Learning to teach in urban schools is difficult, particularly when prospective teachers come from different racial, ethnic and/or class backgrounds than their students. The task of urban-focused teacher education programs is to prepare prospective teachers to learn and enact practices that enable them to teach successfully in under-resourced districts that offer both opportunities and constraints. In this article, we report on a 2-year ethnographic study designed to investigate how new teachers enacted a listening stance in teaching that was introduced in their preparation program. Taking a listening stance implies entering a classroom with questions as well as answers, knowledge as well as a clear sense of the limitations of that knowledge (e.g., Cochran-Smith & Lytle, 1999; Lytle & Cochran-Smith, 1992; Schultz, 2003). The article focuses on how four teachers attempted to adopt a listening stance in their classroom practice, while also responding to the constraints of the standardized curriculum of their district. We conclude that the process of negotiating among teachers' beliefs, practices introduced in a teacher preparation program and district mandates is a critical practice for teachers to learn. We further suggest that in the current climate of high-stakes testing and mandated curriculum, explicit teaching of negotiation skills is likely to support more teachers to enter into and remain in classrooms.