How Ready Is Your Company for AI?
Twenty questions across six dimensions produce a scored readiness profile — and a clear picture of where to start.
- A scored profile across 6 dimensions — see exactly where you're strong and where the gaps are.
- Your biggest opportunities, mapped to specific next moves.
- A personalized video walkthrough from Shawn (optional) — a real read on your results.
Most AI initiatives don't fail in the model — they fail in the preparation. An honest AI readiness assessment looks past the hype at the things that actually determine whether artificial intelligence will pay off for your company: the state of your data, the clarity of your strategy, who owns the work, how fast you can decide, and whether your architecture can integrate AI at all.
This free assessment scores your organization across six dimensions and returns a clear readiness profile in about seven minutes. It's built from 27 years of technology leadership across Fortune 500 and growth-stage companies — the same lens a fractional CTO or fractional CAIO would bring to your first conversation.
What the AI readiness assessment measures
Readiness is not a single number — it's a profile. The assessment scores six dimensions independently so you can see exactly where you're strong and where the gaps are: Data & Infrastructure (can your data actually feed an AI system), Strategy & Alignment (has leadership defined what AI is for), Team & Talent (can someone own and run the work), Process & Governance (can you deploy AI safely and repeatably), Technology & Architecture (can your stack integrate AI), and Investment & Velocity (can you fund and decide fast enough). The final question maps the specific business processes where automation would pay off first.
Why AI readiness matters before you invest
Companies that rush into AI without the foundations spend their first budget proving the obvious: that a model trained on messy, inaccessible data produces unreliable results. The organizations that capture real value treat readiness as the first deliverable — they fix data access, define a bounded use case, and put an accountable owner in place before they build. A readiness profile turns a vague ambition into a sequenced plan, and it tells you whether your constraint is technology, talent, data, or simply decision speed.
What you get at the end
You'll see an overall AI readiness score, a band that describes where you stand (from Pre-Foundation through Execution-Ready), a per-dimension breakdown, and a map of your highest-value automation opportunities. From there you can request a personalized video walkthrough — a short, recorded read on your specific results and what a fractional CTO/CAIO engagement would do for your situation. No generic sales deck.
Frequently asked questions
What is an AI readiness assessment?
An AI readiness assessment is a structured evaluation of whether an organization has the data, strategy, team, governance, technology, and investment capacity to successfully adopt artificial intelligence. Rather than measuring AI knowledge, it measures the preconditions that determine whether an AI initiative will deliver value or stall.
How long does the assessment take?
About seven minutes. It's 20 scored questions across six dimensions plus a final opportunity-mapping question. Your progress auto-saves, so you can leave and resume without losing answers.
Is the assessment free?
Yes. The assessment and your scored results are completely free. You can optionally request a personalized video walkthrough of your results, which is also free.
Who is this assessment for?
It's built for executives, founders, and operators at mid-market and growth-stage companies who are weighing an AI investment and want a clear-eyed read on whether they're ready — and what to fix first if they're not.
What happens after I get my score?
You'll see a full readiness profile with per-dimension scores and your top automation opportunities. If you'd like, you can share a few details and receive a personalized video walkthrough explaining your results and what a fractional CTO/CAIO would prioritize for your specific situation.