This paper explores certain dilemmas in the professional preparation of school administrators, particularly in developing nations. The paper begins by reviewing the issue of specialist preparation and development for educational administrators, examining arguments for and against specialist training. A discussion of the extent of Canada's commitment to professional training for educational administrators provides a context in which to describe a framework developed in Manitoba for planning the preservice and continuing development of administrators. This framework hinges on the establishment of a strong link between the purposes of and the delivery methods for professional training. The framework assumes the existence of a continuum of skills important to administrators, the need to assess an administrator's progress along the continuum, and the need to develop preservice and inservice programs that take both the skills to be taught and the skills already learned into account. Although preservice programs should probably focus on basic "survival" skills and inservice programs on skills for handling problems developing in practice, the traditional content of such programs is usually the reverse, as a discussion of Manitoba's system illustrates. The paper concludes by applying these observations to the unique situation found in the Caribbean. (PGD)