This is the time of year when schools across the country announce their new Heads of School and Prefect teams. At Oakham, we have recently said farewell and thank you to our outgoing Decem team and welcomed the incoming one – the Oakham Torch passed with pride and promise.
As a Head – and a former Housemaster – this is a moment of bittersweet transition. It is always hard to see familiar faces move on, yet one of the great joys of school life is its built-in cycle of renewal. Each year, we ask: What went well? What could we do better? What should we do differently? These are questions for staff and pupils alike.
It is amazing to see how far our leaving Decem have grown in a year. At our recent breakfast ‘handover’ meeting you can see their reluctance to quite let go, but also excitement for their friends and desire to pass on what they have learned.
We begin that process with reflection: What has surprised them? What did they find harder or easier than expected? What are they proud to pass on? This feedback is golden, not only for shaping the year ahead but also for nurturing a culture of service and continuous improvement.
For any new team, there is the need for a balance of optimism – we want energy, ideas, youthful drive and ambition, but this must also be tempered with realism; considering resources and timescales, the ‘why’, and bringing others with you. Leadership is not just about ideas, but about execution, influence, and teamwork.
Communication is often the biggest, unexpected hurdle. Within the team, across the pupil body, and between staff and pupils, the challenge lies not just in the message but the medium – WhatsApp, Snapchat, email, social media, Assemblies, one-to-ones all have their place. How do you channel and harness ideas, how do you get good conversation, and engage multiple voices – how to get things started and keep momentum amidst the busy rhythm of school, to overcome resistance, to hear feedback, to adapt and regroup – not be knocked if it does not work out.
The longer I serve as Head, the more convinced I am of the lifelong value of these leadership experiences and how similar they are to my own. Pupils don’t just learn how to speak in Assembly or chair a meeting (though they do that too); they learn to lead up, across, and down. “Managing up” is a pleasure – senior staff love to see pupils take initiative. “Managing down” is meaningful – working with younger pupils, inspiring and mentoring them. But the hardest, and most revealing, challenge is “managing across”: working within the Prefect Team and across the peer group – equals, friends, allies and critics.
The learning curve is steep. From how to plan meetings to the perils of pre-planning (‘pro-bouleusis’ as the Greeks would call it), we see pupils develop in character, confidence, and competence. But the foundation of all pupil leadership remains the same: show up, look the part, wear the badge with pride and confidence, work hard, stay humble – lead by example, be a role model. Keep up the activities that helped make you a prefect in the first place.
What was clear in all the interviews when we were selecting the Decem is the love of the School. There is gratitude and recognition of opportunity and staff guidance, and a real desire to give back – Service. Even the interview process is powerful. I begin by reminding them it is ok to sell oneself – they are here because we think they are good enough, but of course there must be modesty and humility too.
And yes, the first week or two in role can feel awkward. There is joy and a desire to start, but the former group are still around, and the transition takes a little time. Just like a pupil on the first day of school proudly wearing their new blazer and shiny new shoes, they need to grow into it quickly, and the shoes need breaking in – pride meets with self-consciousness, but that’s ok.
In the end, what does success look like? Not a list of accomplishments, but a feeling: I have done my best. I have contributed, I can look everyone in the eye and feel proud of myself. I have learned, I have grown, I have been myself, I have set high standards, I can pass on the Torch with pride. I hope they have enjoyed it too.
Last year, Oakham hosted our first Heads of School Conference for schools across the East Midlands. It offered shared learning, inspiration, and, perhaps most importantly, solidarity. Sharing experiences with those in similar positions of responsibility generate ideas and seek reassurance.
Building the team in the early days and weeks is vital; it takes trust and empathy. Within the team, we see natural roles emerge: the energisers, the organisers, the quiet doers, the thoughtful challengers. The goal is to build an environment where everyone speaks, where groupthink is avoided, and a sense of shared purpose binds the group together.
As Head and a former Housemaster, I never lose sight of how important these processes and appointments are. I love appointing pupils, but I dislike having to disappoint others. That said, I am always full of pride in those who step forward – whatever the outcome. And I take enormous joy in supporting, challenging, and cheering on our new leaders as they grow in confidence and maturity.
So, to all new Prefects across the country – well done for stepping up, and good luck. Serve with humility, support each other with strength, and never forget: leadership is not about the badge, but what you do with it.
