Purpose: The purpose of this paper is to examine a model linking school principals' strategic, interpersonal skills and teachers' participation in decision making (PDM) to predict teachers' skill flexibility (SF) during the implementation of educational reform. Design/methodology/approach: From 113 randomly selected elementary schools in Israel that had undergone a reform called "New Horizon," 1,482 teachers participated in the study. Data were analyzed through the multilevel structural equation modeling. Findings: Results showed that only principals' strategic skills lead to teachers' PDM, which in turn predicts teachers' SF. Furthermore, based on the upper echelon theory (Hambrick and Mason, 1984), principals' strategic skills promoted teachers' SF through teachers' PDM. Research limitations/implications: This research enables expanding the theoretical upper echelon model, both in the context of leaders' skills and in their relation to change outcomes. Practical implications: Using of strategic skills will help principals influence teachers to participate in decision making, adapt to the reform and promote their ability to use skills according to changing needs. Originality/value: The results of this research emphasize the strategic role of school principals as the leaders of organizational change and promoters of its outcomes.