[erikcw]

We've been using skype chat almost elusively for 3 years. At first, I loved the work flow, but in our case it has devolved into an email replacement for one of our team leads. He daily sends reams of chat messages into the room with the expectation of a synchronous response. Messages routinely get lost in the shuffle. I'm working to get him to use email for these sorts of issues -- status, in progress.

If skype had threaded chat conversations, it would be much more manageable. Until then, I miss gmail... :)

Use the right tool for the job.

[technomancy]

Skype has a pretty awful UI for chats. If you get people set up using a bouncer then it's pretty easy to get persistent conversations over IRC, and then people get to use the client of their choice. Plus it's a lot easier to automate with bots.