Rule of thumb for who, humans or chatbots? For a human, who has their own wants and values, I think it makes perfect sense to wonder what on earth made the interlocutor ask that.

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DharmaPolice an hour ago | parent [-]

Rule of thumb for everyone (i.e. both). If I ask you a question, start by assuming I want the answer to the question as stated unless there is a good reason for you to think it's not meant literally. If you have a lot more context (e.g. you know I frequently ask you trick or rhetorical questions or this is a chit-chat scenario) then maybe you can do something differently.

I think being curious about the motivations behind a question is fine but it only really matters if it's going to affect your answer.

Certainly when dealing with technical problem solving I often find myself asking extremely simple questions and it often wastes time when people don't answer directly, instead answering some completely different other question or demanding explanations why I'm asking for certain information when I'm just trying to help them.

	▲	vintermann an hour ago \| parent [-]
		Sure, in a context in which you're solving a technical problem for me, it's fair that I shouldn't worry too much about why you're asking - unless, for instance, I'm trying to learn to solve the question myself next time. Which sounds like a very common, very understandable reason to think about motivations. So even in that situation, it isn't simple. This probably sucks for people who aren't good at theory of mind reasoning. But surprisingly maybe, that isn't the case for chatbots. They can be creepily good at it, provided they have the context - they just aren't instruction tuned to ask short clarifying questions in response to a question, which humans do, and which would solve most of these gotchas.