The Enron film really gives some great insight into how bad decisions happen. Another good documentary deals with Coke's decision to create and release New Coke.
A couple of other good documentaries-
'Control Room' - This really shows how the govt and news organizations impact how we see the world. It follows the crews of Al Jezeera as they make their decisions about news.
'Dogtown and Z-Boys' - This really took me back to when skateboarding swept the country in the 70's. I was a skater back then and again in the 80's so this was particularly interesting for me.
WANTED - Solid-Boxed WGSH's, C.8 or better.