Jason Cohen created a list of “wild” questions to generate ideas in business1:

  1. If you were forced to increase your prices by 10x, what would you have to do to justify it?
  2. If all our customers vanished, and we had to earn our growth and brand from scratch, what would we do?
  3. If you were never allowed to provide tech support, in any form, what would have to change?
  4. What would be the most fun thing to build (has to be related to our product and market)?
  5. If our biggest competitor copied every single feature we have, how do we still win?
  6. What if we are forced to ship a full, completed (at least MVP) new feature, in just two weeks, that would delight and surprise some fraction of our customers. How would we do that?
  7. What if you were forced to charge customers in a completely different manner?
  8. If you were not allowed to have a website, how would you still grow your business?
  9. What if you made your most introverted teammates’ dreams come true: No more synchronous meetings, ever again?
  10. If we could never talk to our customers again, how would we figure out what to build?
  11. What if it didn’t matter how unprofitable you were?
  12. What if you could change anything, regardless of what anyone thinks or feels?
  13. What externality has the potential to kill the entire company?
  14. What if you could only ship one thing this year?