This research examined challenges faced by novice principals in Colombia in connecting to their school communities through their socialisation processes. Interviews with 37 newly appointed principals in rural and urban schools revealed that the complexity of their school contexts accentuated the need to work on the relational dimension of their jobs. Forging relationships with teachers and parents based on trust and communication, introspection and knowledge about their school communities emerged as crucial factors to foster social justice and to transcend deficit views of their communities. The article questions the role of supporting services for novice principals, emphasises the importance of organisational socialisation, and stresses the role of preparation programs in providing principals with tools for learning during this phase of their professional careers.