Teachers and caregivers are the people who are the most invested in a child’s success. Creating a working relationship between the two where they can collaborate together to align expectations, information, aspirations, and goals can provide constructive support for the child. The purpose of the study is to identify how school leaders can achieve this relationship dynamic between each student’s caregiver and teachers. Two schools who have had success in achieving teacher/ caregiver relationships provided the setting for this study. The data was collected through semi-structured interviews. One school leader, one teacher and one caregiver from each school who had engaged with the teacher/ caregiver relationships were interviewed. The participants were asked to share their experiences and perceptions of teacher-caregiver relationships, barriers and enablers and the role of the leadership. Four themes emerged from the data. The culture of care was the overriding theme and was embedded in the other three themes. The second and third theme: building relationships and communication, provided the foundation of evidence that enabled the fourth theme: collaboration, to be achieved. The themes that emerged from the data will be useful for understanding how school leaders can develop effective working relationships between teachers and caregivers in their schools.