This chapter aims to contribute to the international knowledge about early childhood education and care (ECEC) leadership by describing the Chilean case, specifically regarding one of its most significant factors: how ECEC leaders promote or manage the relationships with children’s families. Through three exemplary cases, it describes how ECEC leaders engaged families with children’s education. To illustrate ECEC leaders’ work concerning children’s family relationships, a qualitative inquiry was followed, carrying out a case study approach. Twenty-one participants were interviewed from three educational settings: one school and two nurseries. The cases analysed in this chapter exemplify effective leadership actions for parents’ involvement in ECEC. These leaders showed deep insight about families as the first educators of children, whose links established with educational centres are critical to the achievement of learning and comprehensive development of children. From the ECEC field and the policy framework that guides its functioning in Chile, these principals also appear to know that the relationship between families and schools contributes to the appreciation of each other in contexts of diversity.