Like other international jurisdictions, New Zealand is facing an escalating recruitment and retention crisis within the school principal workforce. However, unlike their international counterparts, New Zealand principals are not required to possess postgraduate qualifications nor are they compelled to complete formal leadership preparation programs prior to appointment. Over the past two decades, the influence of school leadership on student outcomes has become evident (Leithwood, et al., 2020). Yet in New Zealand, programs to prepare Aspiring and First Time Principals were stopped. Given prior experience in a school leadership role is often deemed the best pathway to principalship, attention is turning to those in middle leadership roles and their preparation for educational leadership. This paper explores leadership preparation in urban and semi-rural schools in New Zealand. Drawing on a multiple case study conducted during 2020-2022, the views of three aspiring leaders are considered with regard to their perceived level of preparedness for leadership in terms of key competencies as outlined by the Leadership Strategy (2018) and the additional challenges to preparation brought about by ongoing and new crises. The paper is framed by research and policy that addresses successful school leadership in New Zealand and research undertaken globally, and aims to contribute to a growing body of international literature about leadership of high-needs schools as evidenced in the work of the International Schools Leadership Development Network (Angelle, 2017; Murakami et al., 2019). The paper builds on other research that seeks to understand the influence of government policy and strategy on school leaders and the educational outcomes of students (Cranston, 2013; Gunter & Thomson, 2009). Insights into leadership preparation in New Zealand are heard in the voices of middle leader participants as they decide whether to step up or step away from school leadership. Thus, the barriers and opportunities faced by these leaders contribute to a discussion about the function of school leadership in the next decade and beyond. Given no current mandatory leadership preparation in New Zealand, this paper contains important recommendations for policy makers and school practitioners.

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