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:
- What is the ideal outcome?
- What outcome(s) do I definitely want to avoid? How can I do that?
- If this is going to fail (or end in a bad outcome), what are the most likely reasons why?
- For each reason, are there likely to be any ‘early warning’ signs?
- Are there any actions I can take that can mitigate those risks?
- If the risk does manifest, what’s my “Plan B”?
- If this ends up going extremely well, what are the most likely reasons why?
- Are there likely to be any ‘early momentum’ signs?
- Say things go really well. Then what? What risks / problems can success cause?
- What steps could I take that might mitigate those?
- How is this likely to affect other stakeholders? What incentives / reasons might they have to support or oppose?
- Why do I think that ideal outcome isn’t possible (if I think it isn’t)?
- For each reason listed in #2, state the opposite. How can I make that true?
- I currently believe X. What evidence would change my mind?
- Is there a way for me to obtain that evidence?
- 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)?
- Who is most likely to disagree with my decision? What is their reasoning? Are they wrong?
- Is there historical evidence or statistics that can help inform how similar decisions have turned out in the past? Why?
- Is there a relevant comparison class? What is the base rate?
- 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?
- When I’m old, what path/scenario am I most likely to regret?
- What are the three most important criteria by which to evaluate this decision?
- Logic aside, how do I feel about each option. Why?
- What are the three pieces of information that would be the most helpful to know?
- Take a step back and think creatively. Is there another option I’m not considering?
- This there a way to ‘test’ one or more options in a low-risk/cost way that gets me more information?
- Is there a decision that provides me more or less optionality in the future?
- What’s the opportunity cost?
- What my real problem here?
- Do I need to make this decision now?
- Am I likely to benefit from delaying making this decision?
- What is the risk of delaying this decision?
- Once I’ve made up my mind, is there any reason I can’t wait 24 hours before acting on it (just in case?)