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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Materials:
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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 means: we track where an exercise has been observed in public sources. We do not claim to know who created it, or how popular it is.
- No efficacy claims: appearing in this library is not a claim that the exercise is proven effective. Facilitator judgment and context decide whether it works for a given room.
- Corrections: if you have evidence of an earlier or more accurate source, read our methodology and trust boundary and tell us.