Here are the steps:

1. Have Skype (make sure it is working)
2. Ask the staff member if he wants to Skype
3. Ask the staff member for his Skype account username
4. Skype the staff member weekly or monthly


NOTE: If you keep Skyping him, be friendly and you may or may not get staff on the server. If you do get staff, be a good staff member and don't be mean!