90-Day Claude Deployment Playbook

From "we have Claude licenses" to "Claude is transforming how we work." A step-by-step guide for rolling out Claude tools across your organization.

Phase 1: Foundation (Weeks 1–2)

Get yourself productive before rolling out to others. Learn the core patterns that make Claude actually useful.

Week 1 Learn to delegate effectively

Install the Delegation Framework — paste it into your Claude Cowork Folder Instructions. Takes 2 minutes.
Practice the three questions on 5 real tasks: What exists when done? What can't change? How will I know it worked?
Notice where your prompts were vague before. This is the #1 reason Claude gives mediocre output.

Week 2 Add memory and structure

Set up the Simple Memory Pattern — create a memory.md file so Claude remembers your preferences between sessions.
Add the Plan-Before-Execute Pattern — prevents Claude from jumping into action without checking with you first.
By end of week 2, you should have 3 patterns installed: Delegation, Memory, Plan Mode.

Phase 2: Connect Your Tools (Weeks 3–4)

Link Claude to the services your team already uses. Each connector takes 10-15 minutes to set up.

Week 3 Connect your documentation hub

Add the Notion connector (if your team uses Notion) or explore other connectors in the catalog.
Test by asking Claude to search your Notion workspace and summarize what it finds.
Security note: Connectors are scoped at the account level, not workspace level. Use a dedicated integration account if your team handles sensitive data.

Week 4 Add your role-specific plugin

Browse the Suggested Bundles for your team's function (Marketing, Product, Finance, Legal, Sales, Operations).
Install the relevant Cowork plugin. Each includes pre-built slash commands for common tasks.
Test the top 3 commands on real work. Note what works and what needs customization.

Phase 3: Roll Out to Your Team (Weeks 5–8)

Now that you know what works, bring your direct reports on board.

Weeks 5–6 Onboard your direct reports

Share the Delegation Framework with your team. Have everyone paste it into their Folder Instructions.
Run a 30-minute team session: "Here are the 3 patterns I've been using and what they do."
Set a goal: each person uses Claude for at least one real task per day for two weeks.

Weeks 7–8 Connect team tools and gather feedback

Help each team member set up the connectors relevant to their work.
Collect feedback: What tasks did Claude handle well? Where did it struggle?
Start a shared document of "what works" — prompts, patterns, and workflows that your team has validated.

Phase 4: Measure and Expand (Weeks 9–12)

Prove the value and expand to other departments.

Weeks 9–10 Measure results

Survey your team: Hours saved per week? Tasks that used to take hours now take minutes?
Document 3 specific wins with before/after timelines (e.g., "monthly report went from 4 hours to 45 minutes").
Prepare a one-page summary for your CEO or leadership team.

Weeks 11–12 Expand to other departments

Share your team's wins with other department heads.
Offer to run the same 30-minute onboarding session for other teams.
Work with IT to review the security assessments for any new tools before wider deployment.
Set up the Scheduled Task Pattern for recurring work that Claude can automate.

Need help with your deployment?

I help teams go from "we have Claude licenses" to "Claude is transforming how we work" — from tool selection and security review to workflow design and team enablement.

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