London


<p>Claire Holloway was appointed head of <a href="https://muddystilettos.co.uk/kids/school-reviews/st-olaves-preparatory-school-new-eltham-south-london-review/" target="_blank" rel="noreferrer noopener">St Olave&#8217;s Prep</a> in January 2017. It might have been her first headship but the school was already in her DNA, having been on staff at St Olave’s for 14 years (her own children were educated there). </p>



<figure class="wp-block-image size-large"><img decoding="async" loading="lazy" width="1024" height="731" src="https://dev.muddystilettos.co.uk/london/wp-content/uploads/sites/24/2026/06/Claire-photo-1-1024x731.jpeg" alt="Clare Holloway " class="wp-image-22696" srcset="https://dev.muddystilettos.co.uk/london/wp-content/uploads/sites/24/2026/06/Claire-photo-1-1024x731.jpeg 1024w, https://dev.muddystilettos.co.uk/london/wp-content/uploads/sites/24/2026/06/Claire-photo-1-300x214.jpeg 300w, https://dev.muddystilettos.co.uk/london/wp-content/uploads/sites/24/2026/06/Claire-photo-1-768x548.jpeg 768w, https://dev.muddystilettos.co.uk/london/wp-content/uploads/sites/24/2026/06/Claire-photo-1.jpeg 1500w" sizes="(max-width: 1024px) 100vw, 1024px" /></figure>



<p>Warm, friendly and ambitious, under her leadership all kinds of great changes have occurred at the caring co-ed in New Eltham, including a new allotment, sports area and stand-alone nursery, plus the kindness agenda has been ramped up to new heights. We sat down with Claire to discover more. </p>



<h2 class="wp-block-heading" id="h-30-second-elevator-pitch-for-your-school-sell-it"><strong>30-second elevator pitch for your school – sell it!</strong></h2>



<p>St Olave&#8217;s is a school where children are known, valued and challenged every single day. We combine&nbsp;the&nbsp;academic ambition of&nbsp;the&nbsp;very best schools with a genuine commitment to childhood. Our children achieve fantastic outcomes, but just as importantly,&nbsp;they leave us as kind, confident, curious young people who know how to work hard, think independently and look after one another. We are small enough to know every child and ambitious enough to help every child flourish.</p>



<h2 class="wp-block-heading" id="h-you-ve-been-given-a-1-million-donation-for-nbsp-the-nbsp-school-what-will-you-spend-it-on"><strong>You&#8217;ve been given a £1 million donation for&nbsp;the&nbsp;school. What will you spend it on?</strong></h2>



<p>Part of me wants to say a never-ending supply of brilliant books! In reality, I&#8217;d probably invest in opportunities and experiences for children. Buildings are important, but&nbsp;the&nbsp;things children remember most are often&nbsp;the&nbsp;moments that spark a lifelong passion, build confidence or open&nbsp;their eyes to something new.</p>



<p>I&#8217;d create a fund that allowed us to offer even more extraordinary experiences: residential trips, educational visits, visiting authors, artists, scientists and musicians, outdoor learning projects and opportunities to explore&nbsp;the&nbsp;wider world.</p>



<p>I&#8217;d also invest further in our outdoor learning provision. Some of&nbsp;the&nbsp;most powerful learning I&#8217;ve witnessed hasn&#8217;t happened sitting at a desk. It has happened in our allotment, working collaboratively on a project, discovering something new in nature or developing resilience through challenge and adventure.</p>



<p>Most of all, I would want every child to leave St Olave&#8217;s with not only an excellent education but also a rich collection of experiences, memories and opportunities that help&nbsp;them grow into confident, capable and compassionate young people.</p>



<h2 class="wp-block-heading" id="h-describe-your-own-childhood-school-days"><strong>Describe your own childhood school days.</strong></h2>



<p>I loved school. I was&nbsp;the&nbsp;child who genuinely enjoyed learning and probably spent far too much time in&nbsp;the&nbsp;library. I wasn&#8217;t&nbsp;the&nbsp;loudest child in&nbsp;the&nbsp;room, but I was curious and hardworking. Looking back, I was incredibly fortunate to have teachers who believed in me and encouraged me to aim high. That&#8217;s stayed with me throughout my career. Schools can change lives because teachers can change lives.</p>



<h2 class="wp-block-heading" id="h-what-was-nbsp-the-nbsp-common-nbsp-theme-of-your-school-reports"><strong>What was&nbsp;the&nbsp;common&nbsp;theme of your school reports?</strong></h2>



<p><em>&#8220;Claire is keen to please&#8221;</em>&nbsp;probably appeared in almost every report I ever received. I was a conscientious child who enjoyed learning and always wanted to do my best. Like many children, I sometimes worried a little too much about getting things right, but that determination and sense of responsibility have certainly stayed with me throughout my career.</p>



<h2 class="wp-block-heading" id="h-what-s-nbsp-the-nbsp-best-school-trip-childhood-or-current-you-ve-ever-been-on"><strong>What&#8217;s&nbsp;the&nbsp;best school trip (childhood or current) you&#8217;ve ever been on?</strong></h2>



<p>One of my happiest childhood memories was a trip to&nbsp;the&nbsp;Europa Centre in Havering, which has sadly now closed. It was designed to bring languages to life and I still remember&nbsp;the&nbsp;excitement of walking down a &#8216;German street&#8217; and ordering food in a café in German. It made everything we had been learning in&nbsp;theclassroom suddenly feel real.</p>



<p>I was also incredibly fortunate to go on a residential trip to Valkenburg in Holland. As a child, travelling abroad with school felt like a huge adventure and opened my eyes to different cultures and ways of life.</p>



<p>Those experiences stayed with me, and&nbsp;they are one of&nbsp;thereasons I am such a passionate advocate for educational visits today. Some of&nbsp;the&nbsp;most powerful learning happens when children step outside&nbsp;the&nbsp;classroom and experience&nbsp;the&nbsp;world for&nbsp;themselves.</p>



<h2 class="wp-block-heading" id="h-your-favourite-book-childhood-university-and-now"><strong>Your favourite book – childhood, university and now?</strong></h2>



<p>As a child, I adored&nbsp;<em>Anne of Green Gables</em>. Anne&#8217;s imagination, determination and optimism captured my heart. I loved reading it with my own children when&nbsp;they were little. At university, my favourite book was probably&nbsp;<em>To Kill a Mockingbird</em>. I was drawn to its&nbsp;themes of justice, empathy and standing up for what is right, values that have stayed with me throughout my career.</p>



<p>These days, I find myself reading a mixture of children&#8217;s literature, educational research and books that encourage reflection. One I return to often is&nbsp;<em>The&nbsp;Boy,&nbsp;the&nbsp;Mole,&nbsp;the&nbsp;Fox and&nbsp;the&nbsp;Horse&nbsp;</em>by&nbsp;Charlie Mackesy. Its messages about kindness, courage and resilience resonate with me both as a&nbsp;Headteacher and as a person.</p>



<h2 class="wp-block-heading" id="h-if-you-weren-t-a-nbsp-head-what-would-you-be"><strong>If you weren&#8217;t a&nbsp;Head, what would you be?</strong></h2>



<p>Something involving books, baking or both. Perhaps I&#8217;d own a bookshop with a café attached. Children could come in to discover wonderful stories while I baked cakes in&nbsp;thekitchen. That sounds rather perfect, actually.</p>



<h2 class="wp-block-heading" id="h-what-advice-would-you-give-your-younger-self-and-your-cu-rrent-students"><strong>What advice would you give your younger self – and your cu</strong>rrent students? </h2>



<p>Don&#8217;t spend so much time worrying about getting everything right. Work hard. Be kind. Be brave enough to make mistakes.&nbsp;Thethings that feel enormous today often become&nbsp;the&nbsp;experiences that help you grow tomorrow.</p>



<p>To our children, I&#8217;d say this: be curious. Ask questions. Read widely. Treat people well. Have&nbsp;the&nbsp;courage to try things that feel difficult. And remember that success isn&#8217;t about being&nbsp;the&nbsp;best at everything. It&#8217;s about becoming&nbsp;the&nbsp;very best version of yourself. </p>



<p><em><strong>Read the Muddy review of St Olave&#8217;s Prep <a href="https://muddystilettos.co.uk/kids/school-reviews/st-olaves-preparatory-school-new-eltham-south-london-review/" target="_blank" rel="noreferrer noopener">here</a>. </strong></em></p>


Meet the Head: Claire Holloway, St Olave’s Prep School

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