Corporate leaders are frequently promoted into senior positions without the requisite capabilities to be successful in such career transitions. A significant proportion fails with substantial negative personal and organisational implications. Incumbents need to adapt through a flexible learning process that transcends superficial change. Transformative learning alters deeply held perspectives and world views and has long-term efficacy, while transition coaching, used sporadically at present, is a personalised learning process. This research created a novel synergy between transformative learning theory and transition coaching using a combination of grounded theory principles (16 participants) and canonical action research (6 participants). The findings yielded two results: the transformative transition coaching framework that appears to facilitates deep, lasting changes in an individual’s perspectives and world views during senior career transitions; and a novel coaching state transition notation that could help coaches to graphically track coachees’ transition progress. By undergoing transformative learning through coaching, transitioning leaders may increase their chances of success in their current and future roles.