Lorraine Riley

Lorraine Riley is Head of School at Marymount in New York, and she knows the school from every angle. She first arrived as a Butler scholar at 14, went on to Georgetown as the first in her family to finish college, taught with Teach for America in post-Katrina New Orleans, and has now led Marymount through its centenary year as a parent of two current students. In this episode, Lorraine reflects on seeing one school through so many lenses, how Marymount uses its faith to push back against toxic achievement culture, and makes the case that a nurturing school and a rigorous one are not competing priorities.

Simon O'Connor is the founding headmaster of Harrow International School Dubai, which opened its doors this September. A former choral scholar at Cambridge, he spent seven years as principal of Jumeirah College and took Deira International School to an "outstanding" rating in eighteen months. In this episode, Simon takes us behind the curtain of launching a brand-new school, explains his concept of "boarding without the sleeping," reflects on why a passport of qualifications isn't enough, and makes a passionate case for pushing technology to the very corners of education.

Dr Tom Kelly has been Head of School at Horace Mann, one of New York's most celebrated independent schools, since 2005. His path there was far from conventional: as a student he spent a semester deliberately living as a homeless person, an experience that left him determined to waste no more time on hate. In this episode, Tom reflects on the hardest shift in school leadership, why partnership has replaced outreach, why the only thing you truly own is your name, and why we should stop telling children they're anxious. Tom also joins us on the panel at Heads & Tales Live New York on 16 November.

Dr Annalies Corbin is the founder and CEO of the PAST Foundation, an anthropologist by training who has spent more than 25 years connecting learning with real life. Her organisation brings schools, industry, research and communities together around hands-on, problem-based education, with students at the centre of the work. In this episode, Annalies argues that children are disengaged not because they dislike learning but because they can't see what it has to do with them, makes the case for mentoring that happens in the messy middle, and shares a controversial opinion that starts with getting rid of the school bell.

Adam Seldon is a teacher and author who has spent almost a decade in the classroom. The son of two teachers, he joined the profession through Teach First and has worked as a head of history, head of year and assistant principal. His new book, Around the World in Eighty Schools, follows his journey to more than 80 schools across six continents in pursuit of one question: what makes a great school? In this episode, Adam shares what he learned from classrooms in South Africa, Ethiopia and New Zealand, makes the case that the best schools treat education as an experience rather than a transaction, and explains why he thinks most school assemblies are a wasted opportunity.

Eugene du Toit is Master of Haileybury, leading around 900 pupils across 500 acres of Hertfordshire. Born in Zimbabwe and raised in South Africa, he came to teaching via economics and PwC, and has since led through St Paul's, Trinity Croydon and Wellington School. In this episode, Eugene makes the case that a child's humanity matters more than ever in a technological world, explains why he leads with belief rather than fear, and argues that the best school in the world is simply the right school for your child.

Shaun Fenton OBE is headmaster of Reigate Grammar School, Surrey's leading co-educational independent day school, and a former chair of HMC. The son of rock star Alvin Stardust, Shaun began his career in accountancy before a conversation with his old teacher drew him into education. In this episode, he makes the case for educating children to be well-educated rather than just well-qualified, argues that happiness and achievement are not a trade-off, explains why he thinks the whole idea of teacher retention is upside down, and reminds us that children won't care what you know until they know that you care.

Ramón Javier is head of school at George Jackson Academy, a middle school for boys on Manhattan's Lower East Side where every family receives financial assistance. A lifelong New Yorker and Prep for Prep alumnus, Ramón grew up on welfare in Washington Heights before attending boarding school, Williams College and Columbia. In this episode, he explains how a school funded almost entirely through philanthropy actually works, why he insists on preserving boyhood rather than rushing boys into manhood, what brotherhood really means to the boys in his care, and why he believes AI is going to make people stupid.

Alex Crossman, now Principal and Chief Executive of St George's British International School Rome, joined us while he was still executive head teacher of the London Academy of Excellence, the state sixth form in Newham that this year sent more students to Oxford and Cambridge than Eton or St Paul's. His own story mirrors the school's mission: he grew up on a West Midlands council estate, knew no one who had been to university, and went on to Oxford and the LSE before a career in finance and then teaching. In this episode, Alex dismantles the lazy criticisms of selective sixth forms, reveals the not-so-secret sauce behind LAE's results, and makes a powerful case for why every state school should prioritise pupils on free school meals.

Sally-Anne Huang is High Master of St Paul's School and the first woman to lead it in its 510-year history. After two decades in girls' education, she took the top job at St Paul's in 2020 and this September opens the St Paul's School Research Centre for the Education of Boys. In this episode, Sally-Anne makes the case for single-sex education at a time when many schools are going co-ed, explains why the conversation around young men has become dangerously catastrophised, and shares why boys need tribe, role models and the freedom to be kind. Most young men, she argues, simply want to do well.