This paper is in five parts. First, pertinent theoretical perspectives are identified from a selective review of distinct but intersecting literatures on school restructuring, leadership, school improvement, collegiality and collaboration as generative principles in the revitalisation of school cultures, schools as organisations and the ongoing professional development of school principals. Second, a succinct account of the policy context of the inquiry is provided and the genesis of the principals' support group described as a means of adequately contextualising the study. Third, the three levels of data that were generated through the research design of this inquiry are described and the process of data analysis outlined. Fourth, three themes that emerged from continuous data analysis are critically analysed. Fifth, the paper concludes that by tracking the evolution of primary principals' professional development longitudinally, it is possible to identify important developmental milestones that provide the basis for a more organic and securely grounded approach to professional well being that is more likely to consolidate gains and sustain organisational and cultural renewal.