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Sounds like this could have been from Office Space where the main character decides to not show up for work, then gets promoted to management. Is this Wally's plan?
@Sordatos, and kinda @Zerotenon
I think the stuff Dilbert says goes way over the boss's head he doesn't realize he's been insulted. Whereas Wally speaks the bosses language and tells him things the boss can't do anything about, so it gets his back up.
Wally must spend days concocting things to say to the boss to drive him nuts...what a job :)