This chapter draws on the available evidence to explore what it means to be a successful school leader within the current educational landscape in Aotearoa, New Zealand. It provides a nuanced understanding of common success factors and the contribution of the school principal’s leadership to that success in context. A set of factors that shape their behaviour and actions is presented that draws attention to cultural relationships and contextual awareness, emphasising not only students’ academic success, but also students’ cultures as vehicles for learning and social change. Findings from this chapter provide insights into how successful school principals consider their entire school as a complex system with interconnected parts, and build social infrastructures that nurture partnerships with multiple stakeholders.