Organizations, whether in the public or private sector, and regardless of their size and nature of activity, have different approaches to the way they create and manage themselves as learning environments. In developing an understanding of the nature of learning at work and the conceptualization of workplace pedagogy, it is necessary to build a picture of the contextual factors that conspire to facilitate or to hinder opportunities for learning. These factors would include an organization’s identity, history and culture, the goods and services it provides, its organization of the labour process, its treatment and involvement of employees and the broader productive system in which it sits (see Braverman 1974; Darrah 1996; Koike 2002; Rainbird et al. 2004a; Fuller and Unwin 2004a; Evans et al. 2006). This chapter explores the ways in which these factors interact over time and space to create different types of learning environment. The term the ‘relational dance’ in the chapter’s title was inspired by Cook and Brown’s (2005) metaphor of the ‘generative dance’ between knowledge and ‘knowing’, which happens when individuals and teams make innovative leaps forward through problem-solving in the workplace.