Dumb boss story
In about 1993, my then boss took the installation floppies of our latest software with him on the train to try out on his laptop (as was his wont).
Cue the usual call for help (over a very bad mobile connection, not helped by train going through tunnels etc.):
Boss: "It doesn't recognise the disc! It says the label is wrong!"
Me:"Change the disc label [it should have been "INST#001 or something]."
(Short while later)
Boss:"It's still not working!"
[I described the correct use/syntax of the LABEL command in DOS]
Boss:"Oh! I'd only changed the writing on the disc label!"
If it had been me I'd have kept quiet about my stupidity, at least. No wonder all his previous companies had gone under...