Chapter 10 analyzes the development of the organizational structure within local healthcare organizations, focusing on the roles and structure between top management and the operational core (clinical middle management). Through interviews with general managers and reviews of the organizations’ documents, the authors studied three cases, two in large metropolitan organizations (ASL Roma 1 and ASL Città di Torino) and one in a local organization that had been subject to a major reorganizational process (APSS di Trento). The evolution of the management figures within these three organizations was driven by the need to oversee the large organizational dimensions and integrate, both vertically and horizontally, the different strategies through decentralization and accountability. In order to carry out the tasks, different performance management instruments were provided, along with organizational development plans and project management. While the structural changes seem to have been established, the “designated human dimension” is an equally fundamental issue at stake. Middle managers: a) consider themselves as representatives of the operating core, while they feel far from the strategic hierarchy; b) tend to isolate the top operational core to preserve the status quo (custodial strategy); c) accept the role for convenience and not for leadership ambitions; d) their loyalty is towards patients and external stakeholders and not towards the organization. It is therefore fundamental for the organizations to invest in engaging middle managers, both in vertical roles (managerial-strategic roles aimed at implementing change and making “difficult” decisions), and in transversal roles (“professional relationship” roles aimed at influencing professionals to pursue integration goals), and in platform management roles.