This article introduces a new method to assess mothers' insightfulness regarding their children's inner world. Maternal insightfulness involves the capacity to see things from the child's point of view, and is based on insight into the child's motives, a complex view of the child, and openness to new information about the child. Insightfulness is seen as the capacity underlying positive parenting and providing the context for secure child–parent attachment. In the assessment of insightfulness mothers view video segments of their interactions with their children and are subsequently interviewed regarding their children's and their own thoughts and feelings during the segments. This article describes how the maternal interviews are coded and provides vignettes of both insightful and noninsightful mothers. Empirical findings supporting the validity of the insightfulness assessment are reviewed, and the implications for children's development are discussed. ©2002 Michigan Association for Infant Mental Health.