What happens when you realize that the smartest AI isn't necessarily the best teacher? At SchoolAI, we discovered that students don't need an AI that knows everything—they need one that knows how to guide them to their own discoveries. In this case study, I'll walk through our process of designing Dot, our AI teaching assistant that emotes, empathizes, and occasionally refuses to help (in the best possible way). From early prototypes that felt robotic to our current system that can detect when students need encouragement versus challenge—and even flag mental health concerns—this is the story of designing AI that feels genuinely human in service of genuinely human learning.

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