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Purpose: In 2003, the advisory dean program at Columbia University College of Physicians and Surgeons was created to better connect students and faculty by supporting student academic progress and improving career advising. With the program in its eighth year, the authors were interested in identifying key factors in maintaining ongoing vitality and effectiveness., Method: In 2011, the authors conducted a reflective analysis to study the program, using available information from dean interviews, student surveys, meeting agendas, and program leader reflections, aided by the Bolman and Deal four-part framework for organizational functioning (structural, human resource, political, and symbolic)., Results: Structural factors included reframing program goals to match program activities, situating the program within broader academic advising and counseling resources, and increasing face time between entering students and their deans. Human resource factors included managing higher-than-expected turnover of deans with dean selection and orientation strategies that balance diversity and consistency, and providing ongoing training to promote continual professional growth. Political factors included balancing resources (e.g., money, administrative support) from the school and departments to help the deans protect and manage their time. Symbolic factors were related to leveraging the deans as symbols of institutional values and commitment to education (e.g., participation in the white coat ceremony), and being aware of "hidden meanings" associated with decisions within other frames (e.g., student-to-dean ratio)., Conclusions: A variety of strategies across frames were used to maintain the program. This report can serve as a guide to program maintenance for other institutions.