Superintendents leading school districts, particularly in hard-to-staff areas, face immense challenges in recruiting and retaining high-quality, well-trained teachers, principals, and district leaders. Many large urban areas as well as their rural counterparts have high concentrations of intergenerational poverty and unemployment. Rural areas are further disadvantaged by the lack of social and cultural attractions as well as fewer health care resources. In North Carolina, many of the lowest performing schools in the state are disproportionately clustered in rural areas. Superintendents leading districts in such areas face serious problems of high teacher and school leader turnover. As a result, superintendents are constantly engaged in an ongoing cycle of hiring new teachers, assistant principals, and district-level leaders. The graying of the school leadership profession further compounds the problem. For example, over the next 4 years in rural, high-poverty schools in North Carolina, an estimated 50% of principals will be eligible for retirement--making succession planning for quality school leadership a critical issue. In this article, we review the research and best practices on succession planning in education as well as in other sectors. Utilizing the theoretical framework of human capital theory, we illustrate how forward-thinking superintendents can partner with universities and other organizations to address the leadership challenges they face by creating strategic, long-term, leadership growth plans that build leadership capacity and potentially yield significant returns in improved student outcomes.