Increasingly complex working environments of school principals inevitably led them to face moral dilemmas in daily life. The aim of this research is to reveal which kinds of moral dilemmas principals fall into mostly, how principals follow the road to making decisions in the moral dilemmas, and if the nature of management affects the decision-making process of their moral dilemmas or not. For data collection process snowball sampling was used. Semi-structured interviews and vignettes which were designed by researchers were used for data collection. According to results, principals in Turkey have experienced moral dilemmas based on self-interests instead of ethic of critique which is experienced by Canadian principals. Moreover, taking into consideration the decision-making process, although principals in Canada follow the same procedure as the Turkish principals, they have two extra steps: “considering the students’ benefit” and “considering teachers’ and parents’ needs.” Lastly, it is seen that the Turkish and Canadian principals’ natures which affect the moral dilemma decision-making process are totally different. The possible reasons for these differences and suggestions were discussed within this context.