This chapter explores middle managers as agents and recipients of change when involved in mergers and acquisitions. We capture the characteristics of middle managers, who, when faced with such radical organisational change, not only have to personally thrive amidst this change, but, moreover, must act as the driving force of this change. The middle managerial challenge is embedded in this double-hatting—simultaneously delivering, while personally living through the same change. We argue that middle managers’ development towards leadership positions depends on their ability to personally undergo and lead such changes when and where they arise. This requires learning to both implement change and personally make sense of change. Going forward, we call for more attention to be given to the ‘inner world’ of change agents.