The university today is a postmodern, neo-liberal, competitive, boundary-less knowledge conglomerate, a far cry from its historical traditional classical and collegial roots. There is a body of literature on deanship that points to its evolving nature in the contemporary academe characterised by complexity and change. Balancing academic demands simultaneously with the requirements for effective performance, leadership and management, lies at the heart of this very challenging bridging role nowadays. Deans are generally former academics, emerging from a traditional collegial space and often catapulted into the relatively unknown domain of executive management, with its related problems. Deans nowadays are required to be more than collegial, intellectual leaders. They are also meant to be fiscal and human resource experts, fundraisers, politicians, and diplomats. Deanship in the Global South: Bridging Troubled Waters is about the deans’ lived reality, as they try to balance the demands of both the academe from which they emerge, and the administration to whom they now need to account. Their lack of preparation and inadequate support points to the need for a more strategic, integrated approach to leadership development within their critical bridging roles between the academe and administration.