When you make an assertion or proffer an argument how do you know if you are being understood as you intend?
How do you know you understand what you hear as it was intended?
IMO the crux of all questions related to meaning and logic.
When people speak your mother tongue, most of it you understand essentially intuitively. That's essentially an unconscious process. Someone not doing it this way would be unable to process the flow of data in any sustained conversation, especially where different people may cut each other or speak at the same time. So, basically, you have to take whatever you understood for granted, just like you have to trust your memory, your logical intuition, as any other perception senses.
Checking will occur with any discrepancy, provided not too much time has elapsed for you to notice.
However, there is something like the semantic focus of your attention. Different people taking part in the same exchange will often focus on very different things in a way which isn't necessarily apparent to other people. This means in practice that you process part of the data flow consciously just like you focus on only a small part of your visual field. It's doable because it's a trickle of data. This should allow you to detect inconsistencies if they affect the data you're focusing on. Otherwise, I think you just won't notice. So, basically, you will notice inconsistencies whenever they relate to things you're focusing on because that's what you're interested in. See, you're smarter than you thought.
Yet, I guess this explains largely why we tend to talk past each other. Essentially, we're not smart enough to pay enough attention.
I think there's nothing you can do about it except train. People whose job is to listen to other people will develop an extra pack of neurons to process a broader focus. However, that may come to the detriment of some other mental functions. So, you need to have a real good reason to do it, like it's your job or something.
EB