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In a work environment, or whenever doing somthing with friends, I just try to keep everybody up to speed on what I'm doing, why I'm doing it, and what my assumptions are. ("Today I'm going out to XYZ to do ABC, but I'll be back in time for OPS. Is that working for you?") And if there's a hidden conflict or issue, my statement usually brings it out of the person who's listening, and we discuss it.
In other words, I talk about what I'm doing -- a lot. Not everybody responds to it, but most do. Some get into the habit and start telling me more about what _they're_ up to.
I actually learned to do this at work. I worked in a field where things could change hourly and where not all requirements were made clear; there was a lot of hidden knowledge. So I found that the best way to get things done was to take my best guess at what needed doing and tell/memo everyone what I planned to do and what my assumptions were. That usually gets the laggards out of the woodwork -- "Wait, you need to allow for -- "
What I have found is that to communicate you need to make a "straw man" (they call it a "straw horse" some places, for reasons I never understood) of reality as you understand it and show it to others. Once they have your total concept -- your work plan, vacation plan, plan for cleaning up around the house, assumptions for how you're going to get finances in order -- they're better able to see how your plans relate to them, and then to respond. When you build your straw man, of course, never present it as the ultimate truth -- just reality as you understand it right now.
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