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Creative Questions to Facilitate Deeper Connections in Workshops E169

Tips to help facilitators ask creative questions and build deeper connections in your workshops

Creative Questions to Facilitate Deeper Connections in Workshops

Facilitators often hold the key to creating connection, curiosity, and collaboration in their workshops. But how do you engage participants on a meaningful level without overwhelming them? Crafting creative questions and using tools like metaphors or visual thinking can transform your sessions. When it comes to facilitating, it's not just about control; it’s about creating space for people to connect, share, and grow.

In this episode, I had the pleasure of speaking with the amazing

, a creative facilitator. Here are five actionable tips from our conversation to elevate your workshop facilitation using creative questions and human connection.

✨ 1. Use Metaphors to Spark Engagement

A great question can be like firing an arrow at the bullseye. Metaphors transport workshop participants into spaces they can relate to, making them more likely to open up and share. For example, instead of asking a basic “How are you feeling?”, you could reframe the question creatively:

  • "If your current state were a drink, what would it be? Energy drink? Matcha tea? Coffee?"

  • "What song would describe how you’re coming into this session today? Is it upbeat or mellow?"

These metaphor-based questions unlock responses beyond the default “good” or “bad,” giving participants a playful yet reflective entry point.

🔗 Related Resource: Check out insights into improving workshop facilitation with metaphors on Facilitation Makes Workshops Work - Myriam Hadnes.

🎨 2. Tap Into Visual Thinking

Visuals are powerful tools when words fall short. Facilitators can incorporate visual metaphors to structure conversations, making abstract concepts easier to grasp. For instance:

  • "If we were to create a visual metaphor for this workshop, what would it be? A garden where we plant ideas? A ship where everyone has a role to sail smoothly?"

  • "Imagine a method you're learning is a bird—what are the wings, what’s the body, and how does it fly?"

These visuals encourage participants to think strategically and synthesize concepts. Instead of relying on dense slides, focus on crafting visual prompts that allow participants to connect emotional and intellectual dots.

🔗 Need more ideas? Discover how visuals enhance collaboration on Facilitation - Make Meetings Fun and Productive.

🗣️ 3. Design Questions to Trigger Reflection and Dialogue

Not all questions are created equal. As a facilitator, your ability to craft thought-provoking questions determines the depth of the group discussion. To foster deeper connections:

  • Pose Reflective Prompts: "From 1–10, how would you rate your ability to convey ideas persuasively? Why that score?"

  • Elicit Creativity With Simplicity: "What was the last thing you created—whether a presentation or a new way to solve a problem?"

Encourage participants to answer in small groups or pairs. This intimacy drives honest conversations, turning a room of strangers into collaborators.

🔗 Learn more techniques to structure workshops effectively by visiting Liberating Structures Facilitation Tools.

🪄 4. Magic and Play as Connection Tools

Facilitators who bring diverse skills into their workshops, such as magic tricks or gamification, create a delightful shock factor that builds trust. Imagine starting a session by asking:

  • "What’s something quirky about you that has nothing to do with work?"

  • Or incorporate an actual card game, like Dixit, as a way to break the ice and explore emotions metaphorically.

Magic and games create cohesion in the group by engaging them at an emotional level, opening pathways for rich, meaningful exchanges.

🔗 For more ways to integrate play into sessions, explore Creative Brainstorming Games.

🚀 5. Refocus Content to Create Space for Stories

Think about your favourite workshops or presentations. Chances are, they struck a chord because they shared relatable stories. As Brené Brown notes, being a “story steward” means valuing and holding space for the stories participants share. Here’s how you can integrate stories into your facilitation:

  • Encourage Anecdotes: Instead of diving straight into theoretical concepts, ask participants, “Can you share a moment where you felt deeply creative or inspired?”

  • Personal Sharing as a Gateway: Lead by example. When you share a personal story, it encourages participants to do the same, fostering a safe and vulnerable space.

Workshops are about people, not content. Striking a balance between providing information and enabling interactions is critical. Prioritise participant experiences over a slide-heavy presentation.

🔗 For more methods to encourage reflective storytelling, see Why Creativity is Important in Technology.

Conclusion

Facilitation isn’t about controlling a session; it’s about creating the conditions for magic to happen. Whether it’s through creative questions, visual metaphors, magic, or storytelling, facilitators have the superpower to guide participants into meaningful connections. These connections turn good workshops into unforgettable ones.

Curious to build your facilitation toolkit? Remember: design engaging questions, make space for reflection, and think beyond the session content.

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Recommended Books for Facilitators:

  • "The Art of Gathering" by Priya Parker

  • "Daring Greatly" by Brené Brown

  • "I Didn’t Do the Thing Today" by Madeleine Dore

Explore these tips, integrate them into your next session, and watch your workshops come to life!

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