Violence and indiscipline within schools is a serious problem which can undermine students’ intellectual, social, and moral development. Principal leadership within schools is a significant factor in changing school culture, including a culture of violence and indiscipline. In Jamaica, the Change from Within (CfW) programme – an intervention to address violence and anti-social behaviours within schools – supports capacity-building and leadership development among principals. In this qualitative study, the role of the programme’s Circle of Friends, a support network for principals and other school leaders, is explored. Drawing on qualitative data gathered from semi-structured interviews of individuals currently participating in the CfW programme and meeting on a monthly basis as part of the Circle of Friends, the research reveals that Circle members identify the need for those leading cultural change from violence and indiscipline as individuals who need to change and challenge their internal ways of thinking, collaboratively craft and communicate vision, and create a physical environment that differs from their students’ home environments. Additionally, research indicates that the Circle offers opportunities for both professional and personal capacity-building. Experiences shared from the programme’s efforts can be useful for those interested in school leadership development and violence prevention within schools.