How One Xec Ignite Change and Deepen Team Insight
In the world of organisational transformation, the questions we ask are just as important as the answers we seek. At One Xec, the art of asking the right kind of questions – specifically, beautiful and wicked questions – is at the heart of facilitating meaningful change. Here’s how these two types of questions work, why they matter, and how you can use them to drive insight and action within your own teams.
What Are Beautiful and Wicked Questions?
Beautiful question: Coined and popularised by Warren Berger, is an open, curious, and often aspirational inquiry that invites reflection, exploration, and positive change. These questions are designed to unlock creativity, empathy, and possibility.
Purpose:
- Inspire new thinking and fresh perspectives
- Encourage honest, open conversation
- Help people imagine what could be
- Surface hopes, values, and aspirations
Characteristics:
- Open-ended and non-judgmental
- Invites curiosity and exploration
- Focuses on possibilities and positive change
- Encourages empathy and understanding
Wicked question: Originates from the “wicked problem” concept by Horst Rittel and Melvin Webber. It is a provocative inquiry that exposes paradoxes, tensions, or dilemmas within a system or team. These questions challenge people to hold two seemingly opposing truths at once, revealing complexity and encouraging deeper dialogue.
Purpose:
- Surface hidden assumptions, contradictions, and tensions
- Help groups navigate complexity and uncertainty
- Encourage systems thinking and collective sense-making
- Move beyond either/or thinking
Characteristics:
- Highlights paradoxes or competing priorities
- Often uncomfortable or challenging
- Forces people to grapple with complexity
- Encourages both/and (rather than either/or) thinking
How One Xec Use Beautiful Questions to Facilitate Change
Through my systemic team and Elephant Rider learning I believe that better questions lead to better listening, deeper understanding, and ultimately, stronger cultures. Here’s how beautiful questions, in particular, are used to spark transformation:
Signal What Matters
The questions leaders and facilitators ask communicate priorities and values. Beautiful questions focus on emotional experiences and aspirations, creating space for people to share what truly matters—moving beyond surface-level opinions.
Unlock Emotional Drivers
Change is often driven more by emotion than logic. Beautiful questions help surface underlying feelings—such as anxieties, hopes, and motivations—that influence how people respond to change. This allows leaders to proactively shape the emotional landscape, fostering buy-in and engagement.
Create Psychological Safety
By encouraging vulnerability and openness, beautiful questions help establish psychological safety. When people feel safe to share their thoughts and emotions, trust grows and teams are more willing to embrace new ideas and behaviours.
Guide Transformative Conversations
Rather than prescribing solutions, beautiful questions invite teams to explore possibilities, reflect on past successes (“bright spots”), and co-create actionable steps forward. This participatory approach increases ownership and commitment to change.
Support Both Rational and Emotional Sides
Drawing on the “elephant and rider” metaphor, beautiful questions address both the logical (rider) and emotional (elephant) aspects of decision-making. Facilitators use these questions to align rational plans with emotional motivation, increasing the likelihood of lasting change.
Beautiful vs. Wicked Questions: A Quick Comparison
| Aspect | Beautiful Question | Wicked Question |
| Purpose | Inspire, open possibilities | Expose and explore paradoxes/tensions |
| Tone | Curious, positive, aspirational | Provocative, challenging, complex |
| Focus | What could be? | How do we hold two truths in tension? |
| Outcome | New ideas, empathy, creative solutions | Deeper understanding, systems thinking |
| Example | “What if…?” | “How can we be both X and Y?” |
How to Action: Using Beautiful and Wicked Questions in Your Team
Start Meetings with a Beautiful Question
- Open your next team session with a question like, “What would it look like if we felt energised every time we experience change?” This sets a tone of curiosity and possibility.
Explore Tensions with Wicked Questions
- When facing a complex challenge, pose a wicked question: “How can we deliver quickly and maintain our quality standards?” Use this to spark deeper dialogue and creative problem-solving.
Encourage Reflection and Sharing
- Give team members time to reflect on their answers, then invite open sharing. This builds empathy and psychological safety.
Co-create Action Steps
- Use insights from these questions to co-design practical next steps. For example, if a beautiful question surfaces a desire for more connection, brainstorm rituals or routines to foster this.
Revisit and Reframe Regularly
- Make asking beautiful and wicked questions a regular practice. Over time, this will help your team navigate both opportunities and complexities with greater insight and resilience
Beautiful questions open doors to new thinking and positive change, while wicked questions illuminate the complex realities and paradoxes that teams must navigate. Both are essential for growth and transformation—beautiful questions for dreaming and designing, wicked questions for wrestling with real-world complexity. By intentionally weaving both into your team’s conversations, you’ll foster deeper understanding, stronger culture, and more sustainable change.