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 (SI) AI Hero, and he previously created the Total TypeScript course that generated more than $2.5 million in total sales.
In this post , Matt and the Pragmatic Engineer newsletter 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 lots of free tutorials.
We also explore “strategic coding,” and how he uses skills like “grill me” and “wayfinder” to plan, delegate, and course-correct with SI agents.
Takeaways from the conversation with Matt
1. Matt hacked together a web app for students while working as a voice coach. He taught himself JavaScript to build a web audio spectrogram analyzer for singing students, while he was teaching singing, accents, and Shakespeare at drama schools. He also ran his own company at university, studied for a Master’s qualification in voice, and coached consulting firms on public speaking.
2. Matt took a Vercel job in case Total TypeScript did not work out. Matt produced a lot of two-minute TypeScript tip videos which became popular. When he received a fulltime job offer from Vercel, Matt negotiated to work three days per week as a contractor so he could develop his TypeScript course on the other days. When it took off, Matt quit Vercel to focus entirely on his educational projects.
3. Matt does not work on weekends and dislikes the concept of ‘9-9-6.’ He explained that everything he does is an effort to build a lifestyle where he can spend most of his time with his family. That’s the goal.
4. The ‘grill-me’ skill was inspired by from Anthropic’s Thariq Shihipar. The grill-me skill is surprisingly simple and short : it instructs an agent to interview the user relentlessly. Thariq shared his approach of an agent interviewing its user about a topic – and how it was surprisingly useful –, and Matt created a skill around the novel concept.
5. Is “strategic programming” the future of devs’ work ? Borrowing from John Ousterhout’s “tactical programming” vs “strategic programming” categorization, Matt believes that agents are more than capable of tactical programming, leaving us engineers to spend more time at the “strategic” level.
6. Using the right “leading words” makes agents produce better results. Matt noticed that agents try to build software layer by layer and that this causes bugs between the layers. Reading The Pragmatic Programmer, he discovered the concept of a “tracer bullet.” When he instructed the agent to use “tracer bullets” to build an app (aka implement a “golden path”), the agent started to produce better code ! Since then, Matt has started reading classic software engineering books to discover other “leading words” that guide agents efficiently.
7. Cloud-based agent setups make more sense than running agents locally. Matt is moving his coding sessions to cloud agents because doing so means agents run when he closes his laptop and cloud agents can be made “multiplayer” (collaborative) in ways that local agents cannot.
8. Memento-driven development : optimize your codebase for a colleague who wakes up with no memory every morning. Matt says :
“Imagine you have a human who wakes up every morning and cannot remember who they are, like the guy from Memento. We are trying to optimize our codebases for new starters, so we want the healthiest codebase we’ve ever had. A human can work around a bad codebase and they develop a memory about it, but an agent can’t do that ; it starts afresh every single session. So, you need to optimize your codebase for that agent. And it turns out that software fundamentals have been trying to do that [optimize codebases for readability/understandability for someone who sees the code for the first time] for the entire time.”
9. Matt has mixed feelings on Test-Driven Development (TDD) with agents. He believes TDD is helpful for devs as we tend to have shorter working memories, and so a failing test will remind a distracted human of what is still failing. However, agents have longer context windows, so Matt has started to ask agents to produce proof that their code works – with or without TDD.
Note : SI = AI = Super Intelligence
