[mrjatx]

I've been a network administrator and had control of everything.

That did NOT mean that I was actively viewing everything and sitting in a tower somewhere cackling at all of the deep dirty news I had. I had to pull data a handful of times during lawsuits or sexual harassment complaints.

You should not be delving into deep personal/sexual conversations on any work tool without having in the back of your mind that it may come up at some point, whether you're at a startup or not. I'm on my 3rd startup and while I know nobody has been monitoring (because I pay for the tools) I still keep the tools somewhat professional. To the point that I couldn't care less if someone looked into my conversations. If we're going to bitch about that, then the fact that my data is on some unknown server at Hipchat is FAR more worrisome to me than my COO looking at my conversations.

You SHOULD trust your employees and if you don't trust one replace them. You should also TRUST your management to not spy on you. But you should also assume that they have the ability, if not, you're daft.