The Boss Of It All by Lars Von Trier

Ravn, the long-time owner of a Danish IT company, is selling his business for a substantial profit but faces a major issue: to avoid being accountable for all his unpopular demands, he's pretended to be a low-level employee for many years, sending emails from a mysterious boss to cover his true identity.

To sell his business, Ravn is forced to hire an actor to play this absent boss, leading to some amusing, and very unsettling, consequences.