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Willpower is a quality that predicts positive outcomes in many areas of life and it is the greatest human strength which can make people go a step further (Baumeister & Tierney, 2011; Karp, 2015). Brunch and Ghoshal (2004) indicate that leaders need more than motivation to spur their actions. This is because difficult challenges underscore the limitations of motivation, and therefore leaders would need to rely mostly on their personal willpower. In leadership research, willpower is a capacity that is less studied and overlooked by researchers, in spite of the fact that many researchers strongly argue that willful leaders achieve more results and are perceived to be more determined in their thoughts and actions. Bearing this fact in mind, and being myself a great believer in this personal quality, enticed me to delve into the importance of willpower in acts of leadership. This chapter is a short account of the present phase of the author’s study which is being conducted with leaders who work in the educational field but who come from different countries, thus embracing diverse cultural backgrounds. The aim is to try to establish if cultural background gives a different perspective to the phenomenon of willpower. Results show that albeit culture has an impact on expected leader behaviour, and national cultures adopt different views on desired leadership qualities, willpower is still a strong phenomenon among educational leaders no matter what their cultural background is.