The Kentucky Community and Technical Colleges System (KCTCS) began hiring diversity officers throughout the system in the mid-2000s. These highest-ranking diversity officers (HRDO) on each campus led their college's efforts to comply with the statewide diversity policy. A phenomenological approach was used to discover how former HRDOs in KCTCS made meaning of their readiness to serve in their roles while working in the system. Individual interviews revealed that rather than being most strongly influenced by individual factors such as education or experience, readiness for former HRDOs in KCTCS was most influenced by the dynamic between both individual and organizational factors. Furthermore, the HRDO position in KCTCS may be different than the CDO position at other colleges and institutions. Finally, former HRDOs provide advice to help those interested in the role be more prepared to serve. [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.]