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We describe the development of and initial psychometric evidence for a set of five constructed response measures designed to assess complex problem-solving skills and knowledge expected to influence leadership. Structured (cued) and unstructured (uncued) problem solving scenarios intended to assess process skills associated with creative problem solving are presented first. Solution construction tasks developed to assess attention to constraints and characteristics in the broader problem context are presented next. Finally, social judgment tasks intended to assess understanding of people and social systems and a task sort to assess knowledge of leadership roles are presented. Preliminary evidence for the reliability and construct validity of these constructed response measures supports their efficacy in assessing skills that underlie effective organizational leadership.