Author: Al Kingsley

Publisher: Routledge (2025) | 256 pages

Reviewed by: Lucy Coy, HeadteacherChat

Why This Book Matters

Every now and then, a book lands on my desk that stops me in my tracks — not because it tells me something entirely new, but because it finally gives voice to things we’ve all been thinking. Al Kingsley’s The Awkward Questions in Education does exactly that. It’s honest, refreshingly human, and, quite frankly, overdue.

If you’re a school leader dealing with inspections, data dashboards, AI hype, and not enough staff to go around, this book will feel like a chat with a colleague who “gets it.”

Who It’s For

I’d recommend this wholeheartedly to:

  • Headteachers and SLT wrestling with accountability versus authenticity
  • Trust leaders looking to build meaningful school cultures
  • Governors seeking a deeper understanding of what really matters in school life

It’s also a great provocation for those involved in shaping policy. If you work in education and you’re fed up with surface-level definitions of “success,” this book is for you.

What’s Inside

Al doesn’t set out to write a textbook. He invites us into a conversation — one based on real experience, careful research, and a deep belief in doing right by children. Themes he explores include:

  • What makes a good school? Not just in Ofsted’s eyes, but from the lived experience of pupils, staff, and parents.
  • Measurement fatigue: The dangers of relying too heavily on things we can count, while ignoring what counts.
  • Inclusion: A beautifully written section on SEND, warm data, and belonging — far more nuanced than policy headlines often allow.
  • Culture and kindness: The schools we all want to work in — where joy, respect, and learning are inseparable.

There’s thoughtful commentary on inspections, curriculum narrowing, and even international comparisons (like PISA and NAPLAN). But it never feels dry. Al blends sector insight with straight-talking reflection: “We all want our learners to thrive, yet we’re expecting them to follow the same path for 14 years and act surprised when some don’t.”

What Stands Out

  • Al's tone — wise, non-judgemental, and collaborative.
  • Inclusion of real voices — from teachers to CEOs — reflecting what makes schools thrive.
  • His focus on human flourishing — backed by OECD research, but grounded in daily practice.
  • He challenges why we do things, without being cynical. There’s a clear sense of hope.

It’s also deeply practical. While not full of templates and checklists, it offers clarity of thought — the kind that can genuinely shape leadership conversations.

A Gentle Challenge

If I had one wish, it would be for even more examples of how schools are already reimagining success. Al hints at lots — but leaders hungry for action might want more scaffolding.

Still, that’s a minor note in what is otherwise a deeply affirming read.

How I’d Use It

This would be ideal for:

  • A staff reading group
  • SLT discussion starter (especially around self-evaluation or inspection prep)
  • A governors’ away day
  • New headteachers thinking about school vision

It gives language to the things we feel instinctively, but sometimes struggle to articulate — and that’s no small gift.

Final Thoughts

Al Kingsley invites us to reflect, to rethink, and to prioritise what really matters.

Buy it. Read it. Talk about it.

About the book

  • Author: Al Kingsley MBE. His publisher biography says he has spent 30 years in education technology and nearly two decades as a school trustee and governor; he is group CEO of NetSupport, an education technology company, chairs a multi-academy trust and sits on the Department for Education's advisory board for the East of England.
  • Full title: The Awkward Questions in Education: The Elephants in the Room from AI to Teacher Retention.
  • Questions the publisher lists: whether students are being taught the right skills for the future; whether more and different spaces would improve attendance and engagement; whether the system is truly inclusive; how to handle AI in classrooms; and how to solve teacher recruitment and retention.
  • Publisher: Routledge, first edition, published 29 April 2025. Paperback, 256 pages, ISBN 9781032883144; also in hardback (ISBN 9781032883175) and as an ebook (ISBN 9781003537168).

Source: Routledge, checked 13 October 2026.