Part of preparing our boys for life, is preparing them for leadership. DHS has a history of producing outstanding leaders in various field including Cabinet Minister Alec Erwin and a former Lord Mayor of London, Sir Gavyn Arthur. In fact, in his book "Little England on the Veld", identifies DHS as the top school in producing South Africa's Leaders.

Grade 8 boys are also formally taught leadership lessons, under the Action Centered Leadership model. Furthermore, Grade 8 and 9 boys are required to perform 12 hours of on-campus community service, and in Grade 10 the boys must compete 20 hours of external community service.