Hx is maybe the wonkiest part of the system. There are many hacks for it.
But it's useful to remember that in mechanical terms, what it really represents is your ability to help or hinder a person. So one way of reading it would be: Knowing them well enough to predict the kinds of things you could say or do, that would either give them confidence or psyche them out.
When you have negative Hx it might be like understanding them TOTALLY WRONG, like a Christian talking to a Satanist, or a Capitalist talking to a Communist...