CEO AI Questions

Strategy & Competitive Advantage

• Which 2–3 AI use cases could create a defensible edge for us in the next 6–12 months—not just incremental efficiency?
• Are we trying to differentiate (new AI-powered offerings) or optimize (cost, speed, quality)? What’s the mix?

ROI, Measurement & Prioritization

• What’s the quantified business case for each use case (time saved, conversion lift, error reduction, margin impact)?
• What’s the fastest path to a live pilot that can prove value in 60 days?
• What guardrails will we use to kill or scale pilots (clear stage-gate metrics)?

Data & Privacy

• What proprietary data do we have that, if organized, would unlock unique value?
• Where is that data today (quality, coverage, access), and what’s the minimum to be “AI-ready”?
• What are our privacy, PII, and customer consent requirements—and how do we prevent accidental data leakage?

People, Org & Change Management

• Which roles are most impacted in the next year, and how do we reskill rather than replace?
• Who owns AI internally (single throat to choke) and what governance forum do we need?

Technology & Build/Buy

• Do we build with APIs on top of leading models, buy platforms, or adopt domain-specific tools? What’s our decision rubric?
• How will we avoid vendor lock-in (model abstraction, bring-your-own-key, data portability)?

Risk, Compliance & Brand

• What could go wrong publicly (hallucinations, bias, IP misuse), and what’s our mitigation plan?
• How do we implement human-in-the-loop and audit trails for high-risk outputs?

Security

• How do we prevent prompt injection, data exfiltration, and shadow AI tools?
• What’s our policy for employee use of public AI tools vs. approved internal tools?

Financials & Budget

• How do we stage investments to de-risk spend while building capabilities?

Operations & Scalability

• What SLAs and monitoring do we need once workflows are in production (quality, drift, cost per task)?
• How will we continuously evaluate model performance and swap models without major rework?

Roadmap & Governance

• What’s our 30/60/90-day plan to ship one high-confidence win and a 12-month roadmap for capability building?
• What principles guide AI decisions (ethics, transparency, human oversight, measurable value)?