Wicked Questions

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.

Examples

• 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?”