As community colleges continue to face challenges in serving an ever-changing student population and a wave of presidential retirements, the next generation of senior community college leaders is surfacing. To prepare these top-level administrators, doctoral-level community college leadership (CCL) programs often serve as a viable mechanism for supporting leaders in their professional practice. Nonetheless, minimal knowledge exists about what benefits and skills alumni -- current community college leaders -- gain from doctoral CCL programs and how such programs and their directors build and evolve programming to meet their students' needs. This qualitative case study employs the theory of planning practice to account for how directors shape CCL programming, ultimately uncovering how doctoral CCL programs' processes contribute to programmatic priorities, curriculum, and evolution. Through interviews with seven doctoral CCL program directors and 16 alumni, our findings show the value of thoughtful program design, intentional curriculum, and evolution of programming to support students. Study implications call for further exploration across many directions, such as the role of an increasing shift to online programming and how alumni play crucial roles in recruiting and mentoring incoming doctoral students to CCL programs.