Principals are instrumental to successful school improvement efforts and positive student outcomes. However, recent workforce trends, increased accountability, demands of the job, and turnover rates for school principals are worrisome. Succession planning is a systematic approach that involves all aspects of identifying and retaining leaders (Rothwell, 2010) including preparation, recruitment, selection, onboarding, induction, development, and retention. Although succession planning is underutilized in public school settings, it is one avenue to address leadership issues and help school district leaders meet their long-term leadership needs. This qualitative study examined the succession practices of five large school districts in Colorado by gathering the perspectives of principals and school district leaders. The findings indicate several actions that educational leaders can take to address the challenges of well-qualified candidates and the do-ability of the principal position. Findings further indicate that leaders may influence principal retention by differentiating support and purposefully fostering relationships. These findings might be used by other educational leaders to strengthen their succession practices and policies and affect the retention of school leaders.