I tend to automatically assume other people didn't understand all the details I'm communicating. Therefore I have a (sometimes annoying) habit to repeat and rephrase. This may be useful in some cases (a prosecutor? a coach?), tolerable in other cases, but how about with a manager?

How about with subordinates?

How about with kids?

With managers, that can come across as pushing-back, negative, lacking can-do attitude. In fact i was trying too hard explaining and highlighting the negative in gory details. A lot of times, the manager already know the issues — perhaps not as much as a foot soldier does, but it's nearly impossible to give them a “deeper” view. I now think many managers don't want a “deep” view but a helicopter view.