In Year 8, Medbury operates a Leadership Programme to further prepare boys for the next stage in their lives. Leaders from the community visit to talk to the boys during the year and each Year 8 boy at some time holds a position of leadership in the School. This is an important addition to the boys' development and self esteem.
School Leaders for 2020
| Head Boy | Henry Hiatt |
| Deputy Head Boys | Ethan Griffin |
| Thomas Gough | |
| Head Boarder | Samuel Pye |
| Head of Sport | Ollie Young |
| Head of Cricket | Luke Mitchell |
| Head of Tennis | Hugo Buchan |
| Head of Rugby | Lachie Beirne |
| Head of Football | Ewan Whiteside |
| Head of Hockey | Jack Bishop |
| Head of Water Polo | Olli Aitken |
| Head of Basketball | Louie Garry |
| Head of Polo | Freddy Scott |
| Head of Hamilton House | James Floyd |
| Deputy Head of Hamilton House | Talan Harrison |
| Head of Creyke House | Felix Stanton |
| Deputy Head of Creyke House | Finnian Chan-Allan |
| Head of Clyde House | Simon Clayton |
| Deputy Head of Clyde House | Oliver Clark |
| Head of Ilam House | Matthew Geddes |
| Deputy Head of Ilam House | Hayden Douglass |
| Head of Music | James Saunders |
| Head Chorister | Jake Elvidge |
| Deputy Head Chorister | Kennedy Xiao |
| Head of Art | Benson Winters |
| Head of Chess | Alex Li |
| Head of Drama | Latham Luke |
| Head of Environment | Che De Luca |
| Head of Kapa Haka | George Mehrtens |
| Deputy Head of Kapa Haka | Lochie Horne |
| Head Librarian | Thomas Blain |
| Head of Peer Mediation | William Foulds |
| Head of Road Patrol | Oliver Finn |
| Head of Science | Hugo Arthur |
| Head of Technology | Tinura Gajamange |
| Head of I.C.T. | George Menzies |
| Head of Community Service | Ben Rowe |