Introduction: The research study deals with the personality of managers in regard to their professional career. The main objective of the study was to find the relationship between the personality dimensions according to the Big Five personality traits model and Holland's typology of the six personality types and work environment types. Methods: The research sample consisted of 121 managers from different levels of the subordinate system in state organizations and private companies in Slovakia. The personality dimensions Neuroticism, Extraversion, Openness to experience, Agreeableness, and Conscientiousness were in this research measured by the NEO Five-Factor Inventory. We have also used the SDS questionnaire - Self-Directed Search to determine the personality types and work environment types - RIASEC codes. The statistical evaluation was performed using the SPSS 20 statistical system, with the data evaluated by methods of descriptive and correlation analysis. Results: There were the highest values recorded in Conscientiousness throughout the research sample. The lowest values were recorded in Neuroticism. We found out that the Summary Code of managers is ESI (Enterprising, Social, Investigative), of male managers is EIR (Enterprising, Investigative, Realistic), of female managers is SEC (Social, Enterprising, Conventional). When comparing the individual RIASEC personality types, we found significant differences between males and females. Males are more realistic than females, more investigative and enterprising than females. Females are more social and conventional compared to males. There was no gender difference in artistic orientation. The RIASEC personality types in the entire sample match the RIASEC work environment types according to SDS, regardless of age. The results demonstrated relationships between the NEO - FFI personality dimensions and personality types and RIASEC work environment types codes according to SDS. Discussion: We can say that managers in our research sample are primarily Enterprising types with leading life orientation. Typical representatives of this personality type are characterized especially by traits such as dominance, ambition, focus on success, self-confidence, sociability, and responsibility. In the context of a manager's success and their effectiveness, or ineffectiveness in work environment, the most predictive Big Five factor for an effective manager is Neuroticism, all effective managers scored low in Neuroticism. Results obtained by the SDS questionnaire - Self-Directed Search confirm our findings of prevalent personality dimensions in the overall personality profile of managers. The overall RIASEC personality code of managers according to SDS is ESI in the whole research sample, thus we can conclude that in the case of the overall personality type - RIASEC code of manager the dominant personality type is Enterprising/leading, followed by the Social personality type and the third is the Investigative personality type. Limitations: One of the methodological limitations of this research is the number of participants in the research sample. We do not consider this number as representative for the purpose of generalizing the results. Conclusions: Research results show that there is a relationship between professional orientation and personality. Some personality dimensions are significantly related to professional orientation types and to professional interests, whereas others are related only non-significantly or not at all. Significant relations were found between the dimension Openness and Artistic, Leading, and Social type, between the dimension Extraversion and Enterprising and Investigative type, and between the dimension Agreeableness and the Social type. Realistic type was not related to any personality dimension. The dimension Neuroticism was negatively related to all professional types. For the career counseling practice and selection of job seekers and manager position applicants, this may mean that despite confirmation of these convergences, there may be different relations between different Holland's professional types and personality dimensions. These findings can be the focus of further research on students in their final year of secondary school when they are deciding on their future professional career. This research study, we believe, has contributed to the understanding of the relationship between personality and professional career. The results confirm that professional orientation and personality interact and influence the professional behavior of a person.