Social work is a globalised field of action, facing theoretical, practical, ethical and pedagogical challenges caused by major global transformations that have given rise to an increasing diversity of socioeconomic, national, ethnic, racial, and religious divisions. This context poses anew the question of the possibility of interconnectedness over or between these divisions. It prompts us to ask, inter alia, do we have to share the same life, the same experiences, the same class, nationality, ethnicity, race, or religion to achieve solidarity and mutual understanding? The German philosopher, sociologist and critical theorist, Jürgen Habermas has shown that this increasing diversity calls for a specific kind of communication to reach mutual understanding and the emancipatory possibilities this entails. He also states that our possibilities for communication are often systematically obstructed. However, Habermas has not been content with stating the problem, he also offers a way to create mutual understanding and cohesion in a rapidly changing world. In such a context, the stakes for social workers (both as practitioners and educators) to communicate or facilitate mutual understanding over socioeconomic, cultural, religious and normative divides, are extraordinarily high. In this chapter the pressing needs of communication across difference and the obstacles to it will be examined in the light of Habermas Theory of Communicative Action.