This article contributes to the limited body of literature pertaining to attempts by educational systems to satisfy the professional learning needs of experienced principals, defined as those with more than 10 years of experience in at least two schools. Specifically, this article illustrates the Catholic Education Office of Western Australia's endeavour to create an innovative, integrated, cross-sectoral program to enhance the leadership capabilities and health and wellbeing outcomes of experienced principals from Catholic, Government and Independent schools in that state. The program comprised four integrated pillars: a 360-degree review of participant leadership capabilities followed by executive coaching to effect improvement; an executive health assessment and coaching with an exercise physiologist to enhance participant health and wellbeing outcomes; a theoretical program based on a nationally accepted standard for principals, developed by the Australian Institute for Teaching and School Leadership; and a group project transacted in a non-educational setting. The article begins with a synopsis of existing literature related to the professional learning needs of experienced principals and the few reported evaluations of programs designed to cater for the unique needs of this cohort. Participant feedback collected at the commencement of the program, its midpoint and conclusion are presented. The article concludes with recommended changes that could be implemented to enhance the efficacy of future program iterations.