Twenty years ago the development of a sports management program at Massey University was then the only one in New Zealand. Professional rugby was still a couple of years away. Kit McConnell, Head of the 2011 RWC and Tournament Director for the IRB, was a Masters student back then. He indicated "the academic staff were doing something new--and special. For me, there was a good balance between having enough structure and learning about the elements of the industry and having freedom within the curriculum to explore what interested me" (cited in Massey University, 2011, p. 15). This paper provides an auto-ethnography related to the author's extensive involvement and self-reflection on leading the development of work based experiential education sport management and coaching related practicum programs at Massey University. Themes and phases of program development are outlined that informed WIL understanding, particularly in the sport context. The research is interpretive in nature and philosophy and employs a collective case study methodology across different educational contexts. The implications are for reflective practice, pedagogy development graduate attributes. [Papers included in this "Asia-Pacific Journal of Cooperative Education" ("APJCE") Special Issue stem from selected manuscripts from the Australian Collaborative Education Network Annual Conference 2012.]