This paper deals with the phenomenon of teachers’ personal initiative in school everyday life as the significant factor of the quality of teaching and learning. Our goal is to explore how teachers assess their initiative - to what extent and in which way they show initiative, and what are the factors that encourage and hinder its demonstration. The first part of the paper analyses the very construct of “initiative” - its determinants and the relation with similar constructs. The second part of the paper presents results of the research that included 182 teachers from urban primary schools from the entire territory of Serbia. Teachers gave their opinion about the presence and demonstration of personal initiative by replying to items in the questionnaire constructed for the purposes of this research. Obtained data were processed using both quantitative and qualitative methods. The results indicate that the majority of teachers consider themselves as persons of initiative. They believe that there is plenty of space to show initiative in creating atmosphere in the class, lecturing and in cooperation with parents and colleagues, while the least space for that is in organizational functioning of school and professional development. Teachers do not think that there are bigger obstacles to demonstrating their initiative; however, they are of the opinion that there is a lack of developed support to such demonstration when it comes to school environment factors. [Projekat Ministarstva nauke Republike Srbije, br. 179034: Od podsticanja inicijative, saradnje, stvaralaštva u obrazovanju do novih uloga i identiteta u društvu) i br. 47008: Unapređivanje kvaliteta i dostupnosti obrazovanja u procesima modernizacije Srbije]