This paper research presentation offers insights from preliminary data analyses of six New Zealand primary and secondary school case studies, in which the work of effective school principals is being examined to determine possible leadership factors in their school’s success. The New Zealand school context will be first explored, in particular the potential influence of the concept of self-managing schools on successful principalships. Beginning in 1989, the management of New Zealand schools was devolved from central government agencies to a locally elected Board of Trustees who are responsible for the teaching of a national curriculum, the employment of staff, property development and the daily operation of the school. As a result, there have been strong links forged in most schools between the principal, Board and members of the wider community. A key question to be asked of the data has been: To what extent is a successful principalship in the New Zealand context contingent upon a successful relationship between a school and its community? The research study sample comprises three primary schools and three secondary schools in two different regions of the South Island of New Zealand. The leadership group under study features four male and two female principals who are spread among four urban schools and two rural schools. The findings from the data analyses will be presented. These findings will detail a brief profile of each school principal; the leadership characteristics exhibited; key strategies or interventions performed by each principal; and contingencies that present themselves as ongoing challenges to even successful principals.