In this conversation, I’m joined by Simon Botten - an Executive Head Teacher in South Gloucestershire, leading two primary schools and serving as Head of Inclusion for a seventeen-school multi-academy trust. He has been a Head Teacher for nearly twenty years and is the author of Head Teachering: A Practical Guide with the Messy Bits Left In.
What does it really take to lead a school and what keeps people going?
Simon was drawn to write because he was worried about how headship was being talked about - the loudness of the difficult narrative and the way that leadership culture more broadly had become a place of edited certainty, where everything that didn’t fit the story is edited out. The result, he felt, was that people who might be excellent Heads were looking in and thinking: that’s not me. ” I could never be that.
We talked about the isolation that sets in when leaders stop looking outward and why that’s one of the things to watch most carefully. About the difference between long hours and useful ones. About what it felt like to arrive at a school at 31 with a young family and, as Simon puts it, bet the farm on it turning out right.
We also touch on the Māori concept of whakapapa - the idea that your ancestors stand in a line behind you and those who come after stand ahead of you and that right now it is your turn to be in the sun. What you do with that moment, and what you pass on, is the question Simon ends his book with.
This is a conversation I think will resonate especially with people who are in or near headship - whether they’re considering it, navigating it, or supporting others who are. But more broadly, it’s a conversation about what it means to lead something you care about for a long time and to do that with honesty rather than performance.
Together we explore:
Why Simon wrote Head Teachering and the question the book is trying to answer.
The edited certainty of leadership culture online and why leaving the messy bits in matters.
Moral purpose as the thing that sustains and what Simon means by measuring success in decades.
Isolation in headship: what it looks like when leaders retreat and why connection is not optional.
The well-being realities of twenty years in the role - compartmentalising, exercise and the difference between long hours and productive ones.
Coaching new heads through overwhelm - arriving with no trust in the bank and learning to live with the chaos long enough to address it.
Whakapapa: the Māori concept Simon draws on in his final chapter about legacy, responsibility and what we pass on.
Simon leaves us with the question:
What would it mean to lead in a way that still matters fifty years from now?
Conversations in Education: a space to think together, through honest conversations about education as it is lived, led and felt.
