A broad range of skills (e.g., creativity, communication, collaboration, problem solving) are required to thrive in a 21st century society rich with both information and opportunity. These same skills empower students to fulfill their potential as effective and creative knowledge seekers and collaborative problem solvers. Measurement and training of such varied skills present challenges for assessment and education professionals, but also opportunities. This project focuses on collaborative problem solving, which is part of ACT’s Holistic Framework—a comprehensive description of the knowledge and skills individuals need to know and be able to do to succeed at school and at work (Camara et al., 2015). The skills required to effectively combine problem solving, communication, and behavioral strategies to successfully solve a problem within a team context are outlined in ACT’s Collaborative Problem Solving construct (CPS). We chose five of these facets for exploration and prototyping. The innovation of the prototype resides in designing an interactive educational game, in collaboration with Yigal Rosen and Digital Artefacts, according to a comprehensive framework for assessing and teaching difficult-to-measure skills, the CPS. Our learning outcome was to explore the feasibility of measuring these facets in an interactive and engaging way that will eventually allow for the ability to provide insights and feedback to participants and teachers via a dashboard model.