Work organisations in the current economic environment are facing unprecedentedhigh energy costs, accelerated information communication technologies (ICT) andbiotechnology changes. However, for most companies returns are increasing, withthe application of knowledge that results in minimum utilisation of resources.Middle managers in these organisations are no longer able to manage workprocesses, market their products or services using the traditional command andcontrol methods. They must refiame their perspectives to conceive new managerialroles based on resolving paradoxes and embracing a more entrepreneurial approach.The corporate managers must not only learn new managerial skills but they must alsoembark on transformative learning to improve their capabilities. Managers mustquestion assumptions, formulate alternatives and continually reform their processes.The research approach adopted by this study is by using the qualitative case studymethod. Sampling of research sites and respondents were based on the criteria ofaccess, industry type and the researcher's familiarity with the particular industry.This study adopted an unstructured interview method and twenty-five respondentswere interviewed individually. The researcher conducted the interviews personallyand the interview results were interpreted using an inductive analysis method.The main findings revealed that the middle managers' behavioural adaptivecapabilities, insights and schemas were the results of their interaction with worksituations and their interactions with colleagues, suppliers and customers, andowners. Learning was triggered not by disorienting &lemmas but by gradualaccumulation of managerial insights and by the slow evolvement of new schemasspanning their working career. This study established the link between anindividuals' transformative learning and their personal career advancements, workexperience and external influence. The nature of transformative learning was foundto be relational, as well as cognitive-rational. The findings contributed to the field oftransformative learning by establishing the use of critical incidents/unstructuredinterviews in elucidating the transformative learning experiences of middlemanagers, and by creating dialogic context for managers to communicate theirlearning experiences. Theoretical contributions of this study included the level oftransformative learning, cumulative layering of insights and true tests oftransformative learning