AI Context Readiness Assessment

Section 1: Foundation Context

Q1. Do you have a written company overview that explains what your business does, who you serve, and how you're different?

Yes, in a structured format (markdown, notion, or similar) that could be copy-pasted into an AI tool Yes, but it's in PDFs, slides, or scattered documents We have something informal or outdated No, it's mostly in people's heads

Q2. Are your products/services documented with features, specs, and pricing?

Yes, in structured text files an AI could easily read Yes, but in PDFs, spreadsheets, or sales decks Partially — some products better documented than others No, you'd have to ask our team

Q3. Do you have a written description of your ideal customer — who they are, what problems they have, and why they choose you?

Yes, in a clean, structured document Yes, but buried in marketing materials or presentations We know it intuitively but haven't written it down well Not really

Q4. Have you documented how you're different from competitors and why customers should choose you?

Yes, with specific proof points in a structured format Yes, but it's in sales decks or scattered notes Somewhat — we know it but it's not formalized No

Section 2: Operational Context

Q5. Are your key business processes documented (e.g., how you onboard customers, fulfill orders, handle support)?

Yes, in structured text that could guide an AI assistant Yes, but in flowcharts, PDFs, or tribal wikis Some are documented, but there are major gaps No, it's tribal knowledge

Q6. Do you have clear guidelines for how your brand should sound — tone, terminology, what to say and not say?

Yes, in a structured style guide an AI could reference Yes, but informal or buried in brand materials Informal guidelines exist but nothing written No

Q7. Is there documentation on compliance, legal constraints, or things that must/must not be communicated?

Yes, clearly documented in accessible text format Yes, but in legal documents or PDFs that are hard to extract Some, but incomplete No

Q8. Do you have documentation of who does what — roles, responsibilities, decision rights?

Yes, current and in a structured format Yes, but outdated or in HR systems/PDFs Outdated or incomplete No

Section 3: AI Readiness

Q9. How are you currently using AI tools (ChatGPT, Claude, Copilot, etc.)?

Regularly integrated into daily workflows Frequently for specific tasks Occasionally, mostly experimenting Rarely or never

Q10. When you use AI, how often do you get outputs you can use without major editing?

Most of the time — AI knows our context well Often, but still needs some adjustment Sometimes — hit or miss Rarely — outputs usually need heavy rework

Q11. Have you given AI background documents about your company to improve its outputs?

Yes, we have structured context docs we regularly use Yes, we paste in company info but it's not structured Tried it once or twice with mixed results No

Q12. What's your biggest frustration with AI tools right now?

This helps us provide more personalized guidance.

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