I've struggled forever to keep my mouth shut. If there is one thing I have tried to work on over the years it's saying less than more. I've been reminded again and again that you often achieve far more value by listening than talking. More so than not, I have left a meeting scolding myself for opening my mouth far too often and not letting the other party speak. I have become far better at this but it is something I try to focus on nevertheless.
The reason this has popped up again in my mind is that I have observed so many meetings and email exchanges in the past couple of years with folks interacting with their superiors in companies or business situations. By "superiors" I mean broadly that one party has something the other wants....VC/Founder, Board Member/Manager, Customer/Vendor and so forth. It's almost painful at times reading emails from one to the other. Get to the point when you want something. Be polite but direct. Do NOT beat around the bush. Just yesterday I saw an email that was almost a page long basically winding it's way around simply saying something had to be approved. The long-winded mail was a bunch of niceties and "I hope's" peppered in-between "It would be great's", "Sorry for's", etc. You all know what I mean and you've all seen or written these emails or had such interactions.
Get to the point! Your superiors, customers, VC's and whatnot usually don't have much time. Further, they've had all the niceties thrown at them. Just say what you want. There is always a fear of being too direct and potentially screwing something up. Trust me...you will never get in trouble asking for what you want. If the other party is offended that you didn't include enough niceties then you may need to rethink the relationship.
Further, when interacting directly, do not fear the silence. Oftentimes it's best to say what you want and wait. Don't say a word after getting to your point. Let the other party think. Let them see that it is their turn to say something. If you've clearly stated what your point was, they have no choice but to speak. If they ask questions, this is good. If they don't react immediately, they are waiting to see if you have something to add. If you know what you want and have stated this clearly, again.....WAIT. So many people are uncomfortable with silence (or succinct emails). Don't be one of them and stop beating around the bush. Let the other side come to you.