Wicked Questions
Wicked Questions is a prompted conversation exercise for relationship mapping: it helps participants build useful connections and understand how people, roles, or ideas relate.
How to run it
- First alone then in small groups, each participant generates pairs of opposites or paradoxes at play in his or her work using the Wicked Question format. 5 min.
- Each group selects its most impactful and wicked Wicked Question. All selected Wicked Questions are shared with the whole group. 5 min.
- Whole group picks out the most powerful ones and further refines the Wicked Questions. 10 min.
- Describe the messy reality of the situation while engaging collective imagination
- Develop innovative strategies to move forward
- Avoid wild or “bipolar” swings in policy and action
- Evaluate decisions: Are we advancing one side or the other or attending to both?
- Make sure that participants express both sides of the paradox in an appreciative form: “How is it that we are and we are simultaneously?” and not in opposition of each other
- Make sure that participants express both sides of the paradox in an appreciative form: “How is it that we are \\\\ and we are \\\\ simultaneously?” and not in opposition of each other
- All methods All authors IAF Library Library Wicked Questions 247 123 You can spark innovative action while diminishing “yes, but…” and “either-or” thinking.
Run this exercise live
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Prompts to use +
First alone then in small groups, each participant generates pairs of opposites or paradoxes at play in his or her work using the Wicked Question format. 5 min.
Each group selects its most impactful and wicked Wicked Question. All selected Wicked Questions are shared with the whole group. 5 min.
Whole group picks out the most powerful ones and further refines the Wicked Questions. 10 min.
Develop innovative strategies to move forward
Evaluate decisions: Are we advancing one side or the other or attending to both?
Make sure that participants express both sides of the paradox in an appreciative form: “How is it that we are and we are simultaneously?” and not in opposition of each other
Run this with your AI assistant +
Works with Claude, ChatGPT, Gemini, or your own local model: paste this prompt and your AI will co-facilitate this exercise with you.
Adapt this exercise for my exact room. Exercise: Wicked Questions. Readiness: Publishable Draft. Core moves: First alone then in small groups, each participant generates pairs of opposites or paradoxes at play in his or her work using the Wicked Question format. 5 min.; Each group selects its most impactful and wicked Wicked Question. All selected Wicked Questions are shared with the whole group. 5 min.; Whole group picks out the most powerful ones and further refines the Wicked Questions. 10 min.; Develop innovative strategies to move forward. Return a concise facilitator script with timing, wording, safety notes, and remote/in-person adjustments.
Origin unverified
- Where we observed it: The strongest current observations come from Liberating Structures; aggregators are listed as additional observations, not origin proof. (2 sources observed, including Liberating Structures, SessionLab.)
- What that does and does not claim: we track where an exercise has been seen in public sources. We do not claim to know who created it, how popular it is, or that it works. See methodology and trust boundary.
- Corrections welcome: if you have evidence of an earlier or more accurate source, tell us.