Communication is extremely complicated. It's also not a solo sport. There are at least two people involved at all times. There are some specific skills that you

Communication is extremely complicated. It's also not a solo sport. There are at least two people involved at all times. There are some specific skills that you can practice which I have found have helped me a lot with this problem. -Empathy/Respect: recognize that people generally are doing the best they can, and try to meet them where they are at/assume good intentions. -Ask clarifying questions like "What I am hearing you say is x". or "I'm having a tough time understanding how this relates to the problem we are trying to solve, can you break it down for me?" or "Just to confirm my understanding here, it sounds like you are suggesting...." To the specific points in your post - I find that the difficulty in clear, concise communication rises considerably when it's a live, realtime discussion vs. when it is asynchronous. Compact and precise language takes a lot of time to formulate (I didn't have time to write you a short letter, so I wrote you a long one). >generally over-complicate matters by wandering off to other related subjects and extending the scope of the discussion This one is a tough one. Sometimes this happens when the structure of the meeting is wrong, or there's not someone who's empowered to say "let's set that aside and focus on x". Sometimes though, exploring the possibility space verbally, even when it's a dead end is just how some people synthesize the problem and internalize it so they can understand it better. Sometimes it's necessary work that needs done before everyone can effectively 'play' with the problem you are trying to solve.