Once Upon a Deputy

The beginning of my journey from Deputy Headteacher to high-level Virtual Assistant.

3 min read

It sounds like a fairytale, doesn’t it? But anyone who has ever held the keys, worn the whistle, carried the radio, or stood on the playground at 8:40am in a torrential downpour knows that the reality of being a Deputy Headteacher is less "happily ever after" and more "how on earth did it get to 5:00 PM and why is there a half-eaten biscuit on my desk?"

After 22 years in education, May half term 2026 marks a massive milestone for me. It is my very last one. Scary? Exciting? Surreal? All of those and more.

Looking back at the long and winding road that has brought me here, and looking forward to the one stretching out ahead as I transition out of education this summer, I’ve been doing a lot of thinking about what it actually means to be the one behind the leader.

The Deputy Head space is a unique, brilliant, and sometimes brutal place to sit. Here is a reflection on what that chapter has taught me and why it’s the secret weapon for my next one.

The Art of the Crisis (that sometimes people don’t see).

As deputy, success is often measured by the things that didn't happen as well as the things which happened brilliantly. It’s the potential timetable disaster that was quietly re-routed. It’s the difficult conversation with a concerned parent that ended with positivity and a shared plan, rather than an escalated complaint. It’s the absolute chaos of a morning staff shortage that gets smoothed over seamlessly so that all classes are covered, everyone is happy and the many other events of the day still go ahead.

A DHT becomes a master of filtering the noise. You learn how to protect the Head's time, protect the staff's energy, and keep the wheels turning without needing (or wanting) a spotlight. It’s strategic, it’s high-stakes, and it requires a level of organisational grit that you just can't learn from a textbook.

The Shield and the Sounding Board

Being a deputy means mastering the art of the pivot. In one single minute, you are a strategic visionary analysing data or preparing for a high-level review. In the next, you are dealing with a broken photocopier, leading a whole school assembly, scheduling the social media content or comforting a child who lost their shoe (yes, really - I’ve had shoes over walls, in trees and in a neighbour’s garden).

A DHT is the shield that keeps the daily operational grumbles away from the big picture, and the trusted sounding board who has to tell the truth when a plan needs work. Being a Deputy Headteacher teaches many skills and you learn how to manage up, manage down, and manage sideways all at the same time. And always with a smile!

Turning the Page

So, why leave? Because 22 years teaching has been incredible and I am proud of all I have achieved, but I am ready for a brand new focus. And being a teacher and DHT has shown me exactly where my passion lies. For me, it isn’t about the titles or the hierarchy; it is about the joy of creating order out of chaos. It is about taking a tangled mess of compliance, calendars, emails and communications, and handing back a streamlined, calm solution. And it has always, ALWAYS, been about support; supporting the Headteacher, the staff, the children and the families.

As one chapter comes to an end I'm realising that the story isn't changing - the setting is. And as Natasha Bedingfield sings: “The rest is yet unwritten.” Oops, am I showing my age there? The exact same skills that kept a school running smoothly are the ones I’m bringing to small business owners and busy leaders through becoming a Virtual Assistant. Except this time, instead of simply protecting a Headteacher's sanity, I’m helping entrepreneurs, consultants, founders and school leaders find theirs! The skills and knowledge are, without a doubt, transferrable and the positivity and calmness are invaluable.

The road ahead is certainly unwritten, and for the first time in over two decades, it doesn't follow a school term diary. And I really and truly can't wait to see where it leads.