[Firm name] Claude Cowork rollout checklist
Replace everything in [square brackets].
Rollout details
| Item | Detail |
|---|---|
| Firm | [Firm name] |
| Rollout owner | [Name, role] |
| Pilot pair | [Partner or manager], [senior] |
| Plan | [Team or Enterprise for a firm] |
| Start date | [Date] |
1. Before you start
- Plan chosen. Cowork is included on paid Claude plans; for a firm, Team or Enterprise, because Pro and Max are personal accounts with no central admin or connector controls. Current pricing checked on Anthropic’s site on [date].
- Client data position settled: we have read the current terms for our plan, checked them against our engagement letters and privacy policy, and our AI data rules say which data may go in.
- Folders decided: Cowork gets a dedicated working folder, never the root of the client file server or anything holding credentials or personal records.
- Approval decided: we start in the mode where Claude asks before each action, and loosen it only after the pilot.
- Heavy users identified: Cowork uses far more of a plan’s allowance than chat, so daily users may need a larger seat.
2. Setup
- Plan bought and the Claude desktop app installed (local file access and browser tasks need the desktop app open).
- Dedicated working folder created: [path]. Work is copied in, not pointed at.
- First session run on a real, low-stakes task (for example, "read these three PDFs and build a comparison table"), with approval on, watching what it does.
- Connectors added deliberately, by an admin, starting with calendar and a scratch document folder.
- Each connector checked for whose permissions it uses: a connector inherits the access of the account that connects it.
- One or two document and spreadsheet skills added from the directory.
- First firm skill written once one job works reliably (for example, our workpaper naming convention or file-note format).
3. Connectors: in order
| When | Connector | Rule | Approved by and date |
|---|---|---|---|
| Week 1 | Calendar; a scratch document folder | Read and write inside the scratch folder only | [Name, date] |
| After the pilot | Xero | Read-only, connected as a user with only the access needed | [Name, date] |
| After the pilot | Read-only or forwarded batches; drafts only, no send permission | [Name, date] | |
| Not yet | Practice management ([Xero Practice Manager, FYI, Kloud Connect, AccountKit, Karbon]) | Our whole client base in one credential. Later, through a scoped integration and a restricted user | [Name, date] |
| Not yet | Ledger write access | No journals posted by an agent unsupervised | [Name, date] |
4. The first five jobs
Document-heavy, low-stakes and easy to review. Tick the ones the pilot runs and note the time saved.
| Job | What Cowork does | Run in pilot? | Time saved |
|---|---|---|---|
| Month-end prep | Builds the prep pack from last month’s checklist and this month’s exports: outstanding items, variance summary, queries to chase. | [Yes or no] | [Minutes] |
| Workpaper summaries | One-page summary of positions taken, open items and anything unusual. | [Yes or no] | [Minutes] |
| Meeting notes into file notes | A structured file note and a draft follow-up email from a transcript or rough notes. | [Yes or no] | [Minutes] |
| Template and letter drafting | Engagement letter variants, fee-increase letters, onboarding packs, from templates in the working folder. | [Yes or no] | [Minutes] |
| Client email triage, drafts only | Categorises and drafts replies for a person to send. No send permission. | [Yes or no] | [Minutes] |
5. Skip until later
- Connecting the practice management system on day one.
- Write access to the ledger.
- Scheduled, unattended tasks, especially during deadline season.
- Send or post permissions for email or any other channel.
- A firm-wide rollout in week one.
6. The rollout
| Weeks | What happens | Owner | Done |
|---|---|---|---|
| 1 to 4: pilot | Two people (a partner or manager and a senior) on two or three of the first jobs. A shared document of what worked, what did not, and actual time saved. | [Name] | [Date] |
| 5: policy | One page: what data may go in, which connectors are approved, the approval mode, and the review rule. | [Name] | [Date] |
| 6 to 8: training | The rest of the team onboarded on the jobs the pilot proved, using the firm skills. A "watch me do it" session for anyone who wants one. | [Name] | [Date] |
The review rule: nothing Cowork produces reaches a client without a person reading it end to end.
7. Review
- Connector list reviewed every quarter, and each one removed when the person who connected it leaves.
- Plan terms re-read when Anthropic changes them, and the date recorded.
- Time-saved figures from the pilot compared with the cost of the seats.
- Next jobs to add, chosen from what the team asks for: [list].
Product details change quickly; check the current Claude plans and Cowork documentation before you rely on any line here. This checklist is general information, not security or legal advice.