What model of the world/way of thinking/worldview generated the things this person is saying?
What game am I playing? What are the rules (or, more relevantly, what aren't) and how do I win?
What is the goal of this conversation? (Note: you must be careful to answer with the actual goal, not the goal you think you should have or the goal you would answer with in public. For instance, if your answer is just "truth seeking" you are wrong with very high probability.)
One useful question per comment, please!
See also: Boring Advice Repository, Solved Problems Repository, Grad Student Advice Repository, Useful Concepts Repository, Bad Concepts Repository
I just got back from the July CFAR workshop, where I was a guest instructor. One useful piece of rationality I started paying more attention to as a result of the workshop is the idea of useful questions to ask in various situations, particularly because I had been introduced to a new one:
"What skill am I actually training?"
This is a question that can be asked whenever you're practicing something, but more generally it can also be asked whenever you're doing something you do frequently, and it can help you notice when you're practicing a skill you weren't intending to train. Some examples of when to use this question:
Many of the lessons of the sequences can also be packaged as useful questions, like "what do I believe and why do I believe it?" and "what would I expect to see if this were true?"
I'd like to invite people to post other examples of useful questions in the comments, hopefully together with an explanation of why they're useful and some examples of when to use them. As usual, one useful question per comment for voting purposes.