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Organizations facing issues related to growth, innovation, and strategy are embracing design thinking, a problem-solving process. This study explores 40 design thinking initiatives and identifies operational practices emerge and empirical categories across various contexts. Quantitative analyses of the initiatives and qualitative interview data are used to distinguish four configurations of action analogous to races: training, emphasizing learning-by-doing; marathons, capturing personal reflection over a long project; relays, highlighting team collaboration; and sprints, reflecting fast-paced product innovation. The initiatives are differentiated as designer-led versus team-driven and, low-urgency versus high-urgency. Implications of practicing design thinking in Organization Development and Change are discussed.