May I Ask a Question?

Image from pixabay by Dean Moriarty, CC0

My friend Ben Collver recently loaned me a book called A More Beautiful Question, by Warren Berger, that arose from some ideas in Warren’s blog. The book is specifically focused on questions that spark business innovations, and his key questions boil down to “Why, What If, and How Might questions that can’t be answered with facts”.

Earlier this year I wrote a post about questions to ask to really get to know people better. And I’m familiar with the value of Appreciative Inquiry type questions.

So I’ve started thinking whether there is some larger question set and question criteria that might, in a broad range of circumstances:

  • Identify the qualities that make for a good question
  • Identify the benefits of asking questions (and when asking a question is most effective and interesting)
  • Identify the types of questions that can best achieve these benefits

Over the past few weeks I’ve read everything I could get my hands on on this subject, and I think I’ve been able to synthesize the results down into something useful.

Building on and generalizing my earlier post, I think the 6 most important Qualities of a good question are:

  1. They elicit honest, thoughtful answers rather than clever, safe, automatic or socially acceptable ones.
  2. They are not so personal, so complicated, or so distressing to think about that they make people hesitant to answer, but they are personal enough, challenging enough, and provocative enough that they elicit sufficient consideration, focus and passion to produce interesting, revelatory and possibly ‘useful’ responses.
  3. They don’t (for most people) require an enormous (ie discouraging) amount of time and energy to ponder to come up with a considered response.
  4. They encourage follow-up questions and deeper explorations into the answers and reasons for them.
  5. The responses to them achieve one or more of the six Benefits listed below.
  6. Both the question and the responses help us learn, and provide knowledge, ideas, perspectives, insights, and/or a deeper relationship with someone, that otherwise wouldn’t have been achieved.

And the 6 most important Benefits of asking, thinking about and responding to high-quality questions are that they help us:

  1. Understand why things are the way they are
  2. Appreciate what we don’t know, need to know, and/or can’t hope to know
  3. Imagine novel alternatives
  4. Iteratively move an idea or process forward or deeper
  5. Learn important and/or interesting things about ourselves and others
  6. Encourage people to articulate and share what they know and care about

Building on Warren’s three types of questions to spark business innovation, I looked through several hundred examples of ‘beautiful’ questions that seemed to have the 6 Qualities, and discovered that they generally had similar syntaxes, depending on the purpose (and hence on the Benefit they potentially delivered). While a few offered more than one of the 6 Benefits, most were clearly designed to offer just one of the 6, so I’m listing them below, sorted by Benefit. Key Question Types:

  1. To understand why things are the way they are
    • Why is it this way? What’s really going on here?
    • Why isn’t it that way? Why has no one (else) done… ?
    • What’s working, and what’s not working, and why?
    • Tell me a story about when things went really well.
  2. To appreciate what we don’t know, need to know, and/or can’t hope to know
    • What’s the ‘problem’ we’re trying to solve (and is it real and do we really care about it)?
    • Tell me a story about when things went badly.
    • What do we need to find out?
    • What are the risks of not knowing… ?
    • Who else should we be talking with or involving in this?
    • What are we missing?
  3. To imagine novel alternatives and workarounds
    • What if we… ?
    • What if things were different in that… ? Can we imagine a better state and then figure out how to get there?
    • How might we… ?
    • How might we begin to… ? What would be the first step forward?
  4. To iteratively move an idea or process forward or deeper
    • What if we… ?
    • Is this really true? Is this really important and useful? Is it actionable?
    • What’s happening here?
    • What are we missing?
  5. To learn important and/or interesting things about ourselves and others
    • What would you do if… ?  Imagine that you… ? What if you could… ?
    • What do you wish… ?
    • What do you think/believe… ?
  6. To encourage people to articulate and share what they know and care about
    • What do you think about this?
    • How do you feel about this?
    • What are your instincts telling you about this?
    • What are we missing?

We should recognize that we’re not all good at coming up with good questions, and we don’t all have the imaginative and creative skills needed to come up with interesting or breakthrough answers. That means assessing who’s good at asking, and who’s good at answering certain types of questions, and drawing on those strengths — and building our own competencies.

Some of the above questions (eg What if we…?) may require great imagination to move beyond the incremental. And answering some of the other questions (eg How might we…?) may require a rare level of imaginative thinking to answer affirmatively at all. Poor questions and unimaginative or ignorant answers are of no value at all.

So here are a few scenarios where asking (and answering) questions might be of particular value, and some sample questions (of the appropriate Type) that might help. I’ve provided one scenario to address each of the potential Benefits (though obviously in any real situation more than one Benefit might be achieved by asking questions, so questions of many Types might be appropriate).

What’s particularly interesting is that sometimes just asking the (right) question confers some, or even most of, the value.

Scenario: You, and someone you love and also work with, have recently been at constant loggerheads, disagreeing about what’s true, what’s good and bad, and what to do. You’re constantly triggering each other, resulting in anger, fear, tears and withdrawal.

Some Benefit 1 Question Types: Why has this been happening? What’s behind it? What’s really going on here? Why aren’t things smooth and easy and any upsets effectively and dispassionately resolved? What are we handling well, and why? What are we not handling well, and why? Tell me a story of when we were at our best. [then you’d move on to Benefit 2-3 question Types]

Scenario: You and your family are entrepreneurs worried about climate change and the state of the economy. You are thinking of moving to a more sustainable place, but there seem practical obstacles to any of the ones you’ve identified, especially with your fledgling business.

Some Benefit 2 Question Types: What’s the real problem we’re trying to solve here? What do we need to find out to make an informed decision? What are the risks of moving, and of staying put, that we might not have contemplated? Who can we talk with to get a better understanding of the situation and options? What are we missing here?

Scenario: You just learned that a new competitor for your small business is using cheap overseas labour and exploiting poor environmental standards overseas to offer products and services possibly comparable to yours for half the price. You have to innovate or your business may not survive. [In such a scenario, different types of questions might help achieve all six Benefits, but I’ve just listed some Benefit 3 & 4 Question Types.]

Some Benefit 3 & 4 Question Types: What if we did nothing? How might we create products and services that no offshore competitor could match? Is it true that this new company threatens us; is there anything we can really do anyway? What if the new competitor didn’t exist; what would we do differently? What are we missing here?

Scenario: You and three other people with complementary skills have recently been approached about a potentially exciting new social enterprise opportunity. None of you know each other, and you’ve convened to see whether you think you might get along well together in such an operation, and personally.

Some Benefit 5 Question Types: (this is one of Ben’s brilliant questions, after seeing the work of a portrait photographer who often placed objects of note in her subject’s hands:) If you were getting a portrait taken, and the photographer asked you to hold something in your hand that told viewers something important about you, what would it be? (the famous Peter Thiel question:) What do you believe that no one else does? (and another famous question) What would you do if you knew you couldn’t fail? (and from my earlier post:) What do you wish you’d learned earlier in life? Of the people you’ve known in your life but fallen out of touch with, who would you most like to reconnect with, and why? If you had to write 200 words that summarize your worldview or philosophy of life, what would they be?  (and finally, a few adapted from Arthur Aron’s famous 36 questions:) Given the choice of anyone living in the world, who would you want as a dinner guest? What would you like to be renowned for? What are you most grateful for? What would you most like to know about your true self, or about your future? What’s on your bucket list, and what’s holding you back? If you knew you were going to die soon, what would you do with your remaining time?

Scenario: Your small enterprise is dealing with a new challenge, but at your meeting a small number are dominating the conversation, and others are clearly feeling unwilling or incapable of proffering their thoughts.

Some Benefit 6 Question Types: (for the wallflowers) What are your thoughts and feelings on this (“Let’s go around the circle.”)? What are your instincts telling you? What’s your sense of what’s going on here? Are we missing something?

There is, unfortunately, no straight-forward checklist of questions, and no easy way to know exactly what to ask. Everything depends on context. And the art of divining and asking the right question, and asking it the right way, can require almost as much imagination as answering the most wicked and challenging question. But perhaps a ‘roadmap’ like the one above might be useful in getting you started and pointed in the right direction. What’s your objective in asking a question in a particular context (ie what Benefits are you striving for)? What Types of questions might achieve that objective and achieve those Benefits? And, once you’ve arrived at what you think are the right questions, before you ask them, ask yourself if they meet the 6 Qualities of a great question.


(Thanks to Ben and to Tree Bressen for their contributions to this synthesis.)

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1 Response to May I Ask a Question?

  1. Chris Corrigan says:

    Lovely exploration Dave. For me contextbis certainly everything and the art of a good question is one that somehow just meets the moment where it’s at. I think you illustrate this well with your examples and conclusions.

    One characteristic of a good question on the personal level is that it comes from genuine curiosity and elicits surprise and delight in thenresponder. Those tend to build friendships quickly.

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