The purpose of this study is to investigate the nature of learning in work role transitions from specialist roles to managerial roles in a context of a large international technology organisation. Prior theorisation of learning in role transitions has been based on quantitative, psychologically-oriented studies prescribing different role and personal attributes related to work adjustment. Personal experiences have received only a superficial or instrumental part in most of the preceding studies. Therefore, this study draws upon a transformative learning theory to outline an interpretative framework and focuses on in-depth, narrative analysis of a small number of role transition experiences. As a result, the study reveals how first-time project managers and team leaders wonder about their abilities and actions; compare "self" with role models; and become aware of the power aspect of managerial roles. Such reflection eventually leads to a perspective transformation regarding "self" and new roles. However, it also involves adaptation to the prevailing organisational norms, values, and leadership ideals. The study will add to our understanding of learning in transitions and inform those working in the human resource development or otherwise involved in the organisational transfer processes. Moreover, it reminds that perspective transformations should not be taken innocently as examples of "empowerment", but critically concern why transformative learning is encouraged at work nowadays and what purposes it serves.