The Wykehamist
Interview with the Headmaster
TD: Headmaster, thank you very much for being here. Our first question is: what does the role of Headmaster of Winchester College involve today, and how do you define success in your position?
HM: I think the role of Headmaster is one of startling variation. [ laughs ] So, you know, you’ re doing everything from picking up the pieces from a tearful, overwhelmed thirteen year-old who has just arrived, to dealing with lawyers about something that will affect the whole school. Particularly with the size and complexity of infrastructure that Winchester has, it can be head-spinning in some ways. I have my favourite pocket of the day where I teach fourth years some A-Level maths, and we do a bit of, say, graph transformations— and then you’ re dealing with some financial question, or some big HR matter. The variation is extraordinary. People see the visible parts, and there’ s quite a lot visible, but then there’ s also a lot of richness behind that.
One colleague described the role to me as the‘ storyteller in chief’. You know, we are a community; Winchester is an institution that is bigger than any of us, and it has that longevity of tradition. I mean, how do you survive for over 600 years? You’ ve got to have very deeply rooted convictions, seriously embedded beliefs and values and so on. And one of the key responsibilities is consistently to be articulating those values to people. When that works well, people don’ t even realise, in a way, that it is being done— they just understand that‘ that’ s how we do it here’, or‘ that’ s who we are’. When you’ re doing it well, it should feel organic; it’ s the antithesis of the corporate, slick tagline. I had a really nice compliment the other day from a don here who said,‘ Oh, loving the website and what I’ ve seen from the school on LinkedIn— I look at it and I think, yes, that’ s so Winchester!’. That’ s really important. It’ s about doing it for the pupils, doing it for the staff, the parents, the prospective parents, the OWs. That’ s one of the wellsprings of culture that keeps this place going.
Another key aspect of the role is filtering out the noise. Particularly in education, there’ s a lot of faddishness, there are a lot of people with bright shiny new things. You can expend a huge amount of time and energy on froth and bubble. I’ ve worked in places where it was almost Orwellian— I remember this story very distinctly early in my teaching career... there was a particular framework for
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