Over the last several decades, the role of the school site principal has shifted from a focus on school management to one on school leadership. Integral to this new focus is the ability of the principal to be an instructional leader, tasked with improving the instructional practices of teachers. Many principal preparation programs have adopted new methods to support aspiring school leaders including the development of effective coaching skills. This qualitative study examined one principal preparation program designed with this goal in mind. The primary research questions that guided this study were: (a) How does the coaching program support the development of coaching skills for aspiring school leaders?, (b) What factors challenged the development of coaching skills for aspiring school leaders?, and (c) What impact did the coaching program have on the aspiring school leaders' perspectives of instructional leadership? The methods used in this study included interviews with aspiring school leaders and document analysis of concept maps constructed by the participants displaying their conceptual understanding of instructional leadership, before and after they received the program's coaching instruction. Observations of the leadership course and analysis of videotapes that recorded the coaching activities of the aspiring school leaders with teachers were also conducted. This research found that: (a) the coaching program supported the aspiring school leaders' development of coaching skills, (b) the development of the aspiring school leaders was limited by certain aspects of the coaching program, and (c) the coaching program challenged, but did not necessarily change the aspiring school leaders' perspectives of coaching and instructional leadership. Since coaching is recognized as an effective method of individualizing and differentiating professional development for teachers, the actual practice of coaching teachers on instruction offers opportunities for aspiring school leaders to develop their capacities for leadership in 21 st Century schools. The findings in this study suggest that coaching programs offer the opportunity for this development and warrant future consideration in the development of instructional leadership capacity for aspiring school leaders within principal preparation programs. [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.]