I have a very roundabout way of getting to my point in a conversation¹, and while my folksy style of communicating would be right at home in an episode of The West Wing, it seems to be a real problem for me in the real world. I don't know why I just can't seem to take Xenophon's advice:

Brevity is the soul of command. Too much talking suggests desperation on the part of the leader. Speak shortly, decisively and to the point [...] Then move on.

I also would choose to be considered witty over tedious any day of the week:

Therefore, since brevity is the soul of wit
And tediousness the limbs and outward flourishes,
I will be brief

--Polonius

I first realized this was a problem in my chosen career path when I attended my first meeting with Plancast's investors. During the course of the meeting, one of our investors asked me a question about how I was planning on hiring more engineers. I began answering the question with a wonderful story about engineers with the intention of segueing into my answer about how we would like to allow prospective engineers do a paid side project for us before offering full employment.

In the middle of my story, the investor cut me off and asked me to get to the point. Since then I've mentally noted numerous occasions where people I'm talking with have finished my sentences or cut me off and just moved on. These mental notes have caused a certain amount of paranoia to follow me into any conversation.

This paranoia to be succinct has also infected other areas of my communication, like emails, where my brevity has led to, on numerous occasions, omitting crucial details the recipient actually needed to clearly understand what the heck I was talking about. Alas, I'm just not good enough to paint gorgeous word pictures as succinctly as Hemingway²:

For sale. Baby shoes. Never worn.

And since I'm often so short on time, I feel like my communication tends more toward that of Blaise Pascal's than not:

I have made this longer than usual because I have not had time to make it shorter.

I guess my point is you should be succinct, but not too succinct that you leave out crucial details or waste too much time dialing up the brevity, something I struggle with daily³. I will say though, I think Twitter has really helped me deliberately practice being more succinct, but I've still got a long way to go. And if I ever do get it right, I can finally leave them wanting more.

https//www.youtube.com/embed/O27RzZEOkeA