Well, I think I do anyway.
It's something I tend to do when people are venting to me and I want to try to get them to think for themselves and to figure out what they need to do to change the situation. Apparently I can sound just like a therapist when I do this...
I think that sometimes when I am really interested in someone and probing for more information I can ask difficult/blunt questions as well. I once asked a guy I'd just started dating why our mutual friend had called his ex-girlfriend a bimbo. I recently said to someone else "You seem to be a bit into self-denial...are you sure you're not atoning for something?"
People usually tell me that they only found me scary when they first met me, which was probably mostly due to the six-foot-tall serious presence. Then they find me less serious and scary when they get to know me better. But I suspect that the difficult questions can be scary.
I have a weird feeling this is one reason I'm not very successful on the relationship front. I don't think most people want to be in a relationship with someone who asks difficult questions or, for that matter, tries to make them think for themselves.
All that said, I shoudn't be hypocritical - I can feel quite pressured when I occasionally get asked similarly tough questions.
I suppose I tend to do this because I ask myself difficult questions. I don't see why others should be spared. I suspect this is an INFJ tendency. Wanting to peel away layers, wanting to help others look into themselves and find what's best for them? That sounds a bit sanctimonious...I don't know, what do others think?