The research goal of this study was to explore the preparation and socialization of beginning administrators as educational leaders, focusing on their leadership growth and development over several years as they transitioned from teacher to administrative preparation participants and, finally, to emergent school leaders. A primary responsibility of school leaders is to implement strategies to move their respective schools forward. Having a desire to enter an administrative leadership preparation program requires one to have the commitment, dedication, and a plethora of leadership abilities that also include being able to support students, faculty and staff, and school-wide initiatives. Through utilizing a phenomenological, or lived-experience, approach for understanding school leadership development from the insights of the participants who experienced the process, the study's results should provide a more thorough understanding of the challenges new administrators in Hawai'i's public schools must navigate regarding leadership, collaboration, appropriate communication skills, classroom instruction, and sustained focus and coherence of school improvement efforts. Results suggested most educators who have transitioned from teachers to school leaders initially had no intention of entering administration; however, over time, they developed a strong desire to influence change and make a difference with a larger impact beyond their specific classroom. Relationships were identified as essential to all parts of the administrative journey--in particular, providing needed program support (e.g., hearing from other principals about their schools, discussions with preparation cohort members) for participants' learning the technical aspects of school leadership and learning to lead through day-to-day experiences and discussions with mentors and others at their school through the leadership transition. Emergent school leaders also suggested the need for greater recognition and inclusion of placed-based educational practice (i.e., sense of where we live, understanding the cultural aspects to our history) within the school leadership preparation experience and greater triangulation that aligns the state, district, and university level to develop educational leaders. Most importantly, this study facilitated the individual voices and the perspectives of school administrative leaders to be showcased as they completed the state's school leadership preparation program and also experienced their initial administrative roles in working closely with students, staff, families, and community members to enrich the lives of their students. [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.]