This paper reports on the methodologies used and the findings of the research done by the Enterprise Social Learning Architecture (ESLA) Task into learning processes occurring in two diverse environments within the Australian Defence Organisation, tactical and strategic. The research focused on identifying factors that enable and facilitate social learning and these factors are discussed in view of the preliminary architecture proposed by the research team and in view of the socio-technical environment within which people work and learn. The paper concludes by suggesting that the development of information systems requires a multidisciplinary approach and needs an understanding of the cultural issues prevalent in work environments.