Most brainstorming sessions suck! Why? Because they inspire creative thinking, challenge the status quo, and inspire bold action. The solution isn’t just bringing in outsiders who don’t think and act like you. It’s to ask provocative questions that drive your brainstorming efforts.

My favorite friends are Why? What If? and Why Not? and you should make them yours too because they never fail to spark creative thinking.

All it takes is a provocative question to help you shift perspective. With that said, here’s a list of 40 disruptive questions you can use to stimulate creative thinking, challenge assumptions, and inspire bold action. Use them to foster innovation and drive positive change within your organization.

1. If we hosted a forum called ‘How Our Products & Services Suck,’ what topics would be on the main stage?
2. Which two things could our competitors do to render our product/services irrelevant?
3. What if we scrapped this approach and tried something else?
4. What would happen if we didn’t do this project at all?
5. How can we think about this problem from someone else’s perspective?
6. If we had infinite resources, what would this look like?
7. What are the unshakable industry beliefs about what customers want? What if the opposite was true?
8. If you could only work on one project for a year to transform the business, what would it be and why?
9. What is the shortest path to the customer? How could we get there in 6 months?
10. What suffers more breakdowns: our products, processes, or people? How could we fix this?
11. What would our dream testimonial from a customer say?
12. If we could hire five more people, what unconventional skills would they have and why?
13. It’s 2025 and we’re the best company to work for in the world: What two things did we do to earn this award?
14. Which parts of your job would you like to kill or eliminate?
15. What can we offer for free that no one else does?
16. You’ve just written a tell-all book about this company: Which secrets does it reveal?
17. How can our services be turned into physical products? How can our products be turned into a service?
18. If we could start over, what would we do differently and better?
19. What if we prioritized radical transparency in all our operations?
20. How might we incorporate principles from completely unrelated industries into our own?
21. What if we flipped the script and made our weaknesses our greatest strengths?
22. How could we disrupt our own business before someone else does?
23. How might we create value in ways that go against conventional wisdom?
24. What if we approached this problem as if we were completely new to the industry?
25. How would Disney / Pixar / Tesla solve this problem?
26. What would happen if we removed all constraints and limitations?
27. What if we did the opposite of what’s expected?
28. We estimate reaching our milestones in 6 months. How might we do it in 3?
29. What if our competitors became our collaborators? In which scenarios would this be true?
30. What if we let our customers run the business? What decisions would they make?
31. If we had to start over with limited resources, what would be the most essential elements to focus on?
32. What are the societal or environmental challenges that our products or services could help address?
33. What are the counterintuitive or contrarian ideas that could give us a competitive edge?
34. If we had to design our processes or products for a completely different audience or context, what would they look like?
35. How can we redefine our industry’s boundaries or expand into adjacent markets?
36. How might we challenge the underlying assumptions that have guided our decision-making?
37. If money and resources were not a constraint, what bold ideas would we pursue?
38. What are the unconventional partnerships or collaborations that could unlock new opportunities?
39. How might we leverage emerging technologies to revolutionize our processes or offerings?
40. How might we create an entirely new business model that disrupts our industry?

Bottom line: Better questions lead to better answers.