In this self-study, the author focuses on ways of embracing and managing a central dilemma of student teaching supervision: balancing assistance with assessment. Drawing on his practice as a field supervisor, the author chronicles conversations with student teachers over a 2-year period in the context of two distinct teacher education programs. Through qualitative methods of data analysis, the author finds that supervisors have access to specific discursive tools and strategies that allow them to balance support with assessment of their student teachers. In this article, he describes and explains five key strategies and concludes with implications for the preparation and support of supervisors that can help them engage in critical dialogue with their student teachers to push their practice forward. (Contains 3 footnotes.)