Communities of Practice (CP) are now being implemented in a variety of workplaces to promote learning and knowledge sharing. The author takes a reflective look at his work as a facilitator and accompanist for the past twelve years of the municipal social development stakeholder Forum at the City of Montreal. This multidisciplinary CP addresses the need to develop collective skills to better meet the social development responsibilities of the cities. By critically assessing the pedagogical strategies used, the author focuses on conditions conducive to learning and a greater transfer of knowledge and expertise in the targeted environments. Finally, he wondered how to exert more influence and ensure sustainability, even if power relations between elected officials, managers and stakeholders (including the facilitator) can sometimes hinder the development of a culture of learning and innovation.