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New principals and novice principals alike must exercise sound professional judgment in order to manage their schools well and lead them to improvement (Cheung & Walker, 2006). This paper, through an explanatory case study design, investigates new principals’ professional judgment in shaping school culture – arguably their single most difficult professional challenge. A critical incident technique is the main method of data collection. Findings suggest that the new principals’ professional judgments predispose them towards particular types of leadership practices and strategies. Their professional judgments in turn were found to be influenced by particular personal attributes, values, role conceptions and their levels of school culture awareness.