The contribution of community engagement towards shaping leadership development in students is an area that is not well explored in research. A study was conducted to establish the type of leadership skills and values that were acquired by a group of students from an established private school in Johannesburg, South Africa, while they served an underprivileged community. The private school adheres to both "Round Square" discoveries framework and the "International Boys' School Coalition's" character education and practices the leadership development programs that have been developed by the two organisations. This was a qualitative research study within the constructivist paradigm with a phenomenological approach. Reflection sheets were used to collect data from 120 students. The data was analysed through discourse analysis, where all recurrent terms were coded, and the codes grouped into themes which were then matched against existing literature, the "Round Square" discoveries framework and the "International Boys' School Coalition's" character education. The study found that community engagement experience helped refine the character of the students, affording them opportunities to develop leadership skills and values that would see them adjust well into the 21st century way of life. The study was, however, not able to determine how other learning areas and developmental fields impacted on the leadership development of the students.