AI Readiness Assessment for Small Business
An AI readiness assessment is a short, structured review of how your business uses AI today and how ready it is to use more. It finds the AI tools staff already use (shadow AI), checks where company data could leak, reviews access and policies, and ends with a prioritized plan for what to fix and what to adopt next.
25+ years in technology and security. No cost, no obligation.
What is an AI readiness assessment?
It is a security-first review of your people, data, tools and policies before (or while) you roll out AI. Most small businesses are already using AI: someone pastes a contract into a chatbot, someone else turns on a meeting note-taker, a vendor quietly adds an AI feature. An AI readiness assessment makes that visible and turns it into decisions you can act on. It also works as an AI security assessment for small business and an AI risk assessment in one engagement.
What does an AI readiness assessment include?
- Shadow AI discovery. We identify the AI apps, browser extensions and built-in AI features your team is actually using. Learn more in our guide to shadow AI discovery.
- Data exposure review. Which files, mailboxes and shared drives AI tools can reach, and where oversharing could surface sensitive data. If you use Microsoft 365, see Microsoft 365 Copilot security risks.
- Access and identity check. Accounts, permissions and sign-in settings that matter most once AI tools are connected to your systems.
- Policy and governance gaps. Whether you have an AI acceptable use policy and clear rules staff can follow, aligned to frameworks such as the NIST AI Risk Management Framework.
- AI risk register. A plain-English list of risks, ranked by likelihood and impact.
- Prioritized roadmap. Quick wins for the next 30 days, then the AI use cases worth adopting safely.
Who is an AI readiness assessment for?
- Small and mid-sized businesses whose staff already use ChatGPT, Copilot, Gemini or similar tools.
- Owners who want to adopt AI but are not sure what is safe to connect to company data.
- Teams preparing for a Microsoft 365 Copilot rollout (see our Copilot readiness assessment guide).
- Startups and growing companies that need answers for customers, investors or insurers about how they use AI.
How does the AI readiness assessment work?
- Free 30-minute call. We learn your business, tools and goals, and confirm scope.
- Discovery. A short questionnaire, a few interviews and a review of your key systems and settings.
- Analysis. We map shadow AI, data exposure and policy gaps into a risk register.
- Readout. You get a written report and a walkthrough of the prioritized roadmap.
- Next steps (optional). We can help put the fixes in place, from policy to AI governance to private AI options.
How is an AI readiness assessment different from an AI security assessment?
An AI security assessment focuses on risk: data leakage, access and attacks such as prompt injection. An AI readiness assessment covers that and adds the business side: which AI uses are worth it, what policies you need, and in what order to move. Our article on the AI security assessment explains the security checks in more depth.
What do you need before the assessment?
Very little. A list of the main business apps you use, an admin contact for Microsoft 365 or Google Workspace, and an idea of which AI tools you want to use. If you have no AI policy yet, start with our free AI acceptable use policy template.
Frequently asked questions
How long does an AI readiness assessment take?
It depends on the size of your team and systems. We confirm scope and timing on the free 30-minute call, before any work starts.
Is shadow AI discovery included?
Yes. Finding the AI tools and features your staff already use is one of the first steps in every assessment.
Will this make us compliant with a regulation or framework?
No assessment can promise that. Our recommendations are aligned to recognized frameworks such as the NIST AI Risk Management Framework, and we flag where you may need legal advice.
Do you need access to our data?
We review settings, permissions and how tools are configured. We do not need to copy your business data, and we agree access up front.
What happens after the assessment?
You get a prioritized roadmap. You can run it yourself or ask us to help with policy, governance, secure AI automation or private AI.
Questions? Email sales@jrsdi.com or call (202) 892-7189.