The purpose of this qualitative study was to explore the connections between principal succession and professional learning through the analysis of the current practices in leader development, support, and retention in two Georgia state school districts. The findings of the cross-case analysis were summarized in five major themes: First, a key component to the overall success of principal professional learning and succession is a visionary superintendent. Second, planning for principal succession, school districts strongly favor local applicants. Third, building leaders from within the district is an effective way to ensure leader continuity. Fourth, developing future principals, school districts express strong preference for the nonuniversity leader preparation programs, designed to address their specific needs. Finally, leader professional development and succession are tightly connected. Implications for research and practice are offered.