Educational literature provides evidence that there are numerous steps school districts must consider in order to recruit and grow qualified individuals for the position of the campus principal. However, it also indicates that there are a number of factors that contribute to the decision-making process that future leaders take in order to decide to apply for the position of the principal. The purpose of this quantitative study is to determine what factors inhibit or encourage assistant principals to pursue the principalship. The researcher utilized a survey to evaluate factors that motivate or inhibit assistant principals' decision to aspire for the principalship. Although surveyed school districts have indicated that have had difficulty filling principalship at all levels (Whitaker, 2001), the number of individuals holding administrative licenses or endorsements exceeds the number of vacant positions each year. The recruitment and retention of qualified and certified administrators is one of the greatest challenges confronting school divisions in Virginia and across the nation (Paola & Moran, 2001). The pressures of high stakes standardized testing coupled with v countless leadership and management tasks have contributed to increased instability in school administration (Hargreaves, 2005; Richardson, 2009). Analysis of quantitative data identified inhibiting and motivating factors in an assistant principal's decisions to pursue the principalship. Four inhibiting factors that were identified were distance from positive impact, roles and responsibilities, external forces, and personal impact. Three motivating factors that were identified were influence on change, challenge, and influence on personal life. Participants indicated that their biggest concerns in pursuing the principalship were the impact it would have on their personal lives and the stress that comes along with the job. The ability to impact change was a factor that participants scored as one of their highest motivators for pursuing the principalship. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]