Justin Reich leads this session from MIT's CMS.595 Learning, Media, and Technology course, examining how standardized and routine assessment practices fail to measure what increasingly matters in a changing job market: critical thinking, creativity, and complex problem-solving. The discussion looks at where artificial intelligence can plausibly assist in grading and evaluation, and where it falls short, particularly in judging persuasive writing, nuanced communication, and emotional intelligence. Reich and participants weigh the tradeoff between efficiency gains from automating routine assessment tasks and the continued need for human judgment in contexts that require contextual insight rather than pattern matching. Running 66 minutes, the session fits into the course's broader concern with how educational technology reshapes teaching and evaluation, treating assessment design itself as a site of pedagogical and ethical choice rather than a solved technical problem.