This article is based on a qualitative case study carried out along the Nyanza-Rift Valley Provinces border in Southwestern Kenya. The purpose of this paper is to examine the context in which school leader's work and operate in southwestern Kenya. We further postulate how best the influence of these contexts can be minimized through the formation of trust, thus enabling the secondary school principals to become more effective in their leadership roles. This exploratory study focused on six secondary school principals in Southwestern Kenya. This research approached the concept of trust and trust-building through multi-case studies. Using a phenomenological approach, data were gathered through in-depth semi-structured interviews, document analysis, and an analysis of school artifacts. Findings showed that the leadership terrain was characterized by dependence, uncertainty and vulnerability. Working in such contexts, principals were faced with the possibilities of failure in their leadership roles. Consequently, to minimize the influence of these contexts, school principals had to improve, develop and sustain high trust relationships with the parents. The article concludes with recommendations for policy.