Leading in a higher education setting is a complex undertaking, largely because the enterprise is like no other sector of our society. It is uniquely structured with a distinctive organizational culture. Colleges and universities are inward oriented, slow to anticipate and make changes, and often unable to address unfolding pressures efficiently, effectively, and comprehensively. In fact, higher education celebrates tradition even though external forces necessitate quick action and reinvention. Restructuring the curriculum and adjusting policies and procedures sometimes requires multiyear time commitments. Practices steeped in conventional processes produce a highly hierarchical environment that few outside the academy can fully understand.