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This paper describes the development and piloting of a series of self-assessment rubrics for school constituents to assess their engagement with four critical dimensions of culturally responsive schooling. The self-assessments come from the perspectives of different school partners, including school leaders, teachers, students, and parents/caregivers. The rubrics are based on the principles of New York State’s Culturally Responsive-Sustaining Education Framework and describe a progression of development across a continuum of key aspects of school and classroom cultural engagement. The rubrics development included a multi-iterative design process, and ‘think aloud’ -scale piloting with different community groups in preparation for a large-scale field trial. Implications include expanding the field’s understanding of developing measures of culturally responsive schooling.