cf Derek Sivers on "how to ask your mentors for help". I take the time to write a good description of my dilemma, before reaching out to them. I summarize the context, the problem, my options, and thoughts on each. I make it as succinct as possible so as not to waste their time. Before sending it, I try to predict what they’ll say. Then I go back and update what I wrote to address these obvious points in advance. Finally, I try again to predict what they’ll say to this, based on what they’ve said in the past and what I know of their philosophy. Then, after this whole process, I realize I don’t need to bother them because the answer is now clear.