Although interest in organizational culture has been growing since the 1980s, research on the relationship between organizational culture and leadership is not extensive, and existing studies have explained this relationship from the perspective that leadership determines and changes organizational culture. However, once organizational culture is established, organizational leaders, as members of the organization, are influenced by organizational culture—a system of shared values and beliefs—and are required to exercise leadership that fits this culture. If leadership is exercised unilaterally without fitting the organizational culture, the culture will constrain such leadership, and the incompatible leadership will also negatively affect organizational effectiveness. Therefore, it is necessary to examine what type of leadership fits a specific organizational culture and how this fit affects organizational effectiveness. This study is an exploratory investigation into whether organizational culture is an important variable influencing leadership. Using a typological approach from the perspective of contingency theory, the study empirically investigated the fit between organizational culture types and leadership types in Korean business organizations, and established a research model and hypotheses to empirically analyze the relationship between behavioral effectiveness resulting from the fit between organizational culture types and leadership types. The results of hypothesis testing showed that specific leadership types are dominantly associated with specific organizational culture types, forming a fit between organizational culture types and leadership types in business organizations. Furthermore, organizations that achieved such fit exhibited higher behavioral effectiveness—namely, higher organizational commitment and job satisfaction—than organizations that did not. Therefore, this study suggests that managers in business organizations should exercise leadership that fits the dominant organizational culture type of their organization, and that such fit is a means of enhancing organizational effectiveness. In other words, when a fit is achieved between organizational culture type and leadership type, the organization's job satisfaction and organizational commitment will be high.