One issue which I seem to be at variance with some others with is the issue of answering questions, specifically doctrinal questions. It seems that some would prefer to ask the enquirer why they ask the question first before answering it. Now, to some extant, this may be helpful pastorally since sometimes there are other questions and issues below the surface. But do we have to always inquire as to the reason why a question is asked before answering it?
There is of course a personal part to this question. In my Christian walk, I have had a few episodes where people seem more interested in why I am (or someone else is) asking a question. One time was a question I had asked a pastor (not my church). Another time was when I was seeking advice when I was counselling someone struggling with a doctrinal issue. Both times I was extremely disappointed when they were more interested in the "why" rather than the "what." When I asked the question, and received a "why" question back, my impression of the pastor immediately went downhill. Here was someone, I thought, who was not interested in answering my question. Here was someone who thought that behind my question laid some personal struggles and difficulties I may have, and thus doctrinal question was merely the symptom for personal struggles. I was very much offended and saw that as someone who belittled me and my inquiry. The good thing at least is that this guy was not my pastor, otherwise if so I might have left the church.
The struggle therefore is how should one go about answering questions. From my experience, I am resolved, as much as possible, that I will NOT speak down to others when they ask doctrinal questions. I will not insult them or their intelligence, by somehow having the "secret knowledge" that their doctrinal questions are symptoms of personal issues. To think as if any and every doctrinal question must be symptomatic of personal struggles is an insult to the inquirer and a belittling of God's truth as something important only to the extant it is "practical," whatever that terms means.
So when should we ask the "why" question? I don't know. It is probably better done in the context of relationships, and NOT when the person is asking that question.