This dissertation aims to understand how leadership practices of early career and more seasoned principals are informed and influenced by their past experiences as vice principals. The overarching goal: increase understanding of how the work experiences of vice principals can be better leveraged as apprenticeship opportunities for future principals. A phenomenological research design was utilized. Interviewed participants were asked to indicate which vice principal experiences were directly transferable to current responsibilities as a principal and to describe how these duties inform their current work. Findings suggest leadership practices of early-career, and highly effective principals were influenced by past experiences as vice principals via pathways to the principalship and through relationships with lead principals. Further, work experiences of vice principals served as training ground for principals, both operationally and instructionally. Identified gaps in leadership training included budget, instructional leadership, special education, and human resources. Due to the lack of succession management systems, school districts might benefit from succession plans for aspiring leaders. Preadministrative opportunities for teacher leaders ensure positive socialization into administration. Former middle vice principals revealed gaps regarding instructional leadership training, yet elementary vice principals did not. Middle school principals would benefit from additional training, accordingly. This paper asks current principals to reflect on their former roles and responsibilities as vice principals and describe how those experiences inform their current work as instructional leaders.