If you’re a premium subscriber, add the private feed to your podcast app at https://add.lennysreads.com In this episode, we dive into the fast-emerging discipline of AI evaluation with Hamel Husain and Shreya Shankar, creators of AI Evals for Engineers & PMs, the #1 highest-grossing course on Maven. After training 2000+ PMs and engineers across 500+ companies, Hamel and Shreya reveal the complete playbook for building evaluations that actually improve your AI product: moving beyond vanity dashboards, to a system that drives continuous improvement. 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 References: • Read the newsletter: https://www.lennysnewsletter.com/p/building-eval-systems-that-improve • AI Evals for Engineers & PMs: https://maven.com/parlance-labs/evals • A Field Guide to Rapidly Improving AI Products: https://hamel.dev/blog/posts/field-guide/ • Aligning LLM-Assisted Evaluation of LLM Outputs with Human Preferences: https://arxiv.org/abs/2404.12272 • Aman Khan: https://www.linkedin.com/in/amanberkeley/ • Anthropic: https://www.anthropic.com/ • Arize Phoenix: https://phoenix.arize.com/ • Braintrust: https://www.braintrust.dev/ • Beyond vibe checks: A PM’s complete guide to evals: https://www.lennysnewsletter.com/p/beyond-vibe-checks-a-pms-complete • Frequently Asked Questions (And Answers) About AI Evals: https://hamel.dev/blog/posts/evals-faq/ • Hamel Husain: https://www.linkedin.com/in/hamelhusain/ • LangSmith: https://smith.langchain.com/ • Not Dead Yet: On RAG: https://hamel.dev/notes/llm/rag/not_dead.html • OpenAI: https://openai.com/ • Shreya Shankar: https://www.linkedin.com/in/shrshnk/ Listen: • YouTube: https://www.youtube.com/@lennysreads • Apple: https://podcasts.apple.com/us/podcast/lennys-reads/id1810314693 • Spotify: https://open.spotify.com/show/0IIunA06qMtrcQLfypTooj • Newsletter: https://www.lennysnewsletter.com/subscribe Follow Lenny: • Twitter/X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ • Podcast: https://www.youtube.com/@lennyspodcast Subscribe • YouTube: https://www.youtube.com/@lennysreads • Apple: https://podcasts.apple.com/us/podcast/lennys-reads/id1810314693 • Spotify: https://open.spotify.com/show/0IIunA06qMtrcQLfypTooj • Substack: https://lennysreads.com/ Follow Lenny • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ • Podcast: https://www.youtube.com/@lennyspodcast About Welcome to Lenny's Reads, where every week you’ll find a fresh audio version of my newsletter about building product, driving growth, and accelerating your career, read to you by the soothing voice of Lennybot. To hear more, visit www.lennysnewsletter.com
