Setting up co-design processes involving several stakeholders is a complex task. In this chapter the authors have looked upon experiences from involving 120 future users in a process of incrementally developing and deploying an electronic assistant for students. The vision is to develop an electronic assistant, an e-Me, that acts as a filter and an agent in the information society. By interviewing some of the future users we have managed to derive some different challenges associated with co-design processes. These challenges have been discussed related to the following categories; perceived usefulness, user involvement in the development process, learning process and critical factors for future development. The authors analyze the empirical data and derive suggestions for possible improvements.