Empathy is theorized to improve the teaching effectiveness of teachers in urban and multicultural classroom settings. However, the field has few models useful for training and preparing teachers to cultivate empathy as a professional disposition. This study examines the academic, behavioral, and social/relational interactions of four White female high school teachers with their Black male students. Findings suggest that empathy, as a professional disposition applied by teachers to negotiate interactions with students, requires two phases of implementation. Phase 1 is the acquisition of new knowledge. Phase 2 is the strategic negotiation of that knowledge and interpretation of student feedback to make the necessary pedagogic adjustments in subsequent student--teacher interactions. Implications for teacher education and professional development are discussed.