Parental Involvement has been associated with better academic achievement. However, some studies indicate that parental involvement diminishes during adolescence. The purpose of this qualitative descriptive case study was three-fold: to explore the nature of parental involvement in children’s education at the secondary level, to determine types of involvement, and to examine parents’ and educators’ attitudes towards parental involvement in private schools in Malawi. Grounded theory, an inductive methodology that uses a constant comparative data analysis process, was used to make generalizations and discover emergent themes from the data. The cross-case analysis portrayed a package of contrasting ideologies held by proprietors, educators and parents. These ideological influences resulted in the formation of perspectives and attitudes, which in turn translated into the schools’ practices and participants’ actions. Based on the findings, recommendations were developed with the intention of improving Parental Involvement in the two Malawian private secondary schools.