This study investigates the preservice teacher learning in the context of conversations about their field-based challenges. First, a review of the literature explores studies that highlight the role of evidence-based conversation as a mechanism to approach the inevitable problems faced by teachers in the classroom. The subsequent case study provides an analysis of how a group of preservice teachers approached a colleague's challenge through a structured conversation and used digital videotapes and artifacts to add specificity to their analysis. The study's implications suggest how constructive and critical conversations between prospective teachers can play an important role in their professional development. (Contains 1 table.)