The institutionalization of community engagement is a lengthy, complex process to which higher education change agents have turned their attention over the past few decades. This study examined the experiences of participants in leadership workshops designed specifically to develop the capacities of campus and community leaders to facilitate this work. Using Conner’s (2006) curve of commitment, this research highlighted factors contributing to and deterring community engagement, and explored the role of leadership development in the institutionalization of community engagement. Findings revealed five critical issues related to this work: administrative support, faculty buy-in, positionality/power dynamics, resources, and embeddedness—with administrative support and leadership serving as a linchpin. In addition to the need for effective leadership development as a pathway to supporting this multifaceted organizational change, the results also underscored the need for a model of shared leadership to guide the purpose, planning, and persistence necessary for institutional change.