Community development, one of critical elements of the sustainable community management, has been increasing its importance in local communities in Japan in recent years. A gradual shift toward decentralization, since in 2003, has been forcing communities to adopt more self-sustaining development policies. At the same time, along with the enactment of the NPO Act in 1998, a variety of actors, including those outside from the communities, have entered grass-rooted activities in local communities. Such an increased involvement of outsiders in the community development process means that they also play an ever-more significant role in the empowerment of the local community. Although most articles discuss the controversial points of outsiders, there have been only a few studies evaluating the positive perspectives. This paper examines the role of outsiders in the community development process by discussing the relations between the working process and outsiders. The result of this study implies that more openly the community is managed, more significantly outsiders can contribute to the community development.