This paper outlines the historical evolution of the post of Chief Education Officer in the education systems of the English-speaking Caribbean, looks at the demands placed on office holders over the last several years, and, against this background, suggests areas in the preparation of senior educational administrators that seem to merit attention in the foreseeable future. The historical review reveals that during the development of Ministries of Education in the Caribbean nations differences emerged in the roles of Chief Education Officers related to policy formation and decision making. Profiles of Chief Education Officers from the Eastern Caribbean show the impact of the experiences and other characteristics of these administrators on the definition of their roles. The growing social and political demands on these administrators have further affected their roles. These factors make the complete professional preparation of Chief Education Officers a necessity. This preparation should provide understanding of political, economic, and social forces and goals; knowledge of communications and human relations; and thorough training in supervision and management. Continuing education based on the pragmatic requirements of evolving conditions should also be available to these administrators. (PGD)