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AI Skills with Matt Pocock

The Pragmatic Engineer

September 17, 2026

• 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.

Speakers Gergely Orosz, Matt Pocock

TopicsTechnologyNewsTech News

Gergely Orosz (0:00)

I got the grilling of my life in building a pretty simple API endpoint using the Grill Me skill. It asked me 35 questions, I kid you not. It was intense, and annoying, and it forced me to think more. Today's guest is the creator of this popular skill, Matt Pocock. Matt is a developer turned educator, well known for his Total TypeScript series, and now for his AI skills and educational videos. Today, we cover Matt's unusual path into tech after years of being a voice coach and building his own DIY coaching software. Matt's popular skills, grill me, wayfinder, and why these skills became so widespread, taking inspiration from decades old programming books to build better software with AI and many more. If you want to understand which software engineering fundamental approaches remain very useful when working with AI agents, this episode is for you. This episode is presented by TurboPuffer, Vector and FulltextSearch built on object storage. It's fast, cheap, and extremely scalable. This episode is presented by Linear, and I wanted to take you back in time to remind you how we used to get work done. Back when every line of code was written by an engineer like you or me, a tracker's job was to keep people in sync without slowing people down.

Linear was built to be fast and low friction, and you could tell.

In last year's The Pragmatic Engineer survey, Linear was the most loved tracker tool, and Jira the most disliked one for its sluggish performance. And data coming from the Pragmatic Engineer audience showed how Linear started to gain traction against existing tools, especially at startups and mid-sized companies. And since then, Linear grew up.

They added all the stuff that larger companies need to manage work, projects, initiatives, roadmaps and customer requests. And large companies started to switch. For example, healthcare company Oscar Health moved 600 engineers from Jira to Linear.

OpenAI started with 100 seats and moved all 3000 staff without any mandate. Coinbase, CashApp, Brexit and Ramp are all on Linear. Many of them saw Linear as a way to consolidate a single tool that brings planning and building together. So now, let's fast forward to today. When you have AI agents inside a company, those agents need context to work well. They need access to things like specs, customer requests, history. Oh wait, these are all already in Linear. So when agents arrived, Linear became the ideal context layer. Today, 80% of enterprise workspaces in Linear have adopted agents. You can use agents like Codex, Claude Code Linear agent or your own agent.

Coinbase and Ramp both built their own internal agents and described Linear as the place that their agent goes and picks up the context before starting work. See how it works at Linear.appslash.pragmatic.

Matt, it's great to have you on the podcast.

Matt Pocock (2:31)

Great to finally be here. I'm a huge fan. I've watched so many of these. I feel like this is like the tiny desk of being a software engineer. You know what I mean? This is big stuff, so I'm glad to be here.

Gergely Orosz (2:41)

And it's also great to reconnect because about a year ago, we had lunch at Microsoft Build as well, which was really fun. But now it's good to jump into this. And with this, I wanted to ask about your background. You, unlike many people in tech and on this podcast, you didn't start out to study computer science, right?

Matt Pocock (3:01)

Absolutely not. So for six years before I became a developer, I was a voice coach. I was a singing teacher working in London and working in Exeter where I went to university.

I was teaching accents. I was teaching singing. I was teaching voice. I did a master's in it. I spent a lot of time thinking that was what my career was going to be. You know, I didn't have any inkling of tech, didn't sort of think about it at all. I sort of ran my own website and stuff. But yeah, so I did that for a long time. And it's been an extremely important influence on my life. And I think my personality as well.

Gergely Orosz (3:37)

Can you get a bit deeper? Where does the voice come from and what do you do as a voice coach? Who are people who came to you for help and what kind of help?

Matt Pocock (3:47)

So I started as a singing teacher.

I was in a band and stuff at university. I sort of had a bit of experience doing singing. And so I set up my own company kind of at university and doing that stuff. And it was people who just wanted to sing better, who wanted to use their voice for choirs, who wanted to just do it as a hobby. It wasn't anything particularly professional. And I went and did a master's in it. And I started going to drama schools to teach people Shakespeare and stuff, and getting people in who wanted to do public speaking. I did a couple of big gigs for consulting companies, going and teaching them how to deliver speeches and how to talk better. It was wild. And the reason I got out of it was because I realized in order to do it at a decent level, you had to live in London. I didn't want to live in London. I tried it for like two years. I just hated it. I hated it. I didn't grow up in London. I wanted to get back to the countryside and where I was from.

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