Liberating Structures

Wicked Questions

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You can spark innovative action while diminishing “yes, but…” and “either-or” thinking.

Wicked Questions engage everyone in sharper strategic thinking by revealing entangled challenges and possibilities that are not intuitively obvious. They bring to light paradoxical-yet-complementary forces that are constantly influencing behaviors and that are particularly important during change efforts.

Wicked Questions make it possible to expose safely the tension between espoused strategies and on-the-ground circumstances and to discover the valuable strategies that lie deeply hidden in paradoxical waters.



Articulate the Paradoxical Challenges That a Group Must Confront to Succeed




    Five Structural Elements

    1. Structuring Invitation
      • Ask, “What opposing-yet-complementary strategies do we need to pursue simultaneously in order to be successful?”
    2. How Space Is Arranged and Materials Needed
      • Groups of 4 to 6 chairs with or without small round tables
      • Paper for recording
    3. How Participation Is Distributed
      • Everyone involved in the work or topic is included
      • Everyone has an equal opportunity to contribute
    4. How Groups Are Configured
      • Individually
      • Small groups (6 people or smaller)
      • Whole group
    5. Sequence of Steps and Time Allocation
      • 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 mins)
      • 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 mins)
      • Each group selects its most impactful and wicked Wicked Question. All selected Wicked Questions are shared with the whole group. (5 mins)
      • Whole group picks out the most powerful ones and further refines the Wicked Questions. (10 mins)

    WHY? Purposes

    • Describe the messy reality of the situation while engaging collective imagination
    • Develop innovative strategies to move forward
    • Avoid wild or “bipolar” swings in policy and action
    • Evaluate decisions: Are we advancing one side or the other or attending to both?
    • Ignite creative tension, promoting more freedom and accountability as the discovery process unfolds

    Tips and Traps

    • 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
    • Use a variety of examples to make the paradoxical attributes accessible
    • Work in quick cycles, failing forward as you make the questions perfectly wicked
    • 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?
    • Avoid data questions that can be answered with more analysis
    • Invite participants to include others in making their questions more wicked
    • Draw on field experience; ask, “When have you noticed these two things to be true at the same time?
    • There are no quick fixes to Wicked Questions and you may need to return to the challenge periodically with additional rounds of Wicked Questions
    • Often a handful of people are very skilled at generating Wicked Questions: let them shine and inspire the rest of the group!

    Riffs and Variations

    • Use Wicked Questions to evaluate and launch Improv Prototyping, Ecocycle, and 25/10 Crowd Sourcing
    • When you have a strong Wicked Question, don’t stop there! Follow with 15% Solutions and 1-2-4-All to generate and sift ideas. Making progress on any one Wicked Question can shift what is possible.


    • For parenting advice: “How is it that you are raising your children to be very loyal/attached to the family and very independent individuals simultaneously?
    • For helping leaders discover how to include everyone in stopping infections: “As infection-control leaders, how is that you have stepped up and stepped back to help a unit take more ownership of prevention practices?
    • For 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?
    • For a functional department, such as HR, finance, legal, etc., to bring to light the Wicked Questions that capture the essence of the function in the context of the department’s organization
    • For surfacing personal Wicked Questions, for instance, with respect to one’s relationship to one other person or in connection to a personal challenge. For instance, “How is it that I am simultaneously dedicated to my work and being fully present for my family?


    Attribution: Liberating Structure developed by Henri Lipmanowicz and Keith McCandless. Inspired by professors Brenda Zimmerman (see Edgeware) and Scott Kelso (see The Complementary Nature).

    Source: Liberating Structures

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    • almost 5 years ago