Since the establishment of American higher education, the presidential profile for institutions has lacked the gender diversity in presidential leadership positions. Though women have taken positive strides as senior executive officers in higher education in the past quarter-century, the conventional post-secondary president is a white, married male with the average age of sixty. Major obstacles lead to the underrepresentation of women as higher education college presidents including the male-dominated culture of higher education leaders and balancing personal and professional commitments. Within all the higher education classifications, community colleges have the highest share of women presidents. As the numbers of women in upper-administration level positions are increasing, it is important to identify possible obstacles they may encounter and what practical leadership solutions may help in their transition through the glass ceiling. This qualitative phenomenological study examines the experiences of six women community college presidents and identifies what leadership skills, attributes, and traits allowed them to transition through the glass ceiling. Also, this study pinpoints various professional, organizational and personal barriers that compose the glass ceiling for aspiring women presidents. Data were collected through interviews and confidential demographic surveys. The findings include emerging themes and implications that add to the breadth of women leadership research, especially in higher education. The findings also provide aspiring women leaders the practical alternatives for overcoming obstacles that arise when leading in higher education. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]