Reliable Agents: Intent-Driven Failure Detection

Hosted by Jason Liu and Ben Hylak

Wed, Oct 22, 2025

6:00 PM UTC (1 hour)

Virtual (Zoom)

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Systematically Improving RAG Applications
Jason Liu
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What you'll learn

Identify Intent-Based Tool Call Failure Patterns

Learn to cluster user intents and analyze failure rates to pinpoint which user goals cause issues.

Build Monitoring Systems for Agent Reliability

Set up automated tracking to detect when tools fail for specific intent categories in production.

Use Failure Data to Optimize Agent Performance

Apply intent-failure insights to improve tool selection and boost user retention metrics.

Why this topic matters

Agent failures cost companies millions in lost users and revenue. Most teams debug reactively, missing systematic patterns. This lesson teaches you to proactively identify which user intents break your agents, build monitoring that catches issues before users churn, and use data-driven insights to prioritize fixes that maximize business impact.

You'll learn from

Jason Liu

Consultant at the intersection of Information Retrieval and AI

Jason has built search and recommendation systems for the past 6 years. He has consulted and advised a dozens startups in the last year to improve their RAG systems. He is the creator of the Instructor Python library.

Ben Hylak

Co-Founder, Raindrop

Ben Hylak is co-founder and CTO of Raindrop, building Sentry for AI

agents, transforming how engineering teams monitor their AI agents in production. Raindrop’s “semantic monitoring” pipeline allows engineering teams to instantly serve massive streams of user interactions to find and monitor issues - like tool call failures, user frustration, and custom issues. Raindrop processes tens of millions of events a day to help AI engineering teams at cutting edge companies like Clay.com, Tolans, Oleve, Websim and more find issues with their agents. Previously Ben was a Human Interface Designer at Apple working on the Vision Pro and did engineering at SpaceX and Google.

worked with

Raindrop
Stitch Fix
Meta
University of Waterloo
New York University

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