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This longitudinal case study reports upon the experiences from three small and medium-sized software product companies implementing Scrum an agile process. Self-management emerged as the key topic that was challenging throughout all projects. When transforming from traditional command-and-control management to collaborative self-managing team, the main challenges were found to be the absence of redundancy and the conflict between team level and individual level autonomy. Our findings are primarily based on qualitative analysis of interviews and observations with developers and product managers. Our findings may give important advice to other product companies considering introducing self-managing teams and agile development practices.