As federal mandates purport to improve the academic achievement of all students, the achievement gap between White students and their marginalized peers has not closed. The persistency of the gap raises the notion that the answer to addressing the achievement gap may not lie in policies or practices. The alternative then is to explore the practices of schools and educators, and the impact each has on students. More specifically, the belief system of those who work with students on a regular basis was the focus of this study. In education, deficit thinking is the practice of holding lower expectations for students with demographics that do not fit the traditional context of the school system. Deficit thinking equates the poor academic achievement of students from low-income and culturally and linguistically diverse communities with factors outside the control of the school. In essence, deficit thinking posits there is little the school can do to “fix” these students so it reverts to providing them with interventions to help them fit the context of the dominant school culture. The literature indicates that trying to “fix” students only further alienates them from the contemporary school setting by perpetuating deficit attitudes and practices toward students who are marginalized. Through a re-positioning of the self, school leaders help educators recognize the harmful effects of deficit thinking on students who are marginalized. This multiple-case study examined the practices and challenges of two secondary school leaders who work to eliminate deficit thinking practices and replace it with notions of a democratic education. Based on the findings, recommendations are made for school leaders to consider the use of deliberate dialogue to create inclusive schools that validate and create space for students who are marginalized. These are presented in an effort to eliminate the practices associated with deficit thinking.