Large language models can explain concepts, summarize readings, and even generate practice problems. But developing professional expertise—the kind of strategic thinking, judgment, and problem-solving that distinguishes novices from experts—requires more than content delivery. It requires coaching. When we wanted to give students more access to expert-level thinking without just handing them answers, we built a custom AI chatbot. But as Matt Beane notes in The Skill Code (2024, p. 7), “If intelligent technologies are going to truly help, the expert-novice bond has to survive too.” That meant training our bot to coach like a mentor grounded in cognitive apprenticeship theory rather than respond like Google.