This paper suggest a different approach to doing skill formation research in the IT industry - one that takes into account the interaction over time of intentions, context, process, and action around formal, accredited on-the-job training schemes. To demonstrate, the paper presents the findings of an empirical study into eight small and medium sized enterprise (SME's) experiences when deciding to participate with an on-the-job training scheme for the first time. The literature on vocational training, and specifically participation with work-place based training schemes, is reviewed. The review indicates a need for process research to complement existing research in the field. Eight case studies were designed around semi-structured in-depth interviews, and were conducted to investigate how and why owner/managers decide to participate with on-the-job training for the first time. The study focused on contextual and process elements as well as the action of key players associated with participation. Grounded theory analysis of the case data produced a structure of conceptual categories and themes related to the participation process within the context of small business in the information technology industry. The theory generated from the empirical findings suggests that the intentions and actions of owner/managers, the processes they enact, as well as the social context into which they are implemented, critically influence what decisions are associated with on-the-job IT skilling. The findings provide insights for policy and practice, detailing the organisational decision-making that are associated with skilling under certain circumstances, and how these might be assessed and managed. Implications for vocational training in small business based on the findings are advanced.