I am very grateful that I am no longer at my last, super corporate job, and that at my current job, I run the IT systems. Why? Because Skype probably would have gotten me fired from my last job. Skype, like every other major instant messaging client, has a conversation history feature. Unlike the others, Skype has a synchronization system. For example, if I am at work at talk to someone via Skype, and then get home and they are logged on from that computer, it will dump the previous chat session's contents to my home PC.
This is all well and good. Rather obnoxious (when the other person signs on, you suddenly get dumped an entire conversation all at once, and it looks like a new message), but harmless. Or so I thought.
Just a few minutes ago, someone I talk to frequently via Skype signed on, using the same PC he was using last night when I talked to him. The contents of last night's conversation (when we were both at home) got dumped to my screen. Some of the language was not "work safe" and some of the contents were not "work safe." Certainly, much of the conversation was something that, even if it did not get me fired, would certainly have me blush if my boss ever confronted me with it.
We do not do any kind of Web/Internet monitoring at my current company. If we did, I would be the one doing it any ways. My previous employer was rather different. All IMs went through a proxy which performed logging, and each manager had full access to the logs of their direct reports. In other words, had this happened at my previous employer, my manager would have been able to read the full contents of that conversation. Even worse, it would have appeared to occur during working hours as the proxy would have timestamped it.
So, if you work for an employer that might be (or definitely is) performing any type of Internet monitoring, I highly recommend that you either avoid Skype entirely as an IM client and use it strictly for its VoIP features, or disable to conversation logging functionality to prevent your "non work safe" conversations from outside the office from leaking into the office. This is yet another example of a new feature that its creators did not consider the implementation of or consequences of before they implemented it.