Powerful Questions

I came to know about powerful questions from Bill Brewer, a colleague of Peter Block. Bill had come to our institution to present a workshop on Block’s Six Conversations. He described powerful questions as having three attributes.

They are personal. This is not to say they are personally invasive, only that when the question is posed, it is unmistakably clear that the question must be considered on a personal level.

They are ambiguous. The ambiguity removes the option to download past thoughts or opinions or theories. The answer is not obvious. The question causes a stop in the normal flow of self-talk. With no obvious quick response available, something inside has to be unpacked in order to frame, or begin to frame, a response.

They are anxiety provoking. Not in the sense of putting one in harm’s way, but to the extent that the answer is not obvious one has to navigate the waters of uncertainty and ambiguity in order to begin to make meaning of the question. There is risk.

Taken together, the three attributes are, in the words of Henry Real Bird, the poet-laureate of Montana, an invitation to think, to move along in thought.

These attributes draw us into asking what experience we expect from considering the question that has been posed, what we expect to learn from the question, how much risk we are willing to take in the course of moving along in thought, and how much the experience of those around us matters.

Powerful questions can be philosophical and complex. They can also be simple in and of themselves, and derive their power from the duration of reflection we give them. Some pull us down paths already traveled but look at the landscape from a different point of view.

Powerful Questions for Individuals

My coach, Katherine Jackson, asked me, “What brought you to now?” “What do you mean by ‘now’” I asked. “Whatever you take it to mean” she replied. She was not being coy.

I realized she was not asking me to simply recount the factual details of a journey. The more I thought about the question the more it brought me to the realization that I was being asked to consider the culmination of all the thoughts and experiences I had ever had, the manner in which they had intertwined with each other, and how and why they had produced the me that was here right now.

Was the now of my life the only possible result of this train of thoughts and experiences? Could I have interpreted them differently? Worked from different deep assumptions? Responded differently? Grown into a different person?

I struggled with the meaning of “now”? Caught between the past and future, is now just a point of transition? A forward reflection of the past and a requirement for the future? Blissfully disconnected from both the past and the future?

The past is fixed but the future is whatever possibility we imagine it to be. Can a reflective journey through the past that delivered me into the now paradoxically free me from reliving the past and open way into future possibilities? Can the totality of all the neuronal activity of my brain be leveraged into new insights and understandings, be burned into my brain as new pathways, and become the hardwiring we tap into without conscious awareness?

Powerful Questions for Organizations

What can powerful question do for organizations, if anything? “What brought us to now?” Can the possibilities for creating shift in individuals be adapted for organizations?

The answers, I think, are no and yes respectively. “No” insofar as organizations have no ability think and reflect separate from the people who populate them. “Yes” insofar as the ability and willingness of persons to each engage in the heavy lifting of inner work and choose to place the fruits of that labor in the community’s awareness. There is, I think, a prerequisite for using powerful questions in organizations.

Making Time to Think

Nancy Kline’s marvelous book, “Time to Think” makes the observation that the common complaint that people ought to do better thinking is rarely met with the intentional practice of making time and place for thinking, actively encouraging people to think, and placing a high value on thinking. In all to many organizations thinking is something one is expected to do in copious amounts so long as it does not interrupt work. Thinking at the expense of productivity is frowned upon in lean continuous improvement circles.

Communities of Learning, Thinking, and Practice

Some years ago I sent an invitation to all the managers and leaders who had attended a week-long course on leadership that I taught. It was a real invitation. I described taking the time to think by considering a question. I let people know that there was a price for attending;  people would have to give up problem solving and negotiating self interest; they may find themselves feeling vulnerable; they should be willing to take some risks (even as the risks were unnamed). I told them I would honor their option to say no and pass. Finally, I let them know I really hoped they would attend.

Of the 120 invitations I sent, close to 90 people responded, 75 said they wanted to attend, 45 said they would attend. Thirty-five people showed up on a Friday afternoon at 4 PM.

I asked one question: “What question inspires engagement in you?” I emphasized that the answer to the question was itself a question. They were not to iterate what inspired engagement but to identify the question that inspired engagement.

We began with personal reflection. Five minutes of silence. People then broke into small groups of three (very difficult to hide in a group of three). They could leave the room, wander the halls, remain at their table, anything of their choosing. They were to share their thoughts in the manner that worked for their group of three.

We reconvened about 25 minutes later. I posed a four part question: “What struck you about the question I asked, what struck you about your experience thinking about the question, what struck you about your small group conversation, and what struck you about the question that, for you, inspires you?”


I was not really interested in the actual questions that inspired them. They would be personal, and to place an expectation in the room that they had to give voice to them was not the work I had hoped the original question would provoke.

I finished (about 45 minutes late, almost everyone still there) with an invitation to offer a closing thought. It was an invitation, telling each person s/he could say no and pass. In one way or another, to greater or lesser degrees, people said they felt different. The afternoon had been hard work, and many said they had to unpack some inner parts of themselves to see the original question through to the end.

A decently large group of people returned to work on Monday with a different view of their own leadership. They now had a group of colleagues with whom they could share their thinking. They understood the people who looked to them for leadership differently. They were, by their own accounts, different people, willing and able to have different conversations in the workplace, willing to ask a few questions of their own, curious to explore leadership while they did their jobs of moving the business of the business forward.

Powerful Questions

I am not known for having original thoughts or ideas. I tell people I fully expect to die without ever having one. So, I do not feel the burden to compose powerful questions myself. I keep a journal, and write down any I hear. Then I plagiarize them to no end to adapt them to the circumstances in which I find myself.

If you know of any powerful questions, or have a gift for thinking of powerful questions, leave a comment and share.


3 thoughts on “Powerful Questions

  1. First, you ask for powerful questions. Here’s one I find entertaining: Where is the dividing line between “me” and “them”?

    Thanks, Bill, for your eloquent and interesting consideration of “time to think”. Some years ago there was an editorial in (I believe) the New Yorker magazine. As I recall, it imagined an art gallery wherein on the end wall of one wing hung a painting of a nineteenth century British magistrate in India and on the end wall of the opposite wing hung a painting of a businessman of the 21st century. The magistrate had received a single mail, sent by long voyage from England. He strolled the Ganges considering his reply – giving it due consideration knowing the reply would not arrive for weeks hence. In contrast, the businessman awoke to a hundred new emails from the night before. He considered how he could reply to them – let alone consider them – before the next night brought another hundred.

    The notion of “time to think” is in transition. Finding integration of the facts alone is daunting enough. Finding time to consider “what’s it all mean” is a struggle. Yet we take the two journeys concurrently: the one of the outside, the one of the inside.

  2. Bill, I know you to be both a thoughtful and decisive person – capable of exploring, judiciously, both the known and unknown. It is in the unknown that our greatest opportunities for change really lie. The ability to expeditiously coach leaders through this uncharted territory is your gift. I look forward to reading (and tweeting) more of your posts. Best regards. Gail

  3. I started to question the question of engagement. A precursor to movement or a small step? I really started to invest when I asked myself ,”What is the driver of your passion?” One may have a singular response or various at that, but passion is a consuming fire, I believe with change it may dim, but never goes out.

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