The goal of this study was to explore the effects of reflective and traditional supervision and training on caregiver insightfulness. Caregiver insightfulness, or caregiver ability to understand “motives underlying the child's behavior in a complete, open, and accepting way” (D. Oppenheim, D. Goldsmith, & N. Koren-Karie, 2004, p. 352) was assessed at two time points with 21 new caregivers at two university-based childcare sites. Trends suggest that caregiver insightfulness was relatively stable while increased levels of components of caregiver insightfulness over a period of approximately 2.5 months were positively associated with reflective supervision and training. These findings suggest that encouraging caregivers to reflect on their interactions with the children in their care fosters caregivers' ability to see from the child's perspective in an open and accepting way.