Lesson 2: The Five Rollout Decisions

Why frame the rollout as five decisions

A Claude rollout is not one large project. It is five linked decisions, each with its own owner. Treat it like commissioning an office building: you agree the floor plan before you issue door keys, and you issue keys before you write the house rules for each room.

The five decisions are:

1. Structure and identity: which plan, how the organisation is set up, how people sign in.
2. Access: which groups of people get which Claude products, and in what stages.
3. Governance: the rules for data, tools and acceptable use.
4. Spend: seats, usage limits and budget controls.
5. Visibility: how you will see adoption, usage and cost.

This lesson gives you the frame and the plan document. Later lessons fill in each decision in detail.

The five decisions and how they depend on each other

Work through the decisions in order. Each one constrains the next.

1. Structure and identity comes first. The plan you choose sets which controls exist at all. For example, Anthropic's current pricing page lists audit logs and SCIM provisioning under Enterprise, not Team. If your governance needs audit logs, that is settled here, not later.
2. Access depends on identity. You cannot give "Finance" one set of products and "Engineering" another until you know how users and groups are defined.
3. Governance depends on access. The rules you need depend on what is switched on. A team that uses chat only needs fewer rules than a team that uses connectors to company systems.
4. Spend depends on access and governance. Cost follows who has which seat and which products. Some controls also depend on structure: per-group spend limits are documented for Enterprise plans.
5. Visibility depends on all four. You can only measure what you have decided to deploy, to whom, and at what budget.

The order is a dependency order, not a strict waterfall. Expect one loop back: a governance or spend requirement can force you to revisit the plan choice in decision 1. Record the loop in the plan instead of working around it.

Do this now: write the five decisions as five headings, in this order, on a blank page.

Assign an owner and a deadline to each decision

A decision with no named owner drifts. A decision owned by a committee drifts more slowly, but still drifts.

Follow these steps:

1. Name one person per decision. Use a name, not a department. That person is accountable for the decision being made, even if others contribute.
2. List who must be consulted. Typical contributors are below.
3. Set a deadline for each decision. Work backwards from your pilot start date, and keep the dependency order: decision 1 is due first.
4. Name a sponsor who resolves disagreements between owners.

Typical owners, to adapt to your organisation:

• Structure and identity: IT administrator or identity lead.
• Access: IT administrator with the operations lead or department heads.
• Governance: security, legal or data protection lead.
• Spend: finance partner or budget holder.
• Visibility: operations lead or rollout sponsor.

In a small company, one person may own several decisions. That is acceptable. Still write the name against each line so nothing is unowned.

Example: a 60-person firm plans a pilot for 1 March. It sets structure and identity for 19 January, access for 2 February, governance and spend for 16 February, and visibility for 23 February. Each date is at or after the one it depends on.

Create the one-page rollout plan skeleton

Create one document that you will complete lesson by lesson. Keep it to one page. Detail goes in linked appendices.

1. Create a document titled "Claude Rollout Plan" in a location that all five owners can edit.
2. Add a header block:
   • Sponsor
   • Pilot start date
   • Date last verified against Anthropic's current pages
   • Version
3. Add this table:

4. Fill in Owner and Deadline today. Leave Decision made blank.
5. Use three status values only: Not started, In progress, Decided.
6. Add a short Assumptions to verify list under the table. Claude features, names and plan limits change often, so each feature you rely on goes here with the page where you checked it and the date.

Check the skeleton before you move on

Use this checklist:

• Every decision has exactly one named owner.
• Every decision has a deadline.
• No deadline falls before the deadline of a decision it depends on.
• The sponsor is named.
• The document fits on one page.
• The "Decision made" column is still empty. You have not chosen a plan or products yet.

If an item fails, fix it now. An incomplete skeleton produces an incomplete rollout.

Key takeaways

• A Claude rollout is five linked decisions: structure and identity, access, governance, spend, visibility.
• The order is a dependency order. Earlier decisions limit what later ones can do, and a later requirement can send you back to decision 1.
• Give each decision one named owner and one deadline, with deadlines that respect the order.
• Keep a one-page plan with owner, deadline, dependencies, status, decision and open questions for each line.
• Record every feature assumption with its source page and date, because plan features change.