The digitalisation of banks is seen as the omnipresent challenge which the banking industry is currently facing. In this digital change process, banks are facing disruptive innovation that requires adaptation of almost all cooperative processes. Digital transformation in the financial industry is associated with obstacles that seem to hinder smooth implementation of digital approaches. This issue has not been adequately addressed in the current academic literature. The main purpose of this qualitative exploratory study is to identify the main perceived obstacles to digital transformation in both the private and commercial banking sectors from a managerial point of view and to analyse them accordingly. The methodology is based on a methodological approach using a combination of contextual interviews with German board members of banks, inductive content analysis, and the exploration of best-practice approaches. The findings revealed that elements of strategy and management, technology and regulation, customers, and employees receive a high level of attention within the digital transformation. The other main barriers can be found in the areas of market knowledge and products, employee and customer participation, and public benefit. Each main barrier is characterised by several sub-barriers of varying importance for the digital transformation of banks and is described in detail.