1- The map is not the territory

• What medium do you use to represents the reality?
• What are the flaws of your representation?
• How do you use this representation?
• Am I looking at a model ?
• Which are the information that I lose ?
• Is my interpretation of the model correct ?
• Is there another models that try to represent this reality ?
• What is the limits of the model ?
• Can I really use this model in this situation ?
• What the model is supposed to do ?
• How I will use the model ?
• Can I built a system robust or antifragile to model error ?

2- Circle of competence

• Is the problem in the boundaries of my circle of competence ?
• Can I expand my circle of competence ?
• Do I have the time to develop my circle of competence in this area ?
• Is there any other people more competent than me ?
• Is the people helping me more competent than my adversary ?

3- First Principles thinking

• Why do I think this? What exactly do I think?
• How do I know this is true? What if I thought the opposite?
• How can I back this up? What are the sources?
• What might others think? How do I know I am correct?
• What if I am wrong? What are the consequences if I am?
• Why did I think that? Was I correct? What conclusions can I draw from the reasoning process?

4- Thought experiment

• What will X cause to happen?
• If Y happened instead of X, what would be the outcome?
• If Y had happened instead of X, would the outcome be the same?
• If X continues to happen, what will the outcome be in one year?
• X happened, could Y have predicted it?
• What caused X? How can we prevent it from happening again?
• If X happens in one year, what would have caused it?

5- Second order thinking

• And then what? What are the second order consequences of your option?
• What could be the hidden consequences linked to your option?
• What are the important parts of your system? How the important part of the system are likely to respond ?
• What do the consequences look like in 10 minutes? 10 months? 10 Years?
• How could you make things more durable ?
• Is your option first order negative and second order positive ?
  • Rational
    • A lot of extraordinary things in life are the result of things that are first-order negative, second order positive.

6- Probabilistic thinking

• What event do you want to assess?
• Have you defined clearly your event in terms of result and timeline?
• What should be true for your event to be true?
• What are the parameters that influence the realization of the event?
• Could you assign a range of probability to each of those events?
• How do you assess your knowledge about the assessment of the probability linked to the event?
• Are you using those probability to plan something?
• Are you fragile to forecasting errors?
• What is the expected value of the event? Is the expected value positive?

7- Inversion

• What do you want to achieve?
• What has to be true in order that you achieved what you want?

8- Occam's Razor

• What is the degree of complexity of my solution ?
• Which are the fewest possible causes to explain what happens ?

9- Hanlon's Razor

• Are you attributing something to the malice of somebody?
• Could it be any other alternative explanation?
• If the behavior is malicious what could be the incentive that led to this behavior?
• What was the context of the action?