The study reported in this article is based on a pilot investigation of the principal's role in Greece and Cyprus. The authors asked newly appointed principals about (1) the nature of the role; and (2) the factors that contribute to or militate against effective enactment of the role. By gathering this information and comparing it against similar information gathered in other countries, the authors hoped to gain cross-cultural insights that would be useful for the professional development of school principals in Greece, Cyprus, and elsewhere in Europe. First, the authors discuss problems and imperatives for developing robust principals and preparation programs. Second, the focus shifts to Greece and Cyprus in a review of their selection process of principals. Third, the investigation of the perspective of newly appointed Greek and Cypriot principals on selected aspects of the role in those countries is described. Fourth, the authors present findings comparing responses from the two groups in the related literature. Finally, conclusions and recommendations are presented. (Contains 3 tables.)