Throughout the last two decades, successful school leadership has been subject to extensive research in Norway and comparisons across countries as part of the International Successful School Principals Project (ISSPP). This paper identifies and discusses how and why Norwegian research on the relationship between school leadership positions and governance regimes comes into play when defining terms such as “success” and “effectiveness”. A critical literature review establishes analysis and discussion as the basis for an improved understanding of the notion of success in ISSPP research in the Norwegian education policy context. The findings show that success is consistently attached to a collaborative, political, and democratic perspective, as well as trust, power, and the definition of quality in education. Furthermore, ISSPP studies of cases in the Norwegian context have contributed to the educational leadership field by positioning school leadership within a combination of local, national, and global political and cultural environments. The differences and similarities between countries that do not share a common cultural heritage or language must be considered. In particular, there is a need to discuss the relationship between national history and policy and the conceptualization of successful school leadership.