I do want to clarify my point of view since there does seem to be some interpretation which I didn't entirely anticipate (wholly my mistake):
1. I'm not claiming that every interaction with a user needs to be turned into a full discussion. There are lots of cases where the answer is "this is what you're looking for, here's a link to the docs". In my experience, this has gone down a lot over time because people tend now to rely on AI much more heavily for those sort of questions in the first place so they won't even reach you. But it does happen and in that case, the best thing for both sides is to point to the documentation and move on.
2. If I am going to employ this strategy, I always try and both give the direct answer to the question and, as a separate point, ask them the context. Quoting directly from the post:
> well the answer to your immediate question is X but that’s a pretty strange thing to ask for because of reason Y. Can you tell me more about the wider problem you’re trying to solve?
3. This does necessitate that you are in some sense an "knowledgeable" on the problem space someone comes to you with: I would never employ this strategy in an area I didn't already feel I was quite well equipped to give my 2c on.
4. If the person I'm speaking to I know for a fact is already knowledgeable on an area, I would be very hesitant to use this approach because I try and be charitable with assuming that people generally know what they are talking about. While yes, I'm not going to be perfect every time in judging this, I think you can get a pretty good sense from the way they ask their question and how clearly they respond to your initial answer whether they are not (ties to 3 as it requires you are good enough in the space to judge this).
5. If someone pushes back, I will always defer to their read of the situation, I'm not here to make people do what I suggest, I will simply say "well I think you should do/not do A because of B reason but at the end of the day your call" and leave it at that. I think it's a good thing to be able to have respectful discussions on topics even if both sides agree to disagree.