In this article we explore how engaging in collaborative self-study resulted in a reciprocal mentorship platform for a mathematics specialist program coordinator and online adjunct instructor. Through the use of our mutually developed norms and a reflective dialogue protocol we examined how we were able to bridge our contexts so that we could equally engage in a graduate mathematics teacher leadership course that only one was teaching. Employing a self-study methodology centered on dialogue, we co-planned and designed learning opportunities in which data was collected using synchronous online tools, agendas, notes and audio recordings from our weekly phone conversations. This ultimately influenced our understanding of what it takes to communicate clearly when conducting a self-study that spans both physical distance, heirarchial rank, and context. The pivotal learning experiences through the implementation of a reflective protocol and collaborative norms will provide other teacher educators who engage in self-study with tools to support their own learning, advance their practice, and promote critical reflection. This study also adds to the literature on adjunct professors in both higher education and self-study.