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This paper explores how faculty members intentionally craft experiences of students of color at elite boarding schools (EBSs) through asking questions around how they operationalize their pedagogical/curricular freedom? This paper highlights three findings about faculty: (1) they need professional development about ways to diversify curriculum, (2) they feel ill-equipped to tackle the issue of racism; (3) they are perpetuating harm through not diversifying curriculum or encouraging the development of racial critical lenses. This paper argues that faculty at EBS need to have teacher activist mindsets and can (re)imagine and (re)direct how equity functions within these institutions. It behooves researchers to focus on what teachers are doing to develop practical implications that improve the experiences of EBS students of color.