25 Questions To Ask When You’re Stuck

by | Process

It’s bound to happen sooner or later. No matter how skilled you are and no matter how well you’ve prepared, you’re inevitably going to find yourself stuck on a tough problem without a clear path forward.

It’s tempting in these circumstances to keep your nose down and continue cranking on the problem. The problem with this method is that you may be digging yourself deeper into an existing rut.

Sometimes it’s valuable to have a set of questions at the ready to help you re-frame, shift, or view the problem through a different window. Below is a set of questions that have been used in various situations to jog new creative thoughts about stubborn problems. The questions can be used on your own, but are especially valuable in the context of a team. (Note: at first glance some of the questions might seem too simple to be of value, but given about fifteen minutes of thought and discussion, they lead to a surprising level of awareness and to potential new paths to explore.) We have to be willing to immerse ourselves in the process in order to get to the deeply valuable ideas that reside just on the other side of stasis.

Questions to ask when you’re stuck:

  1. Is an assumption in the way?
  2. What is the worst-case scenario?
  3. Could I do the opposite?
  4. How can I thrill the end user?
  5. What am I afraid of?
  6. Do I understand why?
  7. Where else has something similar been done?
  8. What is expected and why?
  9. Who has something to lose?
  10. Who is the enemy and how do we foil them?
  11. Who could solve this problem with ease, and how?
  12. How would my favorite super hero do it?
  13. How would my favorite movie character do it?
  14. Could I change the medium?
  15. Could I ask the question differently?
  16. How would a 3rd grader approach this problem?
  17. What question do I need to answer first?
  18. Is there a resource I’m lacking?
  19. How would I describe the problem in three words?
  20. Are there sub-problems to the main problem?
  21. What’s the world like once the problem’s solved?
  22. Who can I call for help?
  23. Can I create a metaphor for the problem?
  24. How would I start over?
  25. What’s primary block and why?

When working individually on a problem write a question at the top of a sheet of paper or in a notebook and spend about fifteen minutes writing an answer to it. You’ll often be surprised by what you write. When working in a group, pose the question to the group and record the answers on a white board or in some other visible place. See what patterns emerge over the course of fifteen minutes.

Don’t get embedded in a rut. Explore the periphery of your problem and stay alert and active. Remember that your best ideas will often come from the least expected places.

Let us know: What other question has helped you break through a creative block? Leave a comment below.

Todd Henry

Todd Henry

Positioning himself as an “arms dealer for the creative revolution”, Todd Henry teaches leaders and organizations how to establish practices that lead to everyday brilliance. He is the author of five books (The Accidental Creative, Die Empty, Louder Than Words, Herding Tigers, The Motivation Code) which have been translated into more than a dozen languages, and he speaks and consults across dozens of industries on creativity, leadership, and passion for work.

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