I've been on both sides as well. But here's the deal... as the spying IT guy, you have to be super careful. Do not be afraid to tell your employer that you do

I've been on both sides as well. But here's the deal... as the spying IT guy, you have to be super careful. Do not be afraid to tell your employer that you do will not do something if you think it puts you personally in a bad legal position. I had one of our legal guys at a job request that I manually review email logs to look for something for him. My response to that was simple, "fuck no." I'll grep for strings and patterns and pull you the emails that come up, but there is no way in hell I am reading someone else's email. The reason is pretty simple too. I don't want to be a part of your lawsuit. I don't get paid to be subpoenaed and deposed. If I quit this job or am laid off I don't want to be getting called up a year, or three down the line just to show up in court and answer questions about why I was reviewing jane and john smith's emails to their kids. Simple fact is, at some point you have to be willing to tell an employer that what they are asking you to do goes way beyond your pay grade. And protecting yourself legally comes before anything related to your career advancement.