This paper presents a history of educational administration among Canada's provinces, discusses the status of university preparation programs, and explores theories of formalized and alternative approaches. Before the 1950's, little interest existed in administrators' formal preparation. Consolidation of schools led to graduate programs, but the lack of requirements for preparation and experience indicates the persistence of the provinces' educational jurisdiction. Historically, administrators and teachers first learned on the job; graduate credentials are not yet completely accepted. Because leadership resides with the ministry and the district, administrators have few opportunities to initiate changes. The importance of schools' geographical and social contexts are not apparent to those observing this limited progress. To formulate a perspective on educating administrators within Canadian cultural contexts, four paradigms illustrate the consequences of preparation programs adopting formalized or alternative approaches. Formalized preservice training emerges within a functionalist paradigm, which delegates administrator control over the organization. The tradition of training following practice is compatible with alternative paradigms--interpretive, radical structuralist, radical humanist--that hold flexible conceptions. This analysis finds no cause for alarm concerning Canada's slow pace of administrator education. Cultural contexts should precede professional ideologies in program design. Forty-three endnotes are included. (CJH)