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Relying on information processing and attribution theories, which relate to the formation of leadership perceptions and attributes, the current study seeks to examine the influence of principal-middle-leaders relational demography variables (gender, education, and tenure) (dis)similarity on middle-leaders Principal System Thinking (PST) attribute and how such relationships are contingent upon the duration of acquaintance between the dyad. Data was collected from 305 dyads (middle-leaders and their principals) from 101 schools. MANOVA analysis showed that PST levels were higher in gender-similar relationships than in gender-dissimilar ones. Hierarchical regression analyses showed that duration of acquaintance moderate the relationship between principal-middle-leaders gender (dis)similarity and PST attribute. These findings may broaden our understanding regarding potential antecedents of PST attributions and its implication for schools.