# Onboarding Design

> When to activate: employee onboarding, 30/60/90 day plans, new hire experience, buddy programs, knowledge transfer, ramp metrics, remote onboarding, role readiness

- Skill: `mattakushi432/onboarding-design` (Agent Skill)
- Install (CLI): `npx skillmds@latest add mattakushi432/onboarding-design`
- Raw SKILL.md: https://api.skillmd.com/api/skills/mattakushi432/onboarding-design/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Coding & Dev Tools
- Author: Mattakushi432 (https://skillmd.com/u/mattakushi432)
- Updated: 2026-09-17
- Page: https://skillmd.com/skills/mattakushi432/onboarding-design

---


# Onboarding Design

## Onboarding Philosophy

Onboarding ends when the employee is self-sufficient and producing at full capacity — not after 2 weeks of orientation. For most roles, meaningful onboarding spans 90–180 days.

**Three outcomes of great onboarding:**
1. Employee is productive faster
2. Employee feels belonging and commits to staying
3. Company culture and expectations are absorbed correctly

---

## Pre-boarding (Before Day 1)

### Two Weeks Before Start
- [ ] Send welcome email from hiring manager (personal, not HR template)
- [ ] Ship equipment — target delivery 3+ days before start
- [ ] Set up accounts: email, Slack, GitHub, ATS, productivity tools
- [ ] Add to relevant Slack channels, meeting series, calendar invites
- [ ] Assign onboarding buddy
- [ ] Prepare 30/60/90 plan draft

### Day Before Start
- [ ] Send "Day 1 logistics" email: where to go / login, schedule, who they'll meet
- [ ] Confirm buddy knows their role and is ready
- [ ] Hiring manager: block first 30 min of Day 1 for personal welcome

---

## Day 1 Schedule Template

```
09:00 — Hiring manager welcome (30 min, 1:1)
         - Reiterate why they were hired, what success looks like
         - Walk through first-week schedule
         - Answer any early questions

09:30 — IT setup (60 min with IT or self-guided)
         - Device, accounts, VPN, password manager
         - Checklist confirmed complete

10:30 — HR admin (30 min)
         - Benefits enrollment deadline
         - Payroll, emergency contact, documentation

11:00 — Onboarding buddy intro (30 min, 1:1)
         - Buddy role: informal guide, not manager
         - Share lunch plans, office norms, unwritten rules

12:00 — Team lunch (casual, no work agenda)

13:30 — Company overview session (60 min)
         - Mission, vision, values — not slides, conversation
         - Business model, how revenue works
         - Where we are in company journey

15:00 — Role deep-dive with manager (60 min)
         - Expectations in first 30/60/90 days
         - Key stakeholders to meet
         - Resources: wikis, tools, key docs

16:00 — Free explore time
         - Read documentation, explore tools
         - Write down questions for tomorrow

17:00 — Day 1 check-in with buddy (15 min)
```

---

## 30/60/90 Day Plan Framework

### Structure
Each phase has 3 dimensions:
- **Learn** — absorb context, relationships, domain knowledge
- **Contribute** — begin producing value within defined scope
- **Connect** — build relationships needed to be effective

### Template per Phase

```
DAYS 1–30: Learn & Listen

Learn:
- [ ] Complete all onboarding modules / readings
- [ ] Shadow [specific people / meetings / processes]
- [ ] Read: [specific docs / books / repositories]
- [ ] Understand: [product, customers, competitive landscape]

Contribute:
- [ ] [Small, defined deliverable — demonstrates capability]
- [ ] [Quick win that helps the team]

Connect:
- [ ] 1:1s with: [list of 8–12 key stakeholders]
- [ ] Attend: [relevant recurring meetings]
- [ ] Join: [relevant Slack channels / communities]

Success criteria (how we'll know Day 30 went well):
- [Specific, observable outcome]

---

DAYS 31–60: Learn & Lead

Learn:
- [ ] Go deeper on [specific domain / process / technology]
- [ ] Understand [cross-functional dependencies]

Contribute:
- [ ] Own and ship: [meaningful project or deliverable]
- [ ] Propose: [at least one improvement to existing process]

Connect:
- [ ] Have informal coffee chats with [N] people outside immediate team
- [ ] Present work to [audience] — practice your voice

Success criteria:
- [Specific, observable outcome]

---

DAYS 61–90: Operate Independently

Learn:
- [ ] Self-identify remaining knowledge gaps and fill them
- [ ] Seek feedback from [stakeholders] proactively

Contribute:
- [ ] Own [full scope of role] with minimal hand-holding
- [ ] Drive [strategic initiative or project]

Connect:
- [ ] Have established cadence with key cross-functional partners
- [ ] Be the person others come to for [specific domain]

Success criteria:
- [Role is fully ramped: performance at expected pace, no manager intervention needed for routine work]
```

---

## Onboarding Buddy Program

### Buddy Selection Criteria
- Same team or adjacent team — not the direct manager
- Tenure: 6 months to 2 years (knows the ropes, remembers what it's like to be new)
- Voluntary — never assign reluctant buddies
- Strong cultural carrier — embodies company values

### Buddy Responsibilities
- Weekly 30-min 1:1 for first 60 days, then bi-weekly to Day 90
- Answer "dumb questions" without judgment
- Make introductions to informal networks (interest groups, lunch crews)
- Surface concerns to manager/HR if new hire is struggling and doesn't want to escalate directly
- Not responsible for technical training or performance management

### Buddy Recognition
- Acknowledge buddy contributions in team meetings
- Include buddy quality in performance calibration conversations (optional but meaningful)

---

## Knowledge Transfer

### Documentation Checklist for Onboarding Wiki
- [ ] Company mission, vision, values — explained in plain language
- [ ] Business model: how money is made, key metrics
- [ ] Org chart: who reports to whom, how to navigate
- [ ] Product overview: what we build, for whom, why
- [ ] Customer overview: key segments, ICP, notable logos
- [ ] Competitive landscape: top 3–5 competitors and how we win
- [ ] Tech stack overview (engineering roles)
- [ ] Key tools: list with access requests and purpose
- [ ] Communication norms: Slack etiquette, when to email vs. message
- [ ] Meeting norms: async vs. sync, how to run meetings
- [ ] Decision-making: who decides what, escalation paths
- [ ] Process guides: per-function SOPs

### "Talk to" Map
For each knowledge domain, list the go-to person:
| Topic | Go-to person | Format |
|-------|-------------|--------|
| Engineering architecture | [Name] | Async OK |
| Customer context | [Name] | Book a call |
| Finance / runway | [Name] | Async only |
| Product roadmap | [Name] | Async OK |

---

## Ramp Metrics

### Generic Ramp Milestones per Function
| Function | 30-day | 60-day | 90-day |
|----------|--------|--------|--------|
| Sales | Pipeline created, first discovery calls | First opportunity advanced to negotiation | First close or on track per quota |
| Engineering | First PR shipped | Owns a feature end-to-end | Operates independently without pairing |
| Marketing | Campaign plan delivered | First campaign live | Measurable results from owned campaigns |
| CS | Owns portfolio with backup | Full portfolio with light oversight | NRR and health score at team average |
| Finance | Completes close cycle with guidance | Leads monthly close | Owns budget model updates independently |

### 90-Day Review Structure
```
Employee self-assessment (complete 1 week before meeting):
1. What have I accomplished in my first 90 days?
2. What have I struggled with?
3. What do I need from my manager to be more effective?
4. Do I have the tools, context, and relationships I need?
5. What surprised me most about the role/company?

Manager assessment:
1. Performance vs. 30/60/90 plan — where ahead, where behind?
2. Feedback on work quality, collaboration, communication
3. Adjustments to role scope or priorities for next 90 days
4. Retention signal: is this person engaged and likely to stay?
```

---

## Remote Onboarding Additions

- Ship swag before Day 1 (creates belonging before they start)
- Day 1 all-video: no one joins audio-only on an engineer's first day
- Virtual coffee roulette: pair new hire with random team members weekly for 4 weeks
- Async video intro from CEO or team lead (Loom, 5 min max)
- Dedicated #onboarding Slack channel for new hire cohorts
- Weekly new-hire group session: answer "what do you wish you'd known?" questions
- Laptop setup guide with screen recordings, not just text
- Test all system access before Day 1 — nothing worse than 4h of IT troubleshooting on Day 1

