A while back (in response to my post on Choosing a Rabbi) I was asked: “for what types of questions do you think a person needs to turn to a rabbi.”
I replied: "What time is it," "Will it rain today," "What is my favorite color," that sort of thing.
My questioner pressed: i don't understand. why would i ask a rabbi those questions?
To which I answered:
"What time is it" - To know when to daven.
"Will it rain today" - To know whether to put on a raincoat.
"What is my favorite color" - To figure out which suit I should get.
All right, fine. It's just my sense of humor. In truth, the answer is that this is a very vague issue, without a clear resolution. I might post on this in the next week or so.
It’s been three months rather than a week, but here are two thoughts on the topic. They're really just common sense, but you asked...
1) Ask the right person
It is popular to ridicule chasidim who consult with their Rebbe about a business venture, or about a medical treatment. People allege that a Rebbe will overstep his knowledge and experience, advising followers with his “Daas Torah” on areas about which he knows nothing.
Many of the ridiculers are simply insecure about their own reliance upon - or non-reliance upon - advice from the Torah. In general, people who ridicule betray a problem of their own. (cf כל הפוסל במומו פוסל - Those who insult others, do so regarding a blemish they see in themselves.)
In truth, though, I do agree that this sort of overreach is a potential problem – but it’s easy to solve: Just choose a humble mentor who knows his own limits. As the gemara (Chagigah 15b) advises, choose a mentor who appears to you like a מלאך, an angel - and angels (with a couple of notable midrashic exceptions) have no ego.
Humility is very easy to identify – pick someone who regularly uses the magic words, “I don’t know,” “I’m not sure,” and the like.
2) Know what sort of answer you expect.
If the mentor knows his own limits, then what remains is for the questioner to manage his own expectations. Ask a rabbi any question you like, but know what you want in terms of an answer.
An answer may be פסק (halachic ruling): מותר, אסור, Do this, Don’t do that.
Example: I can ask about basketball on shabbos, or mixed swimming, or organ donation, and expect a clear halachic analysis.
An answer may be חוות דעתו (expression of his opinion): Based on my knowledge of Torah and my life experience, consider X path.
Example: I can ask about schools for my children, and my mentor can give me the benefit of his experience.
An answer may be Food for thought: Here are a few aspects to contemplate.
Example: I can ask a mentor about a potential move - expecting my mentor to point out issues of potential concern.
And an answer may be Guidance: Assistance in figuring out the right questions to ask, as well as the right answer.
Example: I can ask my rebbe about dating, and my rebbe can help direct my thinking.
So know what type of response you seek. Also, make sure to convey that information as part of the question. This is important so that your rabbi will not feel pressed to extend his advice beyond his reliable pool of knowledge.
Once you have both of those elements - the humble mentor and a clear understanding of what type of answer you expect - ask any question you like. Business, medicine, where to live, halachah, hashkafah, anything is safe.
And, by the way: It’s 10:00 AM, weather.com says it will rain here today, and your favorite color is pine green. Or puce; I'm humbly uncertain.