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Andrew Sobel & Jerold Panas

Book Report by Gary Tomlinson

A Book Report on

Power Questions – Build Relationships, Win New Business and Influence Others

by Andrew Sobel & Jerold Panas


(Book Report by Gary Tomlinson)





What do you think most engages a prospective client or makes a lasting impression on someone you’ve just met?  The popular belief is that we win business by being clever and quick on our feet and that our brilliance – saying just the right thing – is what attracts others.  But as Power Questions compellingly demonstrates, knowing the right question to ask is actually far more important than having a ready answer.


Power Questions can immediately help you win more business, deepen your relationships and connect with people more rapidly that you ever thought possible.  It shows you how to use thought-provoking questions to engage prospects and uncover their most pressing issues.  It gives you the tools to get inside the heart and mind of anyone you meet.  In thirty-five inspiring chapters, you’ll meet a fascinating group of men and women.  Through these riveting, real-life stories, you’ll learn exactly how each power question was used and the impact it had.  You’ll discover how you can transform your daily conversations – and even someone’s life – through powerful questions that anyone can master.



Good Questions Trump Easy Answers:  We’re sitting comfortably in a sun-filled office on the fourth floor of a Chicago skyscraper.  We ask the CEO, “What most impresses you when you meet someone who is trying to win your business?  What builds trust and credibility with you early on in a relationship?”


This executive runs a $12-billion company.  We are interviewing him about his most trusted business relationships.  These are the service providers and suppliers his company goes back to again and again, the individuals who are part of his inner circle of trusted advisors.


“I can always tell,” he says, “how experienced and insightful a prospective consultant, banker or lawyer is by the quality of their questions and how intently they listen.  That’s how simple it is.”


Good questions are often more powerful than answers.  Good questions challenge your thinking.  They reframe and redefine the problem.  They throw cold water on our most dearly held assumptions and force us out of our traditional thinking.  They motivate us to learn and discover more.  They remind us of what is most important in our lives.


We use the phrase power questions as the title of this book.  That’s because the questions we select have the power to give new life to your conversations in unexpected and delightful ways.  They are powerful tools to get directly to the heart of the matter.  They are the keys to opening locked doors.


Learning to use the power of questions can dramatically increase your professional and personal effectiveness.  This book will help you build and deepen relationships.  Sell more of your products, services and ideas.  Motivate others to give more effort than they ever thought possible.  And become more effective at influencing clients, colleagues and friends.



If You Don’t Want to Hit Bottom, Stop Digging the Hole:  When someone says, “Tell me about your company,” get them to be more specific.  Ask, “What would you like to know about us?”  Similarly, if someone asks you, “Tell me about yourself,” ask them, “What would you like to know about me?”


“What would like to know about us?”  When someone asks us a question, we rarely ask them to clarify exactly what it is they want to know.  Have you ever watched someone give a five-minute answer to the wrong question – to a question they thought they heard but which wasn’t actually asked?  It’s painful.


Always clarify what the other person is looking for.  If someone says, “Tell me about yourself,” you could start with your birth – and talk for hours.  Or, you could ask them what part of your background would most interest them and start there.


When to use the question:

  • When you are asked a general question that could potentially require a long answer.

  • When time is short and you want to be sure that your very brief answer will be right on target.


Alternative versions of the question:

  • “What part of my background interests you?”

  • “What aspect of that situation would you like me to focus on?”

  • “Before I answer that, have you had any experience with our organization in the past?”

  • “What if I started by describing a couple of examples of recent work we’ve done for clients like you?”


Follow-up questions:

  • “Does that answer your question?”

  • “Is there anything else you’d like me to talk about?”



The Four Words:  People want to be heard.  Studies are quite clear that we care about people who listen to us.  The question “What do you think” is powerful.  You are seeking an opinion.  The person you are talking with wants you to listen.  You’ve heard about people who talk too much.  You never heard about a person who listens too much. 


This may sound counterintuitive, but asking questions and then listening put you in control of the conversation.  Because your questions require an answer, you are in the position of power.  Good listeners are not only popular everywhere, but after awhile, they learn a thing or two.  Develop your reputation as a great listener.  Draw others out and show you care about them by asking, “What do you think?”


When to use the question:

  • Whenever you are discussing a dilemma or planning a course of future action.

  • After you have shared your views or presented a proposal.

  • When someone comes to you with a problem.


Alternative versions of the question:

  • “I value your opinion.  Can I get your reaction to this?”

  • “Would you be willing to share your views?”


Follow-up questions:

  • “What has influenced your thinking about this the most?”

  • “Are there any other perspectives I ought to be aware of?”



When the Sale is Stuck:  A sale of a service, a product or an idea requires an investment of scarce time and resources.  You must be determined and committed.  Before you exhaust yourself trying to get the sale, you must ask the question, “Are they ready to buy?”


Have you heard this before”  “We talk and talk but nothing happens.  They won’t get off the stick and buy!”  When people are ready to buy, it is a delightful experience.  They reach out toward you.  They relish the interaction.  But they won’t buy your product, your service or your idea if the four conditions have not been met.


Condition 1: Is there a problem or opportunity? As the person such questions as:  “What is this costing you right now?”  “If you don’t fix this problem, what will the consequences be?”  “What do you think this opportunity is worth?”  “Is this one of your highest priorities?”


Condition 2: Does the person “own” the problem?  Ask them questions such as:  “Who owns this problem?”  “Are you responsible for fixing this?”  “Who would authorize an expenditure to address this?”  “Who needs to be involved in a solution to this issue?”


Condition 3: Does the buyer have a healthy dissatisfaction with the current offering or the rate of improvement?  Ask them:  “Is this a minor irritant or something you’re truly fed up with?”  “What would you say is missing?”  “Why do you feel that now is the time to put extra resources against this?”  “How effective have your own efforts been to address this?”


Condition 4: Does the buyer trust you and believe you’re the best alternative they have?  Ask questions such as:  “What other solutions are you looking at?”  “How do you feel about our capabilities in this area?”  “What concerns to you have about us or our approach?”



Mission Isn’t Important.  It’s Everything:  It is your true north.  When someone is making a big move – a significant decision – check to see if it is consistent with who they are.  Ask: “How will this further your mission and goals?”


Our mission and goals are absolutely at the heart of who we are and who we want to be.  This is true at both an institutional and personal level.  Yet, we often stray from them.  We get engrossed in our day-to-day lives and we lose sight of the forest for the trees.  It happens because it is very human to be drawn into things that fulfill our hunger for achievement, wealth, power and fame.  But these don’t often nurture our hearts and souls.


When to use the question:

  • When you see someone doing things that are inconsistent with their core mission.

  • When someone is making a decision to invest significant time and resources in a new direction.

  • When you suspect the other person has not thought through what their mission and goals really are.


Alternate versions of the question:

  • “Can you remind me of your mission and goals?”

  • “Is this consistent with your values and beliefs?”


Follow-up questions:

  • “Why or why not?”

  • “Are there other ideas or initiatives you’re considering that would also support your mission – which also merit consideration?”



Get Out of Your Cave:  In a sense, power questions are our tool for helping to see the true reality around us instead of shadowy representations of it.  Socrates was a master at asking power questions.  Instead of lecturing, he taught by posing his students a series of thought-provoking questions.  Through these, he engaged his students’ minds in the learning process.  He uncovered their assumptions.  He slowly but surely got to the heart of the issue.


You can use the Socratic Method to great effect in your day-today work and personal life.  First, start with questions rather than statements, assertions or commands. Consider these examples:


Instead of: “We need to improve our customer service!”

Try: “How would you assess our customer service levels today?” or, “How is our service impacting our customer retention?”


Instead of: “You know, if you don’t get a job this summer, we’re not paying you an allowance.”

Try: “What ideas do you have for what you’d like to do this summer?” or, “I’m interested to hear about how your job search is going.  What are you looking into?”


Instead of: “I’m fed up with your anger.”

Try: “when you get angry, how do you think it affects your relationships with the people closest to you?”


Second, ask fundamental questions about the things that everyone else takes for granted – questions that will, perhaps surprise others.  For example, someone at work says, “We need more innovation.”  Ask, “Can you describe what innovation means to you?”  When there is a call for more teamwork, ask, “What do you mean when you say ‘teamwork’?”


Adopt the Socratic mindset and get out of your cave!  Questions assumptions.  Question the very definition of words that others take for granted.  Use questions to launch those around you on an invigorating journey of learning and discovery.  Here is a contract that will help you understand this mindset:


Instead of:                                          You:


Telling                                                Ask thought-provoking questions

Being the expert                                 Invite others to contribute expertise

Controlling knowledge                       Help draw out others’ experiences

Assuming meaning                             Ask about the meaning of words

Mandating solutions                           Solicit solutions from others

Showing how smart you are               Show others how smart they are

Analyzing                                           Synthesize and look at the big picture



Begin at the Beginning:  You can truly engage with someone, draw them out and learn their story by asking “How did you get started?”  Of all the questions you might ask, what’s best about this one is the joy, passion and inspiration it brings to both you and the teller.


When to use the question:

  • Anytime, to invite someone to share how they got started in their career – or in any other part of their lives.


Alternative versions of the question:

  • Of a couple: “How did you two meet and end up together?”

  • Of an artist or musician: “Who taught you?  How did you learn your craft?”

  • If anyone: “Where did you grow up?  And how did you end up in…?


Follow-up questions:

  • “How did you decide to do that at the time?”

  • “What was the toughest lesson you had to learn?”

  • “If that had fallen through…what do you think would have happened?



Start Over:  It may feel awkward, but it’s a bold, gutsy strategy to restart a conversation from scratch.  It could be with someone at work or a family member at home.  When you get off on the wrong foot, ask, “Do you mind if we start over?”  People are forgiving.  They want to have a great conversation with you.


When to use the question:

  • When a conversation gets off to a very bad start.

  • If you get into an unproductive, emotionally charged argument with a friend of family member.


Alternative versions of the question:

  • “I’ve gotten off on the wrong foot.  Do you mind if I begin again?  I haven’t done this justice.”

  • “Can we step back from this?  What should we be talking about?”


Follow-up questions:

  • “Thanks.  Do you mind if I ask you a question?”

  • “The reason I’d like to start over is that I put my foot in my mouth.  Can I give it a second try?”



You Can Overcome Anything If You Understand Why:  When you’re trying to define an organizational role, to restore a sense of purpose and pride, or just understand what makes people tick, ask: “Why do you do what you do?”


We do things for many different reasons.  But when you put “should” in front of those reasons, you can be certain all the pleasure and excitement will be soon drained away.  You will not find passion associated with the word should.  No one gets excited about should.  In contrast, when you unveil the true why of someone’s work and actions, you will find passion, energy and excitement.


When to use this question:


  • When you want to understand what motivates and drives the other person.

  • To help reenergize other people about their vocation.


Alternative versions of the question:


  • “What are the most exciting parts of your job / of what you do?  Why?

  • “What are you most passionate about in your professional life?  Your personal life?  Why?


Follow-up questions:


  • “Why are you especially passionate about that?”

  • “What gets in the way of your satisfaction?”

  • “What would make it even more rewarding?”



In a Hushed Moment:  Try this question with your friends, colleagues and family.  Ask them, “What in your life has given you the greatest fulfillment?”  Then sit back.  Just listen.  You will uncover a treasure of conversational gems.  A sense of fulfillment is different from a feeling of accomplishment or happiness.  Fulfillment comes from achieving your hopes and dreams.  It reflects a state of completeness or wholeness.  It’s when you have a sense of deep satisfaction.


When you ask someone about what fulfills them, it opens the door to exploring something that is invariably very special to that person.  It creates a powerful connection, like sharing a relaxed meal or spending an intimate evening together.


When to use the question:


  • To build a more personal connection with someone at work or in a professional setting.

  • To get to know any of your friends and family better.


Alternative versions of the question:


  • “What in your life gives you your greatest sense of satisfaction?”

  • “What is the most fulfilling… (relationship, experience, job, etc.) that you’ve ever had?

  • “What experience affected you the most in your life.?”


Follow-up questions:


  • “Say more about that.  What was especially fulfilling about it?”

  • “Is there anything else that has also been deeply fulfilling for you?”



Is This the Best You Can Do?  When you want to push someone to exercise their abilities to the maximum – when you need their best possible work, ask: “Is this the best you can do?”  You should reserve this question for occasions when it is especially desirable for someone to do their very best and push themselves to their strained and stretched limits.  Often, we settle for mediocrity when we do need our best.  This question can spur the other person to greater heights and make them focus on what their best really is.


When to use the questions:


  • When you’ve asked someone at work to complete a task or project for you.

  • When trying to get a child to raise their effort to the next level.

  • Best of all, when you’re working on an important project, whatever it is, ask yourself, “Is this really the best I can do?”


Alternative versions of the question:


  • “Is there still room for further improvement?”

  • “In what ways could this be even better?”


Follow-up questions:


  • “What’s stopping you?”

  • “Do you think this would be worth your ‘best’?”

  • “What’s the best part of this?  What can be improved?”



No Gorilla Dust:  When you want a clear, unequivocal answer, ask an unequivocal, closed-ended question.  Ask, “Is it a yes or a no?”  When you are trying to pin someone down on an issue or determine their commitment, there are many ways you can ask the question.  There are soft, inquiring approaches like “What would you think of …?”  Sometimes, you must leave no room to wiggle.


A closed-ended question is potent when you want a direct, unvarnished response.  Is it a yes or a no?  When asked purposely, in an appropriate way, the closed-ended question is a powerful and demanding ally to the asker.


When to use the question:


  • To find out whether or not someone is fully committed.

  • To draw out any doubts or hesitations.


Alternate versions of the question:


  • “Can you commit fully to this?”

  • “Are you on board or not?”

  • “Can you make a final decision now?”


Follow-up questions:


  • “What excites you most about this?”

  • “What are your biggest doubts or reservations?”



Bury the Clichés:  When you want to understand a leader’s issues, don’t ask tired cliché questions like “What keep you up at night?”  Engage them in a discussion about their critical challenges.  Ask about the impact of current events.  Ask about the future.  Let me give a few examples that will stimulate your thinking:


  • “Where will your future growth come from?”

  • “How do you think your current strategy is going to change, given … (e.g., the success of new competitors, the rise of low-cost imports, deregulation, etc.)”

  • “If you had additional resources, which initiatives would you invest them in?”

  • “Sometimes a ‘breakthrough’ requires a ‘break-with.’  Are there any things you need to deemphasize or stop doing?”

  • “Why have you been successful so far?  How will that change in the future?”

  • “Which organizational or operational capabilities do you need to strengthen in order to achieve your goals?”

  • “As you think about the future of your business, what are you most excited about?  What are you most concerned about?”


Don’t ask lazy clichés like “What keeps you up at night?  Instead, ask informed questions about the future.  Questions that capture the imagination.  Questions about the other person’s aspirations, priorities and reactions to the world around them.



Don’t Let Anyone Steal Your Dreams:  Absorbed by the details of our day-to-day lives, we are rarely allowed to dream.  Invite a friend or loved one to share their heart with you.  Ask: “What are your dreams?”  This is a deceptively simple yet powerful question that most of us are afraid to ask, perhaps because we think it would be too intrusive. 


It can be a magical moment for others when you invite them to share their dreams with you.


When to use the question:


  • When you want to connect with and get closer to a loved one or friend.

  • When you want to help someone reconnect to their passion and their aspirations.


Alternative versions of the question:


  • “What things would you like to do in your life that you haven’t gotten around to yet?”

  • “If you had no constraints – children, money, your spouse’s job, whatever – what would you like to do?”


Follow-up questions:


  • “What would be most rewarding about that for you?”

  • “What could make that possible?”

  • “What’s getting in the way of doing that?”



Silence Can Be the Best Answer:  There are times when you don’t have to give advice.  In fact, in some situations you mustn’t.  When the choice is deeply personal, ask: “What do you feel is the right decision for you?”  Be quiet.  Don’t fill in the silence.  Allow the other person to find the correct solution.


Sometimes, your job is to help others go deeply into their hearts and recognize their own decision rather than push them in a particular direction.




When to use the question:


  • When the choices are extremely close.  (When someone cannot make up their mind about two alternatives, more logical analysis may not help.)

  • When the decision is a very personals one that may also affect loved ones.  (You cannot quantify the impact of moving to a new city on a child.  Only the heart can understand that.)


Alternative versions of the question:


  • “What does your heart tell you?”

  • “How will this impact your family (spouse, children, loved ones)?”

  • “With each of these choices, what regrets do you think you might have – either way – in two years?”


Follow-up questions:


  • “What would you say is the deciding factor for you?”

  • “What’s your next step from here?”



The Greatest Teacher:  People often race headlong from one activity to the next, never pausing to reflect.  To help someone get the most out of their experiences, ask: “What did you learn?”  This may surprise you:  We often do not learn from our experiences.  This has been demonstrated repeatedly in research studies conducted by social scientists.  We attribute our successes to our own capabilities and performance, whereas we pin failures on other people or external circumstance beyond our control.


The U.S. military is one of the few organizations that systematically tries to learn from experience.  The “after-action review” is a staple of all military operations, including training exercises.  Commanders are brutally honest.


Remember to ask not just, “What did you learn?” but also “What did you learn about…?”  Perhaps there is a lesson about motivating people, trust or organizational politics.


When to use the question:


  • Any time someone is sharing an experience or event with you.

  • After any meeting, interview or visit.

  • When you are mentoring or coaching someone.


Alternative versions of the question:


  • “What’s the most memorable thing you took away from that experience?”

  • “What did you learn about…?”  (people, trust, human nature, motivation, planning, etc.).


Follow-up questions:


  • “Do you think that’s always true or is this situation particular?”

  • “Can you say more about that?”



Push Open the Flood Gate:  Gain more information and open the other person up by asking, “Can you tell me more?”  Tell me more is the magic key to open up the next layer of the other person’s thinking and experiences.  Ask this question often.  It is to conversations what fresh-baked bread with soft creamery butter is to a meal.


When you make the conversation all about you, others may think you are cleaver.  But you will not build their trust.  You will not learn about them.  You will squander an opportunity to build the foundations for a rich, long-term relationship.


When to use the question:


  • Often and everywhere.

  • As a general prompt to encourage someone to go deeper and say more.


Alternative versions of the question:


  • “Can you say more about that?”

  • “What do you mean by…?  (ask them to define their terms more carefully)


Follow-up questions:


  • “When…?”

  • “What…?”

  • “How…?”

  • “Why…?”



The Essence of Your Job:  To get someone to reflect on their job (or their life), ask:  “What parts of your job do you wish you could spend more time on and what things do you wish you could do less of?”  Many factors influence how we spend our time: Historic accident, other people’s demands and our tendency to follow the path of least resistance.  By stepping back, we can often see the forest and not just the trees.


This question is a wonderful way to get people talking about their job – whether it’s running a company or running a household.  You’ll lead them down a path of reflection that may result in joyous and transformative changes.


When to use the question:


  • To invite another person to talk about their position and their role in an organization.

  • In particular, around the time of someone’s anniversary in a job – one year, three years and so on.

  • To explore a friend, colleague or family member’s life and help them understand how they might refocus their time.


Alternative versions of the question:


  • “Which are the most enjoyable parts of your job and which parts do you find least enjoyable?”

  • “If you had an extra couple of hours in each week, how would you spend them?”

  • “What do you wish you could devote more time to?”


Follow-up question:


  • “What’s getting in the way of making that change?”

  • “I know it’s difficult to drop or spend less time on some of those things you mentioned…but what might possibly enable you to do that?”



A Tempest-Tossed Topic:  We often learn the most when we experience intense pressure – when we are stretched and pushed.  Learn from the deepest recesses of someone’s experience by asking, “What is the most difficult question you have ever asked?”  This question almost always creates a flowing stream of conversation.


When asked the questions, what you will most often find is that the person stops and says, “Okay – what’s going on here?  Let me think.  Wow!  That’s a tough one.  In my heart of hearts, what is the answer?”


When to use this question:


  • When you want to plumb deep into the person’s psyche.

  • When you want to know much more about the character and makeup of the person.


Alternative versions of the question:


  • “What is the most profound question you have ever been asked?  That you have ever asked someone?”

  • “Tell me, have you ever been asked a question that really stumped you?”

  • “Have you ever been asked a question that embarrassed you or have you ever asked a question that turned out to be embarrassing for the person you’re talking with?”


Follow-up questions:


  • “What kind of an impact did the question make on your life?”

  • “Sometime later, did you feel you gave the right answer?”

  • “If you were asked the same question today, would your answer be the same?”

The Road Taken:  To help someone reflect on what they’d truly like to do in their lives and how they’d like to be remembered by others, ask:  “If you had to write your obituary today, what would you like to say about you and your life?”  Obituaries are normally for those who stay behind.  They help the family and friends of those who have departed celebrate their lives.


An obituary can become something important to the living in another way.  Envisioning it ahead of time can help shape your life.  It can bring what’s most important to you – and what you truly enjoy – into sharp focus.  Writing your obituary now will highlight the choices you are making and can make.


When to use this question:


  • When coaching or mentoring someone.

  • When a young person is making career and life choices.


Alternative version of the question:


  • “Looking ahead in your life, what do you think will give you the greatest sense of achievement?  The most personal fulfillment?”

  • “What are some things you haven’t done but which you would like to do before you die?”


Follow-up question:


  • “Why did you put those particular things in your obituary?”

  • “What could get in the way of accomplishing that?”



Who Do You Say I Am?  Are you a leader in an organization?  A business professional?  A parent?  A teacher?  In any of these roles, you need to know if those around you understand who you are.  You need to know if they truly appreciate the beliefs and values that define you.  They need to know what you stand for – and what you don’t stand for.  Ask them this direct question:  How do you see me as a leader?” (…or, as a colleague, friend, parent?).


We take for granted that the people who work for us or with us understand and respect what we stand for – that they appreciate our values and approach to work.  The same goes in our personal lives, with regard to family members and friends.  But do they know who we really are?  How do we know?  You can create a truly intimate and inspired conversation by asking this question.  You may learn something unexpected.


When to use this question:


  • Any time you want to know how others perceive your leadership.

  • To discover if those closest to you – family, friends, colleagues – understand who you are and what you stand for.

  • To shake people up who are on the fence about your intentions.


Alternative versions of the question:


  • “What do you think I stand for?”

  • “If you were to summarize the principles or values I exemplify, what would some of them be?”


Follow-up questions:


  • “What have I done that has really reinforced that?”

  • “What else could I do to better communicate and be a role model for these things?”

  • “Why do you think that?”



That Special Moment in Life:  Dig deep and learn something special about the other person.  You’ll bring a smile to their face when you ask, “What’s has been the happiest day of your life?”  This question can illuminate a darkened room and brighten someone’s black mood.  The other person may not even be able to answer it – or provide a single answer.  That’s okay!  You will set their mind in motion, flipping through the most pungent memories in their life.


Whether the answer is a revelation or just thoughtful silence, this question always has a positive if not thrilling impact.


When to use this question:


  • Any time you want to deepen your understanding of the other person and build a stronger relationship with them.

  • To understand the important events that has shaped someone’s character.


Alternative versions of the question:


  • “What was the greatest day of your life?”

  • “What event in your life has brought you the greatest joy?”


Follow-up questions:


  • “Why was that so special for you?”

  • “Are there any other days or events that stand out for you?”



Your Plans or Their Plans?  Don’t start by talking about your own plans.  And don’t start by talking about your plans for the person.  First, ask them, “Can you tell me about your plans?”


To be a great listener, follow these three principles:


Humility:  You must believe you can learn from every person you encounter.


Curiosity:  As we grow older, our curiosity dies.  The average five-year old asks 200 questions a day.  How many do you ask?  Approach every situation with an intense sense of curiosity and you will listen more.


Self-awareness:  Your biases and prejudices will prevent you from listening to others.  Women often make the decisions about which new car to buy – yet, in a typical car dealership, the salespeople pay far more attention to the husband.  Know yourself!


When to use this question:


  • Before you tell someone what you think their plans should be.

  • When you need to understand the other person’s intentions and priorities.


Alternative versions of the question:


  • “How do you plan to approach this?”

  • “What is your strategy?”

  • “What are your ideas for where you want to go in the future?”


Follow-up questions:


  • “What process did you use to arrive at that?”

  • “What things have you decided not to do?”



Never Look Back Unless You Plan to Live That Way:  Sometimes, the right solution to a dilemma you have with someone will present itself when you contemplate a reversal of the roles.  When you are asked for your advice about a dilemma, explore all options by asking:  “If the circumstances were turned around, how would you like to be treated?”  It’s a question you can’t run away from.


Everyone loves the adage, “Do unto others as you would have them do unto you.”  It’s warm and fuzzy.  It makes perfect sense.  But it’s easier to agree intellectually with the sentiment than to live it.  Living it is very tough.


When to use this question:


  • When someone asks you for counsel about a difficult situation involving another person or about a perplexing dilemma.


Alternative versions of the question:


  • When someone has done something wrong or that is hurtful toward you, you can reverse the roles in yet another way.  Ask, “If you were me, what would you do?”  This may make the other person accept your decisions more willingly.


Follow-up questions:


  • “Why do you feel that would be right?”



How to Stop the Snorting:  A good question can be like an elixir that softens a bad mood, melts anger and pulls the other person back to the truly important issues.  People often complain about others and insist that they need to change.  You have to shift them from criticism to solutions by asking, “What do you wish they would do more of?”


They have to change!  That’s a common criticism.  And criticism is contagious.  If you can get the other person to be specific about the behaviors they wish to see, however, you’ll achieve a powerful redirection of the conversation.  You’ll move from complaints and cynicism to productive dialogue about how to move forward.  You will help sharpen the other person’s understanding of the problem.  Don’t fix the blame, fix the problem.


When to use this question:


  • Whenever someone at work complains.

  • When an individual is singled out and criticized.


Alternative versions of the question:


  • “If you could get your people to do just one thing differently – one action that would have a big impact on performance – what would it be?”

  • “In what ways do you wish they would change?”


Follow-up questions:


  • “Why do you think they aren’t doing those things?”

  • “Are they not doing the right things because they lack knowledge and skills, because the organization gets in their way or because they don’t have the natural ability?”



Dig Deeper.  Deeper.  Still Deeper:  Whenever someone says, “I want this,” you have to find out what they really need.  You do this by asking “Why?”  You can ask this question as many as five times, starting with “Why do you want to do that?” or “Why is this happening?”


“Why?” can be a terrible question if used at the wrong time and for the wrong reason.  It can communicate underlying disapproval.  It can sound critical, carping and nagging.  It can make the other person feel bad about themselves.


“Why” can also be a powerful question.  It can make others think more deeply about what they are doing and help them get to the heart of the issue.  “Why?” can make us stop, reflect and examine our actions instead of just mechanically going about our lives?  Use careful judgment in asking “Why?” but ask it often.


When to use this question:


  • When you genuinely want to understand someone’s motivations.

  • When the other person wants something but you’re not sure they really need it.

  • When you are trying to understand what are the root causes of a problem.


Alternative versions of the question:


  • “What result are you expecting from that?”

  • “How did you decide to take that approach?”

  • “Why do you think you should start there?”


Follow-up questions:


  • “Why is that?”

  • “Why do you think that’s happening?”

  • “How do you know that?”



Always Faithful:  To understand someone’s inner being and learn what has been most important to them, ask: “What is the greatest achievement in your life?”  This question has many levels to it.  It contains the potential to create deep, multi-layered conversations.  It raises additional questions:  Is it possible to define a single greatest achievement?  Do we mean professional achievement or in any sphere, such as personal and family life?  How do we define achievement, after all?  It is a powerful question that provokes deep thought and dialogue.


Even if the other person has difficulty citing a single experience, you will learn a great deal about them.  (And by the way, be prepared to answer this question yourself, as it may get quickly turned around on you!)


When to use this question:


  • When you want to deepen your relationship with someone and learn more about what is important to them.


Alternative versions of the question:


  • “What is your most personally gratifying achievement?”

  • “What is the one achievement you are proudest of?”

  • “In thinking about all of your achievements, which one do you think other people will most remember and why?”



Follow-up questions:


  • “Say more about that.  Why did you choose that particular one?”



I Used to Be Indecisive – But Now I’m Not Sure:  Start creating a culture of decisiveness.  Before you begin each meeting, ask: “What decisions do we need to make today?”  After every meeting ask:  “What have we decided today?”


In many organizations, procrastination rules.  (“I would do something about my procrastination – But I can’t get around to it?”)  People are afraid to make decisions.  They are concerned about upsetting powerful, established interests.  It’s easier to play it safe than make a decision for which you may ultimately be accountable.  Creating a list of benign action steps, which don’t really take you anywhere important, is easy and low risk.


When you make decisions together, it binds the group with a public affirmation.  The result is firm commitment to follow through on agreed actions steps.


When to use this question:


  • After any meeting.

  • After discussing an important issue with a family member or friend.  (“So, have we decided anything?” or, “What have we decided to do?”)


Alternative versions of the question:


  • When someone comes to you with a problem or issue:  “Is there a decision that I need to make or that I can help you make?”

  • At the start of a meeting:  “What decisions do we want to make today?”


Follow-up questions:


  • “What is needed in order for a decision to be made on this?”

  • “Do we all agree about that?”



Blah Blah Blah:  When someone approaches you for advice and is vague or starts to give you too much background information, ask:  “What’s your question?”  This is a tough love question.  People will resist it – often strenuously.  But you must ask it.


When someone asks for advice or wants to “bounce something off you,” you can help them immeasurably by asking this question.  It forces them to crystallize their thinking.  It makes them take the first step toward clarifying what the issue it and what advice they really need from you.


By asking this question, you’ll also help reduce the amount of posturing that people do with you.  You’ll move faster toward an authentic conversation.


When to use this question:


  • Whenever someone says they have a question for you but then doesn’t get around to asking it.

  • When you’re asked for advice, but the problem statement is so general that you really don’t know what you’re being asked for advice about.


Alternative versions of the question:


  • “There must be a question in there somewhere…what is it?”

  • “What would you like me to give you advice about?”

  • “You’ve mentioned several issues.  What’s the most important one you are struggling with?”


Follow-up questions:


  • “What have you tried?”

  • “What do you think your options are?”

  • “What’s the thing you are most concerned about?”



Why Is This Day Different?  Invite others to share their most treasured moments with you.  Help them relish and savor their days by asking, “What made this day more special than any other?”  This is an extraordinary question to ask over dinner, when entertaining friends at a cocktail hour or with the family at the close of the day.  The responses are almost always positive.  People stretch to think of all the good things that have transpired.  What makes this reaction special is that when joy overflows their cup, it tends to spill over onto everyone else.


Should the day’s tidings be negative – and this doesn’t happen often – just be aware that there are no rainbows without a cloud or storm.  Tomorrow will be a better day.  In either case, the question leads to revealing discourse.


When to use this question:


  • At the end of any day, when you are talking to just about anyone!

  • When someone has come back from a trip, adventure or outing.


Alternative versions of the question:


  • “Would you tell me about your day?”

  • “What happened today that made you smile?”  Did anything make your frown?”


Follow-up questions:


  • “Why was that particularly special for you?”

Never Too Late:  Compliment a client, colleague or friend on their achievements.  But don’t stop there.  Draw out their deepest, most heartfelt aspirations.  Ask:  “Is there something else you’d like to accomplish?  Is there a dream you’ve yet to fulfill?”  Almost everyone has an unfulfilled aspiration or dream, not matter where they are in their career or their life.  Rarely, however, do others invite them to share it.


Anyone can carry on a conversation about plans, reports and recommendations.  Go deeper and create a sublime moment by asking this question.


When to use this question:


  • When you’ve already had the chance to meet the other person a few times and want to start to deepen the relationship.

  • At any stage of someone’s career.

  • With a leader who will be stepping down in the next few years.


Alternative versions of the question:


  • “Is there a dream you’ve yet to fulfill?

  • “Do you have something in mind for your next act?”

  • “After this, is there a particular challenge that excites you?”

  • “What are your most important aspirations for your career?”


Follow-up questions:


  • “What will the timing of that be?”

  • “Do you think that will stretch you in a different way?”

  • “If you do go in that direction, what’s the next step you’ll take?”



Take Stock of Your Life:  The great management thinker Peter Drucker used to pose five questions to his clients, focusing on Mission, Customers, Value, Results and a Plan.  These clients were large corporations but also major nonprofit organizations like the American Red Cross and the Girl Scouts.  His five questions were:


  1. What is your mission?

  2. Which are the most important relationships you want to invest in?

  3. What are the essential priorities and goals of those closest to you?

  4. What are your expectations of the people around you, and what do they expect of you?

  5. What is your plan?


Now, turn these questions onto your own life.  Use them to challenge yourself.  Make the implicit explicit.


Use all of these questions when you are coaching or mentoring others.  Use just one of them according to the situation.  If someone is trying to build a key relationship, ask “Do you know what that person’s priorities and goals are right now?”  If the other person is in a leadership position – as either a professional or a parent – ask “Do others know what you expect of them?  Have you made that clear?”



The Heart of the Matter:  When the other person is distracted or disengaged or when you feel you are not talking about their highest priority issues, you must ask:  “What’s the most important thing we should be discussing today?” 


If what you are talking about does not align with the other person’s most urgent priorities, they are going to wish they were elsewhere.  You will dramatically increase your relevance and influence if you spend more of your conversations focused on what is most important to the other person.


When to use this question:  Here are some occasions when you may need to refocus the discussion:


  • In update meetings with a client or your boss.

  • When making a sales pitch.

  • With your spouse or significant other.


Alternative versions of the question:


  • “What would you like to talk about today?”

  • “What’s on your mind?”

  • “We’ve got 20 minutes left…is there anything we haven’t covered that we ought to discuss today?”

  • “What aren’t we talking about that we should be addressing?”


Follow-up questions:


  • “Can you say more about that?”

  • “What’s behind that?”

  • “Why is this important to you now?”



Capture the Moments:  Invite someone to think deeply about their priorities in life and how they want to spend the remainder of their days.  Ask:  “If you knew you had only three years to live, what would you hope to achieve personally and professionally?”


You must engage the day, ravish the moment.  Wrest and wring from life all that is good and all it will yield.  Your objective should be to die young – as late as possible.  That is why this is such a powerful question.  If you knew you only had three years to live, how would you spend the time?  You will uncover unexplored, unexpected responses no other question elicits.


Carpe diem!  That says it all.


When to use this question:


  • With your friends, family, business colleagues and just about anyone you know.

  • To shake up other peoples’ thinking and pull them out of the day-to-day minutia of their lives.


Alternative versions of the question:


  • “What are the most important things in your life?  Are you spending enough time on them?”


Follow-up questions:


  • “What’s stopping you from doing this – now?”



An Additional 293 Power Questions:


In this section, we share another 293 questions.  Thoughtful, probing, provocative questions you should be using every day – at work, at home and with your friends.  Even with strangers you meet on the airplane.  They are listed under nine topics to help you do the following things:


  1. Win new business

  2. Build relationships

  3. Coach and mentor others

  4. Resolve a crisis or complaint

  5. Engage your leadership

  6. Engage your employees

  7. Evaluate a new proposal or idea

  8. Improve your meetings

  9. Ask for a gift


Use these questions to add zest and meaning to your conversations and to deepen your relationships.


1: Win New Business:  What is the secret to winning a sale?  To convincing a potential buyer to go with you?  A buyer is created when a clear need is identified, a trusting relationship is established and value is demonstrated.  The most successful salespeople in the world create these conditions by asking great questions.


They don’t build their credibility with prospective buyers through fancy PowerPoint presentations.  Instead, they use thoughtful, informed questions that implicitly demonstrate their knowledge and experience.  They use questions to uncover hidden needs.  To identify whether or not there is a problem or opportunity they can address.  The best salespeople also use questions to connect on an emotional level – to get to know the other person and show they care.


It doesn’t matter whether you’re selling a product, a service or an idea.  When you first meet someone, power questions quickly earn respect for you.  And that’s the first step toward building a trusting relationship.


Holding Effective First Meetings:


  1. From your perspective, what would be a valuable way for us to spend this time together?

  2. What would be useful for you to know about our firm?

  3. What prompted your interest in our meeting?

  4. In talking to my clients in your industry, I’m struck by a couple of particular issues they are grappling with.  These include: (give examples).  How would these resonate with you and your management?

  5. How is your organization reacting to…? (a recent, important development in this client’s industry or function).

  6. How are you handling…? (new competition, low-cost imports, a new regulatory framework, etc.).

  7. Is there a particular competitor you admire?

  8. Can you tell me what your biggest priorities are for this year?

  9. What are your most significant opportunities for growth over the next several years?

  10. What exactly do you mean when you say…? (“risk-adverse,” “dysfunctional,” “challenging,” etc.).

  11. Who would you say are your most valuable customers?

  12. What would your best customers say are the main reasons they do business with you?

  13. Why do customers stay with you?

  14. Why do customers leave?

  15. When customers complain, what do they say?

  16. How have your customers’ expectations changed over the past five years?

  17. How would you describe the biggest challenges facing your own customers?

  18. What’s the driving force behind this particular initiative?  (What is behind the drive to reduce costs, design a new organization, etc.?).

  19. What would “better” (risk management, organizational effectiveness, etc.) look like?

  20. How did you reach the decision to seek outside help?

  21. How much agreement is there, internally, about the problem and the possible solutions?

  22. From your perspective, given everything we’ve discussed, what would be a helpful follow-up to this meeting?


Developing a Need:


  1. How much do you think this is costing you?

  2. What do you think it’s worth to fix this?

  3. How is this affecting other aspects of your business? (sales, costs, productivity, morale, etc.).

  4. How do you know that…? (turnover is high, productivity is low, risks are not being well managed, etc.).

  5. Who in your organization really owns the problem?

  6. If an effective solution is found, how will it affect your own job?

  7. Why is this important to you right now?

  8. Is this one of your top three or four priorities?

  9. How much time do you personally devote to this issue?

  10. Can you give me an example of that?

  11. If you do not address this (problem/opportunity, etc.), how might your business be impacted?

  12. What solutions have you already tried and how successful were they?

  13. What kinds of organizational resistance will there be to this change?

  14. Is there anything I haven’t asked about that you think is relevant to understanding this issue?


Understanding Aspirations and Goals:

  1. Where will your future growth come from?

  2. How much do you think your current strategy is going to change, given trends such as…?

  3. Why have you been successful so far?  How will those reasons change in the future?

  4. You’ve already reached some important milestones and accomplished an enormous amount.  Where do you go from here in terms of future improvements in performance?

  5. How much of your growth will come from existing customers versus new customers?  What’s your thinking behind that?

  6. If you had additional resources, which initiatives would you invest them in?

  7. Are there any things you need to de-emphasize or stop doing?

  8. What more might you ask for if you were not afraid of getting “no” as an answer?

  9. How would you say your priorities have changed over time?

  10. How will your own performance be evaluated at the end of the year?

  11. Are there any organizational or operational capabilities that you need to significantly strengthen in order to support your future strategy?

  12. What demands will your future strategy make on the quality and quantity of people that you need?

  13. As you think about the future of your business, what are you most excited about?

  14. As you think about the future of your business, what are you most worried about?

  15. You’ve been very successful in your career.  Is there something else you’d like to accomplish?

  16. What are your dreams for the future?


Discussing a Proposal:


  1. We had planned to cover the following areas.  What parts of our presentation will be most valuable for us to emphasize and spend time on?

  2. Can you restate, in your own words, what you hope to gain from successful completion of this program?

  3. Given what we’ve set out in our proposal, and thinking about value to you, can you say something about what you’d like to see more or less of?

  4. What do you like most about the approach we’ve outlined?

  5. What aspects concern you?

  6. In what ways does this capture what you’re trying to accomplish?

  7. In thinking about choosing a partner to work with on this, what’s most important to you?

  8. May I ask, who else are you talking to?

  9. Can you walk me through your decision-making process?

  10. Who will make the final decision about choosing a firm to work with?

  11. How will the funding for this be determined?

  12. If two providers are evenly matched in terms of technical ability, experience and price, how will you make your decision?

  13. I sense you do have some hesitation.  Can you help me understand what is behind this?

  14. Is there anyone else who we ought to discuss this with or hear from before we finalize our approach?


Before Meeting with a Client: Questions to Ask Yourself:


  1. Have I thoroughly discussed the client’s needs and expectations for this meeting?

  2. If substantive information or recommendations are being presented, have we previewed these in advance with all the right constituencies?

  3. Are the right people – from their side and from our side – coming to the meeting?  Do I know who they are and how many there are?

  4. If more than one of us in attending, have we discussed and clarified the roles that everyone is going to play?

  5. What are the most prominent messages or ideas that I want to get across?  How would I summarize these in one minute or less?

  6. What are the different options for presenting our ideas?  Can we use flipcharts rather than PowerPoint?  Do we have some engaging stories that can help to illustrate our points?

  7. Is there anything I can give to them beforehand (e.g., pre-readings) that will make this meeting more productive?

  8. What’s going on in this person’s world right now?  What pressures are they feeling (at work, at home, etc.)?

  9. How will they react to what I have to say?

  10. Is there enough flexibility built into the schedule to have a vibrant, give-and-take discussion, and/or to pursue other issues that the client may want to discuss?

  11. What additional information do we need (about the individuals who will be attending, other important data, etc.) before this meeting?

  12. What are the three or four thought-provoking questions that I plan to ask at this meeting?

  13. What do I think will be the likely follow-up to this meeting?


2. Build Relationships:  How do you move from an acquaintance to a meaningful relationship?  A relationship deepens when two people get to know each other better.  This means you must share important experiences, reveal yourself personally and connect on an emotional, not just professional, level.


Relationships are dynamic.  They rarely stay the same.  They either improve and evolve or they wither on the fine.  This particular set of questions will help you ensure that your relationships continue to grow, deepen and prosper.


Connecting Personally:


  1. What would you like to be remembered for?

  2. What has been your greatest accomplishment?

  3. What has brought you the most fulfillment in your life?

  4. What was the happiest day of your life?

  5. What do you wish your younger self had known about (success, relationships, being a parent, etc.) that you know today?

  6. Can you tell me something about your own career and how you got to your current position?

  7. What do you like best about working for your organization?

  8. In terms of your own effectiveness and how you spend your time, what would you like to do less of and on which activities do you want to spend more time?

  9. Tell me about your family.  How old are your children?

  10. When you’re not shaking things up here at work, how do you spend your free time?

  11. What do you think about (a current event, the election results or anything else)?

  12. Who have been influential role models or mentors to you?

  13. Where did you grow up?  What was that like?

  14. What were your parents like?  What did you learn from them?

  15. If you hadn’t gone into (business, teaching, medicine, etc.), what do you think you would have done instead?

  16. If you had to write your obituary today, what would it say?

  17. What’s the most memorable book (movie, concert, etc.) you have ever read?

  18. Do you think you are an extrovert or an introvert?  Why do you say that?

  19. In thinking about e-mail, the telephone, written correspondence, face-to-face meetings, social media and so on – how would you describe your communication style and preference?

  20. I don’t know much about your early career, can you tell me about what you did during the first five years or so?

  21. How did you get your start?

  22. What do you think are your boss’s most pressing issues right now?


Understanding the Other Person’s Agenda:


  1. Can you tell me about your work?  What kinds of activities take up most of your time?

  2. At the end of the year, how will you be evaluated?

  3. What is your organization looking for from you this year?

  4. What are the major projects or initiatives you’re working on?

  5. What’s important to you right now?

  6. What are you most passionate about in your life right now?

  7. What are the most important things you’d like to accomplish this year?

  8. If you had a couple of extra hours in the week, what would you spend them on?

  9. What are the favorite things you like to do when you’re not…(at the office, taking care of your family, etc.)?


Empathizing with Others:


  1. Tell me, how are you?

  2. Can you say more about that?  What’s going on?

  3. What do you mean when you say you’re feeling…?

  4. Why do you think that happened?

  5. How did you feel about that?

  6. I’m trying to imagine what you’re feeling.  I think it’s (angry, embarrassed, proud, etc.).  Is that right?

  7. How (angry, embarrassed, proud) would you say you are right now?

  8. Was what happened difficult for you?  I imagine it was challenging. (Never be dismissive – take everything that’s said seriously.)

  9. Do you feel that was the right thing to do?  Or, Do you think that was the right response?  (Don’t judge.  Judgment stops empathy dead in its tracks.  As the other person what they think!)

  10. It seems like there are really two different issues going on here, is that right?  Or, It seems like you feel stuck between a rock and a hard place…is that right?  (Paraphrase and affirm.  Summarizing what someone has said is boring and tedious.  Paraphrasing or synthesizing, is far more powerful.)

  11. What are you thinking of doing?  Or, What do you think your options are?

  12. I had a very similar experience.  Can I share it with you?

  13. Is there anything I can do that would be helpful?


Getting Feedback about a Professional Relationship:


  1. From your perspective, how do you feel our collaboration is going?

  2. Could you give me an honest assessment of our work together?

  3. Is there anything that you’d change about our relationship?

  4. What should I be doing more of?  Less of?

  5. Are there individuals in the organization with whom I need to spend more time?

  6. Is there sufficient communication so far?

  7. Am I doing an effective job at linking our work to your key priorities?

  8. What have I done that has been most helpful to you?

  9. In what ways am I helping you to achieve your goals?

  10. Do you feel I am working on the most central and critical issues for you?

  11. How can I make your life easier?

  12. How could I make doing business with me easier?

  13. In what ways could I be a better listener to you and your organization?

  14. Art there any aspects of your business or parts of your organization that you think I should understand better?

  15. Overall, how can I do a better job of helping you meet your own objectives?

  16. Are there any other issues that we ought to be aware of or thinking about for you?

  17. Do you have any other concerns that you’d like to put on the table?

  18. On a scale of 1 to 10, how enthusiastically would you recommend me and my firm to a friend or colleague?


3. Coach and Mentor Others:  Who in your life, right now, is benefiting from your experience and wisdom?  Your age doesn’t matter.  Mentoring and coaching others is an extraordinary service you can provide, whether it is part of your professional or your personal life.


Power questions are especially valuable when you are coaching someone.  They help you guide the other person to a solution rather than mandate a direction.  They help you bring out the other person’s hopes, fears and dreams.  Power questions enable you to challenge them in a way that is empowering rather that constraining.


  1. How can I be of the greatest help to you in our relationship?

  2. What’s the best mentoring or coaching experience you’ve ever had?  Why was it so effective for you?

  3. What are your most important goals right now?

  4. What questions are you grappling with now?

  5. What questions can I help you answer?

  6. What are you most excited about in your life right now?

  7. Is there something that you feel is very difficult to do, but which, if you could do it, would substantially increase your success?

  8. What is your time frame for achieving these goals?

  9. What will you have to accomplish in order to get where you want to be?

  10. What are you most afraid of as you think about trying to achieve these goals?

  11. What are the most important obstacles you’re facing?

  12. Is there anything at all you can think of that would remove those obstacles?

  13. Can you give me an overview of the problem?  How did it get to this point?

  14. What have you tried so far?  How has that worked?

  15. What’s the best resolution to this that you can imagine?

  16. Have you ever dealt with anything similar before?  What happened in that case?

  17. What don’t you know in this situation that you wish you knew?

  18. Can you give me an example of what you just stated?

  19. Looking back, what have you been the most successful at?  Why?

  20. When can you remember being truly satisfied at work?

  21. What parts of your work, today, are the most satisfying to you?

  22. What are your greatest abilities?

  23. What do you value most?

  24. What are some of the things you need to let go of in order to move forward and accomplish your goals?

  25. What is your dream for the future of your career?

  26. What’s been the most helpful to you in this conversation?

  27. Based on this discussion, what do you see as your next steps?


4. Resolve a Crisis or Complaint:  When someone complains, the first reaction often is to argue the point and try to show them that they don’t have all the facts.  To set them straight.  You become intent on proving you are right.


When a person is upset, however, emotions are like facts.  People want to be heard and understood.  Rational argumentation will not win the day.  Worse, it will inflame the tension.  When there is a disagreement, your goal is to win the relationship, not the argument!


During the first phase of any crisis or problem situation, you must lead with questions.  By doing so you will learn essential information – most importantly – create an ally in solving the problem.


  1. Thank you for raising this with me.  Can you tell me everything you know about the situation?

  2. Can you say more about that?

  3. Really?

  4. What happened then?

  5. What has their reaction been?

  6. How do you think it reached this point?

  7. What else can you tell me?

  8. I’m sorry this happened.  What would you like to see done at this point?

  9. This is extraordinary important to me.  How soon can we meet to discuss this in person?

  10. Would it be helpful if I did some additional fact-finding and then we could meet face-to-face in the next couple of days to discuss some proposed actions to address this?

  11. If anything else surfaces in the meantime, can you let me know immediately?


5. Engage Your Leadership:  What is it about someone’s performance and attitude that instills confidence in their leadership?  Just as a client is impressed with strong, thought-provoking questions, your boss or organization’s leadership will be too.  Your capacity to handle your work effectively and achieve your goals is essential.  But just as important is your attitude and outlook.


Are you a know-it-all?  Or are you someone who exhibits a healthy curiosity and desire to learn?  Are you a lone ranger?  Or do you consult with your colleagues and superiors on a regular basis?


These questions will help you engage with your leadership and demonstrate the hallmarks of a truly curious and committed member of the organization.


  1. What are the most critical initiatives for the organization over the next 12 months?

  2. What are your own priorities for the next 12 months?

  3. What does your boss expect from you this year?

  4. In terms of accomplishing our goals, where are we on track or ahead of plan and in which areas are we behind?

  5. Is there anything I can do to support you as you pursue your goals?

  6. How can I be helpful to you as you make this decision?

  7. How can I be helpful to you as you implement this decision?

  8. Can you share with me how you and your leadership reached that decision?  What other options did you consider?

  9. What are the major challenges you see yourself facing in the future?

  10. What gets you excited about the future?

  11. As you look back over your career, what has characterized the outstanding performers who have worked for you?

  12. From your perspective, what do you think my most important priorities should be in the short, medium and long term?

  13. If, at my next performance review, I wanted to exceed your expectations for me, what would I need to have done between now and then?

  14. What do you think are my three greatest strengths?  My biggest weaknesses or developmental needs?


6. Engage Your Employees:  Great leaders ask great questions.  They know that if they come up with all the answers, the chances of having anyone else buy into the solution are next to zero.  But if their employees come up with the answer – if they feel ownership of it – there is a good chance it will bear fruit.


Telling, commanding and stating the truth as you see it will not engage or empower.  Answers make you feel like a leader, but questions create real followers.


  1. Are we doing anything that is no longer important or effective and that we should stop?

  2. What ideas do you have to help grow our organization?

  3. How can we improve this?

  4. What do you think is the single most important action we can take to make our organization more successful?

  5. Do you know why we do it this way?

  6. What do you think is the real problem at the bottom of this issue?

  7. Is there anything getting in the way of you performing your job effectively?

  8. What ideas can you suggest for…? (reducing costs, growing revenues, improving productivity, improving innovation, etc.)

  9. What would make your job more interesting and exciting?

  10. Where would you like to go in our organization?

  11. What additional information or resources would allow you to be more effective?

  12. Where do you see me being the most effective and having the most impact?

  13. What do you love about your job?

  14. What are the most challenging parts of your job?

  15. Based on your experience, how would you describe the culture of this organization?

  16. What makes you proud to work here?

  17. Can you point to a recent management decision you didn’t understand or wish you knew more about?

  18. What could leadership do to communicate more effectively to the organization?

  19. Who in our organization do you wish you knew better?

  20. What are we hearing from our customers lately?


7. Evaluate a New Proposal or Idea:  How do you determine whether a new idea is good or bad?  If it has promise or if it is completely unrealistic?  Every day we are bombarded with ideas and proposals.  Someone who reports to you at work may propose a new initiative requiring investment.  Or, one of your children may have an idea about a new sport they want to take up or a career path they want to follow.


Whether you’re talking to a client or a family member, these questions will give you the ability to learn, engage and assess what they are proposing.


  1. Why are you doing this? (What appeals to you about doing this?)

  2. What is your mission?

  3. What is important to you about this?

  4. What are your most important goals?

  5. What, specifically, do you hope to achieve?

  6. What will the results look like?

  7. What outcomes do you seek?

  8. What will success look like?

  9. How will this affect…? (customers, employees, suppliers, support staff or others.)

  10. What changes do you think this will create?

  11. Do you think there could be any negative consequences?

  12. How could this limit your ability to act in other ways or other places?

  13. What are your most important assumptions?

  14. What are you assuming about…? (any number of variable that may impact the decision.)

  15. How could you verify that assumption?

  16. What if one of your key assumptions is wrong?

  17. What’s your plan?

  18. How are you going to approach this?

  19. What help or resources do you need to accomplish this?

  20. When do you plan to start?

  21. What factors are governing your timing?

  22. Are there advantages to starting sooner?  Later?  Disadvantages?

  23. Who will decide or influence the timing?

  24. What could go wrong?

  25. What are the risks of waiting or doing nothing?

  26. What are the two or three most important thinks that have to go well in order for this to succeed?

  27. Which risks can you control and which are uncontrollable?

  28. What else have you considered?

  29. If you had no constraints whatsoever, what would you do?

  30. How does this compare to other alternatives?

  31. What’s the next-best alternative?  Is there anything that could change to make that one look like the best alternative?

  32. Is this consistent with your mission?

  33. Is this consistent with your beliefs and values?

  34. Is this consistent with what you’ve been saying publicly?

  35. How consistent will this be with other initiatives that are going on in the organization?


8. Improve Your Meetings:  At their worst, meetings are where you spend minutes and waste hours.  Talk to anyone who works for a large organization (or a small one, for that matter) and you will hear about how much time is spent – and often wasted – in interminable meetings.


By asking these questions – starting with, “Is there an alternative to having a meeting?” – you will increase the effectiveness and productivity of the meetings you participate in.


  1. What is the purpose of this meeting?

  2. What do we hope to achieve?

  3. Who else will be there or should be there?

  4. How long does this need to be?  Why?

  5. Can we do this in 30 minutes? (rather than an hour.)

  6. Is there an alternative to having a meeting?

  7. What decisions do we need to make?

  8. Do we know enough to make a decision?

  9. What decisions have we made?

  10. How do we feel this meeting went?

  11. Was this a good use of our time?

  12. Did we accomplish what we had hoped?

  13. In retrospect, should we have held this meeting?


9. Ask for a Gift:  We estimate there are more than 30 million men and women in the United States who serve on boards of nonprofit organizations.  You may be one.


These directors and trustees carry as one of their major responsibilities the raising of funds for their organization.  Here are a few power questions that you may use with someone you are calling on for a gift.  What will flow is a stream of conversation that will help you get inside the heart and spirit of the person.


  1. How do you feel we can most effectively serve our community (patients, students, the homeless, etc.)?

  2. If you were the CEO and knew you could achieve any objective, what would you undertake for our organization?

  3. How do you feel about the services of this organization?  What would you suggest they do to expand their outreach?

  4. How do you like to be told about the results of your gift?

  5. When did it first occur to you that philanthropy was important in your life?

  6. If you were a board member, how do you feel we could most effectively use your funds?

  7. What would you change about our organization?

  8. In what ways could we serve better and more effectively?

  9. Why do you think we are one of the better-known organizations in our community?

  10. How can we become even better known?

  11. How can we do a better job of telling our story?

  12. What qualities and attributes do you like best in the CEO of our organization or of another organization that you know and work with?

  13. You’re a graduate of our college.  In what way have we helped you prepare for life?

  14. How important is recognition to you?

  15. What is your idea of perfect recognition for a gift?

  16. How do you like to be thanked for your gifts?

  17. What has been your experience with our organization?

  18. How do you feel about our organization?

  19. How do you feel about this project?

  20. What aspect of our program do you like the most?  And why?

  21. What is the best way to get your attention with the material we sent?

  22. Why did you make your first gift to us?

  23. You stopped giving to our organization.  Why?  How have we disappointed you?

  24. When did you start giving money away and what made you begin?

  25. What organization is the recipient of your largest gift?  How much have you given to them?

  26. What would have to change to get us higher on your giving priority list?

  27. What gift has given you the greatest joy?

  28. How has the economy affected you?

  29. Tell me what gift has cause the greatest disappointment?

  30. What motivates you to give to the organizations you do?

  31. What do you want most in life to achieve?

  32. How would you like to be remembered?



Message from Gary Tomlinson:


I hope you enjoyed reading this book report.  It’s important to understand that this book report should not take the place of you reading; “Power Questions – Build Relationships, Wine New Business and Influence Others.  Sobel’s and Panas’ book contains a lot of stories and examples that are not contained in my book report.  This is an incredible book and will serve as an excellent resource for the rest of your life.  You’d be doing yourself a disservice if you didn’t buy it and read it cover-to-cover.  You can learn more at


Enjoy the education and wisdom contained within this book report and feel free to share it with others because the “illiterate of the 21st Century will not be those who cannot read or write, but those who cannot learn, unlearn and relearn.”


You can engage Gary at To read his other book reports
or book reviews visit his website at

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