I do meet some guessers are good at guessing, but quite a few are bad at it and carry on anyway. At their best, guessers can be empathetic and thoughtful. At their worst, they're people who don't ask questions because they prefer their own internal narrative.

There's a manager at my current place who's been loudly blaming a couple of twenty-something interns in another department for making mistakes, instead of looking into the management structure there and seeing what's going on. Drives me frothing mad, though I have to conceal it. Admittedly, that's more a case of him being an arse than being a guesser.

A more pertinent example would be a colleague who, as I was about to leave at the end of a year's fixed-term contract, said "I'm sorry to see you go. Though you're kind of mysterious..." Well, she'd had the whole year to ask me questions about whatever she thought was mysterious about me, and I'd have answered. But I didn't talk much about my life outside work because I assumed no one was interested. It didn't bother me, since it's probably better to be mysterious than boring!