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David Mamet has a great way to explain the urgency of being specific, "We can infer the general from the specific, but not the other way around."
I have also found it's useful to start with the most important thing you have to convey. When writing a first draft we tend to put it the last paragraph. But the clarity is almost always improved by making the last paragraph the first paragraph. Even if you are stating a seemingly ridiculous proposition, it seems best to get it out, then back it up.
If you don't put the most important part of the message first, there's a disconnect that can be utilized for comedic effect. But -- and I think that this is your point -- those disconnects are a huge obstacle to convey concepts. Now your reader or listener's brain wastes a lot of attention trying to figure out what's going on.
E.g. "You know those drapes you just bought? The blue ones. Yeah, they're on fire. And so's the rest of your house."
I use the term "conceptual hook" explaining that you've got to give people a hook to hang their understanding on. How does it link or anchor to the real world?