Before I engage seriously with something someone is saying, I'm usually running a quick classification. Is this substantive? Is this person reasoning from things they actually know, or working from a general impression? Are we trying to get somewhere, or just talking?
Ray Dalio's above/below the line framework is one tool I use for this. Above the line is the actual claim being made. Below the line is the detail that supports it. Someone who can move between them, who knows what they're arguing and can back it with specifics, is in a different conversation than someone who jumps to detail without a coherent main point, or holds a confident conclusion with nothing underneath it. The second type is usually riffing, even if they don't know it.
How to Win Friends & Influence People adds the other dimension. Even when the logical conversation is real, there's usually a relational layer running underneath — someone protecting a position they've already committed to, a face they need to save. Carnegie's point is that treating that as if it were purely factual is a mistake.
If I pick up on any of this (riffing, vibes-based confidence, relational stakes that override the argument) I don't push. There's no point applying pressure when the other person isn't in a mode where they'll update on anything. Once I've classified the conversation, how hard to engage mostly answers itself.