With the financial crisis threatening the most diverse aspects of urban life, cities have to cope with the uncertainty that any modifications in their economic, cultural, or spatial status quo may generate. Cities encompass inertial resistance to change, bureaucratic decision loops, and budget constraints. In most cases, cities operate by reducing the risk of decisions; however, processes of urban transformation still occur. In the light of this technical pragmatism, the following chapter outlines a discourse on ‘effectiveness‘ in urban transformations: what implies in inclusive practices, why matters in compromising, and how decision making might be alternatively approached.