WorkshopBank logo
Free WorkshopsNewsletterPricing
Request DemoSign in
WorkshopBank logo
Free WorkshopsNewsletterPricing
Request DemoSign in
Workshop Framework

Wicked Questions

Wicked Questions is a structured technique that helps groups surface the paradoxical challenges sitting at the heart of their strategy, culture, or way of working. Participants craft questions that hold two seemingly contradictory truths in tension, using the format "How is it that we [do X] and [do Y] simultaneously?"

45 minutes
6-40 people
intermediate
Get Full AccessSee What's Included

✓ Created by former KPMG & McKinsey consultants

Wicked Questions
  1. Home
  2. Workshops
  3. Wicked Questions

What You'll Achieve with the Wicked Questions Workshop

Real outcomes that transform your team

1

Participants gain clarity on complex challenges they face.

2

Fosters an environment for honest, open conversations.

3

Equips teams with a shared language for discussing tensions.

When to Use the Wicked Questions Workshop

Perfect for these situations and team challenges

When a team is grappling with conflicting priorities after a merger.

At the beginning of strategy discussions to identify underlying tensions.

How the Wicked Questions Workshop Works

A step-by-step breakdown of the workshop process

1Setup

Prepare the environment by introducing the Wicked Questions formula and relevant examples to guide participants in understanding the concept.

2Step 1: Introduce the Concept

Explain the nature of Wicked Questions, emphasizing the paradoxical truths that need to be managed rather than solved, and introduce the specific topic of focus.

3Step 2: Generate Questions in Small Groups

Participants form small groups to collaboratively craft Wicked Questions using the formula, encouraging them to engage deeply with the tensions present in their work.

4Step 3: Share and Sharpen

Groups post their questions for collective viewing, allowing participants to read, discuss, and refine the questions together, enhancing clarity and depth.

Key Topics Covered in the Wicked Questions Workshop

wicked questionsparadoxical challengesstrategy workshopgroup facilitationorganizational changeboth/and thinkingtension management

Ready to run workshops that create real change?

Two ways to get started:

Choose the path that works best for you

MOST POPULAR

Do it Yourself

Perfect for facilitators, leaders and managers

  • Instant access to sample frameworks
WorkshopBank logo

Team workshops, frameworks and templates you can modify in seconds with our AI

Copyright © 2026 - All rights reserved

Workshops
Premium WorkshopsTeam BuildingChange ManagementAction PlanningPrioritization ActivitiesRisk ManagementProcess ImprovementConference ActivitiesProject ManagementMotivational Activities
Company
PricingRequest DemoTerms of servicesPrivacy policyRefund policy
4

Encourages a shift from binary to integrative thinking in problem-solving.

During organizational change to articulate unspoken paradoxes.

When teams are frustrated with recurring issues that signal deeper polarities.

In planning sessions that produce unchallenging objectives and need revitalization.

Team Problems the Wicked Questions Workshop Solves

Say goodbye to these common team challenges

Binary thinking that limits strategic discussions.

Recurring conflicts that stem from unaddressed paradoxes.

Superficial objectives in planning that fail to address real challenges.

Frustration with unresolved tensions in team dynamics.

5Closing

Facilitate a reflection on the insights gained from the questions, emphasizing the importance of holding paradoxes consciously in ongoing work.

Get the Complete Workshop Framework
  • Experience AI customization firsthand
  • No credit card required
  • Start free trial

    Get a Demo

    See it in action with an expert

    • Watch AI customization live
    • Get personalized recommendations
    • Ask questions about your use case
    Book a demo

    Join 200,000+ facilitators and leaders who've transformed their workshops