Purpose: This paper aims to reflect on the opportunities and challenges of the learning process in practice and explores the case of a local authority school Pilot Wellbeing Programme (PWP) intervention. The aim of the PWP was to create the best workplace conditions and circumstances for people to flourish and mature, both individually and collectively. Findings show that the socio-physical environment plays a significant and leading role in supporting this work, as does the consistent modelling of higher level behaviours including integrity, respect and acceptance by intervention managers and school leadership teams. It was also important that the change processes were continually tailored and nuanced to meet the evolving needs of the staff and organisation throughout the intervention. Emphasis was also placed on encouraging individual involvement and commitment by implementing inclusive measures that fostered trust and openness. Design/Methodology/Approach: The intervention worked to the organisational learning process model. Findings: Headteachers (HT) are still playing a key role as caregivers to their staff. Wellbeing is something people in school generally expect to be "done" to them. Personal accountability for one's own health and wellbeing is still a growth area in schools. Any change processes implemented to support this process need to be continually tailored and respectfully nuanced to meet the evolving needs of the staff and organisation throughout the intervention. Accruing quantitative evidence to support the effects of wellbeing work in schools is painstaking and challenging. Practical Implications: HT have traditionally taken the role of school staff "caregiver", overseeing staff wellbeing often to the detriment of their own wellbeing. This situation is becoming unsustainable as HT' capacity for this kind of work is diminishing. School staff need to accept an increasing role in the maintenance of their own personal-professional wellbeing. Social Implications: School staff who do not mind their own wellbeing act as a poor model to their pupils who may ultimately emulate their behaviour. Additionally, as staff sickness absence due either directly or indirectly to stress becomes a growing issue in schools, educational standards will be increasingly difficult to attain and maintain. Wellbeing mechanisms need to be put in place now to stem this possibility. Originality/Value: The intervention is unique in as much as it took a deliberately holistic approach to school staff wellbeing by including all school staff in the change programme. Previous similar programmes have targeted professional staff only, excluding non-teaching classroom staff and school support and maintenance staff.