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.
> Rule of thumb for everyone (i.e. both).
That's never been how humans work. Going back to the specific example: the question is so nonsensical on its face that the only logical conclusion is that the asker is taking the piss out of you.
> 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
Context and the nature of the questions matters.
> demanding explanations why I'm asking for certain information when I'm just trying to help them.
Interestingly, they're giving you information with this. The person you're asking doesn't understand the link between your question and the help you're trying to offer. This is manifesting as a belief that you're wasting their time and they're reacting as such. Serious point: invest in communication skills to help draw the line between their needs and how your questions will help you meet them.
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.