R' Dovid Orlofsky gives an excellent talk here on the topic of how to respond to questions about Yiddishkeit. He makes some excellent points about communication and does so with his trademark humor which can be the laugh-out-loud type at times and excellent examples.
You should really watch the talk but in case you don't, or you want a summary of his points even if you do, here are some notes I took:
You don't teach subjects, you teach people.
You need the right answer for that person.
Some people have dedicated their lives to a question, they are so invested in the question that there is no answer for them like a Holocaust survivor who wants an explanation for the Holocaust.
Others, only a few, are truly interested in hearing an answer.
The rest, 95%, don't want to know the answer to questions they ask!
Ask "what do you mean" to clarify matters because people don't even know what they're asking!
We love to share information but s'yag l'chochma shtika, the less you say the better.
The hardest question to answer is the question you haven't answered for yourself.
People make statements, acknowledge it; they are not questions and there is no point in arguing with statements.
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