We've learned not to expect short inferential distances when explaining ideas we understand. We've also learned that leaping too far ahead when explaining ideas like transhumanism can freak people out.

I want to be really really good at explaining ideas. Does anyone have recommendations about how to figure out what the next inferential step is in another person's mind?

Categories which are not answers themselves but are areas in which I expect to find answers:

Asking filter questions
Social contexts
Verbal cues
Body language

Ideally, I would like to find conversation-independent answers to this question; not just answers that fit for explaining transhumanism.