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.