In our research, we have investigated the influence of tall- and flat organizational structures on authentic leadership in the Swedish- and German context. The research was approached by the systems view and the data were analysed through Grounded Theory. Our aim was to research in which dimension authentic leadership is enabled or restricted to a larger extent – tall- or flat organizations. We discovered that authentic leadership can be performed in both, however it might be more or less encouraged. Hierarchical structures could be seen as a tool for performing authentic leadership – which we were able to confirm in the German context. While flat organizational structures could enable leaders and followers to act according to their true inner selves as well – which we were able to observe in the Swedish context. Interesting differences between tall- and flat organizational structures in Sweden and Germany were observed in terms of authentic leadership performance.