Relying on the contingency theory, the present study examines the influence of school characteristics and principal-teacher gender (dis)similarity on the relationship between principals' systems thinking (PST) and teacher withdrawal behaviours of absenteeism and intent to leave. Data were collected from two sources: 111 school management team members and 109 teachers (220 participants in total) randomly chosen from elementary schools in Israel. Hierarchical regression analyses showed that principal-teacher dissimilarity and a bureaucratic school structure moderate the relationship between PST and teachers' withdrawal behaviours. These findings indicate that the organisational conditions under which principals practise systems thinking can affect teachers' withdrawal behaviours. Therefore, this study may advance theory and practise regarding the implications of PST on withdrawal behaviours, which are an important determinant of teachers' performance and a school's success.