Well according to the Gervais principle, there are two likely possibilities here. If it's a Loser insulting his Clueless boss then he probably has little to lose and probably enjoys the risk of his boss finding out while sharing a good laugh with his friends. On the other hand if it's a Clueless insulting his Sociopath boss then, well, there's probably a good indicator of why he's stuck in the Clueless caste.