Research background: One of the main duties of entrepreneurs is to create a favorable and comfortable work environment for their subordinates or employees. It is, therefore, necessary for them to enhance managerial and leadership skills and in this context to deem tendencies to bossing as dangerous in their entrepreneurial activities. Purpose of the article: The main objective of the presented research is to examine the possible existence of statistically significant correlations between the selected leadership styles and the tendencies to bossing. Methods: The research data were obtained from 197 respondents aged from 21 to 67 years (M = 34.57 years), 55% women and 45% men from various areas of business. To assess the preference of the examined attributes, two methodologies were used: Paternalistic leadership scales (to assess leadership behavior) measuring the factors of Benevolent, Moral, and Authoritarian leadership, and the BOSS methodology (to assess downward workplace bullying, i.e. bossing), which measures Communication-Aimed and Psyche-Aimed Bossing. Findings & Value added: The results confirmed existence of several statistically significant links between leadership styles and tendencies to bossing of the respondents, pointing to behavioral errors commonly found in the workplace among managers and employees, or supervisors and subordinates. The necessity to study these errors has, thus, been accentuated, particularly in the context of entrepreneurship, where these deviations were found to occur.