The entrepreneurial involvement of educational institutions at the elementary and the secondary educational levels has not been systematically analyzed in the existing body of literature, although the decentralization and autonomy of educational institutions have been emphasized in educational policies since the 1980s. This study provides an empirical analysis of the entrepreneurial orientation, as related to the schools in Croatia and Bosnia & Herzegovina and their principals. The influence of this orientation is analyzed from the perspectives of principals’ personal job satisfaction, perceived contribution to the society and the perception of the social role/influence of principalship. The empirical findings show that the entrepreneurial orientation of schools and their principals in Croatia and B&H are closely inter-related. More enterprising principals are also more satisfied with their jobs, and they feel to be contributing to the society more. However, the same does not apply to their perceived social standing/status, which could be attributed to their intrinsic motivation, but such a conclusion needs to be verified by further research. The results of this study show that the entrepreneurial orientation(s) of schools and school principals should be considered as useful descriptors of individual and institutional behaviour in the educational systems of South-East Europe.