AI Readiness Triage Worksheet

15 questions. Five readiness pillars.

Check every statement that's true for your business right now. Be honest — the result is only useful if it reflects reality. No one sees your answers.

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Pillar 01 AI Use Policy → Homepage: Do you have a written AI policy?

I know which AI tools my employees are currently using at work — including ones they found on their own, not ones I introduced.

Shadow AI is the norm, not the exception. If you haven't asked, assume they're using tools you don't know about.

I know what data my employees are allowed to share with AI tools — and I've told them explicitly.

Customer records, financial data, internal documents, employee information — does your team know what's off-limits?

I have reviewed the AI or data-use policies of my key vendors — the software I rely on daily — to understand how they use my business data.

Your CRM, your accounting software, your email platform — many have quietly added AI features that process your data.

Pillar 02 Opportunity Identification → Homepage: Have you mapped 3+ AI opportunities?

I can name at least three tasks in my business that take significant time but follow a predictable pattern each time they're done.

Repetitive, pattern-based tasks are the primary target for AI. If you can't name them, you haven't done the audit yet.

I have identified at least one area where I'm paying for labor that is mostly about processing, formatting, or routing information rather than judgment.

Data entry, scheduling, drafting routine emails, generating reports — these are high-value AI targets in almost every small business.

I have mapped which decisions I make repeatedly — and asked whether the information gathering for those decisions could be partially automated.

Pricing decisions, vendor selection, scheduling — when the same decision comes up weekly, the research behind it is an AI opportunity.

Pillar 03 Team AI Literacy → Homepage: Has your team received AI training?

My team understands that AI tools produce confident-sounding output that can be entirely wrong — and they know not to publish, send, or act on AI output without verification.

Hallucination isn't a bug being fixed — it's a fundamental property of how these tools work. If your team doesn't know this, you have exposure right now.

At least one person on my team has personally caught an AI tool producing incorrect, fabricated, or misleading output — and that experience has been shared with the rest of the team.

If nobody has ever caught AI being wrong, it doesn't mean it hasn't been wrong. It means nobody was looking.

My team knows the difference between tasks where AI output can be used directly with light review, and tasks where AI should only be used as a starting point for human work.

Not all AI use is equal. A draft social post and a legal document are not in the same category. Does your team know the difference for your specific business?

Pillar 04 Competitive Awareness → Homepage: Do you know what competitors are doing with AI?

I have noticed competitors producing content, proposals, or customer communications at a pace or volume that seems faster than what their team size should allow.

Speed and volume mismatches are the most visible signal that a competitor has deployed AI in their workflow. Have you seen this?

I have asked my clients or customers whether AI — in any form — has come up in their experience with other vendors or providers in my industry.

Clients often notice before you do. If they're seeing AI-powered speed or personalization from others, it's already a comparison point.

I understand how AI adoption in my specific industry is likely to affect pricing pressure, turnaround time expectations, or customer service standards over the next two years.

AI doesn't change every industry the same way or at the same pace. Do you know what it means specifically for yours?

Pillar 05 Adoption Planning → Homepage: Do you have a 12-month plan with accountability?

There is a specific line item or informal budget allocation for AI tools in my current business expenses — even if it's just $50/month for a subscription.

If AI isn't in the budget at all, it isn't really in the plan. A budget line — any budget line — signals intention.

There is one person in my business — even if it's me — who is explicitly responsible for staying current on AI tools relevant to our work and reporting back to the team.

Without a named owner, AI adoption stays in the "we should look into that" category indefinitely.

I have set at least one concrete AI-related milestone for my business this calendar year — something specific enough that I'd know in December whether I hit it or not.

"We want to use more AI" is not a milestone. "We will have AI handling first-draft customer emails by Q3" is.

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Find out exactly where your AI readiness breaks down.

15 questions. Five readiness pillars.

Take it with you.

The Roadrunner Cybersecurity,
AI, and Privacy Brief

Find out exactly where your AI readiness breaks down.

15 questions. Five readiness pillars.

Take it with you.

The worksheet shows you where the gaps are.

The Roadrunner Cybersecurity,AI, and Privacy Brief

The Roadrunner Cybersecurity,
AI, and Privacy Brief