We interviewed eight principals from Bermuda and Florida about how they identify and manage their most pressing challenges. Their challenges are composed of both adaptive and technical work, requiring leaders to learn to diagnose and manage them. Challenges focused on change and were traced to accountability contexts, yet accountability was not the driving force for all principals. Neither external demands nor principals themselves dictated whether the problem was technical or adaptive; instead, it was the nature of the problem itself. Leadership preparation programs are encouraged to provide a framework to address managing phases of adaptive, technical, and mixed challenges.