Yes, been there and done that in my previous role in education.
From the business manager who bought a sign in system without doing any research or comparisons (guess what - didn't integrate with our MIS, wasn't very good, and there were much better and cheaper alternatives available) to the new school group "server guy" who bought a new server to replace ours, only for us to find out it was hopelessly underspecced for our needs - but I was already on my way out by then!
Bes one was an officious depty head who had recently insisted everyone read certain policies - this week it's first aid, next week it's pupil code of conduct, etc. As well as having some fun pointing out how out of date everything was (the "site rental" policy had a fax machine available, despite the line being disconnected five years previous) I managed to knock him back in front of half the school at lunch.
DH "This is Bill, who will be starting as an English teacher next term. You are getting a laptop ready for him?"
Me "Yes of course, in fact it's ready now"
DH "Good, then hand it over"
Me "Sorry, thats in breach of the staff laptop policy - which says you don't get a device until your contract starts - and also the staff acceptable use policy, which says issing a laptop needs Appendix A signing and countersigning"
Wandered off and finished my lunch...