Roger Outwin-Flinders

The headmaster of Hallfield School, Roger Outwin-Flinders recalls challenges of the past – including snapping his Achilles twice – five happy years in Brum and his exciting, forthcoming ‘escape to the country’


I was born in Suffolk – I’m a lifelong Norwich City (Canaries) fan! I studied Physical Education, Maths and Geography at St. Paul’s College, Cheltenham and I have taught in a range of independent day and boarding schools in London, the south coast, and the Midlands. I wanted to teach to ‘make a difference’ to children’s lives and I have particularly enjoyed developing the ‘hidden curriculum’, organising out of school activities, holiday clubs and trips. These all provide valuable experiences for children, increasing their confidence and helping them to reach their full potential academically, socially and emotionally.


I have just completed my fifth year as headmaster of Hallfield School – and my twenty-fourth year in total as a headmaster. In September, I will be starting my fourth Headship, at Brooke Priory School in Oakham, Rutland, where my family and I are very excited to be ‘escaping to the country!’


I still enjoy my role as a headmaster and at Brooke Priory I will be focusing on driving teaching and learning forward and increasing pupil numbers – which I have successfully achieved in my previous three headships. The move to Oakham will also mean that we will be closer to family.


At 33, I was one of the youngest headmasters in the country when I was appointed to Wycliffe College Junior School in 1993. After eight years it had been transformed from a failing school with 219 pupils to a highly successful school with 406 pupils. In 2006, while I was headmaster of Fairfield Preparatory School in Loughborough, during an ISI Inspection, the school achieved ‘outstanding in all aspects’ with no areas for improvement – an extremely rare achievement. At Hallfield, Year 6 children have achieved an astonishing total of 164 scholarships in the last five years and, this year, 83 per cent of children have gained entry to select entry local authority grammar schools. On a personal note, I cycled Land’s End to John o’ Groats followed by Coast to Coast in 2002 – two years after rupturing my Achilles tendon (twice!).


I firmly believe that honesty, hard work and integrity are the most valuable qualities in a person. However, I have discovered that not all people in authority share the same high moral compass and values.


As a family, we have enjoyed the rich culture and diversity of this vibrant city and the warmth and friendliness of the Birmingham people. Tania and I look forward to returning to visit for our favourite Birmingham Balti!


As a workaholic, I am looking forward to reducing my current 18-hour working days to normal hours! It will be fantastic to have time to enjoy the stunning Rutland countryside and way of life, with my wife and family.


It has been a pleasure working in partnership with my wife at Hallfield School; she has transformed marketing and communications at the school beyond recognition and she has fully supported my role and the accompanying long hours! She deserves a huge thank you.