Ben_LandauTaylor comments on Questioning and Respect - Less Wrong
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I agree when it comes to asking questions about the facts of the situation. On the other hand, asking nonjudgmental questions about the person's feelings is a good way to establish rapport, if that's your goal. (See also)
Absolutely, but you have to be sensitive. If you genuinely are a little skeptical of the accuracy of the story or the reasonableness of the person's reaction to what happened, you can easily slip and sound condescending, disbelieving and dismissive.