Paths of Glory is one of my favorite films, after hearing David Simon speak about how it's essentially a movie about middle management and the dangers of being giving a task that's impossible to complete yet will still let down the people who look up to you!

Much better than movies or shows on the subject is Herbert Simon's work on Administrative Behavior. Unlike David Simon's work it gives people a way to think about problems and approaches to problems where their skills, resources, rationality aren't enough - https://en.wikipedia.org/wiki/Herbert_A._Simon