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.
Cómo ejecutarlo
- 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.
Consejos
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.
Variaciones
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.
Casos de uso
Planifica tu próximo taller con IA
Workshop Weaver te ayuda a combinar métodos como Wicked Questions en una agenda completa y cronometrada en minutos.
Probar gratisMethod 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.