This naturalistic inquiry sought to obtain the "essence" of select administrative chief diversity officers (CDOs), by exploring their participant profiles, organizational realities, and career reflections. Participants self-identified as their institution's senior most chief executive, were poised executively, and charged to facilitate an institutional diversity agenda. Data was collected through in-depth interviews and the review of archival documents and analyzed through linear, themed case analysis. Findings were displayed by research question, and interpreted into three categories: "participant profiles," "organizational realities," and "career reflections." Important findings exposed personal stories, career sketches, leadership preferences, and diversity and equity competencies; organizational realities revealed institutional need for CDO leadership, CDO roles, administrative strategies, reporting structure and feedback, diversity office staffing, organizational commitment and funding, organizational partners, administrative actions and program initiatives, and lessons learned; career reflections reported career accomplishments, legacies, job satisfaction, professional next steps, the strengths, challenges, opportunities and benefits of the CDO leadership capacity, and provided insight into the future of CDO leadership. The growing literature on academic diversity officers calls for "new mental models" to help further facilitate understanding around the unique and dynamic leadership posture of the CDO. The dynamic "Sustainable Practice Integrating Diversity and Equity" [SPIDER] model, is offered. Its utility is the organizational identification of its working parts. SPIDER is comprised of a nucleus, legs, and arrows; it depends heavily on access, commitment, collaboration, resources, and status. As SPIDER must evolve, it must be regularly assessed and adjusted. It will be ambiguous and transparent, as it is charged to integrate an institutional inclusion platform across and between its "web," the institution's chart of organization, which requires substantial institutional commitment. SPIDER will be "window-dressing" if it is not driven by research, robust support, and buy-in. It goals are that of the institution as articulated by the strategic diversity platform. SPIDER does not operate in isolation as progression of the institutional agenda depends on organizational ownership. Recommendations for theory and practice are discussed that draw upon the need to further understand the complex change leadership of the CDO, amidst a changing landscape. [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.]