AI Readiness Checklist | CMIT Solutions of Silver Spring

A 10-point self-assessment for small and mid-sized business owners — check each box honestly, it takes about 5 minutes.

How to score: check a box only if you can answer “yes” confidently today. Your result appears as you go.

Part 1 — Data & Security

Do you know which AI tools your team is already using — including free personal accounts?

Unapproved “shadow AI” use is the #1 hidden risk for small businesses.

Is multi-factor authentication (MFA) enforced on email and all business apps?

AI tools inherit the security of the accounts behind them.

Do you have a written policy for what company data may (and may not) be typed into AI tools?

Customer data, financials, and contracts need clear rules.

Are sensitive files access-controlled, backed up, and quickly recoverable if something goes wrong?

AI adoption multiplies both productivity and blast radius.

Has anyone in your business used AI for real work in the last 30 days (ChatGPT, Copilot, etc.)?

Even small experiments show where AI fits your workflows.

Have you identified 2–3 repetitive tasks where AI could save time (drafting, summarizing, support, reporting)?

Concrete use cases beat vague ambitions.

Do you know which AI features are already included in tools you pay for today?

Microsoft 365, CRMs, and accounting platforms often include AI you’re not using.

Do you have one person who owns AI adoption (a champion, even part-time)?

Initiatives without an owner stall within a month.

Is your team open to a little training, and do they have time for it?

Willingness plus 30 minutes of guidance is enough to start safely.

Do you have a plan or budget for AI adoption in the next 12 months?

Even a modest, deliberate budget outperforms random tool purchases.

Your Result

Count only the ones you can answer confidently today.

8–10 · AI-READYYou have the foundations in place

5–7 · GETTING THEREClose the gaps before expanding

0–4 · NOT READY YETFix the security basics first

Book Your Free AI Readiness Assessment 30 minutes · no obligation — or simply reply to the email that brought you here and we’ll set up a short call.