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My AI Kept Pushing Me to Ship, So I Asked It Why

My AI Kept Pushing Me to Ship, So I Asked It Why

Andrew Stellman· ·23 min read · 0 reactions · 0 comments · 11 views
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Radar > Topics > AI & MLMy AI Kept Pushing Me to Ship, So I Asked It WhyI finally got fed up with it bullying me into shipping a project that had no deadline. I was using Claude Cowork as the orchestrator: planning scope, dispatching instructions to a worker agent, reviewing what came back. And keep in mind that there was no deadline on any of it: It’s an open source project; I’m the only one setting the schedule, and I’d decided early on that every outstanding fix in the backlog was going into the current release before we moved on to the next one.I’d told the model exactly that.

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O’Reilly Media · Andrew Stellman
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Original publisherO’Reilly Media
Canonical URLhttps://www.oreilly.com/radar/my-ai-kept-pushing-me-to-ship-so-i-asked-it-why/
Publication timeSun, 20 Sep 2026 23:18:01 +0000
Retrieval time2026-09-20T23:28:47.157Z
Last seen2026-09-20T23:28:47.157Z
Headline sourcePublisher (no WeSearch rewrite)
Excerpt sourcepublisher body
Excerpt methodFirst ~120 words (~800 chars) of extracted publisher body, fair-use limited.
SummaryWeSearch · cerebras-chat (WeSearch summarizer)
Summary source textcontentText
Citation coverageSummary is a WeSearch-generated derivative; primary citation is the original publisher URL.
Cluster2d0w0xr-PwZJ · 1 stories
Cluster logicGrouped by semantic title/content similarity across sources within a rolling window. Same-publisher template collisions are excluded from coverage comparison.
Ranking reasonStory pages are not engagement-ranked. Hub feeds use recency, with optional source-diversified chronological ordering (cap consecutive stories per source). No personalized ranking.
Publisher visitYes — open original
Substitutes article?No — link-out required for full text

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Opening excerpt (first ~120 words) tap to expand

{ "@context": "https://schema.org", "@type": "BlogPosting", "@id": "https://www.oreilly.com/radar/my-ai-kept-pushing-me-to-ship-so-i-asked-it-why/#BlogPosting", "mainEntityOfPage": "https://www.oreilly.com/radar/my-ai-kept-pushing-me-to-ship-so-i-asked-it-why/", "headline": "My AI Kept Pushing Me to Ship, So I Asked It Why", "description": "I’ve been working on the Quality Playbook, my open source AI skill that uses quality engineering to find bugs that normal AI code review misses, and I recently had a batch of work that turned into a long run of point releases.

Excerpt limited to ~120 words for fair-use compliance. The full article is at O’Reilly Media.

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