This article examines the available evidence on 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 shaped 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 article provide insights into how successful school leaders consider their entire school as a complex system with interconnected parts and build social infrastructures that nurture partnerships with multiple stakeholders.