The study examines the combined effects of key elements in parental leadership on academic performance. In the wake of inadequate learning resources, parental leadership becomes an indispensable learning input for children’s academic performance. The discourse utilized data collected from 2005 to 2010 in a longitudinal study involving 1,549 children who sat for the national standardized examination in Kenya. Our findings showed that monitoring and aspirations are essential elements of parental leadership and have direct and positive effect on children’s learning achievement. The effects were stronger among children from urban informal settlements compared with those from urban formal settlements. The effect of parental aspiration on children’s performance was mediated through parental support and monitoring in informal settlements. The study provides evidence on the extent to which parental leadership enhances academic performance. This is useful to parents, teachers, and policy makers in their efforts to secure effective mechanisms for improving learning outcomes.