If you’re hiring a chief AI officer, don’t start by asking what tools they use. Ask this instead. What real systems have you owned? Not demos, not slide decks. Systems that actually ran inside a business.
Then ask this, what broke? Because anyone who’s built real systems has failure stories, data issues, scaling problems, security concerns, bad assumptions.
And finally, ask this. How do you think about risk? AI isn’t just about capability. It’s about governance, cost, compliance, and knowing when not to automate.
If someone can’t answer those three questions clearly, you’re not hiring an AI leader. You’re hiring confidence.
