Introducing James Chesterton, Deputy Head of Senior School
This term, we are delighted to welcome James Chesterton to Radnor House Sevenoaks as Deputy Head of Senior School. Bringing more than 20 years of experience in independent education, James joins Radnor at an exciting point in the school’s development, with a strong belief in academic ambition, individual support and preparing young people to thrive beyond the classroom.
James joins Radnor following 17 years at Eltham College, where he held a number of academic and pastoral leadership roles. Having initially joined as Head of Geography, he went on to become Deputy Head of Middle School, with responsibility for Years 9 to 11, before serving as Assistant Head (Lower School) from 2022.
His career began in the South West, training to teach in two secondary schools in Devon, before taking up his first full-time teaching position at St George’s Weybridge in Surrey, where he taught Geography from 2004 to 2009.
An ambitious school with the individual at its heart
For James, the opportunity to join Radnor came at an important point in both his own career and the development of the school.
“It was a great opportunity to join the Senior Leadership Team of an ambitious, innovative school making plans for a bright future. Having spent much of my career working closely with families and supporting students individually, I really appreciated Radnor’s focus on celebrating each individual student.”
It is this balance between ambition and knowing the individual that James believes is fundamental to an exceptional Senior School education.
Strong academic outcomes matter, he explains, because they open doors to future education and careers. But education must also equip young people with qualities that cannot be measured by examination results alone.
“A successful Senior School is one which ensures that students are ready to thrive in adult life. It should offer a broad and enriching curriculum leading to strong academic outcomes, alongside a wide co-curricular programme where every student can find something beyond the classroom that they are passionate about.”
Just as importantly, James wants pupils to leave school as interesting, engaged and grounded young adults: “I want them to be kind, polite, hardworking and reliable, with the social skills and confidence they will need throughout their lives.”
Preparation for Life
This philosophy closely reflects Radnor’s guiding principle of Preparation for Life.
For James, preparing pupils for life means giving them both the qualifications that create opportunities and the human qualities that will allow them to make the most of them.
“Young people need to leave school well-grounded, earnest, kind and reliable. These are the human skills that make you a great employee or leader, regardless of the career you choose, and they will become increasingly important in a changing world of work.”
Central to developing these qualities are the relationships pupils build with their teachers.
James has already been struck by the strength of those relationships at Radnor and believes the school’s smaller class sizes, alongside its investment in teachers’ professional development, create an environment in which pupils can be genuinely known and supported.
“Relationships between students and teachers are absolutely fundamental to academic success. I have already seen that Radnor pupils greatly appreciate this aspect of their education and have seen glimpses of the school’s talented staff body at work.”
Looking to the future
As Deputy Head of Senior School, James will play a central role in the day-to-day leadership of the Senior School, helping to create the culture in which both pupils and staff can perform at their best.
“My role will be varied, but fundamentally I want to ensure there is a culture of strong standards and that the Senior School runs smoothly, enabling students to apply themselves to the best of their ability and staff to deliver high-quality lessons and co-curricular opportunities.”
James is also keen to remain firmly connected to classroom life. A passionate geographer, he will continue teaching alongside his leadership responsibilities and is particularly looking forward to contributing to Radnor’s House system.
He joins with considerable ambition for what Radnor can achieve in the years ahead.
“Radnor genuinely delivers on its commitment to celebrate the individual and has made incredible progress in a competitive educational landscape in a relatively short space of time. I am excited to play a part in the leadership of an ambitious, forward-thinking school and to help its reputation continue to grow.”
For James, that reputation should ultimately be measured in more than academic data. His ambition is for Radnor to be known both for excellent outcomes and for the young people it sends out into the world.
“I want our pupils to be truly impressive ambassadors for the school – young people who have achieved academically but who also have the character, confidence and values to make a positive contribution wherever they go next.”
Getting to know James
Away from school, James is married to Helen, who is also a teacher, and they have two primary-school-aged children, Poppy and Harry. A former hockey player, he now prefers golf – often playing with his son – and is a Fulham FC supporter. Pupils may also discover that their new Deputy Head is, in his own words, “a bit of an aviation geek” and spent part of his childhood in New Zealand.
His own school days have also shaped some of the advice he gives young people today. James describes himself as a quiet but capable pupil who was sporty and conscientious, but admits he sometimes stayed too comfortably within familiar territory.
That experience informs the one piece of advice he would give to a pupil beginning Senior School:
“Try a co-curricular club that you have never tried before. Step outside your comfort zone and give something new a go.”
A warm welcome to Radnor
James’ appointment brings considerable experience to the Senior School at an exciting time for Radnor House Sevenoaks. His commitment to academic ambition, strong relationships, character and opportunity closely reflects the education we want every Radnor pupil to receive: one which celebrates who they are today while preparing them for everything they might become.
We are delighted to welcome James to the Radnor community and look forward to the contribution he will make to the next chapter of our Senior School.
