This essay explores the underlying dynamics that inform postsecondary English teacher development efforts. In particular, it argues for a more expansive understanding of “context” in order to emphasize the inevitability of conflict and the productive potential of surfacing the meaningful contextual differences of our teaching lives. Such differences include varying philosophies of teaching and learning, competing motivations and expectations for participation in teacher development, and differing institutional teaching contexts where very different values might inhere. The essay offers strategies for engaging such differences with a view toward discerning collective (as well as individual) commitments. Such an orientation toward teacher development is crucial in the current climate, where plans for reform increasingly locate the work of remaking higher education outside of postsecondary classrooms. The kind of postsecondary teacher development work this essay calls for, then, seeks to support teachers' growth as agents of educational change.