So they won’t let me play with the 20 year old ROLM PBX at work as I am just an IT guy who can’t possibly be trusted with knowledge of the phone system. 
Thanks said I was enlisted to help verify outgoing caller ID buy picking up the phone and dialing a feature code plus a number associated with the trunk I want to use and then a number to dial on the outside. So my question. Does asterisk have the same feature? Or would I have to code the dial plan to do it?
Thanks All!!