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This study, based on contingency theory, examines the influence of school structure (bureaucratic vs. organic) on the relationship between principals' system thinking (PST) and academic achievement and school violence, accounting for students' socioeconomic backgrounds (SES). Using a three-source survey design with self-report and non-self-report data, data were collected from 423 participants across 71 elementary schools, including senior management team members and teachers. Data were aggregated at the school level of analysis. Hierarchical regression analyses revealed that organic structure moderates the PST-academic achievement relationship, while bureaucratic structure moderates the PST-school violence relationship, both beyond SES impact. The study provides evidence for aligning PST with school structure to improve student outcomes, regardless of SES, contributing to strategies for addressing educational inequality.