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Data-Based Decision-Making (DBDM) initiatives often yield inconsistent results because data tools lack contextual information about learning environments. This is particularly true in complex settings like schools for the Deaf and Hard of Hearing (DHH) education, yet there is a lack of qualitative research exploring teachers’ practices. This paper addresses this gap through a qualitative study of teachers using a web-based progress monitoring software. Using semi-structured interviews, this study investigates teachers' classroom routines, decision-making processes, and perceived barriers. Findings from the study suggest potential for revealing strategies that teachers use that leverage contextual knowledge with data representations and their interpretation, highlighting the need for a teacher-centered, participatory design paradigm for designing more equitable and effective data tools.