The aim of this chapter is to explore how middle managers in the construction industry conceive of their work life and to identify some of the major challenges that site managers are grappling with. This is of interest from a knowledge-management perspective because site managers play a central role in managing, directing, monitoring and leading construction projects. Site managers strongly influence the effectiveness of the construction project, therefore, the support and help directed towards site managers are part of a broader knowledge-management system helping construction projects exploit its accumulated knowledge. However, the point of departure for this study is the rather negative view of middle management in much management literature. Research on middle managers remains one of themostmarginalized fields of interest inmanagement studies (Floyd andWoolridge, 1997; Thomas and Linstead, 2002). In comparison to the massive literature on leadership, the body of texts on middle managers is miniscule. Moreover, in comparison with the so-called labour process studies tradition, emphasizing the worker’s position and everyday worklife experiences, the middle manager is a marginal figure. In cases where middle management is examined, it is portrayed in the bleakest of terms. Middle managers are on the way out, continually being reduced in numbers when organizations are rationalized and adopting a flatter structure. They are stressed and burned out, and endure a work-life situation wherein they are stuck between the demands of top management and those of their co-workers and subordinates (Dopson and Stewart, 1990).