If you’re like me, when a retirement card does the rounds for a much-loved teacher or headteacher, you’ll take a sneaky peek at what others have written.
You might see messages like, ‘You knew every family,’ ‘You always knew what to do,’ or ‘You made this school feel like home.’ It’s often a reminder of just how greatly this person will be missed across the whole school.
But from a leadership perspective, those messages also tell us something else.
If all that knowledge, confidence and culture sits with one person, what happens when they leave?
Beyond the handover notes
When a long-serving headteacher retires, the knowledge that leaves with them is far from just practical memos.
It might be the relationship with the parent who finds school difficult because of their own childhood experience. The quiet understanding of which member of staff needs a nudge, and which one needs space. Knowing why a particular tradition means so much to the community, or why a decision made five years ago still affects how people feel today.
Alongside relationships, personalities also lend themselves to a particular school culture. You will probably recognise a few of these characters in your own corridors:
The Parent Whisperer: Can calm a tricky conversation before it becomes a complaint.
The Pedagogy Mastermind: In a quick classroom visit, can influence better learning opportunities.
The Fix-it Felix: Can sort the timetable, or the glitchy parents’ evening booking system.
The Agile Alchemist: Helps the team adapt, think differently and create a more inclusive environment for pupils.
These are all valid qualities that every school needs. So, if those strengths only sit with one individual, the school can feel very different when that person is no longer there.
At the Diocese of Chelmsford Vine Schools Trust, we often ask our governors: if that person left tomorrow, what would we struggle to do?
When to start planning
Succession planning should be led by ongoing staff development, not by a leaving date.
In any school or Trust, this means looking beyond job titles and asking where talent, confidence and potential are already showing up. This might be through leadership pathways, mentoring, coaching, CPD or wellbeing support.
People are much more likely to step forward when they feel both challenged and supported.
We also need to look honestly at performance and potential to make sure we are investing in the right people, in the right ways. Talent management tools, such as a 9-box grid, can help show where colleagues may benefit from further training, development, or secondment opportunities.
The aim is to notice potential early and grow leaders who can continue a school’s vision, values and ethos, not simply fill a vacancy.
We learnt the importance of this through experience. In one difficult-to-recruit area, we moved too quickly to replace a headteacher and later realised the fit was not right.
It took time to rebuild relationships and restore confidence, and it taught us that no appointment is better than the wrong one. Now, we don’t wait until there is a gap before looking for the people who could fill it. We tend to grow our own leaders, so if someone retires, their successor is likely to have been developing within our Trust for years.
Scouting future leaders
One thing I have learned is that future leaders rarely identify themselves, particularly women. This is reflected in the Sustainable School Leadership: Final Report, 2026, which found that a large proportion of heads (between a quarter and a third in each UK nation) describe their pathway to headship as accidental. I know mine was.
To me, this is where coaching, mentoring and secondments can be so powerful. Spending time with colleagues helps us recognise potential that may otherwise have been missed.
We can see who has the judgement, care and integrity to take the next step, and while leadership skills can be taught, values cannot. Sometimes this leads to ambassador roles or new responsibilities; just as importantly, it helps people understand the kind of leader they are becoming rather than trying to copy someone else.
A recent example is a senior teacher who was seconded into our improvement team and developed a strong relationship with one of our schools. When the school later needed deputy headteacher cover, she was ready to step in, and is now preparing to take on the role of head of school.
Protect what must stay
When a headteacher leaves, the aim is not to find someone exactly the same. New leaders need room to be themselves, but schools must be clear about what should stay consistent.
At one of our smaller schools, the headteacher changed, but we had a very clear understanding of what needed to stay. We listened to staff, children and families, who told us how important German, Forest School and the wraparound care club were to them.
These might sound like small details from the outside, but to that community, they were part of what made the school feel like itself. So, we made sure they remained under new leadership. That, for me, is the balance. Protect what makes the school special, but give the next person room to lead in their own way.
So, perhaps the retirement card can offer more than a lovely keepsake, with its sentiments reflecting not only the difference a leader has made, but the legacy they leave behind.
Emma Wigmore is CEO of The Diocese of Chelmsford Vine Schools Trust, where she leads 21 primary schools across Essex.
