Norman F Dixon on "The Psychology of Military Incompetence" is very instructive, even if he is more than a little biased in his views.
Leadership has never been better described than the Mask of Command by Prof John Keegan. In fact there isnt a better military history book than Face of Battle by Prof Keegan.
Apollo The Race to the Moon (Charles Murray and Catherine Bly Cox) is the handbook of management of complicated organisations.