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While data-driven decision-making (DDDM) is increasingly prioritized by policymakers in education reforms, its implementation often follows a one-size-fits-all logic that overlooks how local contexts shape practice (Spillane, 2012). This comparative case study explores how principals in Azerbaijan, Estonia, and Finland engage with DDDM amid differing systemic conditions. Drawing on semi-structured interviews with four principals from each country, the study examines how governance structures, infrastructure, and policies influence school leaders’ data use. Findings reveal distinct barriers: limited technology access in Azerbaijan, fragmented data systems in Estonia, and restrictive privacy laws in Finland. The study underscores the need for contextually responsive data policies and contributes to the global educational leadership discourse on equitable and effective school-level data use.