The principal of a school is the driving force for instructional success and academic propelling of students. Research shows that other than instruction in the classroom, leadership is the critical factor within the school's control that influences student learning. Much attention has been paid to how school leadership directly influences students; relatively little attention has been paid to how leadership indirectly influences student learning through their relationships with faculty and staff members. Using a qualitative approach, the researcher explored the influence of a principal on aspiring administrators with whom they work. Given the growing shortage of principal candidates in American schools, the field of K-12 education needs infrastructure to develop and encourage currently qualified faculty members to pursue leadership positions. The researcher interviewed assistant principals about their experiences with their principal and how their principal influenced their desire to aspire to the position. Results from this in-depth study highlight the specific areas that draw leaders to higher pursuits of professional growth. Conversely, the results elucidate the role current leadership plays in situations where assistant principals who hold principal certification choose not to pursue the principalship. Understanding the role of leadership in these situations can facilitate healthy relationships between leadership and their staff members as well as identify opportunities for improvement regarding how to support and encourage potential educational leaders as they advance to administrative positions. [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.]