The role of middle management in continuous improvement and similar organizational changes is a very challenging one. In this essay, we identify three different ways of looking at middle management: (a) middle managers are no longer needed; (b) middle managers have insufficient potential; and (c) middle managers occupy a unique position that connects the top management and operational levels. Subsequently, we look at the roles of middle managers in organizational change initiatives such as CI. The conclusion is that middle managers often find themselves in a Bermuda-like triangle, in which they are expected to lead change, implement change and change their own behavior. We conclude by exploring the future of the middle manager in the context of the rise of new organizational forms and the digitalization of work processes.