Community colleges provide access to higher education and workforce development opportunities for a significant portion of the nation's population. This vital sector is facing unprecedented challenges related to declining public appropriations and enhanced external scrutiny. Relevant outcome measures for the sector have changed, and there is a large chief executive officer retirement bubble on the horizon. These chief executive officers, operating from a subordinate position, are required to provide leadership for a board of trustees, who operate as the chief executive officer's supervisor. This study expressly recognizes the unique power dynamics that exist between community college chief executive officers and their politically appointed boards of trustees. This study captures perspectives of successful community college chief executive officers and compares and contrasts them with the perspective of an unsuccessful chief executive officer, as it relates to providing effective leadership for a politically appointed board of trustees. The author provides a series of themes and findings regarding optimal leadership styles, strategies, and tactics that while arguably are applicable across a spectrum of sectors, can specifically be deployed by community college chief executive officers. In addition, the author provides recommendations for future studies, for higher education professional development, and formal academic curricula. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]