Cross-walking our findings from books two and three about leadership preparation and sustainable success, the authors consider the practical implications of those factors that influence a school’s ability to remain successful over time, especially high need schools. Utilising the core dimensions of setting direction, developing people, redesigning the school and leading the instructional program (Leithwood & Riehl 2005); Day’s notion of ‘layered leadership’ (Day, Jacobson, & Johansson, 2011), and the potential need for governance change (Jacobson, Johnson & Ylimaki, 2011), the authors find common individual and organizational characteristics that may be necessary for sustained success. For example, resilience is one such trait and regardless of the school a principal is leading, the very nature of the role and work means that they have to have some way of coping with the difficulties of the work so that they can sustain their level of positive influence. Often resilience is accompanied by commitment, persistence and a sense of clear-minded optimism, even in the face of daunting challenges. In terms of preparation, this means making potential aspirants aware of the nature of principal’s work in order to realistically inform their career choices and by providing then opportunities to explore difficult situations through role play, simulations teamwork and clinical placements.