This reminds me of of the times when I have to compile reports for users from our database. I started requiring that everyone gives me a reason why they want the reports. Most of the users aren't technical people so half the time I need to give them exactly what they asked for and half the time I need to give them something completely different. I've started preemptively adding the reason why I want something into my questions, and I have stopped bothering to guess why people want something. Now I go straight to asking questions.
Communication is hard.
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.