Modern organizations are investing heavily in information technology (IT) with the objective of increasing overall profitability and the productivity of their knowledge workers. Yet, it is often claimed that the actual benefits of IT are disappointing at best, and that IT spending has failed to yield significant productivity gains -- hence the productivity paradox. Evidence is fragmented and somewhat mitigated. This paper argues that the current state of empirical research results from a failure to understand the interplay between IT and managerial work. It addresses this issue by analyzing patterns of association between IT usage and the nature of managerial work in different organizational contexts. Fifty-nine semi- structured interviews were conducted with middle line managers in three large companies: a Bank, a Telecommunications company, and a Utility. In addition, daily activities and IT usage were logged. The data indicate that the relationship between the level of IT usage and the nature of managerial work was stronger in the two organizations that were reorienting their strategies (Bank, Telecommunications) than in the one pursuing its existing strategy (Utility). It was also found that the pattern of the relationship between IT usage and the nature of managerial work depended on the kind of strategic reorientation implemented by the firm. For instance, in the Bank, the level of IT usage was associated with the amount of time spent by managers on information-related activities (e.g., reading reports, gathering information) and on disturbance handling activities (e.g., resolving conflicts, managing crises). In the Telecommunications company, IT usage was associated with more time spent on information-related activities and less on negotiation-related activities (e.g., discussions with colleagues on resource sharing, discussions with subordinates on performance standards). This finding suggests that heavy IT users paid greater attention to and spent more time on the roles they performed best with the technology (information-related activities), and may in fact have been embarking on an over-specialization trajectory.