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This Article, prepared for the Saint Louis University Law Review’s 2013 Symposium on Teaching Employment & Labor Law, explores the use of the problem method in employment law instruction. Drawing on my experience teaching the basic employment law course, I suggest that those areas of the field that require transactional lawyering skills are perhaps best taught contextually through a hypothetical problem, rather than through cases. Adopting the problem method in such circumstances not only gives students a richer understanding of the law and how it operates, but also the opportunity to cultivate problem-solving skills and professional judgment, thereby advancing the goal of graduating more “practice-ready” lawyers.