The 6 Questions
1. "What is our technical debt exposure in dollars?" If the CTO can't answer this, you have a measurement problem.
2. "What is our engineering innovation ratio?" Below 40% is a warning sign.
3. "What would it cost to replace our top 3 engineers?" If the answer makes you uncomfortable, you have a key person risk.
4. "What is the cost of delay for our current top priority?" This reveals whether engineering is working on the right things.
5. "What are our AI costs as a percentage of COGS?" AI costs that aren't in COGS are hidden liabilities.
6. "When is our next technical insolvency date?" If nobody knows, it might be sooner than you think.