While the evolution of digital technologies in human-related aspects changes the approach to organisational issues, artificial intelligence enables complex decision-making and supports strategically important evaluations. Management behaviour, decisions and activities at all organisational levels cause consequences of varying degrees. Recent developments across management related processes require a paradigm shift regarding the application of assistive technologies. Hitherto, the trends in evaluation of leadership parameters have been rather unpredictable and restricted to the application of a limited number of technologies. Leadership as a phenomenon is multifarious. In our exploration, we limit our scope of investigation to the degree of leadership as one of the decisive components for successful entrepreneurship and ranks as one of the organisational development indicators. In this paper, we discuss the current situation exhibited in publications on researched topic and propose a holistic approach to predict the defined leadership parameters over time, based on a regression decision tree model. In order to evaluate our proposed approach, we present selected implementation examples pursuing the identified goals of analysis. Subsequently, we discuss the proposed approach with a focus on the potential benefits, ob-stacles, limitations and perspectives.