While independent schools are a small sector of the American school system, they educate a significant cross section of society. Creating equitable models of leadership in their top administrative positions is important as students see those models and equate them with what leaders look and act like. This study examined leadership styles of heads of independent schools, focusing on the spectrum of transformational and transactional leadership. It examined general and specific factors leading to gender inequity in top JK-12 educational administration. It offers a foundation for discussion about education and educational administration by presenting the history of the American educational structure. The literature review includes research about educational administration and leadership, as well as the explanation of three theories emerging from the study of leadership differences between men and women. A discussion of leadership styles follows, highlighting literature focusing on the barriers women encounter in attaining leadership roles. The voices and stories of those women who have attained top educational leadership positions conclude the literature review, providing a full spectrum of issues ranging from the inception of the educational system to the reasons for the current disparity of women at the head of school level. This study presents a national study of independent school leadership. Using a mixed methods approach, the study includes quantitative data about leadership styles of heads of school, as well as other demographic indicators that highlight their paths and leadership roles. The qualitative portion of the study culminates in one-on-one interviews with eight female heads of school to examine their experiences in achieving top educational administration positions. The study results demonstrate that heads of independent schools are generally transformational leaders in their styles. Further, it illuminates the fact that female heads demonstrate more transformational leadership styles than their male counterparts. It also indicates that male heads of school ascended to headship faster than women. Finally, it outlines how the individual voices of female heads collectively indicate that female heads' natural styles of leadership, which are based in relationships, lend themselves to the characteristics of transformational leadership. [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.]