01 Strategic Clarity

Which best describes your company’s current view of AI?

We haven’t formally addressed it yet We’ve experimented with tools (ChatGPT, Copilot) ad hoc We have an AI strategy on paper but haven’t operationalized it We have a working strategy and are executing against it AI is integrated into how we operate, and it’s compounding

Could you name the top 3 places AI could most impact your business in the next 12 months?

No, we haven’t analyzed this I have intuitions but no analysis Yes, but they’re scattered across departments Yes, and they’re prioritized Yes, and we’re actively executing on them

Who in your organization owns AI strategy?

No one IT / a technical leader A committee or working group A specific operations or business leader The CEO/COO with a dedicated owner reporting in

02 Operational Readiness

How well-documented are your core operational workflows?

Mostly tribal knowledge in people’s heads Some documentation exists but is outdated Documented for some teams, not others Well-documented across most of the business Documented and continuously updated

How accessible and structured is your company’s data?

Scattered, in silos, mostly unstructured Some systems are integrated, most aren’t Most data is in modern systems but not connected Core data is connected and queryable Integrated, structured, and accessible to AI tools

How does your team relate to new technology?

Resistant — change is hard here Mixed — some embrace it, others don’t Open but cautious Most adopt new tools willingly Genuinely curious; tools spread organically

03 Use Case Maturity

How many AI use cases are in production (actively used, producing measurable value)?

Zero 1–2 3–5 6–10 More than 10

What’s your largest AI win to date?

We haven’t had one yet Individual productivity (someone using ChatGPT for drafts) A single team’s workflow (e.g. marketing content) A cross-functional process improvement A measurable business outcome (revenue, cost, cycle time)

04 Investment & Capacity

What is your company’s annual revenue range?

Under $5M $5M–$15M $15M–$30M $30M–$100M $100M+

Approximate annual EBITDA?

Under $1M $1M–$3M $3M–$7M $7M–$15M Over $15M

Your appetite to invest in AI over the next 12 months?

Minimal — focused elsewhere Exploratory — small experiments Active — budget allocated, seeking the right partner Aggressive — a priority, resourced accordingly Strategic priority — board-level commitment

Who would lead an AI initiative if you launched one today?

Honestly, no one — no capacity Someone would have to be hired or contracted An existing leader could, but it’s not their core role We have the right person, partially focused on it We have a dedicated owner with capacity

05 Risk & Governance

How would you describe your AI governance?

None — no policies, no guidelines Informal — verbal guidance, no documentation A basic policy exists but isn’t enforced Documented policies, training, and oversight Mature governance with audit, monitoring, compliance

Your biggest concern about deploying AI more aggressively?

Employee resistance or job displacement Accuracy and trust in outputs Data privacy and security Cost vs. measurable value Regulatory or compliance exposure None of the above — we’re confident

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