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 | |
| Head of Cricket | |
| Head of Tennis | |
| Head of Rugby | |
| Head of Football | |
| Head of Hockey | |
| Head of Water Polo | |
| Head of Basketball | |
| Head of Polo | |
| Head of Hamilton House | |
| Deputy Head of Hamilton House | |
| Head of Creyke House | |
| Deputy Head of Creyke House | |
| Head of Clyde House | |
| Deputy Head of Clyde House | |
| Head of Ilam House | |
| Deputy Head of Ilam House | |
| Head of Music | |
| Head Chorister | |
| Deputy Head Chorister | |
| Head of Art | |
| Head of Chess | |
| Head of Drama | |
| Head of Environment | |
| Head of Kapa Haka | |
| Deputy Head of Kapa Haka | |
| Head Librarian | |
| Head of Peer Mediation | |
| Head of Road Patrol | |
| Head of Science | |
| Head of Technology | |
| Head of I.C.T. | |
| Head of Community Service |