AI is not an oracle — it is a question machine.

In this episode, Samraj Matharu speaks with Cassandra Sibilin, Philosophy Lecturer at CUNY (City University of New York) and a leading practitioner in AI-assisted education.

Cassandra works at the intersection of philosophy, pedagogy, and emerging AI tools, helping educators and students move beyond fear, hype, and automation toward deeper thinking. Rather than treating AI as an answer engine or oracle, she argues for a different framing: AI as a question machine — a tool that challenges assumptions, surfaces multiple perspectives, and sharpens human judgment.

Together, they explore why philosophy has become essential AI literacy, how “flipping the interaction” with AI changes learning outcomes, and why critical th ...