Given that both culture and gender are social constructs and are subject to change in all social processes, they play a significant role and are important variables in the intersection with leadership. This research has shown that gender and culture function in symbiosis and have parallel dynamics in relation to leadership. On the one hand, leadership is the result of a certain cultural context, be it general culture or organisational culture in companies or government and state institutions. On the other hand, leaders and leaderships are shaped by various forms of socialisation through, which social scripts, rules, and expectations imposed on women or men in leadership positions are being adopted. The Balkans Labyrinth demonstrates what challenges women face in the post-socialist patriarchal culture in this part of Europe.