This article presents findings from an exploratory study that described and analyzed the professional growth of 18 educational practitioners while participating in a principal preparation cohort program. The goal of the study was to add understanding to the nature of transformations that occur as teachers prepare to become school principals, and thus, researcher propositions guided the design and focus of this yearlong investigation. Analysis of the exploratory case study data suggests four major themes influencing practitioners' growth toward becoming principals: (a) role conceptualization of the principalship, (b) initial socialization into a new community of practice, (c) role-identity transformation, and (d) purposeful engagement based on career aspirations.