Given the substantial challenges of the principalship and the high turnover of school principals, school districts have sought out assistant principals as a major source of leadership talent to take up the role of principal. In this qualitative dissertation, I explored how principals and assistant principals from a southeast urban school district described and understood their roles in developing future principals or their current position as assistant principals, respectively. Specifically, I examined what they deemed as professional learning experiences that shaped their journey to becoming principals and how, if at all, their prior knowledge supported them in their current role. [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.]