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Questioning the Questions

I know when my fascination with questions started. I was watching a video in a training session as a young adult. On screen, a skilled facilitator was facing resistance from a man whose understanding of the world didn’t jive with the lived experience of one of the other group members. “What would it mean if what he said was true?” the facilitator asked the resister. Opening up to the possibility and realizing the pain behind it, the resister broke into tears.


“I need to get myself some of THOSE questions” I said to myself. If questions are crowbars to create space for change, I coveted the longest ones.


It’s worth remembering in all kinds of organizational change - our good efforts will have limited impact if the questions we’re framing keep us in the status quo. In Fran Peavey’s landmark work on Strategic Questioning, she recalls the story of the Emperor’s New Clothes. The Emperor and the adult citizens were blinded by assumptions and habits of thinking, but one child’s question – “Why doesn’t he have anything on?” – opened up the possibility for new relationships and possibilities for everyone. Fran imagines a fruitful set of follow-up conversations busting other paradigms: “What kept us from asking this question? What allowed the child to ask this question? How might we move towards wiser government? Could we all go without clothes?”


As we turn the page on the year with all the possibilities it represents, how do we set ourselves up to be asking the longest crowbar questions about our future? I’d recommend listing all your questions, and then using a few techniques from “The Art and Architecture of Powerful Questions” to give them more heft.


  • Architecture: Find language or constructs that are narrow (close-ended questions, or questions often starting with who/when/which) and substitute constructs that are broader (questions starting with how, why, or what might)

  • Scope: Try recrafting the question with a larger scope – for example, moving from “How can we increase donations?” to “How can we create an environment where people are excited to share their gifts?”

  • Fresh Perspective: Powerful questions challenge assumptions. Consider what assumptions are embedded in your questions - for example, “How can we serve more students?” assumes a particular kind of relationship with students. Then, experiment with alternatives.

  • Energy: Powerful questions generate energy and focus. Sometimes this means shifting from a focus on deficit to a focus on possibility – e.g. from “Why aren’t we being successful?” to “How can we work together better?” and “What do we need in order to bring our whole selves to this mission?”

I hope – as we all do – that 2022 surfaces some robust and life-giving answers. But I also hope that in all our groups, it gives us an opportunity to practice redefining our questions.



Question mark on misted window

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