Advice on Communicating Concisely

Just guessing here, because I have a similar problem. You need to know your audience, so that you can skip the parts they already know, and only communicate the new part.

Also, depends on whether it is a monologue or dialogue; in monologue you err on the side of saying more, in dialog you can expect some "if they don't understand, they will ask".

.

For example, I sometimes realize that I am needlessly defensive, that I am unconsciously expecting the most uncharitable misinterpretation of anything I say -- that's because I have spent a lot of time offline with people who were like that -- so I am trying to make my argument ironclad, include all kinds of disclaimers, etc., which results in many extra words.

On the other hand, it is easy (and frequent) to err on the side of saying too little, making your message ambiguous without noticing it [? · GW]. Sometimes people appreciate that I include some extra context; I have been explicitly praised at work for writing great documentation.

I also have suffered from this (and still do, really). I will share some lessons that I have picked along the way, followed by a couple of book recommendations.

The lessons:

• Focus: Most of the time the issue is you are trying to communicate way too many things. Now I try to contain my message to one single point. This helped me immensely.
• Message House: A framework in branding and PR, I advise you to do a quick web search on this. With my previous bullet, I "construct" my message house with these components whenever possible: (1) Anecdote, preferably a personal one. Kicking it with a very short story that is central to your idea helps capture people's attention immediately; (2) why this matters, why I am telling you about this; (3) Sizzle, or a very quotable quote. If people wanted to tweet one sentence from your "speech" this is it; (4) Data point or one last anecdote to enforce the central theme.
• Fluency: You might know what you are talking about, but if you are not fluent about it, it takes a lot of time to put stuff together, and it feels like you don't know what you are talking about from the outside. To overcome this, you can drill things down. Anecdotes or data points you occasionally use; you can create word blocks of your world view that signals where you are looking at things from; you can have identity related short blocks and exercise on them constantly to get yourself fluent on very specific little blocks, which then you can use as springboards or solid middle- or end-points in your speech.

Book recommendations:

• Smart Brevity by Jim VandeHei, Mike Allen, and Roy Schwartz
• You've Got 8 Seconds by Paul Hellman

What specific kinds of ideas are making this problem noticeable?

Are you talking about conveying specialist knowledge to a lay-audience - for example, good luck trying to get me to understand what an Eigenvector is or the points system in Cricket - I've tried. Likewise, to explain to a friend what Sub-Surface scattering was, I first had to introduce him to the mechanics of Ray Tracing. Luckily he was a musician so I could just use analogies to the diffusion and travel of sound waves.

Or are you talking about more personal preferences and experiences, for example recently someone asked me "why do you prefer to be behind the camera rather than a performer in front of it?" - apparently they thought I was such a ham I should be a comedian not a director - I didn't know where to even begin.
Likewise many people who "kind of fell into doing this" for their current profession will stumble if you ask them how they "got into it" because there's often a meandering narrative and confused chronology because even to themselves it's not clear.

Another question I have is - are there any patterns in the assumptions, misunderstandings or tangents which people you're trying to explain exhibit in reaction to your explanations?