The current work employs the use of multiple lenses to illuminate the integral role of the Educational Assistant (EA) in a Canadian school district's transition from a segregated to inclusive service delivery model for students with special needs. Often compatible, but also distinctive viewpoints and understandings shape the role of EA in this journey towards inclusive practice in the context of a district that deployed Inclusion Coaches to support educators over the course of five years. Through deductive analysis, qualitative data (interviews, focus groups, blog-style reflections) were analysed from EAs (n = 6), elementary and secondary school teachers (n = 31), and Inclusion Coaches (n = 13). Findings indicated that the voices of EAs, teachers, and Inclusion Coaches all align on three main themes: necessity of collaboration among educators, coordinated and dedicated time for programming and redefining relationships within the inclusive model. During the transition from segregated classrooms to full inclusion, it is imperative that the role of the Educational Assistant (EA) is understood by administrators, teachers and the EAs themselves. With a more clearly delineated and mutually understood role, EAs and educators can develop collaborative relationships, working towards incorporating differentiation and supporting all students in a diverse learning and social community.