The study addresses the correlations within the selected leadership model in the educational environment. The goal of the research study was to verify the relationship between the general self-esteem in Slovak teachers and their pupil leadership style in terms of D. McGregor’s theory. Besides teachers’ self-esteem, the study also addresses the concept of leadership and other contextual variables (age, length of teaching practice, school type, and managerial experience). The method of available selection was used to build the research sample of form teachers working at the secondary level of education. Two questionnaires were administered to collect data: The RSES/Rosenberg Self-Esteem Scale (Halama & Bieščad, 2006) and The X/Y Leadership Style. The study has confirmed the assumed positive correlation between teachers’ general self-esteem and pupil/student leadership style in terms of the Y Theory. This result is consistent with other research results (e.g. Whitney, 1990; Matzler et al., 2015; Ďuricová & Šugereková, 2017), thus confirming the importance of leaders’ positive self-esteem.