This study evaluated and analyzed medical school executives' perceptions of the low level of advancement of women into the healthcare c-suite. As well, medical school executives' recommendations for increasing the number of women entering and experiencing sustained success in executive positions were assessed. Related to these observations were several purposes for the execution of this dissertation. The core purpose was to identify strategies to increase the number of women in the healthcare c-suite for future generations. This study looked at some of the barriers women faced as well as helpful factors when attempting to reach executive levels. Additionally, this study sought to determine how educational backgrounds, specific opportunities, and early mentoring interventions affect the promotion and maintenance of c-suite level positions for women. An extensive literature review was conducted to examine the history of women and specific populations including ethnic minorities and people with disabilities, entering the professional job market from the civil rights era of the 1960s, to their inclusion in medical colleges, state and local government, federal government, corporate America, and recommendations for future generations. The study sought to add to the academic literature in terms of consideration for current healthcare executives' expertise and recommendations for improved strategies to promote women. The findings suggest that c-suite executives interviewed saw a correlation between the organizational culture of medical colleges and the promotion and maintenance of women in executive status positions. The interviewees concluded that, for women to obtain and successfully maintain c-suite positions, they need substantial mentoring throughout their careers. This study further revealed that mentoring beginning from the time potential executives are in school and particularly in the early phases of their career will result in increased identification of female medical college leaders. Although findings also supported the perception of a glass ceiling for women, results reflect that there are feasible strategies to assist women to advance to the c-suite in medical schools and the healthcare industry. [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.]