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This chapter presents the opportunities, strategies, and challenges related to an effort to embed a leadership coaching culture into the culture of an academic institution in Nairobi, Kenya. That effort has been the work over the past several years of four Certified Organizational Effectiveness Coaches trained by Coach Development Institute of Africa. Each tells the story of how and why she moved into coach training and why she views coaching as key to driving social change. The chapter describes the strategies they are using to address opportunities they see and challenges they have encountered. The chapter also presents their preliminary thoughts on a coaching model influenced by both Western approaches and African cultural beliefs, values and attitudes.