I often find that when a boss is stuck in the dark ages of technology, the best route is to work around them. If they don't expicitly tell you how to do someth

I often find that when a boss is stuck in the dark ages of technology, the best route is to work around them. If they don't expicitly tell you how to do something, do it the way you want, but be prepared to fix it if something goes wrong. If they do tell you to use some antiquated method and won't budge, then do it that way. When it doesn't work, they'll move on to the next bad idea. Eventually, they'll exhaust all of their options and will choose the best of the worst. Your job is to be out of there by then.