Effective school-parent partnerships are in the child’s best interests. Nevertheless, the complexity of the parent-teacher relationship requires the teachers to be trained in parent communication skills. Here, we explore factors that affect the parent-teacher relationship from the perspective of education trainees, who were required to communicate with parents to help children with difficulties with their social skills. In this qualitative research, we used thematic analysis of semi-structured interviews with four trainee kindergarten teachers, three kindergarten teacher trainers, and three parents, all involved in such communication processes. Our findings reveal that many teachers minimized parent-teacher communication to avoid potential conflict with parents, and this was mimicked by trainees. However, more experienced kindergarten teachers, confident in their skills and in the respect of parents, were open-minded about communications between trainee teachers and parents, mediated these communications, and found them useful. The findings support the idea mentioned in other literature that training of teachers in future should focus on supervised practice of parent-teacher communication skills to promote a ‘sharing dialogue’.