Unless you have an exceptionally paranoid workplace, a much easier way to compromise your boss's computer is just to walk over to it and pop in a livecd after he's gone home for the day.
By the way, ten minutes I wrote the grandparent to this comment, a coworker IMed me and asked me to break into his workstation :-). He was working remotely, trying to SSH in, his system had gotten wedged due to what turned out to be disk errors, and he needed me to rescue it.