Workbook: Challenge Five
Asking Questions More Open-Endedly & Creatively

A chapter in The Seven Challenges Workbook
A Guide to Cooperative Communication Skills for Success at Home and Work
by Dennis Rivers, MA -- 2023 Edition

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cartoon illustration about asking questions more open-ended-ly Summary (repeated from Introduction) In order to coordinate our life and work with the lives and work of other people, we all need to know more of what other people are feeling and thinking, wanting and planning. But our usual “yes/no” questions actually tend to shut people up rather than opening them up. You can encourage your conversation partners to share more of their thoughts and feelings by asking “open-ended” rather than “yes/no” questions. Open-ended questions allow for a wide range of responses. For example, asking “How did you like that food/movie/speech/doctor, etc.?” will evoke a more detailed response than “Did you like it?” (which could be answered with a simple “yes” or “no”).

Consider the difference between two versions of the same question, as each might occur in a conversation between two people in a close relationship:

“Well, honey, do you want to go ahead and rent that apartment we saw yesterday?”


“Well, honey, how do you feel about us renting that apartment we saw yesterday?”

The first version suggests a “yes” or “no” answer, favors “yes” and does not invite much discussion. A person hearing such a question may feel pressured to reach a decision, and may not make the best decision. Both versions imply a suggestion to rent the apartment, but the second question is much more inviting of a wide range of responses. Even if our goal is to persuade, we can’t do a good job of that unless we address our listener’s concerns, and we won’t understand those concerns unless we ask questions that invite discussion. When your are under time pressure, it is tempting to push people to make “yes-no” decisions. But pressing forward without addressing people’s concerns has played a key role in many on-the-job accidents and catastrophes (such as the Challenger Space Shuttle explosion). On the next page you will find some examples of open-ended questions that could be helpful in:

  • solving problems in a way that meets more of everyone’s needs,
  • getting to know and understand the people around you better, and
  • simply creating richer and more satisfying conversations.


  • “How comfortable are you with Plan B?”

  • “How could I modify this proposal to meet more of your requirements?”

  • “What kind of information do you need in order to go forward?”

  • “How did you like that movie?”

  • “What do you think about … moving the office to Boston?”
    (rather than “Is it OK with you if we…  ?”)

  • “How are you feeling about all of this?”

  • “How ready are you to …?” 
    (rather than “Are you ready to …?”)


First exercise for Challenge 5: Take each of the examples given above and use it to write an open-ended question that includes some content from your life.


Second Exercise for Challenge 5: Translate each of the following “yes-no” questions into an “open-ended” one. What problems can you imagine arising from each of the “yes-no” versions?

(On talking with a person who looks disappointed…) “So you didn’t like that, huh?”   
Your open-ended version:


(A pilot to a new co-pilot…) “D’you know how to fly this thing?”   
Your open-ended version:


(A nurse to a patient…) “Have you been taking your medication?   
Your open-ended version:


(Parent to teen…) “Don’t you think it would be better if you did your homework first?”
Your open-ended version:


What questions in your life could be translated into an open ended style and what would they sound like in that new style?

Part 2: Asking questions more creatively.  Summary (repeated from Introduction) What sort of questions are truly worth asking? When we ask questions we are using a powerful language tool to focus conversational attention and guide our interaction with others. But many of the questions we have learned to ask are totally fruitless and self-defeating (such as, parents to pregnant teen, “Why???!!! Why have you done this to us???!!!”). In general it will be more fruitful to ask “how” questions about the future rather than “why” questions about the past, but there are many more creative possibilities. Of the billions of questions we might ask, not all are equally fruitful or illuminating; not all are equally helpful in solving problems together. In this section we will explore asking powerfully creative questions (with the help of researchers in many fields). Please note: Some of the questions discussed below, if asked without any preparation, may be experienced by others as demanding or as invading one’s privacy. Start by asking these questions of yourself first. Before asking them of others, practice the “introductions to a conversation” described in the Challenge Two chapter.

Question-asking in everyday life. As we wrestle with each new challenge in life, we ask ourselves and others a continuous stream of questions. Question-asking is one of the main ways that we try to get a grip on whatever is going on, but we are usually not very conscious of the quality of questions we ask.

“How could we work together to solve this problem?”  

is probably going to produce lots better results than

“Why are you always such a jerk?”

As noted above, not all questions are of equal value. Many are a waste of effort but a few can be amazingly helpful. Learning to ask conscious, fruitful questions of others, of oneself, and about one’s situation or task at hand, is an important part of the training of many professionals: psychotherapists, engineers, architects, mathematicians, doctors and others. All of these groups ask deeply penetrating questions. They do so in order to apply a body of knowledge to solve problems in a way that respects the unique elements of each new situation, person, piece of land, broken leg, canyon to be bridged, and so on. (A structured kind of self-questioning is also part of the communal life of the Quakers, as I have observed in attending various Quaker meetings, and part of Jesuit religious practice, as a Jesuit friend shared with me.)

“How could I have been so stupid?”


“What could I learn from this experience?”

A tool for everyone. Asking conscious, creative and exploratory questions is not just for professionals; it is for all of us. We are each engaged in the process of trying to build a better life, a better family, a better workplace, a better world, just as if we were trying to build the world’s tallest building. We can apply in our own lives some of the styles of creative questioning that engineers use to build better bridges, psychotherapists use to help their clients and negotiators use to reach agreements.

How am I going to nail that cheater?


What would be best for me in this situation?

The many examples of exploratory questions given by Donald Schön in The Reflective Practitioner suggest that we use questions to make a kind of  ‘space’  in our minds for things we do not know yet (in the sense of understand), or have not decided yet, or have not invented yet, or have not discovered yet. “Hmmm,” an architect might think, “how could we arrange this building so that it follows the contour of the land?” The answer will involve a complex mix of discovering, inventing, understanding, and deciding , all pulled together partly by the creative power of the question. This thinking process is easier to imagine when we use visual examples, such as designing a house to blend into a hillside (but not cause a landslide!). But these same elements are present in all our cooperative problem-solving activities. Asking questions can allow us to start thinking about the unknown, because questions focus our attention, and provide a theme for continued exploration. Questions are like the mountain climber’s hook-on-the-end-of-a-rope: we throw the hook into the unknown, and we pull ourselves into the future. But we need to learn how and where to throw, so that we pull ourselves into a better future.

How can I do this without anybody finding out?


If I do what I am thinking about doing, what kind of person will that help to make me?

As far as I know, there is no straight-forward set of rules about how to ask questions that are more helpful or more tuned to the needs of a particular situation, but there are many wonderful examples, from which we can draw inspiration and intuitive insight.  The exercise that follows will give you a chance to try out some of the best questions ever asked.

Questions of power. In many situations you may not have the emotional, social or political power to ask creative questions. Political power often works to narrow the range of permissible questions and narrow the range of who is allowed to ask them. For example, it is difficult to get US decision-makers to consider the question “Now that the Cold War is over, why is the United States spending more money than ever on nuclear weapons?” Totalitarian governments, modern advertising agencies and abusive families all want us to obey in unthinking silence rather than to question and explore possibilities.  Learning to ask creative questions, in a compassionate and conciliatory way, can be a large step forward in reclaiming your lost power as a person, a family member, a citizen and a problem-solver.

Third exercise for Challenge 5: Expanding your tool kit of creative questions The list of questions presented below contains the most intense and creative questions I have been able to find, drawn from the works of many deep question-askers. Next to each question in the table below I have given the field in which I have encountered that question. Take each question on the list and imagine a situation in your life in which you might ask that question. This is a demanding exercise. You may want to break it up into several sessions. (In real life, as discussed in Chapter 2, it works better if you let people know what kind of conversation you want to have, before you start a conversation that includes challenging questions or intimate inquiries.)


Source fields

When and where you could ask these questions in your own life?

1. How does this feel to me?

2. What (am I / are you) experiencing right now?

Gestalt therapy and general psychotherapy.

3. How could I have done that differently? How could you have done that differently?
4. What could (I / you) learn from this… (situation, mistake, painful experience)?

General psychotherapy.

5. What kind of explanations do I give myself when bad events happen?

6. How easy would it be for me to view this difficult situation as temporary, specific to one location and partly the result of chance?

Martin Seligman’s research on learned helplessness, optimism and explanatory style.

Note: Seligman found that over-generalizing plays a key role in making people feel depressed. When bad things happen, pessimists are more likely to say to themselves “That’s how it will always be, everywhere.” and “It’s totally and completely my fault.”

7. What is the most important thing that I want in this situation?

8. What solutions might bring everyone more of what they want?

9. What is my best alternative to a negotiated agreement?

10. What kind of self-fulfilling prophecy to I want to set in motion in this situation?

Conflict resolution, negotiation, management, especially Getting to Yes.(Note: A self-fulfilling prophecy is a stance that generates its own validation. For example, a person walking down a crowded street screaming “You will not like me!” at passersby is making their statement come true.)

11. What possibilities would be suggested if I were to look at this situation as if it were an airplane… a car… a circus… a movie… a Broadway musical…, etc.?

12. What does this situation remind me of?

Creative problem-solving in the arts, architecture, engineering and management.

13. If I do what I am thinking about doing, what kind of person will that help to make me?

Social constructionist communication theory.(Note: In the social constructionist view of being a person, a sense of self is the overarching story that persons tell to make sense out of their actions and the events of their lives. Each of our actions supports the development of some stories and inhibits the development of others.)

14. What were the times like when we all got along together just fine, when we didn’t have this problem? How did that work and what did that feel like?

15. (focusing on success) Looking back on this accomplishment, what seem to be the turning points that made this possible?

16. What were all the details of that moment of success?

17. Reviewing all these moments of success up to now, what kind of future could be possible?

Narrative therapy. (These are typical questions from narrative therapy that I have translated into a first person inquiry.)

Note: The central concern of narrative therapy is that the stories we tell ourselves to make sense of our lives and our life difficulties tend to leave out the kinds of events in our lives that might support a more energizing story. Narrative therapy tries to bring these “sparkling moments” into the foreground of attention, and to use them as a basis for creating a story that emphasizes strength and resourcefulness rather than illness, dysfunction and disability.

Reading for Challenge Five:  Radical Questions for Critical Times by Sam Keen

Rumor has it that on leaving the Garden of Eden, Adam said to Eve: “My dear, we are living in an age of transition.” Ordinarily, life proceeds ordinarily. We dwell securely within the garden of the protective myths, values, and paradigms of our society; our questions are about making a living, purchasing the things we have been taught to desire, raising our children, and keeping up with the neighbors. But times of crisis challenge our comfortable assumptions about who we are and force us to ask more radical questions. Carl Jung reached such a point at midlife when he realized that he didn’t know what myth he had been living.

Since permanent change is here to stay and crises and transitions are an inevitable part of the human condition, a wise person will hone some of the skills necessary for thriving in troubled times. Think of the crises every Adam and Eve must negotiate as composed of three interlocking circles: identity crises, love crises, social crises. It follows that the radical questions we most need to ask in times of transition (when our world is burning) are those addressed to the solitary self, those concerning the intimate relationship between I and thou, and those that have to do with the commonwealth within which we live and move and have our being.

Herewith, a selection to get you started. (Please send others that trouble, challenge, and inspire you to: Sam Keen, 16331 Norrbom Rd. Sonoma, California 95476)


What is happening to me?

What comes next for me?

What is the source and meaning of my restlessness, dissatisfaction, longing, anxiety?

What do I really desire?

What have I not brought forth that is within me?

What have I contributed to life? What are my gifts? My vocation?

What ought I to do? Who says?

What does my dream-self know that “I” don’t?

What story, myth, values, authorities, institutions inform my life?

What is my ultimate concern?

How faithful am I to my best vision of myself?

At whose expense has my wealth, security, and happiness been purchased?


Whom do I love?

By whom am I loved?

Am I more loved or loving?

How intimate are we?

How close is close enough?

What are we doing together?

Do we help each other broaden and deepen the reach of our caring, to become more compassionate?

What clandestine emotions fear, anger, resentment, guilt, shame, sorrow, desire for revenge – keep us from being authentic with each other?

When do our vows and promises become a prison from which I and thou must escape to preserve the integrity of our separate beings?

Can we renew our passion and commitment?

When is it time to say goodbye?


Who is included within the “we,” the community, the polis that encompasses and defines my being?

Who is my neighbor?

For whom, beyond the circle of my family, do I care?

Who are my enemies?

To what extremes would I go to defend my country?

Can I be just, loving, merciful, and be loyal to my profession, my corporation, my country?

If we were to measure our success by Gross National Happiness (the national standard of Bhutan) how would our economic, political, educational, and religious institutions change?

What would have to happen to convince sovereign nations to wage peace rather than expending their wealth and creativity in producing more deadly and genocidal weapons?


If you doubt that asking a new question is a royal road to revolution, transformation, and renewal, consider what happened when Descartes asked, “Of what may I be certain?” or when Newton asked, “How is a falling apple like a rising moon?” or when Marx asked, “Why were men born free but are everywhere in chains?” or when Freud asked, “What is the meaning of dreams?”

Your question is the quest you’re on. No questions — no journey. Timid questions — timid trips. Radical questions — an expedition to the root of your being.

Bon voyage.

Sam Keen, philosopher, teacher and author, has written many books about being human, including Apology for Wonder, Fire in the Belly, To Love and Be Loved, and Faces of the Enemy: Reflections of the Hostile Imagination. The above article is reprinted here with the author’s permission. For information about Dr. Keen’s workshops and his latest thoughts about life, please visit his web site at

Editor’s note: In presenting Dr. Keen’s essay to you, I would like to include the following advice:  Asking questions is a powerful human activity, and because of the power of questions, they can be sometimes be experienced as rude or invasive by those who receive them. If you decide to ask someone one or more of the deep questions proposed in the above article, it would help your dialogue if you would begin with the kind of conversational openers described in the Challenge Two chapter of this Workbook.  In general, when you want to have a conversation that will demand much effort from another person, it helps to announce your intent to explore a particular topic and invite the consent of your prospective conversation partner.

Sam Keen has generously consented to the inclusion of this article as a reading in the Seven Challenges Workbook.  Text of this essay copyright  2000 by Sam Keen.

Recommended Reading list (with book-buying links) on the topic of creative questioning. 

Article (free): Open-Ended Questions: Stretching Children’s Academic and Social Learning
By Paula Denton — Responsive Classroom Newsletter

Article (free): How to Use Open-Ended Questions to Get Kids Talking
By Lela Davidson (

book cover: the 7 powers of questionsThe 7 Powers of Questions: Secrets to Successful Communication in Life and at Work
by Dorothy Leeds


? demand

? stimulate thinking

? give us valuable information

? put us in control

? get people to open up

? lead to quality listening

? get people to sell themselves

They’re an essential tool of the seeker and the problem-solver, and in our personal and professional lives, they can make the difference between getting what we want and going without. Questions have power-and by harnessing that power, we can change our world. This unique book reveals the seven powers of questions-and shows how to use them most effectively. Learn how questions can improve relationships, help determine what people really want, uncover opportunities, persuade others, and get more out of every business or personal encounter.


1. Why a Book About Questions?
2. Power Number One: Questions Demand Answers
3. Power Two: Questions Stimulate Thinking
4. Power Three: Questions Give Us Valuable Information
5. Power Four: Questions Put You in Control
6. Power Five: Questions Get People to Open Up
7. Power Six: Questions Lead to Quality Listening
8. Power Seven: Questions Get People to Persuade Themselves
9. Sell, Lead, Think: Use Questions To Transform Your Organization
10. Closer Knit Than Ever: How Questions Can Draw Families Together
11. Rediscover Questions: Recapture and Redefine the Essential You
12. The Fifty Smartest Questions

WORLDCAT.ORG: Find this book in libraries thru WorldCat -- includes reader reviews
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BOOKFINDER.COM: Find low-cost used and new copies of this book in many online bookstores.
(We have no financial affiliation with, but they have the widest selection of used books.).

Questions That Work: How to Ask Questions That Will Help You Succeed in Any Business Situation

by Andrew Finlayson

Written by a seasoned business reporter and TV news manager, this provocative “questioning manifesto” and practical “how-to” book gives people the insights and tools to ask effective questions that get results in every realm of their professional lives. It is also a powerful tool that will help business leaders create a progressive environment where questions flow freely and creatively-boosting knowledge and performance increase at all levels of the organization.

“Do you know how to raise your IQQ? (Intelligent Questioning Quotient!) It’s not enough just to ask questions. It’s knowing which questions to ask and how to ask them that gets you results–in the form of better information, enhanced career prospects, and more competitive organizations. Written by a seasoned business reporter and manager, this provocative “questioning manifesto“ and practical “how-to“ book gives people the insights and tools to ask effective questions that get results in every realm of their professional lives. It is also a powerful tool that will help business leaders create a progressive environment where questions flow freely and creatively–boosting knowledge and performance at all levels of the organization. Best yet, the book supplies hundreds of carefully crafted questions that readers can use to find the right job, negotiate salary and benefits, inspire creativity within a group, make a better presentation, get a promotion, and much more. When people master the art of asking smart, meaningful questions, they not only make an excellent impression, they also improve their performance. In the words of the author: “Your success depends on what questions you ask. Workers of the world, question!“ “

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BOOKFINDER.COM: Find low-cost used and new copies of this book in many online bookstores.
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Change Your Questions, Change Your Life: 12 Powerful Tools for Leadership, Coaching and Results  (4th Edition — 2022)
by Marilee G. Adams, Ph.D.

Change Your Questions, Change Your Life is an international bestseller that has sold over 400,000 copies in twenty-two languages. People have discovered that, when we’re looking for answers, we often forget to take the time to ask the right questions. But, as Dr. Marilee Adams shows, intentionally using questions helps us make wiser choices, find solutions, and transform our personal and professional lives.

Dr. Adams uses a highly engaging fable to illustrate how great results begin with great questions. The book’s hero, Ben Knight, learns such breakthrough insights and undergoes a transformative journey. As we read how his coach takes him step by step through the twelve powerful tools of Question Thinking, we also learn how to apply the same information and practical skills in our own lives. At the center of this work is the Choice Map, which provides a simple yet powerful image to predict the likely results of the questions we ask ourselves and others. It tells us how to change our questions and our mindsets for the most rewarding outcomes.

The book contains a new chapter delving into what neuroscience reveals about managing our stresses and fears more effectively using methods such as those described in this book. It includes powerful and practical tools that help readers switch from a constricting Judger to an expansive Learner mindset, achieve the results they desire, and foster breakthroughs.

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BOOKFINDER.COM: Find low-cost used and new copies of this book in many online bookstores.
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