it depends on how they monitor you, I run a Server 2008 R2 enterprise cluster and several hundred client machines on Windows 7. I use several different methods of 'watching people', I have a internet filtering 1U server box that all traffic passes through which blocks and/or logs everything going through it, so if John Smith goes on x x x.com it logs the username, pc and the website. I also have centralised screen / keyboard capture running on the network, this software logs all the keystrokes on each pc, so that if for example John Smith types in hotmail.com it will automatically take screenshot's to see what they are up too, this also logs any swear words and anything else I care to put into the filter, e.g the words youtube etc.
By the way I work in an educational establishment, hence the overkill filtering.
We use Impero for our keyboard / screen filtering, but there are plenty of alternatives, e.g Ranger etc
Using software like the above you don't need to hack around doing anything with certificates etc as you are filtering the keyboard input at source, you can also get it to start recording video or taking screenschots when certain keywords are triggered.