This article outlines success factors of six New Zealand primary and secondary school principals. These factors are grouped under principals' personal characteristics, leadership skills that connect with their teachers, leadership strategies that impact positively on school stakeholder needs, and factors that sustain leadership success. Emerging themes that link to the educational leadership literature and to International Successful School Principalship Project (ISSPP) cross-country findings are conceptualized around the notions of critical self-reflection, responsive leadership, building relational trust, and personal resiliency. The article concludes by exploring implications for principals' personal learning, and subsequent challenges for those charged with the responsibility for preparing and supporting our school leaders. (Contains 3 tables.)