# Questions for the Team During Onboarding

> Source: <https://simonwillison.net/2026/Mar/6/ally-piechowski/>
> Published: 2026-07-09 09:47:33+00:00

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

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