Onboarding Plan Skill

Onboarding Plan Skill

Creates a complete, structured onboarding plan tailored to a specific role — covering the first 90 days with clear milestones and success criteria.

Required Inputs

• Role and level of the new hire
• Team and manager
• Key stakeholders they will work with
• Top 3 priorities for their first 90 days
• Tools and systems they will need access to
• Company stage (startup / scaleup / enterprise)

Output Structure

Onboarding Plan: [Name] — [Role]

Start date: [Date] | Manager: [Name] | Buddy: [Name]

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Before Day 1 (Manager checklist)

• IT setup: laptop, accounts, email, Slack, key tools
• Access provisioned to key systems
• First week calendar blocked with key meetings
• Buddy assigned and briefed
• Welcome message sent with Day 1 logistics

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Week 1: Orient

Theme: Listen, learn, do not act yet.

Day	Focus	Key activities
Day 1	IT setup, team intro	1:1 with manager, team lunch
Day 2	Product deep dive	Demo, key docs to read
Day 3	Process and tools	Shadow key workflows
Day 4	Stakeholder intros	3-4 intro 1:1s
Day 5	Week 1 debrief	Check-in, questions logged

Week 1 milestone: Can describe what the company does, the team role, and their top 3 priorities.

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Days 8-30: Learn

Learning goals:

• Deep understanding of product from customer perspective
• Know key metrics the team is measured on
• Understand current projects and status
• Map key stakeholder relationships
• Complete all compliance/HR training

30-day milestone: All stakeholder 1:1s complete. 2-3 early observations shared with manager.

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Days 31-60: Contribute

Goals:

• Own at least one project end-to-end
• Make one meaningful contribution
• Build cross-functional relationships
• Identify one process improvement

60-day milestone: Delivered one tangible output. Manager says "this person is contributing."

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Days 61-90: Lead

Goals:

• Operating independently on core responsibilities
• Has formed and shared a point of view on priorities
• Building reputation with key stakeholders

90-day milestone: Ready for formal review. Clear 6-month plan in place.

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90-Day Review Questions

Manager: Meeting expectations? What to double down on? What to develop? New hire: Have the clarity, tools, support needed? What surprised you? What would you change about onboarding?

Quality Checks

• Before Day 1 manager checklist is complete (IT, access, buddy, calendar)
• Each phase (orient/learn/contribute/lead) has a clear milestone
• 90-day review questions are included for both manager and new hire
• Plan is tailored to the specific role and level (not generic)
• Key stakeholder 1:1s are listed by name or role

Anti-Patterns

• Do not produce a generic plan that could apply to any role — the plan must reference the specific role, team, tools, and priorities provided, not use placeholder text
• Do not skip the Before Day 1 manager checklist — IT access and system provisioning failures on day 1 destroy first impressions and waste the new hire's first week
• Do not set milestones without distinguishing between the orient, learn, contribute, and lead phases — collapsing phases produces plans where new hires are expected to lead before they understand the product
• Do not omit the 90-day review questions — the review is the accountability mechanism for the entire plan, and skipping it makes the milestones meaningless
• Do not treat the plan as a task list — each phase should have a clear theme and a milestone that describes an observable capability, not just a set of completed activities

Example Trigger Phrases

• "Create a 30/60/90 day plan for a new [role]"
• "Write an onboarding plan for [name] starting as [role]"
• "Build a first 90 days roadmap for our new hire"