The purpose of this qualitative study was to gather insights from current parochial school administrators who experience the day-to-day operations and expectations of the position. The role of the parochial principal has transitioned over the past decades to be a position requiring a variety of skills and abilities. Data collection occurred through the collection and analysis of surveys, individual interviews, and a focus group discussion. All participants within this study are current parochial school administrators with five years or less experience and have participated within the Van Lunen Executive Management Program. Data collection was designed to gain insights from those experiencing the day-to-day expectations of the position. Phase 1 data analysis revealed four primary skills, which are visionary leadership, relational, communication, and operational oversight. The two secondary leadership skills are educational philosophy and finance. In Phases 2 and 3 of this study, the researcher used interviews to gain insight into how these skills are developed. Data analysis exposed the emphasis of skill development through contextual experiences, mentorship, and a growing trend to transition away from the autocratic leadership model. Continuing education was also noted as an area for future improvements through the updating of curriculum. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]