to politely ask this person to make one change?; Who could mediate?; How might I create distance?

Questions for Stronger Leadership: What can we do to right this wrong?; What is the twenty-first century demanding of our students, and how can the school provide that?; How do you instill a sense of possibility in young people living amid poverty and hopelessness? How do you keep underpaid, overworked teachers from burning out?; Why do I choose to lead?; What if we said to our would-be leaders, “Take this role only if you care desperately about the issue at hand?”; Why do I want to lead this endeavor or these people?; Why would they want me to lead them?; Does the answer to the first question also work as an answer to the second?; How do you want to leverage your special gifts and interests to make the world a better place?; Am I willing to step back from individual achievement—in order to help others move forward?; Do I have the confidence to be humble?; Can I learn to keep learning?; Do I seek to create an organization in my own image?; Am I courageous enough to abandon the past?; How might I stimulate my own curiosity?; Do I surround myself with inspiring, sometimes even odd, big thinkers? Is my schedule packed with meetings and daily decisions, or freed to explore new frontiers? Do I use every interaction, from the colleague to the driver, to ask new people about how they think and feel?; Am I bringing together diverse people who can share points of view that I might be missing?; Why must I retreat in order to lead?; What could I have done differently?; Does my thinking sound right to you? Does it sound like me? Am I missing something?; What is my code?; When have I been at my best? What drove or inspired me at those times?; What have I learned about working with other people (in doing so, when have I been effective, and what caused that?); When have I taken a principled stand? What have I gone out of my way to defend?; When have I failed to effectively meet goals or lead others—and what did I seem to be doing wrong? When did I fail to take a stand—and why?; Who are my formative influencers?; When have I come up short—and why?; What is my story? What is my logline?; Did I live up to my own code? In what ways did my behavior fail to match my stated values? How would I do it differently?; (Organization Mission Questions): Why are we here in the first place?; When have we, as an organization, been at our best? What have we stood for throughout our history?; Why do we matter, and to whom?; If we disappeared tomorrow, who would miss us?; What do we do that other organizations can’t or won’t do?; What are we against?; How might we be not just a company but a cause?; What is our higher calling?

Questions for Making Better Choices: What is the least I can do?; Why do otherwise successful people get tripped up by the trivial?; What if we stopped celebrating being busy as a measure of importance?; Which problem do I want?; Is this necessary? If we add this, what do we stand to lose?; What do I want to go big on?; What should we stop doing?; Why does this rule (or this process) exist in the first place? If it made sense once, does it still make sense now?; What stupid rule would you most like to kill?; At this moment, what is the highest, best use of my time?; What truly matters?; What is the one thing I can do that would make everything else easier or unnecessary?;

(Visionary Questions): If an oracle could tell you what’s going to happen three years from now, what would you most want to know?; How can we become the company that would put us out of business? What might this predator look like, and why would it have an advantage over us?; What if we had the capability to do what we now do much faster and more efficiently—what might that enable us to achieve?; What if we created the ideal workplace for our employees—what might their workday look like?; Who do we want our customers to become?; How can we brace ourselves for the third wave?; What would the seventh generation think about what we’re doing?; How might I make tomorrow visible?; What is our “vision question”?; Who are you spending time with? On what topics? Where are you travelling? What are you reading?; What are the implications of this decision ten minutes, ten months, and ten years from now?; What’s going on out there—and how can I help?; What is going well? What are we doing right?; Why are you still here? (sitting in your office); What should I ask all these people?; Am I looking for what’s broken … or what’s working?; Help me understand what led to the deadline issues? How might we expedite the work without compromising quality? How can I help?; How can I make sure the conversation is about them—their needs, their interests—and not about me?; Am I seeking their thoughts, instead of just offering my own? Am I focused on their priorities, not mine?; Am I offering them choices and options, instead of telling them what to do?; (Questions Not to Ask Employees): How’s it going?; Why did you ___?; Who screwed up here?; Haven’t we tried this already? (Questions You Should Ask Them):What’s the biggest challenge you’re facing?; Are you making progress?; Help me understand what led to ___?; Is it clear what we’re doing and why?; How can I help?; Did you do your best to make progress today?; What are we doing that’s getting in your way?; What are you working on right now that you’re most excited about?; What inspired you to take this approach?; How would you like to see yourself growing in this role?; Would my employees, if asked, be able to articulate the company’s vision and priorities?; What do you do in your life outside work that is most inspiring? What do you do to keep learning and growing as a person?; What if we could take that passion you have for X and somehow bring it to life here? How might we do that?; Do I really want a culture of curiosity?; Why would a leader want to encourage more questioning? Why open the lid and release a potential torrent of employee questions?; If people start asking more questions at your company, what will you do with those questions? What if you don’t like the questions your employees are asking?; Am I ready to announce “Bring us the problems you’ve noticed?”; What is the culture I want, and what actions and conditions are likely to produce such a culture?; How can we make questioning safe? How can we make it

Here is a summary of the questions:

  • Do effective questioners shift into questioning mode when needed?

  • Did you ask the important questions you’re supposed to ask?

  • How might I reward myself for questioning?

  • How can I warm up my questioning muscles?

  • Can I build a better question?

  • How might I test my built-in baloney detector?

  • Is this bad feeling I have really true? Is there another way of viewing this situation?

  • What if I looked at the world around me with a fresh eye?

  • What if Attila the Hun was plopped down in Silicon Valley? What if a potato peeler were combined with gloves?

  • What’s interesting about it, and what doesn’t work? Is there a similar but different combination that might be more interesting?

  • How (and with whom) shall I break the ice?

  • What if I approached this party as if I were a journalist, looking for stories about the people in attendance?

  • (L.I.F.E. Exercise Questions): What weird LITTLE thing sticks out in your mind from this week? What piece of INFORMATION did you learn this week? Is there anything you tried and FAILED at this week? What memorable EXCHANGE did you have this week?

  • (Self-Interview Questions): About life’s biggest dreams, childhood aspirations, failure responses, how you treat people, life in one sentence, life’s purpose, getting better at things.

  • Can questioning help bring my family closer together?

  • (Family Heritage Questions): About ancestors, family origins, family traditions, family stories, family difficulties, family accomplishments, family lessons, family jokes.

  • (Family Purpose/Mission Questions): About family meaning, differing family views, most interesting family member, family values, family greater purpose, family “how might we” question, contributing to family mission.

  • What if I trade my resolutions for “questolutions”?

  • How might I meet more interesting people this year? How might I get myself to drink more water?

  • How might I encourage others to question more?

  • Izzy, did you ask a good question today?

  • What is my one “big beautiful question”?

  • Where and how might you find your big beautiful question?

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About Matheus Puppe