onboarding

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

1. 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.

1. 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.

1. 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.

1. 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.

1. 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 /