For families with toddlers approaching their third birthdays, parent-child playgroups provide opportunities to support children's school readiness skills and to prepare both children and parents for changes they are likely to encounter during the transition to preschool. However, all transitions are unique; they depend on families' needs and resources, and must be carefully planned and individualized. This article describes a Parents Interacting With Infants (PIWI)-Inspired Playgroup as a way to provide individualized learning opportunities during various playgroup routines that may be similar to those children encounter in preschool. Many of these ideas can be implemented in other settings, such as Early Head Start socialization groups, community playgroups, and families' homes. The key factor is that parents are able to provide the amount of support their children need, and professionals are available to modify or adapt activities and the environment to address individual differences. A selected list of resources on the PIWI Intervention Model is appended.