My ex-boss who had 35 years of experience in IT Industry, didn't know one single fucking coding language, obviously had no clue about source control or anything even remotely related to computers, and had been project manager of a project having over 1 million lines of totally undocumented code split into 389 files with no apparent structuring. All variables were either alphabets or names of programmers who developed them.
Code was in Python 2 and had bugs/line ratio ~= 5.
He asked to write a 'wrapper' class and somehow run it in Java and fix all bugs automatically. (insert Shia LaBeouf's magic GIF here)

When I said it doesn't make sense, he said you should put in hard work and do it, and not give excuses.
Time given to do this - 1 hour :-P

Good thing I quit that shit place and that pathetic moron. Love my new job and life! :D

Seriously managers should trust their developers and allow some degree of freedom. It helps a lot.