The community college system is beginning to see waves of retirements at all levels of the administrative structure. These retirements, in conjunction with expected growth in administrative positions, will result in system-wide administrative vacancies. Community colleges not already seeking new leaders are likely to find themselves in the midst of a leadership crisis. With candidates from outside the community college system difficult to find, colleges will need to look internally for future leaders. Despite the clear need for succession planning programs, colleges have been slow to adopt formal succession planning procedures to train and advance faculty into much needed administrative positions. This phenomenological research study investigated the experiences of nine retired northern California community college administrators to explore their lived experiences and perceptions surrounding informal succession planning at their colleges, their perceived role as administrators in encouraging and preparing faculty to take on new management positions, as well as their experiences working with newly promoted administrators. Study participants confirm the complexity of the dean position within the community college system, along with the inherent lack of control associated with entry-level management which discourages faculty from seeking advancement into administration. This study identifies common transformational experiences that help prepare faculty with aspirations of administrative careers for success within community college administration, and further emphasizes the value of peer mentoring for neophyte administrators. The results of this study, based on findings resulting from the stories shared by the participants, include: the importance of leadership skills for entry-level mangers, the confirmation that preparing for advancement is incumbent on the faculty, succession planning is misunderstood or poorly communicated within many institutions, and finally, preparation and desire alone do not ensure a successful transition into administration. This study concluded by recommending colleges clearly define succession planning within their institution and provide resources and opportunities for interested faculty to gain the skills, both managerial and leadership, needed to be successful as an academic dean. [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.]