I think that, as with many areas, deliberate practice has helped.
If my dad says, "Son, never date girls who are hippies", that probably means that he himself was burned from an experience like that. While reading it plain would have given me a catch-all theory that is not necessarily true, reading into the reasons told me two extra factoids: my dad doesn't want me to get hurt, and he has dated a hippie girl and that ended badly.
I can't really give specific examples, but it really is a daily thing, where I remind myself to follow things to their logical conclusions, in order to know how to proceed with a task/project/question/etc..
I honestly think most people like this have no idea that they are hard to talk with, or if they do they have not interest in fixing it, and just want to be left alone: The "I thought doing this job meant I didn't have to speak to people?" types.
I think I can handle most things, but the real detail of negotiating funding, or even being "forceful" enough in a first impression worries me.