This paper examines the complexities surrounding teacher evaluation in general, and the evaluation of preservice teacher educators affiliated with a university teacher education program in particular. It focuses on the purposes of evaluation, whether those purposes are complementary or in conflict with one another, how the evaluation is related to reflection, and how the actual act of evaluation is negotiated between teachers and supervisors. The paper begins by relating the story of one particularly troubling evaluation incident. Next, it examines the context of evaluation, viewing teacher evaluation as a professional challenge and discussing the shift from K-12 teacher evaluation to preservice teacher educator evaluation. Finally, the paper describes a pilot evaluation process for teaching assistants in one teacher education program, highlighting the goal-setting, evaluation process, and re-assessment phases of the effort. This pilot process puts teaching assistant preservice teacher educators in charge of the design and implementation of their own evaluation through a reflective portfolio process. This promotes a sense of professionalism and competence and creates a mutually supportive community of self-confident preservice teacher educators. (SM)