Leaders in the healthcare sector, frequently find themselves attempting to improve service provision by adopting evidence based-best practices, as requested by policy. Notwithstanding, change implementation is often not straight forward. As an insider-turned-researcher I initiated a Maltese National Healthcare Service-wide doctoral inquiry into the lived experience of leaders during change and transition, to gain insight into which leadership styles and managerial skills characterise an effective transition leader from a psychotherapeutic perspective. The inquiry was divided into two phases, using mixed methods with an action-research element. Arising themes indicating the need for individual proactive self-actualisation, development at an emotional-transferential level and the undoing of identity following organizational/personal shifts, provided a platform for the co-creation of a Training Manual focusing on self-reflexivity. Training using the Manual was offered to the participants facilitating their looking more closely at how power relations stalled personal and organisational growth by hindering change implementation processes. Encountering the need to unblock shame, some met impasse, others modified their underlying metaphor/identity enhancing a change in behaviour while retaining the power inherent in their previous identity, while others yet noted that the training enhanced their managerial skills. The Training Manual was well received in the healthcare field and beyond. The results of the inquiry suggest that self-reflexivity is an essential element when planning training for leaders and that self-actualisation, and self-reflexivity are essential managerial competences supporting transitions while enhancing creativity and interdependence. This implies that self-reflexivity needs to be introduced in mainstream managerial training.