Communities of practice are emerging as an innovative approach to faculty development. While collaborative learning is becoming popular in the classroom, autonomy and individualism continue to dominate the culture of higher education for faculty. However, as we begin to recognize that old solutions to new problems are no longer effective, there is a growing desire for innovative engagement requiring the embrace of multiple perspectives. This takes the development of new habits of mind and discourse. For my dissertation, I engaged in a qualitative study with my colleagues where we experimented with generative approaches to dialogue in a community of practice. It became apparent that creating supportive, collegial spaces where we can explore beyond the edge of what we currently know can help us bridge across differences, harness the potential within diversity, and step into the emerging future. However, it also became apparent that this quality of dialogue is not easy.