Honestly, that’s pretty out of character for Michael Scott. For a character who otherwise repeatedly makes the same mistakes over and over again, to show even that tiny bit of insight is a pretty big plot twist that maybe he’s not completely the bumbling oaf he lets on.
I’m not saying he’s secretly a Machiavellian genius, but his stupid antics belie what seems to be a pretty high emotional IQ at times (in sales and management, at least).
To add to the previous comment, Michael was also well known for making bad choices that did damage to his own life.
But then again, Michael having an inconsistently high emotional IQ is a recurring theme. When he’s in “sales mode”, he’s really good at making an emotional connection with people and making them feel like they’re buying from a friend.
I dunno. It’s an interesting conundrum the series presents and obviously doesn’t dig into too deeply since it’s a sitcom. Michael is sometimes unnaturally attuned to someone’s feelings and other times extremely oblivious to them.