This paper builds on recent scholarship on the gendered nature of educational work to argue that while conceptualisations of the principalship are underpinned by scholarship and policy assumptions that construct the work of the principal as a male domain, women have responded to opportunities presented by changing historical, political and social contexts, creating professional spaces for themselves as principals in primary and secondary schools within both state and Catholic school systems. It details how in the years prior to 1975, a time when the majority of state primary and secondary schools were led by men, the principalship of New Zealand Catholic schools was a largely female endeavour. The experience of Catholic Sister Principals was framed by the fact that they were women leading schools in a world dominated by men. Implicit in this arrangement were the ecclesiastical authority structures and their subjection to the convent hierarchy. Nevertheless, Sister Principals learned a range of strategies that enabled them to negotiate with Church and religious authorities and to undertake the diverse tasks associated with the leadership of Catholic schools.