I had one company director trying really hard to get me to let him around our security measures - I finally said 'Is this a test?' which made him stop and think and finally give up.
Then there's the big guy who had the corporate security team hack into peoples' gmail accounts, there was a lawsuit about that case last year because the security guy quit after he refused to hack into the big guy's ex-wife's email and later sued for wrongful dismissal or something as a result. Come on guys - boundaries!