In this paper, we discuss how we attempt to build classroom environments that are conducive to positive civil discourse. Utilizing the framework of cultural proficiency (Lindsey, Robins, and Terrell, 2009), we argue for an inside-out approach through self-exploration to help deconstruct worldviews we develop through the years. In coupling this approach with the benefits of a liberal arts education, we are then able to provide preservice teachers with a deeper sense of how to move critical conversations forward within their work.