Wicked Questions

Articulating the paradoxical challenges that a group must confront to succeed

Overview

A wicked question is used to elicit a thought-provoking examination of the sometimes paradoxical nature of the challenges which a group have to tackle. E.g. “How come we are simultaneously integrated and autonomous?” This approach shines a light on conflicting circumstances and unearths possibilities that are essential for a successful outcome, even if they are not intuitive. A sense of freedom and accountability is brought about by the creative tension each participant experiences as the discovery process unfolds.

 

How to use it

A wicked question is used to elicit a thought-provoking examination of the sometimes paradoxical nature of the challenges which a group have to tackle. E.g. “How come we are simultaneously integrated and autonomous?” This approach shines a light on conflicting circumstances and unearths possibilities that are essential for a successful outcome, even if they are not intuitive. A sense of freedom and accountability is brought about by the creative tension each participant experiences as the discovery process unfolds.

How to apply it

Start:
  • Ask a question like “What opposing yet complementary strategies do we need to pursue simultanously in order to be successful?”. Use a variety of examples to make the paradoxical attributes accessible, such as in the examples reported below:
  • In parenting advice, “How is it that your children are loyal/attached to the family and are very independent agents in the world?
  • Managing large global operations, “How is that we are always and never the same… an organization with a singular global identity and we are uniquely adapted to each local setting?  How is it that we are integrated and autonomous?
Setting:

Participants sit around a table or in a circle. Work is first carried out individually, then in small groups (less than six) and then the whole group works together.

Materials:

Notepad.

Time/Steps:
  • 5 minutes: Each person generates pairs of opposites or paradoxes at play in their work using the Wicked Question format.
  • 5 minutes: Participants then divide into small groups, and share their most wicked questions.
  • 10 minutes: As a whole group, participants choose the most effective pairs and hone the WQ further.

How to adapt it

Use to evaluate and launch Improv PrototypingEcocycle Planning, and 25/10 Crowd Sourcing.

Tips

  • Make both sides appreciative, “How is it that we are ____ and ____ simultaneously?”
  • Work in quick cycles, learning from mistakes as you make the questions perfectly wicked.
  • Avoid questions that may suggest judgment or be unbalanced on one side.
  • Avoid data questions that can be answered with more analysis.
  • Draw on field experience; ask “When have you noticed these two things to be true at the same time?”
  • There are no quick fixes and you may need to return to the challenge periodically.
  • Everyone should be given an equal opportunity to contribute, yet use a peer to peer model if skilled WQ participants are present.

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