Having served as Headteacher of Reigate Grammar School since 2012, just within the last few months, Fenton has been selected as a winner of the Pearson National Teaching Award’s Headteacher of the Year, listed within 2026’s ‘Top 100 Influential People’, and is a finalist of the TES School Awards 2026. You wonder where he’ll store all the trophies.

Despite the accolades – (which also include an OBE, awarded in 2020) – Fenton is keen to emphasise, somewhat nobly, that these will always come second-place to student experience. ‘‘No nomination, award or trophy is ever as important as the daily experience of a child in our care. That’s the most important thing. It’s about the children who turn up every day ready to make the most of the opportunities, it’s about the teachers who are motivated to care for and support children to do better, it’s about the parents who support what we’re doing. It’s about whether or not the child who came to school this morning goes home this evening saying, ‘I had a great school day, great day at school, Mum.’ If that happens, I’ll swap that for any award.’’

The school, which includes former Prime Minister Keir Starmer, Fatboy Slim, and Romesh Ranganathan among its alumni, opened its gates in 1675 –with just four boys enrolled. Today, Fenton has around 1500 students in his charge – a sprawling family, some might say. Others, plain hard work. But despite the noise you might expect from cohort the size of three jumbo jets, the campus is surprisingly quiet. Students are absorbed in getting to their lessons, and leaving to the next.

Fenton has made his home in an office that overlooks the playground. When it’s cold and wet, he tells me, girls and boys will ‘come in and sit at lunchtime’, using it as a ‘sort of extra space’. He warns me to watch out for balls bouncing off the window, but the students outside are striding with purpose toward their next period, pausing only briefly to chat.

Fenton’s journey to education began after he decided to leave a career in accounting – which albeit being a little unconventional, perhaps exposed even more deeply the ‘moral purpose’ he longed to fill. Undertaking a PGCE, he finally ‘found his fit’. ‘‘I just remember thinking, ‘This is joyful. This is the future.’ I’m working with some of the most amazing people as teachers and got the privilege of looking after children. I’ve never regretted it once. I’ve loved every day of it.’’

In his fourteenth year as headteacher, Fenton is clear-eyed about the culture he wants to foster. ‘‘Happy children do great things. This isn’t a school which is driven by exam results. It’s a school which is all about relationships, not about results. It’s about children’s happiness, not about their outcomes.’’

Fenton acknowledges the ability to focus on experience over outcomes is a privilege not all schools can work with – indeed, his decision to work within the independent sector was partly motivated by a frustration from the uncompromising framework of Ofsted, a lack of resources, and league tables that ‘create anxiety and difficulties in the school community’. ‘‘In an independent school, my accountability is to that child, and to their mum and dad. It’s about the dreams that they brought with them as they brought their child to the open day. And when they started their first day of school, with a blazer slightly too big; the hopes for the future. Each and every child needs to have a life-changing experience in my school, not because of what Ofsted said, not because of what league tables say, not based on some funding formula from the Department for Education. But because of the trust that family puts in us to help make a difference to their child.’’

This pursuit of a ‘life-changing’ student experience is a complex, and evolving task, perhaps more so now than ever. With the looming presence of social media, ramping unemployment rates in the young, and fears of job security due to the increasing influence of AI, how does Fenton inspire his students, while preparing them for a world that, at times, can feel deeply hostile to their success?

‘‘The last thing we do before students off to do their exams at GCSE or A level is turn the whole school into a fair with fancy dress. Their last day at school before they do their exams is, as a result, a day of cementing lifetime memories. Equally, it’s crucial that we adapt to a changing world. New technologies offer huge opportunities to transform the way we do things in the world. But, they also present huge challenges that we need to educate the children about so that they can use new technologies responsibly and safely. They’ll be prepared for a world where the job market and the employment scenario are very different to what they were a generation ago. In the future, maybe some of the jobs of the past will have changed or gone. In the future, maybe the grades you got at school might not be so important as they once were. But it will be more important than ever, or as important as it’s ever been, that today’s children become young adults who can work collaboratively, be creative, think empathetically, problem-solve, deal with difficulties and learn from them.’’

In much of our cultural memory, schools are a locus of control. Whether it’s Mrs Trunchbull’s reign of terror in Matilda, or the ‘mystery meat’ served in Grange Hill, schools are shown as a place where you are marched through corridors, told to be silent, served food that is hard to identify, and even harder to swallow. It is a place in which the spirit is one of containment, rather than encouragement.

Fenton, whether or not reflective of his own experience, said his ambition was to build a school ‘around the child – and adapt what you do so it fits their needs.’ ‘‘One of the early things that I tried to remove from the culture at Reigate Grammar School was this notion of, “That’s the way we do things.” Or, “If we do that for one child, we might have to do it for other children. So we better say no.” We should amend the way we do things so that it works for every child. I think that’s what I’ve learned from being a child myself and being a dad is that one size doesn’t fit all. We need to keep changing.’’

For Fenton, his happiest moments as headteacher are not necessarily found in the students’ achievements, but in the moment of courage that leads toward them. ‘‘Say they’ve been camping out for two or three nights on a Duke of Edinburgh expedition, and they’ve still got another three hours trudging in wet shoes. Or they’re about to be on the stage for the first time in a drama production, and they’re standing in the dark in the wings, wondering whether they can step out into the light. Or the night before a big hockey match against a local rival school when there’s a feeling in their tummy of nervousness about whether they’re going to do well for themselves and for their team.’’

It is this resolution, that is dictated as much by their learned behaviours as their inherent qualities, that he is proudest to watch. And, Fenton says, it marks the beginning of a positive course for the rest of their life – that they will be able to do better tomorrow than they have ever done before.