This paper presents the findings of an interpretive study of eight small and medium sized enterprise's (SME’s) experiences when deciding to participate with Australia's New Apprenticeship system for the first time. The study focused on contextual and processual elements as well as the action of key players associated with participation. A series of case studies were designed around semi-structured in-depth interviews with owner/managers. Grounded theory analysis of the case text produced a structure of conceptual categories and themes related to the participation process within the context of the information technology industry.