Leadership in Africa remains an elusive and contested phenomenon on which general agreement is highly unlikely. Despite this understanding, few studies have taken into account the possible cultural influences on leadership styles, the differences in leadership approach that are practiced, and how generalizable they can be in national and continental development. The aim of this paper is to examine how culture is core in influencing western Kenya leadership for national and continental development. The study utilized Complexity System Leadership Theory, which confirmed that leadership is a system function that operates to change the rules of interaction among people or groups within a complex adaptive system of interactions, both in terms of ends- where the system is going; and means- how to get there. The study used descriptive and cross-sectional designs and relied on a mixed methods approach. The target population was two cultural groups of western Kenya (the Luhya and the Abagusii, found in two administrative Counties of Kakamega and Kisii in Kenya. A sample size of 361 respondents from the general population, 25 Key informants, 16 focus group discussions and 25 direct observations were used to generate data. Methods of data collection included: Questionnaire, Key Informant Interviews, Focus Group Discussions and Observation checklist. Quantitative data was analyzed descriptively and using inferential statistics with the aid of SPSS software. Qualitative data was analyzed by content analysis and constant comparative meaning oriented analysis using thematic means. Quantitative and qualitative data were presented in a mixed way that reinforces each other. The study found that cultural values, beliefs and expectations influence how leaders are identified, chosen, developed and the leadership styles they adopt. Traditional leaders are also regarded as both County and National leaders especially by Abagusii people in Kisii County.