Questions for the Team During Onboarding

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

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