It's a struggle for me, too. People sometimes rest on their assumptions even though new technologies and paradigms can invalidate old rules (I'm sure everyone has lots of examples).

I found that constant communication and scenarios help bridge the gap between how they think things work and how you do. It doesn't always work - a lot of time people don't care to discuss things in detail.

But sometimes it worked and the other person came to realize a new way of thinking. Sometimes the discussion made me realize I was the person using invalid assumptions :)