Re: "Has your boss ever exempted themselves from rules imposed on others?"
In one company I worked for the best way to get something radical past management was to have a conversation with the MD down the pub along the lines of "I've had an idea but I'm not sure whether it's workable, so what do you think about ...". 2-3 days later the MD would announce this brand new initiative that he'd come up with, and the techies would all grin at whoever's turn it had been to speak to the MD.