This chapter examines the major issues and questions that managers face concerning websites and information technology (IT). The chapter starts with a look at the questions and issues concerning websites, and then turns to the larger issues of information technology management. It then examines the matter of financing information technology projects. The chapter aims to deal with the management of these issues rather than the technical issues themselves. In this section, it relies on the insight of IT professionals who deal with the frequently occurring questions of IT issues. A data management strategy is the way to cut across these different customer descriptions. In the discussion, commonly used approaches are introduced which are used in IT investment decisions. To illustrate with an analysis of a typical IT project, it uses cost effectiveness analysis. This chapter has framed the most common yet consequential questions about technology at work.