Is there a meaningful discussion of working conditions here? The article doesn’t have a lot of other context. If this is all that the employee in question said, I would not call it discussion of working conditions.
Yes, the "joke" only works because the implication is that the CEO is out of touch with the lives and working conditions of the average employee. It's pretty overt in meaning.
Should employees be required to discuss things explicitly? Without the natural way people talk? Especially the natural way Americans talk? Seems pretty rigid if you ask me