In today’s world of global wicked problems, constraints and imperatives imposed by an external and uncertain environment render strategic action a quite complex endeavour. Since the 1990s, within community initiatives and philanthropic projects, the construct of Theory of Change has been used to address such complexity. Theory of Change can be defined as the systematic and cumulative study of the links between the activities, outcomes, and context of an intervention. The area of focus for this paper is to explore whether Theory of Change can support more strategic approaches in design. In particular, the paper examines how Theory of Change was applied to DESIGNSCAPES - a project oriented, among other things, toward offering a supporting service for all those city actors interested in using design to develop urban innovation initiatives that tackle complex issues of broad concern.