Urban and rural grandmothers (n = 20) in Botswana participated in focus groups to learn their expectations for the acquisition of skills by preschool children. Their expectations for self‐care, traditional politeness, and participation in household chores were dramatically earlier than developmental timetables reported for Western middle‐class populations. There are some differences, however, in the urban and rural grandmothers’ expectations. Rural grandmothers had earlier expectations for self‐care skills and participation in household chores, and they had more specific expectations for mastering Setswana cultural customs. In addition, some urban grandmothers, who were generally more educated, described using more reciprocal communication, and they believed in playing with their grandchildren, whereas the rural grandmothers’ communication was more instructional, and they insisted that children should play away from adults. Strikingly, there was no mention of school readiness goals or activities by either group, suggesting a “cultural misfit” between the standard early childhood curriculum, largely imported from the United States and other Western countries, and the cultural backgrounds of Batswana families. To create a more workable partnership between preschool teachers and grandparents—important caretakers of young children, both traditionally and currently—will require efforts to acknowledge and promote the values and expectations of both groups.