EPISODE · Aug 14, 2026 · 1H 30M
How AI is changing software development with Simon Willison
from Talking Postgres with Claire Giordano · host Microsoft
What’s your gold standard for deciding whether AI-written code is ready for production? In Episode 42 of Talking Postgres, Simon Willison—creator of Datasette, co-creator of Django, and prolific open-source developer—joins Claire to share how AI is changing the way he builds software today. We dig into why his test for shipping AI-generated code is “Could I explain this to somebody else?”, how engineering management skills can be surprisingly useful when managing AI agents, and how the bottleneck is no longer writing code but understanding it. Also: personal credibility, deep research, the Winchester Mystery House, slop proxies, and Simon’s observation that “Features are cheap. That doesn’t mean you should build them all.”Previously on Talking Postgres:Talking Postgres podcast Ep 30: AI for data engineers with Simon Willison Links mentioned in this episode:Blog: Simon Willison’s BlogProject page: Datasette, for finding stories in dataGitHub repo: sqlite-utilsBlog post: Release of alchemy-utils 0.1a0 (featuring Postgres & DuckDB)Blog post: There are no lossless transformations of natural-language text, by Sophie AlpertPodcast episode: The Open Weight Revolution with Simon Willison, on Oxide and FriendsPodcast episode: An AI state of the union, on Lenny’s Podcast Wikipedia: Winchester Mystery HouseIdea in Mythical Man-Month: Conceptual integrityBlog post: SQLite compressed text-history prototypes, by Simon WillisonTools: Simon’s miscellaneous tools repoIn this episode, we covered:00:00 Intro & music04:00 A week of work before breakfast09:12 Red-green TDD makes agents exercise every line14:42 A million lines mean nothing if you don’t understand it18:28 Finding low-hanging fruit among open PRs & issues22:07 Getting work done while walking the dog23:01 Gold standard: “Could I explain this to somebody else?”28:27 Slop proxies add no value at all30:49 Aggressive nitpicking reviews35:01 Everything in software engineering is about trade-offs41:16 Racoon heist game is only fun for 1 minute 15 seconds43:46 New Year’s resolution to be more ambitious48:11 You have to learn to throw things away51:57 Features are cheap. That doesn’t mean you should build them all1:00:45 Engineering management skills are so useful1:04:44 QA specialists should be having a great time1:07:53 Writing is thinking, don’t outsource it1:08:23 Skill atrophy is a choice you make1:10:07 I believe in people who are motivated1:11:55 Systems are not set up to deal with this volume1:18:48 Research agents stopped being absolute garbage1:21:49 The whole point of the “human in the loop”1:26:10 Dream: I want there to be more small businesses
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How AI is changing software development with Simon Willison
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