1. Why don’t our customers like us?
  2. If our company went out of business tomorrow, would anyone who doesn’t get a paycheck here care?
  3. How can we become the company that would put us out of business?
  4. Are we  relevant? Will we be relevant five years from now? Ten?
  5. If we weren’t already in this business, would we enter it today? And if not, what are we going to do about it?
  6. What is the smallest subset of the problem we can usefully solve?
  7. Who, on the executive team or the board, has spoken to a customer recently?
  8. If I had to leave my organization for a year and the only communication I could have with employees was a single paragraph, what would I write?
  9. What do we need to start doing?
  10. What are the most difficult questions you could ask a business?