This article pushes back against the evalu-centric view of improvement (Hazi, 2018; 2020) in the supervision literature by advocating for a democratic pedagogy and supervision framework developed to support instructional supervision and evaluation dialogue between teachers and leaders. This democratized approach honors and centers the teacher’s expertise and learning as well as the leader’s in the observation, debrief, and reflection process. Through this decentering of expertise in the instructional supervision cycle, our goal is to build leaders’ and teachers’ mutual capacity to develop, implement, and sustain democratic instructional supervision cultures in classrooms and schools. Additionally, we illustrate our framework through a subject/discipline-specific case of instructional supervision in secondary mathematics instruction. Through this illustrative case, we demonstrate how the framework provides school leaders and teachers with specific, shared pedagogical language to engage in standards-based mathematical dialogue during the instructional supervision process. Finally, we discuss the implications of our questioning framework for democratic school leadership, supervisors’ leadership content knowledge, teachers’ discipline-specific work of teaching, and instructional supervision practices, which are often stifled by accountability-driven teacher evaluation education policies that suppress schools’ leadership capacity to apply democratic instructional supervision standards and principles.