Wicked Questions

Purpose

Wicked Questions surfaces the paradoxical tensions that groups live with but rarely articulate. By naming two seemingly contradictory truths that coexist, teams move beyond either/or thinking into creative both/and strategies. Use it when a group is stuck, polarised, or avoiding an uncomfortable complexity.

At a glance

• Group size: 6–40 people
• Duration: 25 minutes
• Difficulty: Intermediate
• Facilitation style: Structured
• Setting: Indoor / Remote-friendly

How to run

1. Introduce (2 min): Explain the format — a Wicked Question has the structure: "How is it that we are BOTH ___ AND ___ simultaneously?"
2. Individual brainstorm (3 min): Each person writes candidate wicked questions on sticky notes.
3. Small groups (10 min): In groups of 4–6, share questions and refine them. Aim for wording that makes everyone in the group nod uncomfortably — both halves must be true.
4. Whole group (10 min): Each small group presents its best wicked question. The full room discusses which ones capture the deepest tension.

Materials needed

• Sticky notes and markers
• Flip chart or wall space
• Timer
• Example wicked questions on a slide

Pitfalls & common mistakes

• Producing simple trade-offs instead of true paradoxes — coach groups to check that both halves are genuinely true simultaneously.
• Being too abstract — the best wicked questions are concrete and locally grounded.
• Trying to resolve the paradox immediately — the value is in naming and sitting with the tension.

Inclusion & accessibility

• The small-group phase allows quieter voices to contribute before plenary.
• Provide written examples so participants with different learning styles can grasp the format.
• In multilingual settings, allow small groups to work in their shared language and translate for the plenary.

Variations

• Wicked Questions + 15% Solutions: After surfacing the paradox, use 15% Solutions to identify actions that honour both sides.
• Wicked Questions Gallery: Post all questions on a wall and let participants dot-vote on the most resonant.
• Wicked Questions as opener: Use a pre-crafted wicked question as a provocative frame for an entire workshop.

When NOT to use this

Avoid Wicked Questions when the group needs clear, unambiguous direction quickly — the method deliberately surfaces complexity rather than simplifying it.

Source & further reading

Developed by Henri Lipmanowicz and Keith McCandless as part of Liberating Structures. See liberatingstructures.com.