Teacher education programs are cognizant of the need to prepare preservice teachers (PTs) to work effectively with children from diverse cultural backgrounds. Well-constructed field experiences can help PTs develop awareness and gain understanding of important cultural considerations related to effective teaching and learning (Sleeter, 2001). This paper describes a unique field assignment created for an Elementary Math Methods course in which 61 PTs were trained to conduct a semi-structured interview with a student whose cultural background was different than their own. PTs transcribed their own interviews and completed a guided reflection on their experiences. Reflections were submitted and analyzed for emerging themes. Analyses suggest that the structured interview component of this field assignment provided PTs with increased insight into mathematics instruction and the learning needs of diverse students. We also discuss the value and limitations of this instructional innovation and propose avenues by which to continue to help PTs grow toward becoming culturally relevant pedagogists (Irvine, 2003).