In western democracies, the critiques of managerialism in school leadership are increasingly common. Feminist researchers have suggested that this recent orientation fits more easily with traditional male leadership than with that of their female counterparts. However, not all men principals are happy with the managerialist turn either. This study investigated how male primary school principals describe their work and respond to the recent changes. While we acknowledge that female principals are also required to deal with emotional issues, this paper points to the stresses experienced by male principals as a consequence of their being men. From this standpoint, our analysis suggests that gender relations form a particular feature of current leadership issues for male principals and we identify the demands placed on them as a consequence. Using data drawn from a series of recursive interviews with 17 experienced male elementary school principals, we propose that emotional issues are centrally involved in the busyness of running a school. While the acknowledgement of emotional responses challenges the stereotypical view of the male manager as impersonal masculine authority, we show that emotional encounters serve to usher in traditional gendered responses in these male school leaders in ways that are experienced as challenging.