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The issue of low math performance, particularly in schools serving historically marginalized communities, requires immediate attention. Despite implementing various interventions, including leadership changes, curriculum updates, and hiring consultants, student achievement in math has remained stagnant at Ida B. Wells Academy (Wells). This case study uses organizational and adult learning theories to examine the leadership actions and organizational changes implemented by the principal to improve student learning through improved pedagogy in daily math lessons. The principal engaged math teachers in rapid, iterative inquiry cycles, using an instructional framework to facilitate math conversations that center mathematical thinking and problem-solving. Teachers also engaged in critical reflection to nurture classroom environments conducive to productive conversations, academic risk-taking, and productive struggle. The study identifies key strategies essential for implementing organizational change and facilitating cognitive redefinition in the context of improving math education. These include iterative disconfirmation, nurturing survival anxiety, collaborating to diagnose needs, and operationalizing trial-and-error learning. Furthermore, leadership actions such as normalizing learning anxiety and unpacking unlearning proved crucial in mitigating challenges during the change process. These findings offer valuable insights and practical tools for equity-focused school leaders seeking to enhance students' experiences and outcomes in middle school math classrooms. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]