Questions for the Team During Onboarding

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.

6th March 2026 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 https://piechowski.io/post/how-i-audit-a-legacy-rails-codebase/ , How to Audit a Rails Codebase Recent articles 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