Wicked Questions

Choose this exercise

Purpose: Articulate paradoxical challenges that require holding two opposing strategies or needs at the same time.

Use it when: Use when a team is stuck in either-or debate, pendulum swings between extremes, or false compromises on strategic priorities.

Skip it when: Skip when the problem is a straightforward technical issue requiring data gathering or a single factual decision.

Group arrangement: Solo reflection, then small breakout groups of 3 to 6 people (for group sizes that do not divide into 4 to 6, use groups of 3 or 7), concluding with a plenary.

Timing: Matches the 25-minute baseline sequence from Liberating Structures sources.

Materials and tools

• Index cards or scratch paper (2 to 3 sheets per participant)
• Pens or markers (1 per participant)
• Flipchart or whiteboard and markers for plenary recording
• Optional printed copies of the Wicked Questions Guide Card (1 per table or small group)

Before participants arrive

1. Arrange seating into clusters of 3 to 6 chairs around tables or open circles. Form groups of 3 or 7 if group size does not divide cleanly into 4 to 6.
2. Write the framing template on a visible board: 'How is it that we are [Side A] and we are [Side B] simultaneously?'
3. Write one clear neutral example on the board.

Say this to open

Often our hardest challenges cannot be solved by picking side A or side B. In this session, we will name the opposing forces that are both necessary for our success. We will use the question template: 'How is it that we are doing X and we are doing Y simultaneously?' Both sides must be valued and needed. Take a moment to think about the tension in our current work.

How to run it

1. Introduce paradox and template 5 minutes

   Explain the concept of paradoxical tensions versus simple trade-offs. Point to the template on the board: 'How is it that we are _____ and we are _____ simultaneously?' Share a neutral example: 'How is it that we provide standard, consistent service and offer customized, flexible care simultaneously?' Emphasize that both sides must be appreciative and necessary, avoiding blame or sarcasm.

2. Draft solo and share in small groups 5 minutes

   Participants spend 2 minutes working silently alone to write 1 or 2 paradoxical questions on scratch paper. For the remaining 3 minutes, participants take quick turns reading their drafted questions aloud in their small groups without debating them.

3. Select one question per group 5 minutes

   Each small group discusses the questions read aloud and selects the single most wicked, impactful question capturing their genuine tension. One person writes it clearly on an index card or large post-it note.

4. Refine and harvest with whole room 10 minutes

   Facilitator collects or reads the selected question from each group (expecting 1 to 6 questions depending on group count). The room tests each question against two criteria: both sides must be essential, and neither side assigns blame. The group suggests minor wording edits to sharpen the paradox. Record the final refined questions on the plenary board.

Debrief questions

• Looking at our final questions, which tension do we tend to over-correct or swing between?
• What becomes possible if we treat both sides of this tension as equally necessary?
• Where in our upcoming decisions can we use these questions as an evaluation checklist?

Finished output: A shared list of 1 to 6 refined paradoxical questions articulating core strategic tensions the group must navigate together.

Remote

Display the question template on a shared presentation slide or digital whiteboard. Run Step 1 in plenary. Run Step 2 with 2 minutes of silent solo typing, then send participants to breakout rooms of 3 to 6 people for 3 minutes just to read drafts aloud. In Step 3, keep them in breakouts for 5 minutes to debate and select their top question, posting it to a shared plenary document. In Step 4, return to the main room for 10 minutes to refine wording live on screen and debrief.

Hybrid

Form in-person small groups and separate remote small groups to ensure natural audio discussion. Remote groups post their selected question into a shared digital document; in-person groups write theirs on cards that a facilitator mirrors into the document. Facilitate plenary wording refinement and debrief by alternating spoken contributions between room microphones and remote audio.

Access and participation choices

• Participants may draft questions by writing, typing, speaking with a peer, or simply considering them quietly.
• In small groups, participants may pass on reading their solo draft aloud and choose instead to help select and polish a peer's question.
• Provide written sentence starters on printed table cards or digital slides.

If the session gets stuck

A participant writes a complaint or blame question, such as 'How can we do good work when management cuts our budget?'

Remind the room that both sides must be legitimate organizational needs. Help reframe it appreciatively: 'How is it that we maintain rigorous quality standards and strictly control operating costs simultaneously?'

A group brings forward a factual question that can be answered by data or research alone.

Ask the group: 'What is the underlying value in tension here?' Help them identify the two competing priorities behind the request for data.

Terms used here

• Wicked Question: A question articulating a paradox by framing two opposing-yet-complementary strategies that must be addressed at the same time.
• Paradox: A situation where two seemingly contradictory principles, needs, or truths coexist and are both necessary.