The learning and development of educators in schools can take many forms. This paper is a critical reflection about the coaching and mentoring practices of the authors, set within the context of a state-wide transition to school initiative in Queensland, Australia. The paper describes the context of the initiative, the role of the authors, critical participatory action research methodology adopted, some of the tasks used, and emerging evidence of the efficacy or otherwise of decisions made. Critical reflection on the processes undertaken, and the rationale for these, have formed the basis for planning coaching and mentoring support through the initiative and constitute the data utilised in this paper.