U.S. intelligence analysts, as well as academics and political risk consultants, struggle to anticipate and assess leadership transitions in sub-Saharan Africa. Judd Devermont (CSIS), Jeffrey Herbst (American Jewish University), Mike Noll (The George Washington University), and Amaka Anku (Eurasia Group) discuss why leadership analysis is so vexing, identify common pitfalls, and recommend critical thinking tools and techniques to sharpen analytic judgments. Examinations of South Africa’s recent corruption scandals and Côte d'Ivoire’s new political dynamic open the episode.