While the business press is awash with claims that investing in enterprise-wide systems is the key to delivering superior economic performance, unfortunately it appears that reaping the benefits of such IT investments is fraught with difficulty. Indeed, the introduction of IT into work organisations is generally marred with persistent reports of underperformance and failure. This chapter critiques the nature of this dilemma and in particular explores the role of diverse occupational groups in its perpetuation over time. This dilemma is sustained over time by the behavioral patterns of diverse occupational groups that have vested but divergent, interests in exploiting IT. Executive management tend to view the introduction of IT as an economic imperative while IT specialists tend to view it as a technical imperative. The coalescent nature of these two imperatives is such that the human and organisational aspects of IT related change are frequently marginalized and ignored. Achieving a more integrated approach to the introduction of IT is inordinately difficult since the narrow perspectives embraced by the executive and IT communities do not naturally attend to change in an integrated manner.