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Quoting Ally Piechowski

Simon Willison Archived Mar 17, 2026 ✓ Full text saved

Questions for developers: “What’s the one area you’re afraid to touch?” “When’s the last time you deployed on a Friday?” “What broke in production in the last 90 days that wasn’t caught by tests?” Questions for the CTO/EM: “What feature has been blocked for over a year?” “Do you have real-time error visibility right now?” “What was the last feature that took significantly longer than estimated?” Questions for business stakeholders: “Are there features that got quietly turned off and never came b

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    Simon Willison’s Weblog Subscribe Sponsored by: CodeRabbit — Planner helps 10x your coding agents while minimizing rework and AI slop. Try Now. Questions for developers: “What’s the one area you’re afraid to touch?” “When’s the last time you deployed on a Friday?” “What broke in production in the last 90 days that wasn’t caught by tests?” Questions for the CTO/EM: “What feature has been blocked for over a year?” “Do you have real-time error visibility right now?” “What was the last feature that took significantly longer than estimated?” Questions for business stakeholders: “Are there features that got quietly turned off and never came back?” “Are there things you’ve stopped promising customers?” — Ally Piechowski, How to Audit a Rails Codebase Posted 6th March 2026 at 9:58 pm Recent articles My fireside chat about agentic engineering at the Pragmatic Summit - 14th March 2026 Perhaps not Boring Technology after all - 9th March 2026 Can coding agents relicense open source through a “clean room” implementation of code? - 5th March 2026 This is a quotation collected by Simon Willison, posted on 6th March 2026. rails 110 software-engineering 62 technical-debt 9 Disclosures Colophon © 2002 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 2025 2026
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    Simon Willison
    Category
    ◬ AI & Machine Learning
    Published
    Mar 06, 2026
    Archived
    Mar 17, 2026
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