Richard Hamming famously used to ask people what the important problems in their field were, and why they weren't working on them.

From this, the Center for Applied Rationality (CFAR) developed the concept of Hamming Questions – questions designed to help you identify and make progress on the most important problems in your life. (See page 139 of the handbook for some examples.) I and other CFAR alumni have found it helpful to work through these questions periodically as a way to surface and tackle key personal problems.

Recently, while trying to get my thoughts straight on a thorny work project, I had the idea to adapt the Hamming Questions model for project planning. This turned out to be very productive, so I'm copying the questions I used here in case anyone else wants to try it. I recommend it especially in cases where you feel like you're missing something important but aren't sure exactly what, or where you have the guiltily ominous feeling that you're avoiding something that matters.

In each case, brainstorm responses to each question until you run out of ideas, then move on to the next question. When you're done, review your answers and identify next actions to tackle those problems. In a week or a month, come back to your answers and see (a) how you're progressing and (b) whether these still feel like key unresolved issues to you – if so, you might want to try some new solutions.

  1. The original question: what are the most important problems for this project, and what is stopping you from working on them right now?
  2. What is the limiting factor on the project’s growth and progress?
  3. What problems in this project are the largest order of magnitude? What changes could you make that would result in a 100x or 1000x increase in this project’s positive impact?
  4. What would the leader of this project (or its successors), looking back from 5 or 10 years in the future, think was the obvious next step?
  5. In the context of this project, what do you feel you’re “not allowed to care about”, e.g. because it feels too big or impossible?
  6. When do you have flashes of envy or impostor syndrome related to this project?
  7. Whose input about this project should you obviously be seeking, that you haven’t yet sought?
  8. What are you avoiding thinking about in the context of this project? Why?
  9. Who are you avoiding thinking about in the context of this project? Why?
  10. If this project were the plot of a novel, what would be the obvious next step? What do you need to do to move the story forward?
  11. What if this project were the subject of an inspirational nonfiction book?
  12. If this project were the subject of a cautionary tale or postmortem, what would be the most important mistake you are making / going to make?
  13. What goals are you already pursuing for this project, but in a bad/convoluted/inefficient/distorted way?
  14. If you say “Everything in this project is going fine, and we’re on track to achieve all of our goals”, what feels untrue about that? What makes it hard to say that sentence out loud?
  15. Now try “Everything in this project is going perfectly”.
  16. What feels most alive to you right now, in the context of this project?
  17. What feels most endangered to you right now, in the context of this project?
  18. What is a small but frequent cost that is draining this project’s progress?
  19. What major part of this project should you drop right now?
  20. What potential major additions to scope or content could seriously improve the impact of this project?
  21. What would you do if you weren’t afraid?

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I really like this selection of questions! I'm not doing any major project planning myself at the moment, otherwise I'd try it immediately. But I'd be interested in an eventual update which of the questions worked best/elicited the most insight for you.

Honestly the first question is typically the most valuable for me. The rest are intended to dig around for stuff that the first question might have missed.

In the project I developed this list for, questions 1, 2, 4, 8, 9, 12, 18 and 21 were probably the most valuable. But I'd expect that to differ between projects, depending on the nature of the most important problems.