Bulgarian society has been going through a very difficult period of transition from Communism to a democratic free-market system. Nowadays, the effective and successful management in Bulgaria is important not only for the organizations, but also for the society as a whole. This empirical study is conducted to explore the main leadership challenges for the Bulgarian manager today including the decision-making process, risk-taking process, motivation, trust and the cultural challenges. The changes in the leadership style of the Bulgarian managers are compared and analyzed according to the influence of the Communism in the past, and the influence after the accession of the country to the European Union in the present. The main findings from the ten semi-structured qualitative interviews suggest that Bulgarian manager today still relies on building relationships, which is an evidence about the influence of the Communism in Bulgaria, when doing any business, starting a company or getting to a management position. The results also show that Bulgarian manager today is willing and prefers to include the subordinates in the decision-making process, to take riskier approaches for accomplishing a task, and to trust their subordinates and business partners. Further, Bulgarian manager today provides more internal motivators to the subordinates, so that they can have the opportunity to develop as individuals, which could be useful not only for the team but also for the company. Keywords: Bulgarian manager; Communism; European Union; Leadership challenges; Career development; Decision-making process; Motivation; Trust.