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Self-Assessment

The AI Readiness Checklist for leadership teams.

Fifteen yes/no questions across five areas: data rules, current AI usage, knowledge hygiene, ownership, and workflow candidates. Ten minutes with your leadership team and a clear read on where you stand.

The fifteen questions

Count your honest yeses. Every question is answerable in one leadership meeting — if a question starts a debate, that's a no.

Data rules

  • Do you have a written rule for what data can never go into a public AI tool?
  • Could every employee name the categories that are off-limits — client financials, privileged material, patient or proprietary data?
  • Has anyone checked what your current vendors' AI features already do with your data?

Current usage

  • Do you know which AI tools your team actually used this week, sanctioned or not?
  • Is there an approved-tools list people can find without asking?
  • If an employee pasted client data into a chatbot today, would you ever find out?

Knowledge hygiene

  • Could a new hire — or a new system — find the current version of your ten most important documents?
  • Does every critical document have a named owner who keeps it current?
  • Is there one place company knowledge is supposed to live, and does anyone believe it?

Ownership

  • Is there one name — not a committee — attached to AI decisions?
  • Does that person report AI progress to leadership on a fixed cadence?
  • If an AI tool breaks a workflow, is it clear who owns the fix?

Workflow candidates

  • Can you list the three workflows that consume the most expert hours?
  • Do you know what an hour of those experts' time actually costs you?
  • Has any AI pilot you've run been measured against a number you'd defend to your board?

How to read your score

12–15 yes

You're readier than most. The question isn't whether to move — it's sequencing: which workflow first, and who owns the roadmap.

6–11 yes

The most common band. You have real foundations and real gaps; this is exactly what the AI Executive Assessment is built to score and sequence.

0–5 yes

You have shadow AI, not an AI strategy. Start with data rules and a single owner — before any tool decision.

Get the scored version

The PDF adds the scoring worksheet and how to run the exercise with your leadership team without it turning into a debate.

You'll get the checklist plus two short follow-up emails on how to score it. No newsletter, no drip campaign.

Prefer no form? Open the checklist PDF directly — the follow-up emails just cover how to score it.