{"slug": "questions-for-the-team-during-onboarding", "title": "Questions for the Team During Onboarding", "summary": "Ally Piechowski published a list of onboarding questions for developers, CTOs/EMs, and business stakeholders to audit legacy Rails codebases, covering areas like deployment fears, production failures, and blocked features.", "body_md": "6th March 2026\n\nQuestions for developers:\n\n- “What’s the one area you’re afraid to touch?”\n- “When’s the last time you deployed on a Friday?”\n- “What broke in production in the last 90 days that wasn’t caught by tests?”\n\nQuestions for the CTO/EM:\n\n- “What feature has been blocked for over a year?”\n- “Do you have real-time error visibility right now?”\n- “What was the last feature that took significantly longer than estimated?”\n\nQuestions for business stakeholders:\n\n- “Are there features that got quietly turned off and never came back?”\n- “Are there things you’ve stopped promising customers?”\n\n— [Ally Piechowski](https://piechowski.io/post/how-i-audit-a-legacy-rails-codebase/), How to Audit a Rails Codebase\n\n## Recent articles\n\n[sqlite-utils 4.0, now with database schema migrations](/2026/Jul/7/sqlite-utils-4/)- 7th July 2026[sqlite-utils 4.0rc2, mostly written by Claude Fable (for about $149.25)](/2026/Jul/5/sqlite-utils-fable/)- 5th July 2026[Have your agent record video demos of its work with shot-scraper video](/2026/Jun/30/shot-scraper-video/)- 30th June 2026", "url": "https://wpnews.pro/news/questions-for-the-team-during-onboarding", "canonical_source": "https://simonwillison.net/2026/Mar/6/ally-piechowski/", "published_at": "2026-07-09 09:47:33+00:00", "updated_at": "2026-07-09 10:13:13.298969+00:00", "lang": "en", "topics": ["developer-tools"], "entities": ["Ally Piechowski"], "alternates": {"html": "https://wpnews.pro/news/questions-for-the-team-during-onboarding", "markdown": "https://wpnews.pro/news/questions-for-the-team-during-onboarding.md", "text": "https://wpnews.pro/news/questions-for-the-team-during-onboarding.txt", "jsonld": "https://wpnews.pro/news/questions-for-the-team-during-onboarding.jsonld"}}