How Do You Evaluate An AI Agent? (The Agents Season, Episode 7)

How Do You Evaluate An AI Agent? (The Agents Season, Episode 7)

From Linear Digressions by Katie Malone

June 1, 2026 · 32 min

About this episode

This episode discusses the challenges of evaluating AI agents and measuring their performance systematically.

Knowing when an AI agent has failed sounds straightforward — until it isn't. Agents have a frustrating habit of finishing confidently while quietly doing the wrong thing, or looping endlessly without ever crashing in an obvious way. This episode tackles one of the thorniest problems in the agentic world: evaluation. If failure is hard to see, how do you measure it systematically? And how do you know when your agent is actually working?

People in this episode

Host: Katie Malone

Topics covered

  • AI evaluation
  • agent failure
  • systematic measurement
  • agent performance
  • technology

Keywords

  • AI agents
  • evaluation
  • failure detection
  • performance measurement
  • technology

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