This paper identifies how deep change in organizations, catalyzed by Appreciative Inquiry, can be the consequence of simultaneous, synergistic Transformative Learning experienced at the individual level and enacted at the group level. It examines the theoretical and structural framework of these two constructivist views of development. Existing literature within the two perspectives is explored to identify inherent strengths and gaps. A new bridging construct, Transformative Appreciative Inquiry, is proposed which enlightens the potential for sustainable, ongoing adaptation based on the tenets of action technology and inspired by inter- and intra-personal narrative and reflection from a generative perspective.