Before you roll Claude Cowork out to a team, run this quick audit. Twenty-seven yes/no questions across the four things that actually decide whether a rollout sticks — licenses and access, data rules, the work you’ll point it at, and a real adoption plan. Count your yeses, check your score, and you’ll know exactly where you stand. It’s free, and there’s nothing to fill in — just download it.
What’s inside — 27 checks across 4 sections
- Licenses & Access — 7 checks
- Data & Security Rules — 7 checks
- Workflow Candidates — 6 checks
- Training & Adoption Plan — 7 checks
Free · no email required · a Word version is at the bottom of this page.
What the Checklist Covers
The full 27 live in the download. Here’s a taste — two checks from each of the four sections:
A. Licenses & Access
Can everyone actually get in, on a plan that includes Cowork, with the connectors they need?
- Everyone who will use Cowork has a Claude account on a plan that includes it.
- Connectors you need (Drive, GitHub, Slack…) are permitted by IT, at least for a pilot.
+ 5 more in the PDF
B. Data & Security Rules
Is it clear what data may go into Claude, who decides, and how output gets checked?
- There is a written rule for what data may and may not go into Claude.
- There’s a rule to review AI output before it’s shared externally or acted on.
+ 5 more in the PDF
C. Workflow Candidates
Have you picked real, recurring work to point Cowork at — and one first win you can land in week one?
- You’ve listed 3–5 recurring, time-consuming weekly tasks.
- You’ve picked one “first win” simple enough to succeed in week one.
+ 4 more in the PDF
D. Training & Adoption Plan
Is someone actually driving adoption, with time booked, wins shared, and a next step after the pilot?
- One named person owns rollout (a champion) — not “everyone, eventually.”
- Leadership is aware / supportive, or you know how to make the ROI case.
+ 5 more in the PDF
How to Use It
1. Score it as a team, not solo.
Sit the people who own licenses, data policy, and the actual work in one room (or one doc) and answer the 27 questions together. The disagreements are the useful part — a “yes” IT assumes and a “no” the champion knows about is exactly what you want to surface now.
2. Count your yeses and read your band.
One point per yes, out of 27. Drop your total into the scoring bands below to see whether you’re Ready, Close, or need Groundwork first — and what the sensible next move is for each.
3. Turn the no’s into a short punch-list.
Every “no” is a rollout risk with an owner’s name on it. Assign each one and put a date on it; that list is your pre-launch plan. Prefer an interactive scored version? The readiness assessment walks you through it.
What to Do If You Score Poorly
| Your score | What it means & your next step |
|---|---|
| 22–27 Ready | Start now. You’ve got the foundations — a workshop mostly helps you move faster and get the whole team consistent from day one. See team training options → |
| 14–21 Close | A few gaps to close first — usually a data rule, a named champion, or a concrete first workflow. Close those, then roll out. Follow a 30/60/90 rollout plan → |
| Below 14 Groundwork | Foundations first. Sort licenses, access, and data rules before you invite the team in — rolling out onto shaky ground is how pilots quietly die. |
A low score isn’t a red light — it’s a to-do list. Most teams that stall don’t stall on the technology; they stall on the unglamorous stuff this checklist covers: no clear data rule, no named champion, no time actually booked to learn. Fix those first and the rollout gets much easier.
If you’re in the Groundwork band, start with licenses, access, and a written data rule — nothing else works until those are settled. If you’re Close, a structured rollout plan will close the last gaps in a few weeks. And if the missing piece is leadership buy-in, don’t guess at the business case — the one-page ROI brief makes it for you. When you’re ready to move fast with the whole team at once, that’s what live team training is for.
Frequently Asked Questions
Is the checklist really free?
Yes — it’s a free PDF download with nothing to fill in. No email, no form, no “book a call to unlock it.” Grab it, score your team, keep it. (We may add an optional emailed version later, but the download stays free.)
How is this different from the readiness assessment quiz?
Same four dimensions, different format. This checklist is the printable, score-it-as-a-team version you can mark up in a meeting. The interactive readiness assessment asks the questions for you and returns a scored report automatically — handy when you’d rather click than print.
What if we’re not ready yet?
Then it did its job. The point of a readiness check is to find the gaps before you roll out, not after. Use your score band for the next step — foundations, a rollout plan, or team training — and re-score once you’ve closed them.
Download the Checklist
All 27 checks, the scoring guide, and how to use it — free, no email required.
Claude Cowork Training for Teams
The complete free course — start it free →
Related Resources
All free resources
Browse the full resource library.
Rollout templates
Copy-paste plans, prompts, and trackers for your first 30 days.
Cowork for teams guide
The complete guide to setting Cowork up for a whole team.
Ready to Roll Out — or Want Help Doing It Right?
If your team scored well, live training gets everyone consistent fast. If it didn’t, we’ll help you close the gaps first. Either way, the next step is a conversation.
Written by Peter Velinov, Claude Certified Architect – Foundations
Claude and Claude Cowork are trademarks of Anthropic. This checklist is an independent training resource and is not affiliated with or endorsed by Anthropic.