Most "AI readiness" checklists were written for companies with a CTO, a data team, and a procurement department. If that's not you — if you're a nonprofit of twelve, a university department, or a ten-person professional services firm — those checklists can make you feel behind before you've even started.
This one is different. It's a self-assessment you can run in 45 minutes with your leadership team and a whiteboard. It doesn't assume you'll hire anyone. It doesn't assume you'll buy a platform. It just helps you see, clearly, where AI fits today — and where it honestly doesn't yet.
The five questions
- 01Where is the real bottleneck in your work right now? (Not AI-shaped — just: where does time leak?)
- 02Who on your team is already quietly experimenting? Start there.
- 03What's one task you'd gladly have a junior analyst help with, if you could afford one?
- 04Where does a mistake cost you trust? Those tasks stay human-led.
- 05What's your honest data hygiene situation? Be specific.
Signals you're not ready yet
Some of these aren't disqualifying — they just mean you start smaller, not bigger. If three or more apply, I'd focus on foundations before tooling.
The good news: foundations are cheaper and faster than pilots. They're also what every AI investment depends on.
- 01No shared place your team actually stores documents consistently.
- 02Key processes live entirely in one person's head.
- 03Your board hasn't had a single conversation about AI this year.
- 04You've already bought a tool nobody is using.
“AI amplifies what's already true. If what's already true is chaos, you get faster chaos.”
How to use this with your team
Block 45 minutes on a Tuesday. Print the one-pager. Walk through the five questions out loud — don't let anyone fill in their own copy silently.
By the end, you should have one thing you're going to try in the next 30 days, and one thing you're explicitly not going to try yet. That's the whole deliverable.
Download the one-page version.
Print it, share it with your board, bring it to your next meeting. Free, no strings, yours to keep.
Get the PDF