Use this skill when designing onboarding programs, creating 30/60/90 plans, setting up buddy systems, or measuring ramp effectiveness. Triggers on onboarding plans, 30/60/90 day plans, buddy programs, knowledge transfer, ramp metrics, new hire experience, and any task requiring employee onboarding design or optimization.
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name
onboarding
version
0.1.0
description
Use this skill when designing onboarding programs, creating 30/60/90 plans, setting up buddy systems, or measuring ramp effectiveness. Triggers on onboarding plans, 30/60/90 day plans, buddy programs, knowledge transfer, ramp metrics, new hire experience, and any task requiring employee onboarding design or optimization.
When this skill is activated, always start your first response with the 🧢 emoji.
Onboarding
Onboarding is the structured process of integrating a new employee into their role,
team, and organization. Done well, it accelerates time-to-productivity, builds
psychological safety, reduces early attrition, and establishes patterns of performance
that persist for years. Done poorly - or left to chance - it costs the equivalent of
6-12 months of salary in lost productivity and replacement risk. This skill covers the
full onboarding lifecycle: pre-boarding preparation, first-week experience design,
30/60/90 day milestone planning, buddy program setup, knowledge transfer methods,
role-specific tracks, and the metrics that prove it is working.
When to use this skill
Trigger this skill when the user:
Needs to design or improve an employee onboarding program from scratch
Wants to create a 30/60/90 day plan for a new hire or for themselves
Is setting up a buddy or mentor program for new employees
Needs to build a knowledge transfer plan for a departing or arriving team member
Wants to design or schedule a new hire's first week in detail
Is defining ramp milestones, success metrics, or productivity benchmarks
Needs to create role-specific onboarding tracks (engineering, product, sales, etc.)
Wants to collect, analyze, or act on onboarding feedback
Do NOT trigger this skill for:
General performance management or PIP processes unrelated to new hire ramp
Long-tenured employee L&D programs or career development outside ramp context
Key principles
The first week shapes retention - Research consistently shows that employees
decide whether to stay within the first 90 days, with the first week being the
highest-leverage window. Investment in day-one logistics, social connection, and
clarity of purpose has outsized ROI compared to any later intervention.
Buddy beats documentation alone - A structured buddy program accelerates ramp
2-3x compared to self-directed reading of wikis and onboarding docs. Buddies provide
context that documentation cannot: unwritten norms, who to ask for what, and
psychological safety to ask "dumb" questions. Documentation supports; humans accelerate.
Clear milestones reduce anxiety - New hires' biggest stressor is not knowing
whether they are performing at the expected level. Explicit milestones at 30, 60, and
90 days replace vague expectations with a shared contract. Both sides know what
success looks like.
Onboarding is everyone's job - The manager owns the plan. The buddy owns the
relationship. The team owns the culture. HR owns the logistics. When any one party
treats onboarding as someone else's problem, the new hire experiences the gap. Define
owners explicitly for every onboarding component.
Measure time-to-productivity - "How did onboarding feel?" is a useful signal but
not the goal. The goal is a productive, engaged employee. Track leading indicators:
time to first meaningful contribution, 30/60/90 milestone completion rate, buddy
check-in frequency, and 90-day retention rate. Use these to continuously improve the
program.
Core concepts
Onboarding phases
Pre-boarding -> First Week -> 30 Days -> 60 Days -> 90 Days -> Alumni Check-in
| | | | | |
Paperwork, Orientation, Learn the Contribute Own work, Assess
access, team, domain, independently validate long-term
welcome kit culture, tools, with some ramp fit
role clarity processes support complete
Each phase has distinct goals. Pre-boarding removes first-day friction. The first week
builds belonging and orientation. Days 1-30 focus on learning. Days 31-60 shift to
contributing. Days 61-90 focus on independent ownership. The alumni check-in at
six months closes the loop.
Ramp milestones
Milestone
Engineering
Product
Sales
Day 1
Dev environment working, first PR open
Product tour complete, first user interview scheduled
CRM access, first shadow call completed
Day 30
First shipped feature (small)
First spec drafted
First discovery call solo
Day 60
Owns a component or service
Shipped first iteration
First deal in pipeline
Day 90
Independent contributor
Roadmap item owned end-to-end
First closed deal or on-track quota
Knowledge transfer methods
Method
Best for
Effort
Durability
Pair sessions
Complex processes, judgment calls
High
High
Shadowing
Customer-facing roles, decision-making
Medium
Medium
Recorded walkthroughs
Tooling, repeatable processes
Medium
High
Written runbooks/wikis
Reference material, SOPs
High
High
Lunch-and-learns
Culture, team history, strategy context
Low
Low
Codelab or guided projects
Technical skills, hands-on learning
High
High
Buddy vs mentor
Dimension
Buddy
Mentor
Primary purpose
Day-to-day guidance, social integration
Long-term career development
Relationship duration
First 90 days (ramp period)
Ongoing, often years
Topics covered
How things work here, who to ask, norms
Career path, skill development, strategy
Seniority match
Peer-level (1-2 years ahead)
Senior, cross-functional welcome
Formal structure
Weekly check-ins, defined agenda
Flexible, driven by mentee needs
Common mistake
Assigning a buddy with no guidance or agenda
Treating mentor as a substitute for a manager
Common tasks
Create a 30/60/90 plan
A 30/60/90 plan is a written contract between the new hire and their manager defining
what success looks like at three checkpoints. It should be co-created, not handed down.
Template:
Name: [Employee name]
Role: [Job title]
Manager: [Manager name]
Start date: [Date]
Last updated: [Date]
--- FIRST 30 DAYS: Learn ---
Theme: Understand the people, product, processes, and tools.
Goals:
[ ] Complete all required onboarding sessions and access setup
[ ] Meet every direct teammate (1:1, 30 min each)
[ ] Shadow 3 customer calls / user sessions / team ceremonies
[ ] Read and summarize the team's top 3 strategy docs
[ ] Complete [role-specific technical or domain training]
[ ] Deliver one small, scoped contribution (PR, spec section, call debrief)
Success looks like: I can describe what we do, why, and how. I have met everyone
and know who owns what. I have shipped something small.
--- DAYS 31-60: Contribute ---
Theme: Apply learning to real work with support.
Goals:
[ ] Own one project or workstream end-to-end (with buddy support)
[ ] Drive at least one team meeting or demo
[ ] Identify one process or area that could be improved (documented, not just noted)
[ ] Receive a mid-ramp check-in from manager; adjust plan if needed
[ ] [Role-specific milestone - see references/thirty-sixty-ninety.md]
Success looks like: I am adding value independently on real work. My manager
trusts me to take on a full project. I am proactively unblocking myself.
--- DAYS 61-90: Own ---
Theme: Operate independently and start contributing beyond assigned work.
Goals:
[ ] Deliver [role-specific 90-day output - see references/thirty-sixty-ninety.md]
[ ] Propose one improvement that was not on the original plan
[ ] Complete a 90-day self-assessment and share with manager
[ ] Identify gaps in onboarding; document feedback for the program
[ ] Begin mentoring the next new hire if possible
Success looks like: My manager considers me fully ramped. I am operating at full
capacity and contributing to team direction, not just executing tasks.
--- REVIEW ---
30-day check-in date: ___________ Status: On track / Needs adjustment
60-day check-in date: ___________ Status: On track / Needs adjustment
90-day check-in date: ___________ Status: Ramped / Extended ramp needed
See references/thirty-sixty-ninety.md for role-specific templates (engineering,
product, sales).
Design a buddy program
A buddy program without structure degrades into an occasional Slack DM. Structure it.
Program setup:
Selection criteria for buddies:
- Tenure: 1-3 years (long enough to know the culture; recent enough to remember ramp)
- Voluntary: Never assign an unwilling buddy
- Same team: preferred for role context; cross-team is acceptable for culture
- Not the direct manager: removes hierarchy dynamics from the relationship
Buddy responsibilities:
Week 1: Daily check-in (15 min). Answer "how does X work here?" questions.
Give a personal tour of tools, channels, and unwritten norms.
Week 2-4: Weekly 1:1 (30 min). Review 30-day milestones together.
Introduce new hire to 3-5 people outside their immediate team.
Month 2-3: Bi-weekly check-in. Shift from "how things work" to "how to thrive."
Buddy training (required before assignment):
- What a buddy is and is not (not a second manager)
- Common new hire anxieties and how to normalize them
- What to escalate vs. handle vs. let the manager handle
- How to give feedback without undermining the manager relationship
Program health metrics:
- Buddy assignment rate: target 100% within Day 1
- Check-in completion rate: target > 80% of scheduled check-ins completed
- New hire satisfaction with buddy: survey at Day 30 and Day 90 (target > 4/5)
- Buddy NPS: would the buddy volunteer again? (target > 70%)
Build a knowledge transfer plan
Use when a key employee is departing, transitioning roles, or onboarding into a complex
domain that requires deliberate knowledge capture.
Plan structure:
Knowledge owner: [Name, role]
Knowledge recipient(s): [Names, roles]
Transfer period: [Start date] to [End date]
Facilitator: [Manager or program owner]
Step 1: Inventory (Day 1-3)
- List every recurring task, project, and decision owned by the knowledge owner
- Classify each as: documented / undocumented / tacit (judgment-based)
- Prioritize by: criticality x undocumented status
Step 2: Document undocumented items (Day 3-10)
- Knowledge owner writes runbooks/SOPs for top 5 critical undocumented items
- Minimum viable doc: purpose, inputs, steps, outputs, failure modes, escalation
Step 3: Shadow and pair sessions (Day 5-15)
- Recipient shadows knowledge owner for all priority-1 tasks
- Pair on at least one real execution of each critical process
Step 4: Reverse shadow (Day 10-20)
- Recipient leads; knowledge owner observes and corrects
- Knowledge owner must not jump in unless the recipient is about to cause real harm
Step 5: Independent execution + Q&A window (Day 15-30)
- Recipient owns all transferred tasks
- Knowledge owner available for questions but does not step in proactively
- All Q&A captured in writing and added to documentation
Step 6: Sign-off (Day 30)
- Both parties confirm transfer is complete
- Any gaps documented as open items with owners and due dates
Create a first-week schedule
The first week is too important to leave unscheduled. A blank calendar signals
disorganization. A packed calendar with no breathing room signals poor culture.
Aim for 60% structured, 40% self-directed.
Day-by-day template:
DAY 1 - MONDAY: Orientation and belonging
AM: Manager welcome (30 min) - role context, team culture, what success looks like
IT and access setup (60 min) - do not leave new hire alone with this
Team intro lunch or coffee chat
PM: Buddy intro (30 min)
Self-directed: read team charter, team wiki, product tour
End of day: manager checks in - "how was today, what questions do you have?"
DAY 2 - TUESDAY: Product and context
AM: Product deep-dive session with PM or product lead (60 min)
Customer story session - watch 2-3 recorded calls or interviews
PM: 1:1s with 2 teammates (30 min each)
Self-directed: explore product as a user, document first impressions
DAY 3 - WEDNESDAY: Process and tools
AM: Team ceremonies walkthrough (standup, sprint planning, retro - observe at least one)
Tooling walkthrough with buddy or team member
PM: Shadow a key team workflow (code review, design review, sales call, etc.)
Self-directed: set up local environment or workspace
DAY 4 - THURSDAY: Deeper domain
AM: Domain deep-dive (technical architecture, market landscape, customer segment)
1:1s with 2 more teammates
PM: First small contribution scoped and started (PR, doc edit, research task)
Self-directed time to work on first contribution
DAY 5 - FRIDAY: Reflection and connection
AM: First contribution review or pair session
1:1 with manager (30 min) - week-in-review, questions answered, plan confirmed
PM: Team social or informal gathering if available
Self-directed: write personal 30-day plan draft; send to manager
Set ramp milestones and metrics
Ramp health dashboard (track monthly):
Metric
How to measure
Target
Time to first contribution
Days from start to first shipped output
< 14 days
30-day milestone completion
% of 30-day plan items completed on time
> 80%
60-day milestone completion
% of 60-day plan items completed on time
> 75%
90-day retention rate
% of new hires still employed at 90 days
> 95%
Buddy check-in completion
Scheduled check-ins completed / scheduled
> 80%
New hire satisfaction score
Survey at Day 30 and Day 90 (1-5 scale)
> 4.0
Manager confidence score
Manager rates new hire confidence at 90 days (1-5)
> 3.5
Onboarding NPS
Would new hire recommend this onboarding to a peer?
> 50
Lagging indicators to watch:
6-month and 12-month retention by cohort
Time-to-first-promotion compared to pre-program baseline
Performance review scores at first annual review
Design role-specific onboarding tracks
Generic onboarding handles the universal layer (culture, tools, HR, company strategy).
Role-specific tracks handle the domain layer. Run them in parallel after Day 2.
Track structure:
Track name: [Role] Onboarding Track
Duration: 30 days (runs alongside general onboarding)
Owner: Hiring manager or team lead
Buddy: Senior practitioner in the same role
Week 1: Orientation to the discipline
- How this role works at [company] vs. industry norms
- Key tools, systems, and workflows
- Top 5 resources every [role] must read/watch
Week 2: Observation
- Shadow 3+ experienced practitioners in real work
- Attend all relevant team rituals as observer
- Review 3+ examples of strong prior work output
Week 3: Guided participation
- Take on one real task with close support
- Pair on at least 2 sessions with experienced practitioner
- Draft your first real output (review before sending/shipping)
Week 4: Supported independence
- Own first real output end-to-end
- Share with team; receive structured feedback
- Self-assess against role expectations; discuss with manager
See references/thirty-sixty-ninety.md for engineering, product, and sales-specific
milestone definitions.
Gather and act on onboarding feedback
Survey cadence:
Day 7 survey (5 questions, < 3 min):
1. I felt welcomed and expected on my first day (1-5)
2. I have the tools and access I need to do my job (1-5)
3. I understand what is expected of me in the first 30 days (1-5)
4. My buddy has been helpful (1-5)
5. What is the one thing we should improve about the first week? (open text)
Day 30 survey (8 questions, < 5 min):
+ Progress and clarity scores
+ Buddy program quality
+ Manager support quality
+ Open: what is still unclear or missing?
Day 90 survey (10 questions, onboarding NPS):
+ Full ramp assessment
+ Would you recommend this onboarding? (NPS)
+ What was most valuable?
+ What should be cut or changed?
Feedback action loop:
Review survey results weekly for new cohorts
Flag scores below 3.5 immediately for manager follow-up
Aggregate qualitative feedback by theme each quarter
Update onboarding program materials based on recurring themes
Publish quarterly onboarding health report to leadership
Anti-patterns
Anti-pattern
Why it is wrong
What to do instead
"Sink or swim" onboarding
Top performers who self-rescue are the minority; most lose 30+ days of productivity and many leave quietly
Build a structured 30/60/90 plan; assign a buddy; schedule the first week before Day 1
Death by documentation
A 200-page wiki read alone in a room does not transfer context, relationships, or judgment
Use docs as reference material; use people for learning; pair first, document second
Buddy assigned with no guidance
Buddy defaults to "let me know if you have questions" which new hires rarely use
Give buddies a structured checklist, a meeting cadence, and clear scope of the role
Onboarding ends at Day 1 orientation
The hardest part of ramp is Week 2 onward when formal orientation is over but new hire is not yet producing
Structure the full 90-day period; schedule explicit milestone check-ins at 30/60/90
Generic plan for all roles
A generic plan leaves the new hire without the domain context, tooling access, or role-specific relationships they need
Layer a role-specific track on top of the general onboarding from Day 2 onward
No feedback loop
Onboarding problems repeat cohort after cohort because no one aggregates and acts on new hire feedback
Run Day 7, Day 30, and Day 90 surveys; assign an owner to review results and update the program
Gotchas
Buddy assignment without a structured agenda defaults to silence - Simply assigning a buddy and announcing it via Slack produces almost zero value. Without a week-by-week check-in cadence, a topic guide, and a clear scope ("help them navigate norms, not replace the manager"), buddies default to "let me know if you have questions" - which new hires almost never use. Require a kick-off meeting template and a check-in schedule at the time of assignment.
30/60/90 plans handed down top-down destroy ownership - A plan written by the manager and handed to the new hire on Day 1 signals "execute this" rather than "own this." Co-create the plan in the first two weeks. The new hire's input on what they need to learn surfaces blind spots and creates accountability that top-down plans cannot.
IT access delays on Day 1 damage the psychological contract - If a new hire spends their first day waiting for laptop setup, email access, or tool provisioning, it signals disorganization and devalues the hire. All access requests must be submitted at offer acceptance, not at start date. Build a pre-boarding access checklist with a manager-owned SLA.
Role-specific onboarding scheduled after general onboarding creates a gap - Starting the engineering or sales track in Week 3 (after "general onboarding is done") leaves new hires directionless during the most critical learning weeks. Run general and role-specific onboarding in parallel from Day 2.
Onboarding NPS surveys sent too late miss the critical signal - A Day 90 survey tells you what you could have fixed 80 days ago. Add a Day 7 pulse survey (5 questions, 3 minutes) that flags problems while they can still be addressed for that cohort.
References
For detailed role-specific templates, load the relevant file from references/:
references/thirty-sixty-ninety.md - 30/60/90 day plan templates for engineering, product, and sales with milestone definitions and success criteria
Only load a references file when the current task requires it.
Companion check
On first activation of this skill in a conversation: check which companion skills are installed by running ls ~/.claude/skills/ ~/.agent/skills/ ~/.agents/skills/ .claude/skills/ .agent/skills/ .agents/skills/ 2>/dev/null. Compare the results against the recommended_skills field in this file's frontmatter. For any that are missing, mention them once and offer to install:
