Wicked Questions
A Liberating Structure that surfaces the adaptive challenges and paradoxes that undermine conventional strategic thinking. A Wicked Question holds two apparently contradictory truths simultaneously: 'How is it that we must [bold aspiration] AND we are currently [contradictory reality]?' Naming the paradox honestly and without resolution is more generative than pretending it doesn't exist. It opens up creative thinking about both horns of the dilemma.
How to run it
- 1
Introduce the concept of wicked questions: questions that hold genuine paradoxes without false resolution.
- 2
Give the template: 'How is it that we must [A] AND [not-A]?' Example: 'How is it that we must move fast AND be deliberate?'
- 3
Participants work individually or in pairs to craft 1–2 wicked questions relevant to the situation (5–7 minutes).
- 4
Share questions with the group. Read each one aloud.
- 5
Discuss: which questions feel most alive? Which generate the most productive tension?
- 6
Select 1–2 wicked questions for deeper exploration.
- 7
Use as input for ideation sessions or strategic discussion.
Tips
The wicked question is not a problem to be solved — it's a paradox to be worked with.
Resist the urge to resolve it.
The best wicked questions generate productive discomfort, not despair.
If the group finds a question easy to answer, it wasn't wicked enough.
Variations
Combine with TRIZ: use the wicked question as the starting point for 'what would guarantee failure?' Sequence with 1-2-4-All to build individual questions into a collective set.
Where it fits
Plan your next workshop with AI
Workshop Weaver helps you combine methods like Wicked Questions into a complete, timed agenda in minutes.
Try it freeMethod descriptions on Workshop Weaver are original content written by our team, based on established facilitation practices. This method was inspired by work from Liberating Structures.