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Addressing the differences of all learners through differentiated instruction has been an emerging topic in education. However, measuring the effectiveness of differentiated instruction is a unique challenge due to a lack of consensus on theoretical and practical definitions of differentiated instruction. In this study, the researchers document and compare the sensemaking of teachers and the principal within the same school context by using a qualitative case study methodology. The findings suggest that teachers and the principal in this school made sense of differentiated instruction differently. While the principal primarily relies on the official definition when evaluating teachers’ effectiveness on differentiated instruction, teachers have more practical approaches to this pedagogy by tailoring their practical definitions.