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NancyLebovitz comments on Rational Communication - Less Wrong
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A model:
Most people parse out 'why' questions as a request for them to give the narrative they've constructed surrounding an incident or set of incidents. In most cases where a person is upset about an incident, it's largely because they haven't worked out an acceptable narrative about it yet, and in such cases asking the person to relate that nonexistent narrative will just upset them, primarily because it comes across as judgmental ("you should have an answer to this question, and it's bad that you don't"). In situations where a person is not upset, but is explaining something or relating a story (even a personal or emotional one), asking 'why' will work much better, because the story being requested already exists.
My impression is that asking "why" tends to sound like "do you have a reason which will convince me that I should agree with you? I'm dubious about what you're doing".
(nods)
I generally assume that people will understand "Why did you X?" to mean "You should not have Xed"... as a challenge, rather than a request for information, since such challenges are frequently expressed as questions of that sort. So if I genuinely want to invite people to reflect on their reasons, I find I have to reframe the question.
Depending on the particulars, that might be "When did you first decide to X?" or "What was your inspiration for X?" or even (though this is a dangerous one, as it skirts the edges of challenge) "What led you to reject Y in favor of X?"