To fully understand the continuing evolution of the community college movement, one must also consider the evolution of its leadership, its changing environment, as well as changing societal needs. This monograph provides some experiential insight into the leadership aspect of the community college, particularly with regard to generational change. Focused topics include needed curricular changes in graduate leadership programs, leadership recruitment and retention, and specific situational discussion. The article concludes with a brief consideration of future challenges for aspiring community college leaders.