Questions for the Team During Onboarding

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A quote from Ally Piechowski

Simon Willison’s Weblog

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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, How to Audit a Rails Codebase

Posted 6th March 2026 at 9:58 pm

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This is a quotation collected by Simon Willison, posted on 6th March 2026.

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