The Pragmatic Engineer The Pragmatic Engineer

AI Skills with Matt Pocock

Sep 17, 2026 · 1h 35m

Summary

Matt Pocock shares his unconventional path from voice coach to TypeScript educator and AI skill creator. He discusses the launch of Total TypeScript and how AI shifted his focus from teaching syntax to strategic workflow design. The episode highlights his popular "grill me" skill, which forces developers to make critical decisions before coding, and his approach to managing AI agents through structured specs and context optimization.

Topics discussed

Intro: Matt Pocock and the grill-me skill Sponsor: Linear's rise in project management Matt's background: from voice coach to software dev Early career: first jobs and learning TypeScript Working at Vercel and the TypeScript community Creating Total TypeScript and the 7-figure milestone The impact of AI on education and Matt's pivot Building AI skills: the grill-me concept Sponsor: WorkOS Airlock for agent security Sponsor: Turbopuffer for agent memory How the grill-me skill works in practice Context management and the Ralph loop The Map: organizing agent state and decisions Day shift vs Night shift: planning and execution Applying engineering skills to non-technical tasks Leading words and using domain language with AI Software fundamentals in the age of AI agents Strategic vs tactical programming and tech debt Hiring in the AI era and organizational feedback loops Remote development and the value of planning Waterfall vs Agile in agentic workflows Test-driven development and automated code review The future of software engineering education Advice for new engineers and the 'gardener' role Closing thoughts and book recommendations
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