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Mr. Nicholas Sampson, the eighth headmaster of Cranbrook School, has been dedicated to preserving the school’s values and forging a vision for the future since the outset of his tenure. He emphasises the uniqueness of each headmaster’s role in maintaining Cranbrook’s diverse ethos. Sampson’s educational journey, from attending a selective school to studying English literature at Cambridge University, instilled in him a deep appreciation for reading and learning through conversation. After briefly venturing into the public service, he discovered his passion for teaching and embarked on a fulfilling career in education. Sampson’s leadership extended to Geelong Grammar School and Marlborough College in Australia and the UK, where he introduced innovative educational initiatives and formed partnerships. Integrity and a commitment to civilised living have been central to his philosophy at Cranbrook, fostering renewal and development while staying true to the school’s founding principles. His innovative leadership is evident in the numerous advancements and events, including the school’s centenary celebrations in 2018. Moreover, Sampson has a unique connection to Marlborough College, sharing ties with other headmasters and individuals associated with Cranbrook.