Higher education is built on a long history of tradition, which, in many ways, has been impervious to outside pressures and influences. Despite having served as change agents for society, colleges and universities have resisted change for decades. Amid unprecedented pressure and scrutiny from outside stakeholders and dwindling state and federal support, higher education leaders are being challenged to rethink the workings of the academy. However, in the absence of experience leading change efforts and a lack of robust empirical evidence to draw upon, transformational change remains elusive. Administrators have been left to muddle through change efforts, which often stall or fail due to long-standing environmental, structural, and cultural challenges inherent to higher education institutions. By drawing up organizational theory to provide the conceptual foundation of common organizational problems, with the literature and lessons learned at one institution, this case study provides practical and immediate implications for today's higher education leaders.