This study explores the issues facing twenty-first century secondary school principals as they face changes in education brought about by the New Zealand Curriculum, and changes in their communities in the face of the emerging knowledge society. The study explores literature on educational leadership, futures thinking and some of the social factors influencing communities today. Data is gathered from semi-structured interviews with four futures-focused secondary principals from a range of schools and localities. Findings are presented in a narrative style that attempts to capture the person behind the principal, while maintaining confidentiality. The major findings from the study indicate that school leadership in the twenty-first century is likely to be complex, and have influence far beyond the school gates. It concludes with recommendations for principals and systems administrators in supporting next steps for leadership.