This Element presents a framework for analyzing the complexities of contracting, how these vary across circumstances, the ways contract managers can address challenges, and the skills of contract managers. The framework is grounded on central concepts. Market frictions are underlying imperfections that cause common contracting problems; contract management activities are the tasks and procedures that contract managers perform to prepare and execute the purchase; and skills are the ability to perform contract management activities that identify and mitigate frictions. These concepts are interdependent – market frictions can influence the efficacy of contract management activities, activities may reduce or increase the presence of frictions, and skills may influence both the choice and effectiveness of activities in addressing contracting challenges. Omitting any of these components is likely to result in misleading accounts of the root causes and potential solutions to contracting challenges.