I love this idea. It can be tremendously helpful for remote workers. I 've tried similar stuff it in the past, but those sessions were about tasks shared by both (or all) of us involved in the session. Your idea is more about just "working with someone", even if that someone is not working on the same task as you. It is more about simulating working in the same office even when you are not actually in the same physical space - and that sounds like a great idea. I will definitely give this a try.