Claude Enterprise Cowork Pilot Plan

To use this plan, copy it with the "Copy page" button above or open the Google Doc version. Read the companion analysis, what the 16 November Cowork switch-on means for your Claude Enterprise rollout, for the thinking behind it.

Claude Enterprise Cowork pilot plan

A free template for CIOs, AI Ops leads, security and finance teams who run Claude Enterprise. Use it to decide what happens when Chat and Cowork unified turns on by default on 16 November 2026, run a pilot by role, and bring evidence to your steering group before you expand. It works on its own; you don't need any platform to use it.

0. Pilot details

• ☐ Organisation:
• ☐ Decision owner (usually the AI Ops lead):
• ☐ Sign-off (usually the CIO):
• ☐ Decision date (before 16 November 2026):
• ☐ Chat capability on? (yes / no)
• ☐ Cloud code execution and file creation on? (yes / no)
• ☐ Cowork or Cowork in the cloud on today? (yes / no)
• ☐ Zero data retention, HIPAA-ready or customer-managed encryption keys? (If yes, the unified experience isn't available yet. Record that and stop here.)
• ☐ Sandbox organisation available? (yes / no)

1. The decision

Pick one and write down why.

If you keep it disabled, set a date to revisit:

2. Role map

Before you turn the organisation setting on, move anyone who shouldn't have it yet to a custom role with Chat and Cowork unified turned off. New custom roles start with all capabilities, so check them too.

3. Settings review

Agree each setting before the pilot starts. Check the names against Anthropic's current admin guide.

4. Retention gaps

Custom retention covers conversations and the cloud sessions Claude starts from them. Decide how you'll handle what it doesn't cover.

• ☐ Cowork cloud sessions a member starts directly (kept until the member deletes them). Our approach:
• ☐ Scheduled tasks and their runs (keep running after the conversation that created them is deleted). Our approach:
• ☐ Cowork history stored on members' computers. Our approach:
• ☐ Memory of members who leave. Our approach:
• ☐ Members told that existing memory moves to a new memory system, and the old memory may be deleted 14 days later.

5. Spend guardrails

• ☐ Pooled group budget for the pilot (monthly amount):
• ☐ Member-level spend limit:
• ☐ Efficient mode on for the pilot role? (yes / no)
• ☐ Stop rule. If pilot spend passes this amount in a week, we will:
• ☐ Reports updated to include the Chat and Cowork unified line in every spend, token and message total
• ☐ Headcount taken from overall active users, not by adding products together

6. Pilot measures (two to four weeks)

7. Opportunity log with ICE scores

Each task people hand over and get back as finished work is a candidate opportunity. Score impact, confidence and ease from 1 to 10 and multiply them for a score out of 1,000.

8. Outcomes

Baseline each process before the team relies on the unified experience, then measure again.

9. Expand, hold or stop

Expand to the next wave only when all of these are true:

• ☐ No unresolved security or data incident from the pilot
• ☐ Spend stayed within the pooled budget, or the overspend is explained by value
• ☐ Retention gaps have an agreed approach
• ☐ At least one outcome is sampled or measured, not just estimated
• ☐ Pilot users would object if it were switched off

Decision and date:

10. Message to staff (draft)

From [date], Claude can do more than answer questions. Ask it for the finished thing: a report, an analysis or a deck. When a task needs it, Claude carries on in a secure cloud workspace and keeps going if you close your laptop. We're starting with [pilot group] and expanding in waves. Please don't put [restricted data classes] into Claude. Tell [AI Ops lead] what you hand over and what comes back, so we can back the best uses.

11. Steering group lines

• Decision on the 16 November default: [enable now / pilot by role / keep disabled], because [reason].
• Pilot: [group], [members], [dates], within a budget of [amount].
• So far: [number] opportunities logged, top ICE score [score] for [opportunity].
• Ask: approval to expand to [wave 2 group] on [date], or [decision needed].

12. Implementation notes

• Check every setting against Anthropic's admin guide before you rely on it. Names and defaults change often.
• Run the pilot in a sandbox organisation if you have one.
• Usage data can take up to two days to appear in analytics.
• If you log opportunities and outcomes in Kowalah, the free plan covers that.
• This is a planning tool, not legal or data protection advice. Agree data rules with your DPO and legal team.