Research shows that, under certain circumstances, people using GSS can be substantially more productive than people who do not. However GSS has been slow to transition into the workplace. This paper argues that the Technology Transition Model (TTM) may be a useful way to explain this seeming paradox. The paper presents a comparison of GSS transition case studies in two organizations — one where a self-sustaining and growing community of users emerged, and one where it did not. Following TTM, it explores the frequency with which users perceived cognitive, economic, affective, political, social, and physical value from using the system. Comparison of the cases reveals differences in perceptions of value along several of these dimensions that are consistent with TTM. The findings suggest the model may be a useful way to explain organizational change, but much more research will be required to test the model more rigorously.