The purpose of this paper is to explore dimensions that relate to training systems effectiveness in a number of industry categories. The training system is taken as part of the reproducer boundary subsystem within the organisation (Miller 1978). In particular this paper seeks to link the concept of the subsystem, namely the training system effectiveness to its environmental characteristics. This is an exploratory study. To my knowledge there is no research work that tests the relationship between the environmental characteristics and and the effectiveness of training systems. This research is in the same 'vein' as that of Lawrence and Lorch (1969), seeking answers to the elusive concept of organisational effectiveness and its relationship to the environment.