This book questions the role and function of the school principal as an instructional leader and/or an entrepreneurial manager. Combining Bourdieusian sociology and a Christian faith orientation, the work applies a unique lens to this educational leadership dilemma. Presenting an analysis of data generated from semi-structured interviews with CSA principals in South Australia, this text examines the core of the school principal role. Using an exploratory design case study, Barnes highlights principals’ competing demands of instructional leadership and entrepreneurial management, the notion of principal frustration and the resolution of the instructional leadership and entrepreneurial management dilemma via an agile leadership approach. This work presents the agile leadership approach as a new theoretical model for educational leadership, adaptable to a variety of educational contexts. It also identifies the impact of the COVID-19 crisis on this educational leadership dilemma, showcasing how principals tended to adopt a dichotomous fragile leadership model. This is an indispensable resource for researchers and postgraduate students working in education leadership.