Students are increasingly expected to prepare for open-ended innovation work, which requires well-developed cognitive, metacognitive, and emotional regulation skills. College learning environments offer opportunities to work on real-world problems--such as in design and engineering--but students often remain unaware of their ineffective work practices and recurring regulation challenges, and may struggle to improve. Coaching from experts can help, but students' practices and regulation behaviors are largely invisible from work artifacts alone and are difficult to diagnose and track without computational support. We introduce Situated Practice Systems (SPS), which provide: (1) an Interactive Context-Assessment-Plan (CAP) Notes tool to support coaches' understanding and modeling students' regulation-informed practices, and (2) Practice Agents that help students develop more effective practices. SPS uses Practice Objects to represent practices and regulation behaviors computationally, and Practice Scripts to automatically present suggested practices to students in relevant situations. In a formative 3-week field study, SPS helped coaches identify recurring regulation gaps and provide tailored practices. SPS also guided students in adopting more effective ways of working on their own and with others. We demonstrate how CSCW systems and learning environments can be designed to support the development of students' work practices and regulation skills, enabling them to lead innovation work.

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