This chapter raises issues concerning information and knowledge sharing in organizations and why such sharing is often difficult to achieve. In particular, it compares an organizational cultural analysis with an organizational political one. The authors believe that the issues raised are not only important but are often insufficiently attended to by practitioners who are attempting to build technological information and knowledge management systems. The driver for the chapter is the fact that despite impressive advances in technology, and its now almost ubiquitous presence in organizations many of the benefits originally expected concerning improved information and knowledge sharing have not materialised as was once confidently expected. One of the authors argues a basic reason for this lies in the lack of attention to the cultural foundations of organizations, while the other contends it is more because matters relating to organizational power and political matters are often misunderstood, overlooked or ignored. These different perspectives are discussed and contrasted in order to tease out the important differences between them and assess the prospects for a synthesis. It is concluded that, while there are important commonalities between the two perspectives, there are also fundamental differences, including concerning what are causes and what are effects and, therefore, how to go about effecting change regarding information and knowledge sharing.