Round Square is based on the theories of experiential educational philosopher Kurt Hahn who believed that schools should have a greater purpose beyond preparing young people for college and university. Dr. Hahn believed that it was crucial for students to prepare for life by having them face it head on and experience it in ways that would demand courage, generosity, imagination, principle and resolution. As a result, he felt that young people would become empowered and develop the skills and abilities to be the leaders and guardians of tomorrow's world. Round Square schools are founded on a philosophy which embraces a series of six pillars or precepts which can be summed up in the word IDEALS. They are Internationalism, Democracy, Environment, Adventure, Leadership and Service. Students at Round Square schools make a commitment to addressing each of these pillars through exchanges, work projects, community service and adventure. The overriding goal is to ensure the full and individual development of every student as a whole person through the simultaneous realization of academic, physical, cultural and spiritual aspirations.

Teaching students both the values of democracy and the importance of active participation in democracy is essential to Round Square schools. Freedom of thought and speech is greatly encouraged and appropriate forums and channels of communication are set in place. Students are also taught to appreciate the importance of self-discipline and are trained and expected to share in the running of the school. Therefore, student government and a genuine sense of responsibility in the management of the school are goals in all Round Square schools.

Building the body and soul through adventure, meeting the physical challenge and developing an appreciation of the outdoors: these are all central to Round Square schools. Each school arranges outdoor and extra-curricular activities that challenge and strongly engage students, individually and within groups – in ways that promote personal growth and self discovery. All students are expected to participate in Outward Bound type activities which will foster a spirit of adventure and the realization that students can be so much more than they might have imagined. Round Square schools also incorporate adventure programmes for various grades into school calendars and invite students from other member schools to join in.

key method used by Round Square to prepare students for life is by the expectation of serving others. Each student is encouraged to perform a substantial number of service hours, either in school-sponsored, regional or international projects. Round Square international projects have been in existence since the early eighties, occurring in developing countries, where both staff and students from all Round Square schools work together in constructing buildings and water systems. Schools are also expected to train students in skills to help in emergency or disaster situations. To help in funding these projects, students raise money for the Prince Alexander Project Fund, to supply construction materials for the projects