This article presents findings from an exploratory study that compared and contrasted leadership succession planning in two large Ontario school districts with focus on three themes: (a) leadership succession planning, (b) recruitment and selection, and (c) professional and organizational socialization of school administrators. Among the findings from the two comparative cases were: (a) a need for financial support for leadership preparation, (b) a need for structured recruitment teams, (b) a need for structured administration preparation and training programs, (c) self-selection, (d) a need to examine policy for rotating leaders, and (e) a need for internal and external promotion.