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 2019
| Head Boy | Nicholas Sharr |
| Deputy Head Boys | Josh Durant |
| Frankie Meates | |
| Head Boarder | Alexander De Luca |
| Head of Sport | Austin Smith |
| Head of Cricket | Felix Huston |
| Head of Tennis | Archie Whithear |
| Head of Rugby | Sam Pickens |
| Head of Football | Jake Hayes |
| Head of Hockey | Ben Harford |
| Head of Water Polo | Matty Hickman |
| Head of Basketball | Carter Stewart |
| Head of Polo | Elliot Lee |
| Head of Hamilton House | Angus Eglinton |
| Deputy Head of Hamilton House | Oscar Ren |
| Head of Creyke House | Callum Fox |
| Deputy Head of Creyke House | Paddy Cochran |
| Head of Clyde House | Oscar Compton-Moen |
| Deputy Head of Clyde House | Miles Clayton |
| Head of Ilam House | Hugo Ranken |
| Deputy Head of Ilam House | Caleb Benton |
| Head of Music | Ted Pitts |
| Head Chorister | Harry Vaughan |
| Deputy Head Chorister | Jin Kim |
| Head of Art | Tom Hansen |
| Head of Chess | William Tavendale |
| Head of Drama | Hugo Sudell |
| Head of Environment | Tadhg McKenna |
| Head of Kapa Haka | Tom Rawstron |
| Deputy Head of Kapa Haka | Max Topham |
| Head Librarian | Alan Chong |
| Head of Peer Mediation | Jack Satterthwaite |
| Head of Road Patrol | Jack Boon |
| Head of Science | Harrison Lehmann |
| Head of Technology | George Grace |
| Head of I.C.T. | Louie Nelson |
| Head of Community Service | Felix Bowden |