You always want to be specific about what you’re asking for. Are you asking for a relationship? Are you asking for advice? Are you asking to follow up with them along the way, and occasionally reach out with a question? I think the best gauge for what’s fair to ask is flipping the tables: How would you feel if somebody approached you and asked this exact same thing? If you feel okay with it, then go ahead and do it. If you feel a little uncomfortable, then try to tweak it in a way that makes you feel okay about it.

