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Powerful coaching questions to get you from stuck to unstuck fast

by | Jan 19, 2024

Stuck in a rut? Facing a creative challenge that seems insurmountable? Don’t despair! Here are 11 of my favourite coaching questions that can help you unlock problems, shift perspective and drive progress in your professional life.

Get a fresh perspective

1. What if the opposite were true? 

  • This question flips the script, forcing you to consider alternative perspectives and expose hidden assumptions. Source: “Thinkertoys” by Michael Michalko)

2. What is the simplest thing that could possibly work? 

  • This question cuts through complexity and focuses on the core essence of the problem (Source: “Simplify” by Joshua Cooper Ramo)

3. What would happen if there were no rules? 

  • By removing constraints, this question encourages radical thinking and leads to innovative solutions. List the rules you ‘think’ are in place – what are they and how could you break them , change them or workaround them? (Source: “Thinkertoys” by Michael Michalko)

4. What would a [role model/expert/unexpected source] do in this situation?

  • This question leverages the wisdom of others and opens up new possibilities. You’re struggling to manage your time effectively? Asking “What productivity hacks does [your favourite CEO] use?” might inspire new strategies for your own workflow. Or go further an step into the shoes of a historical figure, celebrity, politician, activist and so on. You can read more about this process here.

Personal inquiry questions

5. What haven’t I considered yet? 

  • This introspective question prompts you to revisit your assumptions and explore uncharted territory. You’re trying to improve your public speaking skills? Asking “What hidden factors might be affecting my audience’s engagement?” might lead to unexpected adjustments in your delivery.

6. How can I make this a win-win situation for everyone involved? 

  • This question shifts the focus from individual gain to mutual benefit, fostering collaboration and building trust. You’re facing a disagreement with a colleague? Asking “How can we find a solution that works for both of us?” might lead to a more sustainable and satisfying outcome. (Source: “The 7 Habits of Highly Effective People” by Stephen R. Covey)

7. The Dr Pepper question. What’s the worst that could happen if I try this? 

  • This question confronts fear and encourages calculated risk-taking. You’re hesitant to launch your new product? Asking “What is the potential downside of trying this, and how can I mitigate it?” might help you overcome your hesitation. A pre-mortem can be a great way to do this in more depth (Source: Dr Pepper ads, lol)

8. What is the most important thing I can learn from this situation? 

  • No-one likes to fall short but if you lose, don’t lose the lesson as someone wise once said. When you’ve got over the initial shock/pain/impact of what has happened this question can help to reframe ‘failure’ as a learning opportunity, fostering resilience and growth. (Source: “Mindset” by Carol Dweck, one of my favourite authors on this topic).

9. Can I break this problem down into smaller, more manageable pieces? 

  • The classic ‘you can’t eat an elephant but you can eat a lot of elephant burgers’ approach. This question tackles overwhelming challenges by dividing them into bite-sized steps. You’re feeling overwhelmed by a large project? Asking “What are the 3 key tasks I can complete today to make progress?” might reduce anxiety and increase momentum. I also like the tip to do the thing you’re most dreading as your first task of the day so you don’t procrastinate and feel better about yourself!

10. What am I grateful for in this situation? 

  • Another questions that might need a bit of distance from the initial event. This question shifts focus from the problem to the positive aspects, fostering optimism and resilience. You’re facing a personal setback? Asking “What am I learning about myself through this experience?” might help you maintain a positive outlook and find strength to move forward. Resilience is not something you have, it’s something you do too.

11. What is the conversation you’re NOT having?

  • My personal new favourite coaching question. Susan Scott is author of a book called Fierce Conversations who says: “Never be afraid of the conversations you are having. Be afraid of the conversations you are not having.” That sounds like a great prompt to help you get unblocked and tackle deeper challenges. (Source: “Fierce Conversations” by Susan Scott.)

The best questions are those that spark curiosity, challenge assumptions, and open doors to new possibilities. So, experiment, ask boldly, and watch your problems transform into opportunities for growth and innovation. My own book In Your Creative Element also features over 100 creative coaching questions to help you move forward.

Don’t let your organization’s creative potential go untapped. Join our small, residential creative leaders programme to up your creative confidence and learn how to lead a culture of creativity underpinned by well-researched principles and methods. Find out more here.