Knowledge Management (KM) and knowledge sharing are important factors that support lifelong learning, and enable people to continue developing throughout their careers. The concept of a Community of Practice ( Wenger, 2000) is attractive in drawing together people whose work shares similar aspects, and consideration is given here to how technology can be used to develop and support such a community. In this paper, concepts from the Community of Practice literature are used to consider the development of a software environment for people working as a community in the area of lifelong learning. The intention was to design the system in an evolutionary way, using a minimal set of essential elements which would be elaborated according to user feedback. Three key design questions are considered: Who can contribute resources to such a system? What happens to existing practices? How is the community engaged? We conclude that, in lifelong learning, knowledge management supported by a software environment offers a good way to bring together communities, resources and experience, but to achieve these benefits, great care needs to be exerted in introducing the system and maintaining existing work practices.