The concept of accessibility offers a valuable professional language to bring stakeholders together in urban strategy-making settings. Most of the recently developed accessibility instruments that aim to do this suffer from low usability. One reason for this is the persisting disconnect between instrument developers and the potential users. Building on the concept of reflection in action, this chapter develops a framework to bridge these two worlds in one ‘experiential learning cycle’. This cycle is used in a wide variety of contexts to improve the usability of accessibility instruments and develop academic insight at the same time.