'Why...?' questions, by their very nature, sound judgmental and can easily imply that you disagree with your buddy's approach, e.g. "Why (on earth) would you do that?"
You will be the most help to your buddy by remaining both neutral and non-judgmental and a great way to do that is to use 'neutral' questioning techniques.
Instead of asking 'why', start your questions with, 'How...?', 'What...?' and 'Who...?' and you'll help your buddy achieve forwards momentum...without getting her back up! :) -RW
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