Nº 002 · STRATEGY · 30 July 2026
5 Hard Questions About Your AI Strategy
If you cannot answer these five, you do not have a strategy — you have a budget line and some enthusiasm.
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Every company has an AI strategy slide. Very few can answer five direct questions about what is actually happening. Ask these at your next leadership meeting.
1. Who owns AI in your company?
A C-level name — not a department, not a committee. If AI sits three levels down, it is not a strategy, it is a side project.
Red-flag answer: “Someone in IT… I think.”
2. How do we measure if it works?
License counts and usage stats are not results. Revenue impact, cost savings and customer satisfaction are.
Red-flag answer: “Well… 800 people have licenses.”
3. Where could an AI-first rival hurt us?
AI is not just an efficiency tool — it is a competitive weapon. If you cannot name the threat, you have not mapped it.
Red-flag answer: “We're keeping an eye on the market.”
4. Which workflows has AI actually changed?
Everyone uses AI; that is not the question. Adoption is easy. Redesigning how work gets done is where the value lives.
Red-flag answer: “We use it for emails.”
5. What data is leaving through AI?
Every prompt is an upload. Customer records, contracts, source code — pasted daily into tools you do not control. A policy is not protection if nobody checks.
Red-flag answer: “We have a policy.”
Then count the clear answers
- 5 / 5 — you're ahead of most. Keep the discipline.
- 3–4 — solid base. Close the gaps this quarter.
- 0–2 — the best time to start was yesterday. The next best is now.
The most revealing part is not the answers. It is the silences.