Senior Leadership Team

How can you say, “The sky’s the limit”, when there are footsteps on the moon?

Mr Andrew De Silva has been the Headmaster at The Oratory Prep School since September 2022 and the quote epitomises the learning journey that the children at the school venture on. Andrew’s educational vision is that all children have outstanding learning experiences and that their potential is limitless; importantly, this is key to the school’s ethos and philosophy, and is also key to the outstanding boarding provision at the school.

Prior to His appointment at The Oratory Prep School, Andrew was Head of the Junior School at St Edmund’s School in Canterbury. Andrew has a wealth of experience, honing his skills through Headships in both the state maintained and independent sectors, in addition to a Master’s degree in Educational Leadership and Management and the NPQH (National Professional Qualification for Headship) and honorary awards for his contributions to music.

Through his experiences, Andrew believes that every child has the ability to succeed and it is the job of schools, working closely with parents, to unlock this ability. He is as a specialist in Teaching and Learning, Curriculum Design and Assessment. However, Andrew very much classes himself as a ‘Head Learner’ rather than a ‘Head Teacher’.

In addition to his role at The Oratory Prep School, Andrew is also on the Strategy board for IAPs and is the chair of the IAPs EDI group (Equality, Diversity and Inclusion).

Born and raised in Derbyshire, James to studied mathematics in Newcastle. He spent eight years in sales and marketing before training to be a teacher in 2010. He taught state secondary until his appointment as Head of Mathematics at Caldicott in 2017. He was appointed as Senior Deputy Head in 2022. He is married to Lucy and has a son Freddie who attends the school.

Hobbies: Golf, skiing, badminton and dabbles with DJ mixing decks.

Chris began his preparatory teaching in Suffolk having been educated at Trent College and undertaking his BSc studies at the University of Liverpool (specialising in Sport Science and Biology). His teaching career began at Loughborough University where he completed his PGCE before joining the staff at Woodbridge Prep School as Head of Games. Having been appointed as Director of Sport to the OPS in September 1999, he joined the Senior Leadership Team in 2006. Chris’ diverse executive role has included academic, pastoral, boarding, and community responsibilities, alongside co-curricular involvement in sports, music, drama, and enrichment, while also overseeing local projects and school initiatives from design to completion, all with a focus on preparing OPS pupils for their dynamic futures.

Chris, married to Abigail and proud of their three adult sons, brings over 30 years of teaching experience, passionately inspiring OPS pupils both in the classroom and beyond, while continuously pursuing professional development to provide the best education and help students excel in their passions.

Poppy began her preparatory school teaching in London, having studied at Oxford Brookes University. Poppy joined the staff at The Oratory Prep in 2024, having previously taught at Wimbledon High School, Abingdon Prep and Oxford High School. Poppy is married with two young daughters.

Hobbies: travelling, gardening and running.

Leanne was educated at the Oratory School in London and went on to study music at Royal Holloway, University of London where she held a choral scholarship.