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Wicked questions

Wicked Questions helps groups unlock deeper strategic thinking by embracing complexity and paradox. 
What Is Made Possible
  • Challenging either-or thinking: Wicked Questions reveal the tensions between seemingly opposing ideas that are both true and necessary, helping teams move beyond binary choices.
  • Surfacing hidden dynamics: They expose the paradoxical forces that shape behavior and decision-making (especially during change efforts) making the invisible visible.
  • Encouraging bold reflection: By asking provocative questions like “How is it that we are both… and…?”, participants confront contradictions in strategy, culture, or practice in a safe, constructive way.
  • Stimulating innovation: The tension in Wicked Questions sparks creative insights and new possibilities that wouldn’t emerge through conventional problem-solving.
  • Aligning action with reality: They help bridge the gap between espoused values and on-the-ground realities, leading to more grounded and effective strategies.

  • Time needed

    25 minutes 

  • Preparation

    1. Miro Board (online) or paper (F2F)
    2. Split into smaller groups (4-6 people) - prepare the rooms online in Teams

  • How to start

    1. Ask, “What opposing-yet-complementary strategies do we need to pursue simultaneously in order to be successful?”

  • Step-by-step and timing

    1. Introduce the concept of Wicked Questions and paradox. Illustrate with a couple of examples of Wicked Questions. Give the following template, “How is it that we are … and we are … simultaneously?” as the sentence to complete by inserting the two opposite strategies that are at play. (5 min)
    2. 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).
    3. Each group selects its most impactful and wicked Wicked Question. All selected Wicked Questions are shared with the whole group. (5 min).
    4. Whole group picks out the most powerful ones and further refines the Wicked Questions. (10 min)

  • Hints

    1. 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
    2. Use a variety of examples to make the paradoxical attributes accessible
    3. Avoid nasty questions that appoint blame or are unbalanced on one side. Here is an example of a nasty question: “How can we focus on our customers when we are forced to spend more and more time on the headquarters’ bureaucracy?”
    4. Avoid data questions that can be answered with more analysis
    5. Draw on field experience; ask, “When have you noticed these two things to be true at the same time?”

  • Examples of use

    1. Describe the messy reality of the situation while engaging collective imagination
    2. Develop innovative strategies to move forward

  • Link with other Liberating Structures

    Link with:

    1-2-4-All

    15% Solutions

    25/10 Crowd Sourcing

    Ecocycle planning

    Improv prototyping

     

  • Link to Liberating Structures page

    Wicked questions

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