The relationship between assistant principals' orientation process and career mobility is examined in this qualitative study, based on the assumption that the assistant principalship is a testing and an opportunity position for both the candidate and the organization. Methodology involved formal and informal interviews with 20 secondary school assistant principals and their colleagues, direct observation, and document analysis. Factors for career mobility were identified; these include school and district norms, relationships with colleagues, career timing and planning, degree of risk-taking ability, and personal drive. The typology provides a framework for viewing the career orientation of assistant principals and the factors influencing their careers and also identifies four emerging themes: organizational influence, site level, the principal, and personal responses. A recommendation is made for using the typology as a basis for structuring recruitment, training, selection, support, and organizational assessment practices. Two tables and one figure are included. (38 references) (LMI)