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90-Day AI Readiness Checklist

22 questions. 5 areas. One honest look at where your business actually stands with AI.

Takes 10 minutes. No fluff. No vendor pitch. Just clarity on what you need to do next.

✓ Covers data, team, tooling & strategy
✓ Difficulty ratings on every item
✓ Instant score + priority guide
✓ No email spam. Just the checklist.

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1 — Foundation & Strategy

You can name at least 3 specific problems you're trying to solve with AI. Quick

Your leadership team agrees on what "good" looks like in 90 days. Medium

You have a budget allocated for AI tools, even if it's small. Quick

Someone internally owns the AI initiative (not just an external consultant). Medium

2 — Data & Systems

Customer and operational data lives in a structured system (CRM, ERP, database) — not just spreadsheets. Medium

You know your data quality status — clean, dirty, or unknown. Effort

You have a backup and recovery plan for critical business data. Medium

Your key systems (email, operations, CRM) can integrate with other tools via API or native integrations. Effort

3 — Team & Process

Your team has basic AI literacy — most people have used ChatGPT or a similar tool. Quick

You have documented processes for your most time-intensive workflows. Medium

Your team would support AI adoption — not resist it out of fear. Medium

You have time budgeted for training and change management — not just buying tools. Effort

4 — Tools & Technology

You know which AI tools you're already paying for (and whether they're actually being used). Quick

Your team has IT-approved ways to use AI tools — not a shadow IT situation. Medium

You have a process for evaluating new AI tools before adopting them. Quick

Your software vendors have a clear AI roadmap or AI features already released. Medium

5 — Security & Governance

You know which AI tools your team is allowed to use and which are prohibited. Quick

You have a policy for handling sensitive company or customer data in AI tools. Effort

Your team knows what AI can and can't do — including hallucinations and bias risks. Medium

You have a process for tracking AI-related decisions and their outcomes. Effort

You have reviewed or are aware of AI-related regulatory requirements in your industry. Effort

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0 Medium/Effort

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