judgement

Most decisions can be ranked along two dimensions: importance and difficulty to reverse. For easy-to-reverse decisions, make them quickly or delegate. Same for difficult-to-reverse but unimportant ones. But for important and difficult to reverse decisions, you need to think carefully. Here are some questions I ask myself when making these kinds of decisions:

Outcome Clarity

1. What is the ideal outcome?
2. What outcome(s) do I definitely want to avoid? How can I do that?

Scenario Planning

1. If this is going to fail (or end in a bad outcome), what are the most likely reasons why?
2. For each reason, are there likely to be any ‘early warning’ signs?
3. Are there any actions I can take that can mitigate those risks?
4. If the risk does manifest, what’s my “Plan B”?
5. If this ends up going extremely well, what are the most likely reasons why?
6. Are there likely to be any ‘early momentum’ signs?
7. Say things go really well. Then what? What risks / problems can success cause?
8. What steps could I take that might mitigate those?
9. How is this likely to affect other stakeholders? What incentives / reasons might they have to support or oppose?

Hypothesis Testing

1. Why do I think that ideal outcome isn’t possible (if I think it isn’t)?
2. For each reason listed in #2, state the opposite. How can I make that true?
3. I currently believe X. What evidence would change my mind?
4. Is there a way for me to obtain that evidence?

External Inputs

1. Who can I talk to/ask that has some expertise in this area (where expertise ideally = has done something very similar with success at least three times)?
2. Who is most likely to disagree with my decision? What is their reasoning? Are they wrong?
3. Is there historical evidence or statistics that can help inform how similar decisions have turned out in the past? Why?
4. Is there a relevant comparison class? What is the base rate?
5. Who are three people that I admire in this domain (dead or alive)? If I can’t talk to them, what do I imagine they would tell me?

Prioritizing

1. When I’m old, what path/scenario am I most likely to regret?
2. What are the three most important criteria by which to evaluate this decision?
3. Logic aside, how do I feel about each option. Why?
4. What are the three pieces of information that would be the most helpful to know?

Meta Questions

1. Take a step back and think creatively. Is there another option I’m not considering?
2. This there a way to ‘test’ one or more options in a low-risk/cost way that gets me more information?
3. Is there a decision that provides me more or less optionality in the future?
4. What’s the opportunity cost?
5. What my real problem here?

Timing

1. Do I need to make this decision now?
2. Am I likely to benefit from delaying making this decision?
3. What is the risk of delaying this decision?
4. Once I’ve made up my mind, is there any reason I can’t wait 24 hours before acting on it (just in case?)