In this chapter we review different approaches on social innovation and leadership. Social innovation is usually conceptualized as a way of improving territorial development in disenfranchised neighbourhoods. However, little attention has been paid to the dynamics by which responses emerge, how social impact or scalability could be achieved and, finally, how social change could be effectively accomplished. Bringing together disruptive theories of social innovation and constructionist theories of collective leadership this chapter delves into the context–agency debate. In so doing, we identify the main challenges for the novel approach to analyzing social change that we develop theoretically and empirically throughout this book.