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?”