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Raemon comments on Mitigating Social Awkwardness - Less Wrong
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I used to operate under a similar heuristic. Eventually I figured out that 90% of the time, if someone didn't respond to me, it's because they couldn't think of anything to say or it wasn't funny or interesting. Occasionally someone might miss something I said, the but the utility-hit of ALWAYS repeating myself (and being annoying 90% of the time) is not worth the benefit of occasionally repeating something useful.
Or put it this way: If you're about to repeat something, first think about how important it is and the consequences of it not having been heard. Then divide that importance by 10. If the result is more significant than sounding annoying by repeating yourself, then go ahead.
It's useful to have this percentage as a guess at my own baseline, and I may fall back on your heuristic as a default. But what I really want is a way to find out before I have to repeat myself whether I've been heard. I refer back to earlier utterances in conversation; I adjust my models of others' intentions based on what information I think they have to work with; sometimes it's a question and the difference between "I didn't hear you" and "I have no opinion" matters for my next action.
This is going to depend a lot on what you're saying and why you want them to have heard it. If you're actually communicating about a problem/project that you're collaborating on, I think there's more room to repeat yourself because the consequences of misinterpretation can be pretty major.
If instead you're navigating a social arena (either for its own sake, or to gain status that you'll need later) then I think it's almost always going to be better to go with the uncertainty.
If you're worried that people DON'T think your statements are valuable, then it's probably better to focus on that. And in that case, it may be worth the status hit to ask point blank a few times:
"Hey, did you hear what I just said"
"yeah?"
"Why didn't you respond?"
"...because I (didn't care/wasn't funny/etc"
"why didn't you care?"
"Uh, because X, I guess"
This is NOT a good general practice. But it may be a necessary cost to figuring out how to communicate better. Save it for people you at least reasonably trust (but who are close enough to the average social person to have advice that is generalizable).
Data point: If you did this with me, then you'd need to be pretty careful not to sound defensive. I tend to shrug, grin, and make a fairly non-specific response because usually when people ask that question, I'm just trying to get them off my back. If you wanted to me to try and give you a thoughtful answer, you'd want to convey curiosity, even prefacing the question with 'I'm curious..."
Yeah, my actual script there wouldn't work very well. I didn't bother trying to do a better one because it'd be incredibly context-dependent, and any "good" specifics I gave wouldn't really work anyway.
I should point out that the 90% number was mostly made up (it's somewhere between 65% and 95%, I haven't done a formal study.)
90% sounds a bit high. But even when not heard (or not comprehended) repeating a mediocre statement can appear mildly needy. If they want to hear they can, of course, prompt you themselves.