Fr. Philip Powell gives some good practical points, and questions that those discerning a religious vocation should ask themselves. These questions to ask when discerning a vocation may be found, together with comments on the Anti-Christ, and the difference between magic and prayer, at his blog Domine, da mihi hanc aquam!
What questions should I ask my vocations director and my postulant director?
Thank you.
Ask about whatever's unclear to you 🙂
Seriously, I don't quite picture the situation you are in or have in mind, and couldn't give you questions specifically fitted for you. Both a vocations director and a novice master (or director for postulants) have two roles. They can help you acquire a more accurate and honest picture of yourself, and they can give you information about vocations or the specific community in which you are that will be helpful in your discernment.
Basically in both cases the important thing is a relationship in which both persons know and trust the other. Then, after speaking to a vocations director about, for example, what you're looking for, hoping for, in a community, you could ask for suggestions on types of community; or if you're further along and have a community in mind, whether he thinks you haven't yet reckoned with certain difficulties you'll experience there, etc. It should be a quite individualized matter, rather than a fixed set of questions.