Public and private universities in Kenya, Tanzania, Uganda, and elsewhere in Africa have been experiencing all-time high expansion since the late 1990s. This rush to expand both public and private universities has seriously impacted both the physical infrastructure as well as the effective leadership that new universities require. At the same time, the private sector has experienced dire shortages of teaching personnel and competent academic leaders. To shed light on these problems, this case study examined the dynamics of leadership roles exhibited in private universities and how leadership styles align to achieve success within Tanzania's Catholic Universities System. A case approach was used to study reports, journals, and interview data collected during 2007-2013 from universities selected purposely in order to understand better the success and effectiveness of academic leaders. The analysis revealed often perplexing assumptions that undergird the expectations of management operations, showed how leadership styles are perceived by incumbent academic leaders, and explained cross-cultural forces that govern, sustain, and sometimes frustrate leadership appointments.