As I am someone who has not yet managed to "get round" to arranging a skype conversation, I have been thinking about what's stopping me.
I know there is a psychological barrier for many of us when jumping into our first conversations. I am nervous of arranging a one-on-one call, but I think if there was a group or several small group calls scheduled I might be brave enough to join in one. Or perhaps beginners could listen in on some skype calls or group calls first to see that it is not that scary (some overlap here with technical ideas in other threads).
Maybe there could be some scripted conversations to try, based on the SSIW lessons or listening exercises, so that learners could practice, eg issue recordings of one half of the conversation? Or is that taking hand holding too far?