This is a reflective paper grounded in practice. It addresses the nature of working alliances in education between colleagues from different cultural, professional and generational backgrounds. The authors are specifically concerned with discussing the significance of accessing peer/cultural support in education, in particular how one colleague mentored another and the way knowledge was exchanged during this process to increase awareness and understanding. This topic is considered in the context of supporting male Aboriginal and Torres Strait Islander students while they study and live away from home to complete their secondary school education at boarding school in Western Australia (WA).