Purpose: The purpose of this paper is to present qualitative evidence on the processes and forces that shape school administrator career paths. Design/methodology/approach: An embedded case study approach is used to understand more than 100 administrator career transitions within the Delaware education system. Semi-structured interview data were collected from 48 principals and assistant principals. Coding and analysis occurred through an iterative process, revealing patterns in processes and forces influencing the careers of school administrators. Findings: While some career decisions are self-initiated, most are influenced in part or entirely by other actors in the system, described as recruiting/tapping, requesting, reassigning, passing over, and removing. In self-initiated decisions to move or stay, a number of "pushes" and "pulls" are identified. Findings also suggest the decision to stay-equilibrium is driven by relationships with students and by district support. Research limitations/implications: Data are limited to Delaware and represent the voices of principals and assistant principals only. Patterns evident in the data suggest a need to further investigate administrator career behavior qualitatively, as well as directions for future research. Practical implications: There is a need to better understand and improve local human resource processes in terms of recruitment and assignment of administrators. Additional research is needed to better identify processes and forces related to career decisions in order to improve leadership recruitment and retention. Originality/value: This research represents the first large-scale qualitative study of administrator career behavior and is an important companion to recent quantitative analyses in this area. (Contains 2 notes, 4 tables, and 2 figures.)