This paper reports on expectations for and community members’ experience in the development of community indicators in a healthy communities initiative (HCI) in Alberta, Canada. The HCI process involved community visioning, the creation of action plans to further the vision by addressing key health priorities and/or community capacity building activities and the development of indicators to monitor and report on progress towards goals. Nineteen semi-structured interviews were conducted with community participants to discuss definitions of success in the HCI and participant experience in developing indicators. Three themes emerged: the formal indicators lacked relevance to community members; the community did not own the HCI indicators and participants instead drew upon measures of success which were largely experiential in nature. The study provides a critically reflective, candid account of on-the-ground work with communities. The findings reveal limitations in the process of developing community indicators in this HCI, which we attribute in part to skills and discontinuities on the staffing side of the health authority and in part to failure to recognize and fully appreciate ‘different ways of knowing’ between communities and agencies.