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Grounded in practitioner inquiry, this paper examines why elementary school principals often leave site funds unspent and explores how financial professional development influences their budgeting decisions. Structured workshops with site leadership teams revealed several key themes: principals struggle with fiscal decision-making due to limited knowledge, lack of experience, and external environmental barriers. Additionally, the learning environment was found to directly influence principals’ financial confidence. The study presents tools, case studies, and protocols that supported the development of financial literacy, improved communication between district and site leadership, and strengthened budget implementation. Findings suggest that targeted professional development can enhance principals’ capacity for fiscal leadership and contribute to more effective resource allocation in support of student outcomes.