The Pragmatic Engineer

AI Skills with Matt Pocock

September 17, 2026·1h 35m
Episode Description from the Publisher

Brought to You By:• turbopuffer – a vector and full-text search engine built on object storage. It’s fast, cheap, and extremely scalable• Linear – the product development system for teams and agents• WorkOS – everything you need to make your app enterprise ready.—Why is the “grill-me” skill so popular, and why does its creator swear by the importance of software fundamentals? Matt Pocock created this widely-used skill – and many others – alongside being an educator, content creator, and engineer. His latest course is AI Hero, and he previously created the Total TypeScript course that generated more than $2.5 million in sales.In this episode, Matt and I discuss his unconventional path from working as a voice teacher to becoming a developer and going all-in on technical education. He reveals how communication skills helped him break into tech, why he took an unusual three-days-a-week contract at Vercel, and how he built Total TypeScript through workshops, courses, and a lot of free content.We also explore “strategic coding,” and how he uses skills like “grill me” and “wayfinder” to plan, delegate, and course-correct with AI agents. Matt explains his “day shift” and “night shift” approach, why splitting context up can keep agents in their “smart zone,” and how concepts from classic software engineering books can guide agents to do better. In this episode, there’s also local versus cloud workflows, whether agents need TDD, how AI is changing the ways that engineers learn the fundamentals, and why humans are still essential in teaching.Timestamps00:00 Intro05:48 How Matt got into tech10:14 How Matt got into open source12:58 Joining Vercel18:39 Total TypeScript23:21 AI’s impact on technical education30:32 Building reusable skills for AI coding agents40:46 The “smart zone” vs the “dumb zone”45:02 The wayfinder skill47:52 Why agents excel at software engineering50:54 “Leading words”1:01:10 Learning the fundamentals1:09:17 Local vs. cloud agents1:12:36 Planning vs. course-correcting1:18:13 TDD and agents1:23:06 Living in the UK1:24:21 Teaching: the human part1:28:36 Advice for junior engineers1:31:07 Gardeners and great engineers1:34:01 Book recommendation—The Pragmatic Engineer deepdives relevant for this episode:• What is "loop engineering?"• The Philosophy of Software Design – with John Ousterhout• Context engineering with Dex Horthy• Are AI agents actually slowing us down?• The AI Engineering Stack• How Codex is built• How Claude Code is built• How Uber uses AI for development: inside look—Production and marketing by ⁠⁠⁠⁠⁠⁠⁠⁠https://penname.co/⁠⁠⁠⁠⁠⁠⁠⁠. For inquiries about sponsoring the podcast, email podcast@pragmaticengineer.com. Get full access to The Pragmatic Engineer at newsletter.pragmaticengineer.com/subscribe

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