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

Tags: technical-debt (https://simonwillison.net/tags/technical-debt), software-engineering (https://simonwillison.net/tags/software-engineering), rails (https://simonwillison.net/tags/rails)