School leaders in the twenty-first century face complexities that frequently make leadership challenging. Many underperforming schools struggle because, among other things, school leaders and their followers lack the necessary skills to guide their institutions to success. Research demonstrates that school leaders today need skills such as self-reflection, collaboration, and eclectic leadership. Furthermore, the ability to deal with ambiguity and paradoxes in leadership are fast becoming pronounced in schools, although there is still inadequate research that examines these concepts. This conceptual study used theory adaptation to examine the propinquity of Janusian leadership and thinking to school leadership. In Roman mythology, Janus is a god with two heads facing in opposite directions. This symbolises the dualities that exist, such as the ability to explore the past and the future simultaneously. The findings show that the skills that school leaders need include complex thinking and the ability to understand the uncertainties in an organisation as they embrace their followers. The major findings demonstrate that school leaders who understand and embrace the ambiguities and paradoxes of leadership are likely to guide successful schools.