Nope, best way to educate the pointy hair boss is to have him watch you when you troubleshoot a problem and, as Jesper pointed out, everything is done online. If you are proficient with troubleshooting, you should be able to move quickly through the various screens looking at various items while you isolate the cause so you can correct it. I had an operator amazed last week when a new machine didn't do quite what he wanted and I added a new function on the fly by updating the functional spec as we talked, adding more code to the controller, updating the HMI, etc.
Printing out programs went away along with hard copies of the programming manual, you can find the answer faster in the online manual than the paper copy by using a search function.
The functional specification is where it's at, even he should be able to read it and possibly understand what is going on even though he can't follow the code.