This study examined how head teachers of two Community-Based Schools (CBS) in Karachi understood monitoring in relation to school yearly plan. The study was conducted within the qualitative paradigm. Two head teachers of local CBS schools (Mountain and City) participated in the study. Interview, observation and document analysis were used as a major research data collection tools. The results of the study revealed that the head teachers have been engaged in monitoring practices. Both of them considered monitoring as a fundamental factor for the smooth functioning of the school activities. However, the way they approached the tasks are different. The head teachers viewed monitoring professional development of teachers, parental involvement to promote students' learning, teaching and learning, and planning as the key areas to be monitored. The data reveal that in the Mountain school monitoring approach is delegated, while in the city school it is mostly the head teacher who carries out monitoring all activities. The study reveals that head teachers' professional exposure and presence of professional capacity in the school determine their monitoring approach. For instance, the principal of the Mountain school has an extensive and professional and academic exposure. He has two professionally trained teachers in his team, to whom he has delegated the responsibility of monitoring by the virtue of their professional assignments as academic head and head of ECD section respectively. While in the City school, the teachers have nominal professional qualifications with some exposure to short term courses. The study identifies some focused areas in the CBS school context for monitoring. Both head teachers do monitoring, but there is no such monitoring strategy as a part of yearly plan. Monitoring finance and teaching and learning are focused. The study identifies planning as the backbone for development of school. The study shows different kinds of planning in both schools. But both head teachers monitor the plan. Finally, the study finds some areas for further exploration for researchers.