This study investigates which subjects teachers talk about with parents in parent–teacher conferences and other contact moments, and how they communicate with regard to these subjects. Fifty-five in-depth interviews were carried out with teachers from special education schools, at-risk schools serving low socio-economic status children and mainstream primary education schools in the southern part of the Netherlands. The results illustrate that (1) two-way communication is used the most in at-risk schools, (2) teachers find it difficult to involve parents in the decision-making process concerning special care for the child, and (3) the teachers’ attitude towards parents is best when it comes to difficult discussion topics. When situations are really difficult, teachers stand alongside the parents instead of addressing them from their expert role, asking them ‘How can we solve this together?’. Teachers should be more aware of this quality, and not be afraid to address difficult subjects or conflicts.