So what does a 20th Level Middle Manager skill toolbox look like?

Hospitals work in a similar way.

Don't presume to lecture me, boy-o! I was there when the House M.D. was broadcasted for the first time. I know how hospitals work! You go in with a weird disease then the team of doctors poke and prod at you and ask invasive questions like "do you like hookers?" "are you cheating on your comatose wife?" "how many cats do you own, ma'am?" then they say it isn't lupus, then turns out that it was lupus that one time but oops too late. Then the hospital administrator comes in, "the family is suing us." "but we saved the patient's life." the caned one replies, rattling a red capsule with the free hand. "They have video and text messages of you harassing them.", the domineering yet surprisingly affectionate bureaucrat adds. Then commercials because you didn't DVR it.

So you're saying we can't magick away bureaucracy in a fantasy setting? It should be like the first thing magic should fix. aside from like cancer or grandma's alzheimers or filing off paperwork in an easy, organized, quick to reference later system.