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This study examines how transformational leadership (TL) influences organizational learning (OL) in schools, focusing on the moderating roles of principal self-efficacy and teachers' perceptions of leadership effectiveness. Using survey data from 1,080 teachers and 31 principals across Hong Kong K–12 schools, multilevel mixed-effects analysis shows that the four dimensions of TL—intellectual stimulation, idealized influence, inspirational motivation, and individualized consideration—positively relate to OL, with effects varying across schools. Notably, when principals report high self-efficacy but teachers do not view them as effective leaders, the relevance of intellectual stimulation to OL is significantly weakened. These findings highlight the complex dynamics between leader confidence and teacher perceptions, emphasizing the importance of the alignment between perceived leadership performance and principal self-efficacy.