This article considers the experiences and perceptions of practising English headteachers and the tensions that they face when juggling government prescription and government initiatives, which may be antagonistic to their educational values and beliefs. Managerial control over teachers work has been particularly acute and destructive to ‘human flourishing’. Headteachers have a moral and ethical responsibility for the welfare and education of pupils. Such professional ethics oblige the professional to seek the good of the pupil and therefore good is viewed as intrinsic to the work of an educator. Thus headteachers are directly involved in negotiating between sometimes contradictory imperatives and drivers. How then does the headteacher cope with what Colley refers to as ‘situated ethics work’? This article presents data derived from written responses from 10 headteachers that begin to open up this question. I argue that it is not uncommon for people to weaken in their values-driven stance when under great pressure. It is however important to recognize the extent to which educational values are constrained by neo-liberal value-based market agendas in order to continually question and re-evaluate what is happening within education rearticulating this for the benefit of pupils.