As one part of a larger project exploring participative democratic forms of municipal governance, this paper will report an organizational intervention designed to create a more collaborative, participative democratic city management. A Directors Working Conference (DWC) designed to empower city managers is examined through a series of follow‐up interviews with participating managers. A total of 10 interviews were conducted, transcribed and coded to synthesize the most common themes. Included is a discussion of the external and internal challenges facing city managers in the current, turbulent socio‐ecological environment.