When did careful planning and execution become un-cool in real life? Probably about the same time it became un-cool in Hollywood. 

Think how the American hero has evolved. He used to be smart, principled and disciplined.  Not anymore.  Where we used to have student-of-the-game Ted Williams, we now have Barry Bonds.  Where we used to have Atticus Finch, Rick Blaine and Jefferson Smith we have hot-headed Lt. Daniel Kaffee (played by Tom Cruise).  Planners and careful executers include heroes as diverse as Rocky Bilboa and Gandhi.  Heroes-who-plan include soldiers from starkly different backgrounds, such as the soldiers in The Great Escape and The Dirty Dozen. 

Modern television and movies don’t offer heroes who intelligently plan and collaborate with others to save the day.  A television show offering this in the 60’s was Mission Impossible.  The Impossible Mission Force was a group of specialists who actually sat down to plan their mission at the beginning of each show. 

Modern heroes rarely sit down to plan their missions.  They bristle at the thought of collaborating.  Modern protagonists are reactive, not planners. Think of Indiana Jones, Han Solo, Terminator II.  These are individualistic hot headed rejecters of collaboration.  When they succeed in the end it is because they got lucky at that last desperate moment, not because they pondered contingencies before setting out.   Interestingly, if you want planning and execution, look to Hollywood’s villains, people such as Hannibal Lecter, Darth Vader or Batman’s Joker.