Why [not] ask why?

When someone asks for help, e.g. in a place like Stack Overflow, they are often met with the response "why do you want to do that?"

People like to talk about the "XY Problem": when someone's real problem is X, but their question is about how to do Y, which is a bad way to solve X. In response, some other, snarkier people sometimes talk about the "XY Problem Problem": when someone's problem is Y, and they ask about Y, but people refuse to help them with it because they're too busy trying to figure out the (nonexistent) value of X.

The other day, I thought about a taxonomy of good responses to the kind of informally-specified request for help that one sees online. I came up with the following:

1. Straightforward answer to the question asked.
2. "Frame challenge" (This is Stack Overflow terminology; the others below are not.)
   • "I understood your question, and I also understood your underlying problem, and I would like to offer an explanation of why I think the straightforward answer to your question does not solve your underlying problem."
   • Although this kind of response doesn't directly answer the question, I think it's good because (1) it's required to directly address why not, which provides something for the asker to disagree with if appropriate; and (2) it provides something that the answerer thinks is more useful than an actual answer.
3. "Safety challenge"
   • "I think your question provides evidence that you are doing something dangerous to yourself or others, and you are not aware of that danger.  A direct answer would endorse or contribute to that danger, so instead I want to warn you about the danger."
   • This can be condescending if the danger is minor, or not real. But again, I think it's good because (1) it directly states why it doesn't answer the question, and (2) it provides some information the answerer thinks is more useful instead.
4. "Assumption challenge"
   • "I think it is not possible to answer your question, because it embeds an assumption that is not true, as follows: [...]"
   • Good, because it clarifies what the assumption is, which gives the asker the opportunity to argue or clarify.
5. "Ambiguity challenge"
   • "I did not understand your question, and I am unable to answer it because I can't figure out what it's asking."
   • This one is interesting and I will discuss it below.

When someone responds to "how do I do X?" with "why do you want to do X?", I think this creates conflict for a few reasons. Primarily, it tends to insult the asker. As certain people on this site would say, it's a status grab: "I know better than you what question you actually need answered, and it is not the one you asked; try again." It sets the answerer above the asker in status.

One of the reasons that "frame challenge" works so well on Stack Exchange is that you have to declare that you're making one. Saying "I would like to challenge the assumptions of your question" comes across as more respectful, and less status-grabbing, than "why would you want to do that? Don't do that." I think "safety challenge" could work similarly. Saying "you shouldn't do that, it's dangerous" will always come with some amount of status assertion, but saying "I think that's dangerous, and here's why" is less of a status grab than "Why would you want to do that?", because it provides an explanation, rather than assuming it's obvious and putting all the burden of communication on the asker.

Another reason is that it provides more information to the asker. For a "frame challenge" to be a valid answer on Stack Exchange, it has to include an explanation of why the answerer thinks the asker's frame is bad. The ball is in the answerer's court to provide the asker with useful information. A bare "why would you want that?" does not.

Stack Exchange's question/answer structure really helps here, compared to other types of discussion fora. In unstructured discussion fora, it's easy for a "Why?" to turn into an angry argument between the original asker and the responder. On Stack Exchange, each answer is a separate conversation thread, meaning that (1) conversation in response to one answer can't prevent someone from giving a better answer, and (2) multiple independent answers can be voted up, so there's room for BOTH "here's the answer to your question" and "here's why I think that won't help you" to be upvoted and discussed separately, on the same question (and I've seen this happen.)

Above I mentioned "the burden of communication", which I think is a big part of what's going on here. It is roughly always the case that a question is ambiguous in some way, or requires some context to understand. This means there will be some burden of negotiating the necessary context between asker and answerer. "Why do you want to do that?" tosses 100% of the burden back on the asker; it expresses "I don't like your question", but makes no effort to bridge the gap. "Why? Well, it all started about 14 billion years ago..." There are always infinite layers of "why", and this is no help in figuring out what the responder feels is missing from the question.

"Ambiguity challenge", which I suggested above, is the least helpful of my suggested responses -- to be helpful, I think it needs to come with some effort to explain what about the question is ambiguous. What form that will take depends on the question. It still beats "why?" because "the problem is ambiguity" is still some information. It means the problem is not safety, or clearly false assumptions. And it's a direct statement that the responder does not understand the question, which implies they aren't being totally condescending ("I understand you, but I refuse to help because I think your request is stupid.")