Lenny's Newsletter
Lenny's Reads
Listen: Building eval systems that improve your AI product
Preview
0:00
-21:40

Listen: Building eval systems that improve your AI product

An audio edition of Lenny's Newsletter post

If you’re a premium subscriber

Add the private feed to your podcast app at add.lennysreads.com

In this episode, you’ll learn:

  • Why most AI eval dashboards fail to deliver real product improvements

  • How to use error analysis to uncover your product’s most critical failure modes

  • The role of a “principal domain expert” in setting a consistent quality bar

  • Techniques for transforming messy error notes into a clean taxonomy of failures

  • When to use code-based checks vs. LLM-as-a-judge evaluators

  • How to build trust in your evals with human-labeled ground-truth datasets

  • Why binary pass/fail labels outperform Likert scales in practice

  • Evaluation strategies for complex systems: multi-turn conversations, RAG pipelines, and agentic workflows

  • How CI safety nets and production monitoring work together to create a flywheel of continuous product improvement

Listen now: YouTube | Apple | Spotify

References:

This post is for paid subscribers