Index of Questions

Introduction: Why Question?

Why question?, here

Isn’t the study of questions as worthy of classification as the study of ticks and mites?, here

What if I just declared myself a questionologist?, here

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?, here

How can questioning help us decide, create, connect, and lead?, here

What am I really trying to achieve here?, here

What can we learn from a four-year-old girl?, here

How does one become a better questioner?, here

What are the five enemies of questioning?, here

Will asking questions make it seem as if I don’t know how to do my job? Will it annoy my colleagues and supervisors?, here

How might a four-year-old see this situation?, here

Am I willing to be seen as naïve?, here

Am I comfortable raising questions with no immediate answers? here

Am I willing to move away from what I know?, here

Am I open to admitting I might be wrong?, here

Am I willing to slow down and consider?, here

What if I find that I have no ready answer for the serious questions I ask myself?, here

Is it really worth taking the time to question?, here

Why is questioning now more important than ever?, here

Can questions bridge the gap between us?, here

Can a leader embrace uncertainty, ask questions, admit vulnerability—and still be seen as a strong and confident leader?, here

What if the future of democracy depends on questioning?, here

Do we even know how to ask skeptical, interrogatory questions? And when we do ask such questions, are we willing to accept information that may conflict with our existing views?, here

How can I see this with fresh eyes?, here

What might I be assuming?, here

Am I rushing to judgment?, here

What am I missing?, here

What matters most?, here

Part I: Questions for Better DECISION-MAKING

Why should I question my own decisions?, here

What am I really trying to decide here? What’s most important? What critical information do I have and not have?, here

Why are we making decisions as if we’re still in the jungle?, here

Should I rely on my gut instinct when making decisions?, here

How can I override those gut instincts?, here

What if we could open up a wider view—using our questioning flashlight to do so?, here

Why do I believe what I believe?, here

What am I inclined to believe about this particular issue?, here

What did I once believe that is no longer true?, here

What would I like to be true?, here

What if my beliefs or assumptions on this issue are just plain wrong?, here

What are some reasons that my initial judgment might be wrong?, here

Am I thinking like a soldier or a scout?, here

Would I rather be right, or would I rather understand?, here

Do I solicit and seek out opposing views?, here

Do I enjoy the “pleasant surprise” of discovering I’m mistaken?, here

Is this someone who would rather be right or would rather be successful?, here

What do you most yearn for—to defend your own beliefs or to see the world as clearly as you can?, here

Why should I accept what I’m told?, here

(Critical Thinking Questions): What is the evidence behind this claim and how strong is it?; Does this evidence come from a solid source? Is there an agenda behind it?; Cui bono?—Latin for “Who benefits?”; What are they not telling me?; Does it logically follow?, here; What’s the other side of this issue? Is there actually another side?; Which of the conflicting views has more evidence behind it?; Does my critical thinking have an agenda?, here

What if this isn’t a “yes or no” decision?, here

How do I open up more options?, here

What is the great, the good, and the ugly?, here

What is the counterintuitive option?, here

How can I “open up” the question to be decided?, here

If none of the current options were available, what would I do?, here

What would an outsider do?, here

If my friend had to make this decision, what advice would I give?, here

What should [my name] do in this situation? (instead of what should I do?), here

What would Warren Buffett do if faced with this decision? (Or for that matter, LeBron James?), here

If we got kicked out and the board brought in a new CEO, what do you think he would do?, here

Does this decision have to be made now? Is this the right time to decide?, here

Is it possible to shoot holes in this decision?, here

If I had to defend this decision at a later time, how would I do so?, here

Where in my life right now am I living under the fog of indecisiveness?, here

What would I try if I knew I could not fail?, here

What are you so afraid of?, here

How can questioning help with something as primal and powerful as fear?, here

What is your earliest memory of this fear? How do you react to it? What has it kept you from doing? How might things change if you were able to overcome this fear?, here

(Courageous Questions): Why would I want to do this thing or make this choice, even though it scares me?, here; Within this scary possibility, what excites me?; What is the worst that could happen?; And how would I recover from that?; If I did fail, what would be the likely causes?; What if I succeed—what would that look like?; How can I take one small step into the breach?, here

How can we generate more ideas?, here

How can we quickly and inexpensively test those ideas?, here

What if cost were not an issue?, here

What would you do if you weren’t afraid?, here

What would “future me” decide?, here

What if we were encouraged to make bolder choices—would we then be happier?, here

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

If I look back years from now, will I wish that I’d made a change when the opportunity was ripe?, here

Which option will allow me to evolve and flourish?, here

(Questions on Whether to Take a Job): Can the little person rise to the top? Can I shape my destiny and have influence in this organization?; How will the boss react to mistakes?; How have others at this company added new skills and expanded responsibilities?; How does the organization encourage “connectedness” between employees?; How does the organization react to mistakes?; Will I be punished for exploring?; Will I enjoy the “small pleasures” of my daily routine?, here

Why are people fully aware that present benefits are important in their current job, and yet expect not to care about those benefits in the future?, here

How would I later explain this decision to others?, here

What are my core obligations?, here

Imagine yourself explaining your decision to a close friend or a mentor–would you feel comfortable? How would that person react?, here

If I’m generally better off saying yes to bold decisions, why not say yes to this one?, here

If I’m saying yes to this, what am I saying no to?, here

How would I feel if I accepted this invitation—and then found out it had been canceled?, here

What if putting experience first makes us happier, more fulfilled, more creative and more memorable people?, here

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

(Passion Questions): What is my tennis ball?, here; How does this help me in the pursuit of my tennis ball?; Should I even be asking “What’s my passion?”, here; What are my signature strengths? What personal strengths did I display when I was at my best?; What are my superpowers?; When was I truly happy and why?; What activity or theme do I keep coming back to?; When do I seem most like myself?, What did I enjoy doing at age ten?, here; What makes me forget to eat?, here; In what way do I wish the world were different?, here; What is my sentence?, here

What is needed and how might I help?, here

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

If I didn’t come into work today, would things be worse?, here

Am I making a difference? Am I making a contribution?, here

How might I apply my signature strengths to a pursuit that is of natural interest to me and helps others?, here

What is your favorite flavor of shit sandwich? What struggle or sacrifice are you willing to tolerate?, here

How would I like to be remembered? What matters most to me? What change would I like to create?, here

Part II: Questions for Sparking CREATIVITY

Why create?, here

What was I put on this earth to do?, here

How can I help as many people as possible rediscover their creative confidence?, here

Why be creative? Why add to the pile? Why take the risk?, here

Am I willing to decide in favor of creativity? And if so, why?, here

Given the benefits, why would anyone not decide in favor of creativity?, here

Where did my creativity go?, here

(Questions Not to Ask About Creativity): Am I creative?; How creative am I?; Where will I ever find an original idea? Hasn’t everything been thought of already?; Where will I find the time to create?; How can I come up with an idea that will make money?, here

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?, here

What if I go looking for problems?, here

In an era of sleek smartphones, why are thermostats still so dumb?, here

Why is it that some of the raw materials we encounter inspire us, and others don’t? And can we seek out the ones that do?, here

(Problem-Finding Questions): What is happening that doesn’t make sense?; What is the story that is not being told?; How might the whole thing be reinvented or turned upside down?; Why might I want to take on this problem and make it my own?; What stirs me?; What bugs me?; What’s missing?; What do I keep coming back to?; What is ripe for reinvention?, here

What’s wrong with this product? Why doesn’t [a better] product exist?, here

What were my most creative ideas this week?, here

Is this a problem that is trying to find me?, here

(Questions to Help You See More): What might I notice if I were encountering this for the first time?; What if I stand on the desk? (to get a different view); What is in the background?; What here would fascinate a five-year-old?; What would Seinfeld be amused by?; What would Steve Jobs be frustrated by?, here; How would a traveler see this?, here

When am I most resonant? What are people responding to in my work?, here

Why should this be my problem?, here

Do I look forward to thinking about this topic?, here

Will I want to commit to this six months or a year down the road?, here

Will I still love this problem tomorrow?, here

Can I make a unique contribution here?, here

What am I adding that somebody else couldn’t?, here

Is this a challenge that I can apply my skills to?, here

If others are pursuing the same idea, what’s my twist? How might my approach differ from others?, here

What is the upside if I do solve the problem?, here

Can I own this problem?, here

How might I create a thermostat as appealing an iPhone?, here

(The Four Whys): Why does this problem matter? Why does it exist in the first place? Why hasn’t someone solved it already? Why might that change now?, here

Where is my tortoise shell?, here

Where will I actually be able to create?, here

When should I take a break to digitally connect?, here

If I must be connected, how can I at least reassert control?, here

What if we saw attention in the same way that we saw air or water, as a valuable resource that we hold in common?, here

If I began to see my attention as a precious resource, how might I better protect it?, here

How can I shift from a “manager’s schedule” to a “maker’s schedule”?, here

Am I pruning the vine?, here

What if I trade the morning news for the “morning muse”?, here

Instead of taking breaks from social media, what if I reverse that?, here

When is my creative prime time?, here

How can we resist the urge to fill in the blank spaces on the calendar?, here

Am I a lark or an owl?, here

How can I fight through that initial period and not give up?, here

How can I put myself in creator’s jail?, here

What is my early release time? Shall I offer myself a brief furlough?, here

What activities distract me a little but not too much?, here

Am I willing to kill the butterfly?, here

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

Do I have what it takes to make the idea actually happen?, here

Who will hold me accountable?, here

Am I chasing butterflies?, here

Am I rearranging the bookshelves?, here

(Questions for Getting Started): How can I lower the bar?; What if I begin anywhere?; Can I make a prototype?, here; What can I do with what I already have?; What small first step can I take to give form to my idea?, here

How do I get “unstuck?”, here

Who would look at this problem from a different angle?, here

What would Lincoln think in a situation like this?, here

If I were to imagine future me, ten or twenty years ahead, how do I imagine I’d look at this problem differently?, here

What if I tried to create a car that is unable to move? Or an oven that can’t cook?, here

Have I ever solved a problem like this before?, here

Have other people with my motivation and ability been able to accomplish something remotely similar?, here

Am I ready to “go public”?, here

Do I want to be done or do I want to improve?, here

(Feedback Questions): Am I coming across?; What do you like least about this?; What would you suggest I try?, here; Is my goal to stay at my current level of skill, or to improve?; Why am I resistant to simply accepting this gift? (of feedback); Who are my trusted advisors?, here; How do you figure out when to listen to other people—and when to listen to yourself?; Is the feedback suggesting that I alter my vision or merely improve upon the execution?; I was wondering about how to improve X or Y—what would you suggest I try?, here; How well did I take that feedback?, here

How do I stay “en route”?, here

How can you keep moving away from what you know?, here

Should a creative person be more like a hummingbird or a jackhammer?, here

What am I willing to abandon?, here

How might I “go electric”?, here

Where is my petri dish?, here

Part III: Questions to Help CONNECT WITH OTHERS

Why connect?, here

Why not do a study on romantic love?, here

How might we, in a laboratory setting, find a way to create instant intimacy between strangers?, here

Could questions be used to rekindle a spark among long-term couples who’d grown a little too used to each other?, here

Could questions strengthen the relationship between people who might have less in common—and might even be adversarial in some cases?, here

Am I genuinely interested in the other person? Am I able to put my ego aside and suspend all judgment?, here

Am I prepared to truly listen, as opposed to just acting as if I am listening?, here

What if we go beyond “How are you?”, here

Why do we go around asking each other such pointless questions?, here

(Ice-Breaker Questions): What was the best part of your weekend?; What’s the strangest/most interesting thing about where you grew up?; What was it like when you first moved to Boise? What’s the single weirdest thing that ever happened to you there?; What’s the best thing that happened to you today?; What are you excited about in your life right now?; What are you most looking forward to at this gathering?; What are you most passionate about?; What problem do you wish you could solve?; What did you want to be when you were growing up?, here

Why did being with a stranger so often mean we couldn’t immediately talk about meaningful things?, here

Why can’t we replace small talk with big talk and ask each other profound questions right from the start?, here

What’s the most in love you’ve ever felt?; Why did you fall in love with your wife?, here

(Intimacy Questions):What would constitute a “perfect” day for you?; If you could change anything about the way you were raised, what would it be?; What does friendship mean to you?; How do you feel about your relationship with your mother?; When did you last cry in front of another person? Or by yourself?; What, if anything, is too serious to be joked about?, here

(Marriage Questions): How compatible am I with this person, and is there potential for something deep and lasting?, here; Did your family throw plates?; What do you envision as our ideal future?; What would marriage offer us that we don’t already have?, here

(Spouse Questions): When did you feel appreciated today?; Will you remember any specific part of today a year from now?; How can I make your day easier in five minutes?; If we were leaving for vacation tonight, where do you wish we were heading?; What made you laugh today?; What do you wish you did more of today?, here

(Questions to Ask Your Kids): What was the most difficult problem you had today? How could you have handled this differently?, here; What have you failed at this week?; If you were an inventor—what would you invent, and why?; What was your first thought when you woke up today?; Who in your class seems lonely?; What do you think is the biggest challenge facing our world today?, here

(Listening Questions): How might I listen with my whole body?, here; Am I ready to listen fully?, What does it mean to listen fully?, here; Why Am I Talking? (the “WAIT question”), here; How can I make sure I’m really hearing what this person is trying to say?; Just to be clear, are you saying x, y, and z?; Can you explain what you mean by that?, I imagine that made you feel __ , right?, here; And what else? (The “AWE” question), here; Is there anything else?, here

What could we try in order to solve this problem … and what else?, here

What issues should our company be thinking about … and what else?, here

What needs to happen for that feeling to feel better?, here

What if I advise less and inquire more?, here

Why are we inclined to advise others on what they should do?, here

How can we use questions to guide the “horse” toward the “water”?, here

(Advice Questions): What is the challenge that you’re facing?; What have you tried already?; If you could try anything to solve this, what would you try?; And what else?; And what else; Which of these options interests you most?; What might stand in the way of this idea, and what could be done about that?; What is one step you could take to begin acting on this, right away?, here

(Criticism Questions): What’s motivating this critical urge?; How am I guilty of the thing I’m criticizing?; How would I react if someone said something similar to me?; What positive result do I hope will come of saying this?; Am I deriving pleasure from criticizing?, here

Take me through what happened on this project: What went well, what did you have problems with, and what can we learn from that going forward?, here

(Questions for Bridging the Divide): What if I replace judgment with curiosity?, here; Why might I want to cross this particular divide?, here; Am I really interested in learning from the other side?, here; What can I learn from those I do not understand?; How might I consider both sides of this dispute?, here; How might I own my own biases?, here; Knowing that I tend to lean in one direction, how might that be altering my view of this new information or situation?, here; What is my culture preventing me from seeing?, here; When you say “freedom,” how are you defining that term?; Can I briefly lay out for you what I think?; Can you find anything in your position that gives you pause?; Is there anything in my position that you are attracted to or find interesting?, here; On a scale of one to ten (one having no value at all, ten being 100 percent right and unassailable), how would you rate my position? And your own?; If you didn’t rate mine a one and yours a ten, why not?; Can we imagine a position that might at least partly satisfy both of us?, here; How might we find one small thing we can actually agree on?, here

How might we form a stronger partnership?, here

The person I love and married is telling me over and over again that this behavior is a problem. Why don’t I believe her?, here

If I knew my marriage would end painfully as a result of something I am doing or not doing, would I continue to make the same choice?, here

Can I try to explain what I think your position is—and then you can do the same for me?, here

Am I missing a bid? (Was that a bid from a loved one that I just ignored while staring at my iPhone?), here

How should I be responding to the various bids coming from my partner?, here

(Questions for Your Best Friend): What do you struggle with on a day-to-day basis?; What have you always wanted to try?; If you could start your own nonprofit, what would it be?; What would be the title of your autobiography?; If you had to live in another country for a year, where would that be?, here

What was going through your mind when you heard the good news? You must have been so proud when you heard about this—what was that like?, here

What new opportunities do you think this might create for you?, here

Do I want to be right or do I want peace?, here

Have you made clear your concerns about the relationship?, here

Would you really be happier without your partner?, here

How might we begin to save this marriage?, here

I’m sorry. I was wrong. Will you please forgive me?, here

Can questioning help us connect in the workplace?, here

How can I ask questions of coworkers without overstepping bounds or putting them on the defensive?, here

What is my job?; How might I do it better?, here

Given all the changes yesterday, what is my job today?, here

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?, here

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?, here

(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?, here

Why is it hard for managers to “question down”?, here

Are you satisfied with your own performance?, here

What do you think is working well, and what is not?, here

What do you not have time to work on, that you’d like to be working on?, here

What questions do you have for me?, here

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?, here

I’m curious, why did you choose to do it this way?, here

What’s the coolest thing you’ll be working on this week? What are you excited about in your job right now?, here

(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?, here

What if we replace the sales pitch with a “question pitch”?, here

What does the world need from us?, here

How might we put our heads together to solve this problem your company is having?, here

What is our mission and purpose (as an organization)? Why are we here?, here

Part IV: Questions for Stronger LEADERSHIP

What can we do to right this wrong?, here

What is the twenty-first century demanding of our students, and how can the school provide that?, here

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?, here

Why do I choose to lead?, here

What if we said to our would-be leaders, “Take this role only if you care desperately about the issue at hand?”, here

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?, here

How do you want to leverage your special gifts and interests to make the world a better place?, here

Am I willing to step back from individual achievement—in order to help others move forward?, here

Do I have the confidence to be humble?, here

Am I willing to step back 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?, here

How might I stimulate my own curiosity?, here

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?, here

Am I bringing together diverse people who can share points of view that I might be missing?, here

Why must I retreat in order to lead?, here

What could I have done differently?, here

Does my thinking sound right to you? Does it sound like me? Am I missing something?, here

What is my code?, here

When have I been at my best? What drove or inspired me at those times?, here

What have I learned about working with other people (in doing so, when have I been effective, and what caused that?), here

When have I taken a principled stand? What have I gone out of my way to defend?, here

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?, here

Who are my formative influencers?, here

When have I come up short—and why?, here

What is my story? What is my logline?, here

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?, here

(Organization Mission Questions): Why are we here in the first place?, here; 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?, here; What is our higher calling?, here

What is the least I can do?, here

Why do otherwise successful people get tripped up by the trivial?. here

What if we stopped celebrating being busy as a measure of importance?, here

Which problem do I want?, here

Is this necessary? If we add this, what do we stand to lose?, here

What do I want to go big on?, here

What should we stop doing?, here

Why does this rule (or this process) exist in the first place? If it made sense once, does it still make sense now?, here

What stupid rule would you most like to kill?, here

At this moment, what is the highest, best use of my time?, here

What truly matters?, here

What is the one thing I can do that would make everything else easier or unnecessary?, here

(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?, here; 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”?, here

Who are you spending time with? On what topics? Where are you travelling? What are you reading?, here

What are the implications of this decision ten minutes, ten months, and ten years from now?, here

What’s going on out there—and how can I help?, here

What is going well? What are we doing right?, here

Why are you still here? (sitting in your office), here

What should I ask all these people?, here

Am I looking for what’s broken … or what’s working?, here

Help me understand what led to the deadline issues? How might we expedite the work without compromising quality? How can I help?, here

How can I make sure the conversation is about them—their needs, their interests—and not about me?, here

Am I seeking their thoughts, instead of just offering my own? Am I focused on their priorities, not mine?, here

Am I offering them choices and options, instead of telling them what to do?, here

(Questions Not to Ask Employees): How’s it going?; Why did you ___?; Who screwed up here?; Haven’t we tried this already, here

(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?, here; 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?, here; How would you like to see yourself growing in this role?, here

Would my employees, if asked, be able to articulate the company’s vision and priorities?, here

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?, here

What if we could take that passion you have for X and somehow bring it to life here? How might we do that?, here

Do I really want a culture of curiosity?, here

Why would a leader want to encourage more questioning? Why open the lid and release a potential torrent of employee questions?, here

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?, here

Am I ready to announce “Bring us the problems you’ve noticed?”, here

What is the culture I want, and what actions and conditions are likely to produce such a culture?, here

How can we make questioning safe? How can we make it rewarding? How can we make it productive? How might we make it a habit?, here

Why not have every manager or supervisor throughout the company participate in a weekly or monthly “Ask me anything” session?, here

How can we make a culture of inquiry stick?, here

What if every meeting began with a question? What if the company held regularly scheduled “question days”—during which groups come together to ask, What assumptions can we challenge today?, here

What if you ask employees to come up with one ambitious question a week, to be shared with their colleagues?, here

I know we disagree on this, but will you gamble with me on it? [Can we] disagree and commit?, here

Whose voice might I have missed hearing—and how might I amplify this voice?, here

Conclusion: The Inquiring Life

How might I begin to act on my questions?, here

Can we simply advise ourselves to “question more” and then expect that shift into questioning mode will happen when needed?, here

Did you ask the important questions you’re supposed to ask?, here

How might I reward myself for questioning?, here

How can I warm up my questioning muscles?, here

Can I build a better question?, here

How might I test my built-in baloney detector?, here

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

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

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

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

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

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

(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?, here

(Self-Interview Questions): What is your biggest dream in life?; When you were a child, who or what did you want to be?; When you have failed, how did you respond?; If people were asked how you treat them, what do you think they’d say?; What is your sentence? (Meaning, if you had to summarize your life in one sentence, what would that sentence be?); What is your tennis ball? (What is the thing that you chase as intently as a dog chases a tennis ball?); What are you trying to get better at?, here

Can questioning help bring my family closer together?, here

(Family Heritage Questions): Where were our ancestors born? When did they arrive in this country?; What might our ancestors have had to overcome to get here?; What are some traditions that have been passed down through our family? When and how did they get started?; What are some family stories that you know? That I know?; In particular, what difficulties did the family have to bounce back from?; What were some of the greatest accomplishments by family members through the years?; What do the stories mean to us today?; What are some classic family jokes or songs?, here

(Family Purpose/Mission Questions): What does it mean to be part of this family?; Is how you feel about being part of this family different than how I feel?; Of all the family members you have either known or heard stories about, who do you think lived the most interesting life? Why?; What are our family values?; What is this family trying to do beyond daily living? What’s the greater purpose of our family?; How might we create a “How might we” mission question for the family?; How might I contribute to the mission?, here

What if I trade my resolutions for “questolutions”?, here

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

How might I encourage others to question more?, here

Izzy, did you ask a good question today?, here

What is my one “big beautiful question”?, here

Where and how might you find your big beautiful question?, here