While many forecasts chart an evolution of artificial intelligence (AI) in taking human jobs, more likely is a future where AI changes the division of labor in most jobs, driving a need for workforce development to shift towards uniquely human skills. Specifically, AI is becoming increasingly proficient at calculation, computation, and prediction (“reckoning”) skills. As such, we will see increased demand for human judgment skills such as decision-making under conditions of uncertainty, deliberation, ethics, and practical knowing. Developing human judgment skills follows well from the broadened conception of learners presented in the earlier briefs in this series. This brief focuses on the important topic of how workforce development can help humans prepare to collaborate with artificial intelligence to do work that neither are capable of in isolation.