I am a team lead, and I am starting to think that I have become poor at technical communication outside of my team. When explaining things to my superiors, or to offsite contractors, a particular scenario plays out again and again.
Imagine that I am explaining task G; A through F are prerequisite knowledge to complete G. I'll believe that A, B, C, and D go without saying, so I'll explain E and F and then G. If the listener is a contractor, what always seems to happen is that they'll then go off and prepare a presentation about C and D, because they had to spend some time figuring it out, and assume it's news to me. If the listener is a manager, the next time the topic rolls around they'll want G explained again, because they didn't actually understand the first time.
If G is a data entry task (a purely hypothetical example), A, B, C, and D would be basic information about data entry: perhaps A is "turn on the computer to use it," B is "the keyboard is for typing," C is "launch Excel by double-clicking the icon," and D is "click in a cell to edit it," while E and F would concern the actual data I needed to be entered. If I were to explain A and B, I am sure I'd insult the listener. But if I don't explain C and D, the listener doesn't always know what's up.
How do I do a better job of judging where to start explaining things without insulting the people I'm talking to?