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]
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
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.
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.
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."
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.
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"