Effective monitoring of learning and development involves integrating multiple perspectives from a child’s parents, carers, family, and their educators. A collaborative approach between educators and families not only recognises the family’s critical importance in their child’s life but it has also been shown to benefit children with learning difficulties, delays and behavioural concerns (Parenting Research Centre, 2012; Prior et al., 2011). Efforts made towards the integration of multiple perspectives can also support stronger inclusion of diverse families into communities of early childhood education and care. However, discussions with parents and carers about issues regarding their children’s development can be a challenging part of an educator’s role (O’Connor et al., 2018). This paper will reveal both obstacles and enablers when it comes to engaging in conversations with parents and caregivers. Bronfenbrenner’s ecological systems theory positions ’mutuality, reciprocity and shared decision-making’ (1979, p. 46) at the forefront of planning for conversations about the learning and development of young people. This paper will justify how this lens has informed the development of a tool to support educators and families to move beyond traditional power imbalances to enhanced and balanced relationships that result in improved holistic student support.