This research is in continuation of the academic and research work led by LIRTES (Interdisciplinary Research Laboratory for Transformation in Educational and Social Practice – University of Paris Est Creteil) and CREAD (Research Center for Teaching, Learning and Didactic Practice – University of Rennes 2) which both hold a common interest in lifelong training and the development of continuing education university programs supporting adult learning. The research which is being conducted this Spring focuses on the transformative journey of ten French organizational leaders of small and mid-sized companies. The purpose is to study the process of transformation and sense-making through their experience and learning of perceived dilemmas. This research is also the opportunity to establish a more intentional bridge between North- American and French research and their complementary approach to transformative learning in the workplace. In the United States, research building on theories studying the individual development of psychological structures such as constructive-developmental theory (Kegan, 1982, 1994) tends to focus on the variations of perception and experience of dilemmas from an individual and subjective perspective. France tends to favor a psycho-sociological approach including an understanding of the contextual factors; the interest is “in the functioning of groups and organizations, in change processes, in power relations, in the understanding of psychological and social conflicts, in the relationships between research and social practices” (Barus-Michel & Enriquez, 2002 p. 9). From this perspective, dilemmas are understood in their socio- organizational and intersubjective dimensions as those influence institutional dynamics and professional practices in place (Lourau, 1970; Hess & Savoye, 1993). The authors therefore propose to create new bridges between those two lines of research through a multi-referential and critical approach. From an epistemological perspective, the goal is to produce knowledge on and for action. Practically, the development of new knowledge will impact the design of university adult learning and training programs on both sides of the Atlantic Ocean. The first section of the paper presents the multi-referential model used by the authors to understand and analyze the question of “transformative dilemmas” within a leader’s professional journey. The model integrates North-American concepts and research based on constructive- developmental theory (Kegan, 1982, 1994, 2000; Faller, 2014, 2017) and French psycho- sociological perspectives inspired by the influential ‘French Ecole Vincennoise” (Eneau, Bertrand & Lameul, 2012 ; Bertrand, 2011, 2014, 2015 ; Eneau, 2017). The second section presents the research methodology and protocol as well as the preliminary exploratory findings related to the types of transformative dilemmas perceived by the leaders and the process of sense-making throughout their transformative journey. The last section opens to a discussion of the epistemological, methodological and pedagogical dimensions of our conceptual model and approach.