I like to teach through telling stories. Yes, this will related to digitization. Trust me.
Our dryer broke on Sunday, meaning that we could wash clothes but not dry them. Today the repairman came and fixed the dryer and also checked over the washer. I had flashbacks to a Star Trek: The Next Generation episode when Scotty (from the original series) is telling LaForge how a piece of equipment should be operated, rather than what's in the manual. Here was the repairman looking inside the washer, telling me how we used it (based on what he saw), then giving me tips on how we could do things better. (For example, how to bleach whites without inhibiting the detergent from doing its job. I never knew!)
Isn't it always the case that we learn best how to operate equipment from other operators or from those who repair the equipment. This is where the real tips and techniques come out. This, too, is where we learn how to handle error messages that seem to mystify.
Of course, what would make a great manual for any piece is to have it written by those who use the equipment, and include suggestions from those who repair it. (We know that doesn't always happen...it often seems like the manuals are written by harried engineers.)
And the tie-in with digitization? First, heaven forbid that your equipment should ever need repair, but if it does do take time to watch and talk to the technician who fixes it. Don't be afraid to ask questions. (We tend to leave repair people alone, but as I child I learned that someone was suppose to be there to watch and answer questions. It is also a good way of learning how to do some minor repairs or even keep the equipment clean.)
Second, if you write procedures for your staff on how to operate or maintain equipment, really write what should be done (and when) and don't necessarily repeat that manufacturer's party-line. Be sure to include helpful hints. For example, in grad school I worked in a copy center and the Kodak copier would overheat during heavy operations. Rather than letting it cool down (and get behind n our work), we found a way of running the copier with the cover over the guts of the operation totally open. That was in no one's operations manual and we never wrote it down, but it is the type of thing that needs to go into group's instruction book.
Finally, this also reminds me of my grandmother's cookbooks. She annotated her favorite recipes, adding and deleting ingredients and making other notes. Do the same thing with you equipment manuals. Okay...probably you're not going to cross things out, but make notes of things that you learn that are not documented. And if you don't write a separate manual for your staff on how things work, then be sure to make notes in the manuals. (Then make sure they can find the manuals!)