Headteachering – OUT NOW!
The Blurb…
The honest guide to the messy job of being a headteacher, including real stories of mistakes made and lessons learned, case studies and practical advice.
These are the bits about being a headteacher they don’t teach you. Headteachering is part instruction manual, part call to arms and part confession of errors from experienced headteacher, Simon Botten.
From being told to ‘f*** off’ at assembly on his first day and being handed a walkie-talkie for calls to break up fights to managing crisis and the pain of failure after success, Simon tells you the stories you don’t usually hear. Packed with brilliant advice for how to lead a school and multiple case studies from experienced headteachers who have been there and seen it all, this book is an essential guide to what it’s really like to be a headteacher, whether you’re an aspiring school leader or you’re currently in post. Humorous, wise and insightful, this book aims to inspire you to be the best headteacher you can be – practically, technically and emotionally.
What’s in the book?
I like to read leadership books on the beach, which annoys my wife no end (especially when I produce a ruler and some highlighter pens). So when the good people at Bloomsbury kindly asked me to share my thoughts on Headteachering I wanted to write something which (hopefully) was informative… but you’d also want to read on a beach…
So each chapter starts with an entirely unvarnished story about the challenges which all headteachers face. It then gives a bit of advice before finishing with a case study by some truly talented school leaders. Finally there are some questions to think about (either on the beach between cocktails or when you get back to school).
Who else is in the book?
I wanted the book to include the voices of Headteachers who had ‘miles on the clock’ and a proven track record for school improvement, so asked some people who I really admire to provide their take on different aspects of the job. Some have provided very clever school improvementy ideas. Others provide deeply personal stories about how they addressed some of the job’s big problems. All of them taught me something.
| Chapter | Case study Author |
| Preface: Why being a headteacher is one of the most important jobs in the world. | Keziah Featherstone (Exec HT, co-founder and trustee of WomenEd, co-chair HT Roundtable & Author Punk Leadership’ |
| Chapter 1: Learning to swim in a storm – Your first 100 days as Headteacher. | Kulvarn Atwal (Exec HT, Author ‘The Thinking School’ & ‘The Thinking Teacher’) |
| Chapter 2: ‘Why does your school exist?’ – The power of vision and values. | Simon Smith (HT East Whitby Primary School & Blogger) |
| Chapter 3: ‘The stories we tell ourselves’ – The importance of Symbols and Rituals. | Sonia Thompson (HT, leader of St Matthews Research School & Author ‘Ethic of Excellence in action’) |
| Chapter 4: ‘Give a little respect’ – Improving behaviour. | Chris Dyson (Ex HT Parklands, Author ‘Parklands’ & Create Trust Deputy CEO). |
| Chapter 5: ‘a hundred tiny steps’ – School improvement planning without the BS. | Ross Newman ( Ex Exec-HT, OFSTED inspector & Leaf CEO). |
| Chapter 6: How to improve teaching | Claire Savory (CEO GLA Trust. Executive Headteacher & National Leader of Education) |
| Chapter 7: ‘How to fail’ – How to learn from failures in Teaching and Learning and address systemic problems. | Ro O’Reilly (Headteacher & Evidence Leader in Education at Somerset Research School). |
| Chapter 8: – How to build and maintain an effective school team. | Dr Vic Carr (HT Woodlands Primary School, Cheshire, Speaker & Author ‘Leading with Love’ & ‘Authentic School Improvement for Authentic Leaders’) |
| Chapter 9: How to build and maintain a strong and supportive parental body. | Dave McPartlin: HT, BGT performer & speaker |
| Chapter 10: Working with governors | Katie Hague, Executive Headteacher |
| Chapter 11: Making the money add up – Strategic financial planning | Deb Beazer (CFO Leaf Trust. Fellow ISBL, and my ex-School Business Leader!) |
| Chapter 12: Strategic Laziness – Coping with the stress of Headship | Kyrstie Stubbs, ex-HT, Deputy CEO & School Improvement Lead at Inspire Partnership MAT, & blogger ‘The Tattooed Headteacher’ |
| Chapter 13: Whakapapa – How will your moment in the sun be remembered? | Brian Walton (Author ‘Lessons from the Head’s office’ & HT of the year nominee 2024) |
Where can I buy this spectacular volume?
Well, as it’s Bloomsbury, pretty much anywhere. It’s available on Bloomsbury, Amazon and Waterstones no plus a heap of other places.
What do others say about it?
⭐️⭐️⭐️⭐️⭐️ (5/5)
” Headteachering deserves to be on the desk of every current and aspiring headteacher. It is part handbook, part therapy session, and part call-to-arms — reminding us that while headship is one of the toughest jobs in education, it is also one of the most vital, impactful, and profoundly human.”
“Whether you’re fresh to headship or have the battle scars to prove your experience, this book speaks to you. I picked it up at 5pm and couldn’t put it down—already on page 113. It’s that good.
Simon’s voice is authentic, bold, and refreshingly unfiltered. Huge thanks to him—and to the brilliant contributors—for creating something that’s not just informative, but genuinely inspiring. Featuring: Mary Myatt Keziah Featherstone FCCT Kulvarn Atwal“
Chris Dyson (Deptuy CEO Create Trust)
Brilliantly honest! Every new head needs this book!
Amazon Review Nov 2025
⭐️⭐️⭐️⭐️⭐️ 5/5
‘I laughed, winced, and nodded all the way through Headteachering. As a new headteacher, it felt like Simon Botten had been secretly following me around school, jotting down every chaotic, funny, and painfully real moment. From the first-day disasters to the tough calls no one trains you for, his honesty is both refreshing and reassuring.
This book reminds me that headship isn’t about having all the answers — it’s about courage, reflection, and keeping your sense of humour intact. I finished it feeling seen, supported, and strangely ready for whatever Monday brings next.’