Liberating Structures

Wicked Questions

Articulate the paradoxical challenges that a group must confront to succeed. Wicked Questions create a clear, shared understanding of the essential tensions your group must navigate—helping teams embrace “both/and” realities instead of getting stuck in false either/or choices.

learn how to run it download free PDF

Wicked Questions

Articulate the paradoxical challenges that a group must confront to succeed.

Reveal

In person & Online

Group & Solo

25 min

What is made possible - What it unlocks

Wicked Questions make it possible for groups to name contradictions that usually stay hidden or uncomfortable. Instead of choosing one priority over another, teams learn to hold both sides simultaneously. This unlocks creativity, deeper insight, and entirely new ways forward. Paradoxes become engines for innovation rather than sources of confusion.

When to use it

When a group is caught between competing forces or values
To clarify strategic tensions (e.g., “control and autonomy”)
At the beginning of planning processes to surface assumptions
When polarization drains energy
To navigate complex, uncertain situations that have no single “right” answer
When a team needs to expand its thinking and unlock new options
For uncovering deeper systemic dynamics driving conflict or stagnation

🛠️ The five design elements of Wicked Questions

Each Liberating Structure consists of five simple design elements to make participation possible for everyone. By shaping these elements with care, you move beyond rigid control or chaos and create space for people to contribute, listen, and co-create.

1. The Invitation
2. Setup & Materials
3. Participation Flow
4. Group Configuration
5. Sequence & Timing

1. The Invitation

How you frame the purpose or question that sets the focus and energy of the group.

Invite participants to explore a core paradox the group must navigate to succeed (opposing-yet-complementary strategies)

Example:

“How is it that we must pursue X and also Y—even though doing both seems contradictory?”

2. Setup & Materials

The arrangement of space and which tools or resources are needed to support interaction.

Space for small-group collaboration
Sticky notes or index cards
Flipcharts or digital canvases
Markers
The context or challenge clearly stated
Optional: “Paradox Principles” overview to keep thinking expansive

3. Participation Flow

Who gets a voice and how everyone is actively included in the process.

Everyone identifies opposites, drafts Wicked Questions, and refines them in groups.
No one owns the paradox; the group co-creates it.

4. Group Configuration

How people are arranged (alone, small groups, or all together) and how this shifts during the activity.

Individuals → pairs → small groups → whole group refinement.

5. Sequence & Timing

The step-by-step flow of the activity and the time given to each step to keep energy and focus.

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)
First alone then in small groups, each participant generates pairs of opposites or paradoxes at play in their work using the Wicked Question format. (5 min)
Each group selects its most impactful and wicked Wicked Question. All selected Wicked Questions are shared with the whole group. (5 min)
Whole group picks out the most powerful ones and further refines the Wicked Questions. (10 min)

Total time: 25 minutes

Online version

Adapted for virtual use, with the same impact

All the steps are the same as described above.

Prepare breakout rooms for small groups to work in.

Total time: 25 minutes

Solo version

Adapted for individual use and personal development

Step 1 – Identify Opposites: (7 min)
Think about your challenge. What important opposites or contradictions do you notice? What competing demands pull you in different directions? List 8-12 pairs of opposites (e.g., “control / freedom,” “speed / quality,” “structure / spontaneity,” “ambition / contentment”). Don’t judge them yet—just notice what tensions are present.

Step 2 – Combine into Meaningful Pairs: (7 min)
Review your list of opposites. Which pairs feel most alive or important right now? Which tensions really matter for your success? Mark 3-5 pairs that have the most energy or significance. For each pair, check: Are both sides genuinely valuable? Would choosing only one side create problems?

Step 3 – Draft Wicked Questions: (7 min)
For each of your 3-5 key pairs, write a Wicked Question using this format: “How is it that I must [first opposite] AND [second opposite]?” For example: “How is it that I must stay focused on one goal AND remain open to new possibilities?” or “How is it that we must move quickly AND build things that last?” Write out the full questions.

Step 4 – Refine & Select: (5 min)
Read your Wicked Questions aloud to yourself. Which one creates the most energy, discomfort, or possibility? Which question, if you could hold it well, would unlock the most? Choose your most generative Wicked Question and refine the wording until it feels precise and powerful. Test it: Does this paradox expand your thinking rather than narrow it?

Step 5 – Integration: (3-5 min)
Sit with your chosen Wicked Question. Reflect: What becomes possible when you stop trying to resolve this tension and instead learn to navigate it? What would change if you gave both sides equal value? How might holding this paradox shift your next decisions or actions?

Total time: ~30 minutes

Order now

All Liberating Structures in 1 e-book

All Liberating Structures (44!) including explanations, visual step-by-step guide, and worksheets in a handy workbook for € 11,-

Simple methods for big changes
Have interactions that truly matter
Build a culture of innovation step by step
Involve and activate everyone in the group

Show the e-book!

Proven over decades

🧠 Why it works

Liberating Structures are not magic tricks—they work because they tap into how people naturally think, connect, and collaborate. Each structure is carefully designed to unlock participation, spark creativity, and build trust, using principles grounded in social science and human interaction.

Attribution: Liberating Structure developed by Henri Lipmanowicz and Keith McCandless. Inspired by professors Brenda Zimmerman and Scott Kelso.

Paradox Mindset

Helps groups move beyond either/or thinking, vital in complex systems where opposing forces coexist.

Cognitive Flexibility

Reduces the brain’s tendency to oversimplify, allowing people to hold multiple truths at once.

Social Sense-making

Reveals unseen assumptions and competing values that shape group behavior.

Generative Tension

Holding opposites without collapsing them stimulates creativity and new possibilities.

Riffs and Variations

Start with creative constraints to learn this structure and then... go liberate yourself and try some variations.

Warm-up paradoxes
Start with simple, low-stakes tensions (“How can we be fast and thorough?”) to help participants get the feel.
List of things to be true
Start with making lists of activities or statements that participants think are both true. Then, let them connect opposing truths.
Pole cards
Write each pole on a separate card and physically place them apart. Makes the tension tangible.
Gallery refinement
Post Wicked Questions around the room so participants can mark clarity, resonance, and missing elements.
Role-based versions
Ask people to craft questions from the perspective of different roles (team lead, client, frontline).
Three-round sharpening
Invite participants to rewrite their Wicked Question three times for increasing precision.

Tips

Lessons learned from other facilitators.

Express both poles appreciatively
Formulate both sides as desirable truths: “How is it that we are ___ and we are ___ at the same time?”
Use examples to make paradoxes tangible
Offer several real, concrete examples so people understand what a productive paradox looks like.
Work in fast, imperfect cycles
Keep drafts moving. “Fail forward” until the question becomes truly wicked.
Invite others into the sharpening
Encourage participants to co-shape each other’s questions — it strengthens clarity and ownership.
Draw from real field experience
Ask: “When have you actually seen both of these things be true at the same time?”
Return to the paradox over time
Some tensions need multiple rounds. It’s normal to revisit and refine.
Let skilled people model it
A few people often “get it” quickly — let them inspire the group with examples.

Traps

Don't make the same mistakes.

Don’t frame poles as opposites or criticisms
A Wicked Question explores two positive intentions, not complaints, frustrations, or blame.
Don’t use ‘nasty questions’
Avoid formulations like: “How can we focus on customers when headquarters keeps drowning us in bureaucracy?” These appoint blame and shut down curiosity.
Don’t turn it into a data question
Questions that can be solved with analysis (“How many clients…?”) are not Wicked Questions.
Don’t smooth out the tension
Avoid wording that eliminates the paradox or makes it one-sided.

Try it with…

The real power of Liberating Structures emerges when you combine them into "strings." Link different structures together to build on insights and create more powerful results. Here are some nice combinations:

1-2-4-All: Generate initial tension pairs
Min Specs: Define minimum requirements for navigating the paradox
Ecocycle Planning: Place each side of the paradoxes on the Ecocycle
Purpose-to-Practice: Connect paradoxes to deeper organizational purpose
Critical Uncertainties: Combine tensions with future scenarios
Conversation Café: Explore emotional reactions to the paradox

Field stories

To get to know Liberating Structures without having used them yourself, it helps to see familiar situations from real-life practice. Chances are that you or your team have faced one of these challenges before. Discover how to approach these kinds of situations in a fresh and engaging way.

Choose a post type and select posts.