Research has shown that the success of urban students of color is strongly linked to the teacher’s Culturally Responsive Pedagogy. Due to longstanding social, cultural, and economic inequities, the field of education has consistently found itself with a often poorly bridged divide between the educator and the student. In order to cross this divide, educators must, not only understand the cultural differences between them and their students, but also be able to reflect on their own cultural relevance and how this may benefit or harm the school community. This Action Research Project acknowledges these empirical ideas and looks at four middle school teachers in a highly diverse school community as they reflect on their current Culturally Responsive Pedagogy. The teachers are assisted through a Cognitive Coaching process that utilizes school academic and discipline data to challenge their thinking about the efficacy of their Culturally Responsive Pedagogy.