A number of studies have shown that although the utilization of interorganizational information systems (IOS) can contribute significantly to organizational flexibility, they do not provide equal benefits to all trading partners. Also, the emergence of new technologies and the increasing use of the Internet in business-to-business commerce challenge the viability of the traditional “hub and spoke” systems and affect the flexibility of the participating organizations. By conducting this study we will try to understand not only how the use of IOS affects flexibility, but also, how organizational, behavioral and political issues influence the application and use of technology. This paper argues that a better understanding of the aforementioned issues, could result by re-examining the notion of flexibility both from a business network and individual firm perspective, and proposes a research approach.