Onboard New Hires

Instructions

1. Send philosophy and context before start date

   • Create a "welcome to the company" document explaining your values, decision-making approach, how you communicate
   • Share 3-5 key company documents (strategy, values, team structure, market positioning)
   • Send link to architecture/codebase (technical roles) with "don't memorize, just orient"
   • Include: time zone of team members, Slack norms (response time expectations), calendar setup
   • Signal: "We want you ready on day one; here's what you should know going in"

2. Design immediate belonging through pairing

   • Don't let first day be sitting alone reading docs
   • Assign an onboarding buddy (peer level, ideally someone they'll work closely with)
   • First 5 days: 2-4 hours daily pairing where buddy explains system, answers questions, normalizes asking
   • Pairing is not about productivity; it's about belonging and accelerated learning
   • Buddy should say: "Here's how I do this. Here's how others do it. What feels right for you?"

3. Teach golden rituals by first Friday

   • Show how you actually work: daily standup format, how you write PRs or share updates
   • Introduce them to your async communication style (Slack threads? Email? Notion docs?)
   • Explain your decision-making process: who talks to whom before deciding?
   • Show the calendar rhythm: all-hands cadence, 1:1 schedule, planning cycles
   • Golden rituals = how we work together; teaching them early prevents later friction

4. Conduct a listening tour in first 30 days

   • Schedule 30-minute 1:1s with 8-12 key people across company
   • Frame: "I want to understand the company from your perspective"
   • Ask: What's working? What frustrates you? What do you wish someone would fix?
   • Listen 80% of the time; don't pitch or defend
   • Take notes; synthesize into "state of the union" they present back to leadership
   • Shows: We value your perspective; your voice matters here

5. Define success at 90 days, 1 year, and 2 years

   • Week 1: Draft 90-day success vision together (what does "ramped" look like?)
   • Month 1: Define what good looks like in their role after 90 days
   • Be specific: "You've shipped 3 features" not "you're productive"
   • Include relationship metrics: "You've worked with sales team; they know you"
   • 1-year vision: Where do they grow into? What new skills?
   • 2-year vision: Where are they on trajectory? Leadership, depth, scope?

6. Engineer early wins for visibility

   • In first 30 days, identify 1-2 projects where they can ship something visible
   • Early wins should be: achievable (don't set them up to fail), visible (team sees them), legitimate (not make-work)
   • Examples: bug fix they understand, small feature, documentation improvement, process tweak
   • After first win, suggest: "You should present this to leadership next week"
   • Visibility + early win = they feel like they're contributing, not learning

7. Have "relationship design" conversation early

   • Ask: What kind of communication do you prefer? Slack or calls? Sync or async?
   • Ask: How often do you want 1:1s? What should we talk about?
   • Ask: What do you need from me to feel supported?
   • Ask: What feedback do you want? How do you like to receive it?
   • Document their preferences; revisit monthly
   • Signals: We care about how you work, not just what you produce

8. Schedule regular 1:1s and hold them sacred

   • 30 minutes, weekly, first 90 days (no cancellations)
   • Month 1: Listening mode (how's the ramp? any blockers? how's belonging?)
   • Month 2: Early work review (shipping things? what's hard? what skills to build?)
   • Month 3: Ownership conversation (what are you owning now? where do you want to grow?)
   • Beyond 90 days: Shift to career development, not logistics

9. Create working agreements together

   • How do we make decisions? (consensus, trust your judgment, ask first?)
   • What does "done" look like? (code review standards, quality bar, testing expectations)
   • Communication norms: response time, escalation path, when to DM vs. public Slack
   • Conflict resolution: how do we disagree? Who do we ask if we're stuck?
   • Document it; refer back when friction appears
   • Collaborative working agreements prevent later resentment

10. Avoid over-promising during hiring

    • If you said "you'll lead this initiative," have that conversation month 1
    • If you promised flexibility you can't deliver, acknowledge the gap now
    • If you oversold stability and reality is chaos, reset expectations
    • Broken promises early destroy trust; honesty early builds it
    • Course-correct in 1:1 before they feel misled

Output Format

ONBOARDING PLAN — [New Hire Name]

Role: [Position Title]
Start Date: [Date]
Manager: [Your Name]
Onboarding Buddy: [Buddy Name]

BEFORE START DATE (Pre-onboarding)
──────────────────────────────────
□ Send welcome email with:
  - Company values and working philosophy
  - 3-5 key company documents (strategy, team structure, market positioning)
  - Slack/communication norms
  - Time zone & team member locations
  - First day logistics (where to be, who to meet, what to bring)

□ Set up:
  - Laptop, desk setup, access credentials
  - Slack, email, calendar
  - Code/project access (technical roles)
  - GitHub, tools, documentation wiki

□ Send "light reading":
  - Architecture overview (technical roles)
  - Recent company blog posts or announcements
  - Team member bios (so they know who's who)

□ Assign onboarding buddy:
  - Send buddy context: new hire background, role focus, prior experience

FIRST WEEK — BELONGING & ORIENTATION
─────────────────────────────────────
Monday (Day 1):
  - 9am: Welcome call with manager (30 min)
    • Set tone: excited to have them, resources available, pace is learning
    • Introduce onboarding buddy
    • Overview of first week
  - 10am-12pm: Pair with onboarding buddy
    • Tour systems, Slack, communication style
    • Answer questions, normalize asking
    • Show where things live
  - 1-3pm: Lunch with team (informal, not work talk)
  - 3pm: Meet other team leads (quick 15-min intros)

Tuesday - Friday:
  - Daily 9am standup (show how we work together)
  - Daily 2-4 hours pairing with buddy
  - 1:1 with manager (30 min) — check in on belonging, any blockers
  - Meetings to observe: team rituals, culture, decision-making (listen, don't contribute)
  - End-of-week: Manager 1:1 debrief

FIRST 30 DAYS — LISTENING & EARLY WINS
───────────────────────────────────────
Week 2-3: Listening Tour
  - Schedule 8-12 interviews (30 min each) with key people:
    • [Name 1, Role] — company culture/values perspective
    • [Name 2, Role] — cross-functional collaboration
    • [Name 3, Role] — technical/strategic context
    • [And so on...]
  - Questions:
    • What's working well? What would you change?
    • What should I know about our [department]?
    • How can I be most helpful?
  - Take notes; synthesize into "state of the union"

Week 2: First Assignment
  - Assign 1-2 small wins (achievable in 1-2 weeks)
    • Project: [First Win Description]
    • Success criteria: [Specific, measurable outcome]
    • Buddy/manager available for questions
  - Goal: Ship something visible by week 3

Week 3-4: Relationship Design & Success Alignment
  - "Relationship Design" conversation (1:1 with manager, 1 hour)
    • How do you prefer to communicate?
    • How often 1:1s? What should we talk about?
    • How do you like feedback?
    • What support do you need?
  - Align on 90-day success vision
    • What does "ramped" look like in 90 days?
    • What skills should you sharpen?
    • What relationships matter?
    • Document the vision together

  - Present first win to leadership/team
    • Quick show & tell (15 min)
    • Visibility signal: they're contributing

MONTH 2-3 — OWNERSHIP & GROWTH
───────────────────────────────
Week 5-8:
  - Increase ownership: bigger projects, less pairing
  - Continue 1:1s (weekly, focus on: work progress, blockers, relationship health)
  - Introduce to customers (relevant roles)
  - Have "how's it going?" conversations with team members
  - Manager input: Are they ramping as expected? Any gaps emerging?

Week 9-12: 90-Day Preparation
  - Review 90-day success criteria (are they there?)
  - Prepare 90-day formal check-in
  - Gather feedback from: manager, buddy, cross-functional team members
  - New hire self-reflection: How do you feel? What's been good? What's hard?

90-DAY REVIEW — CALIBRATION & NEXT PHASE
──────────────────────────────────────────
Manager 1:1 (60 min):

✓ What's gone well?
  - Specific examples of their contributions
  - Where they've exceeded expectations
  - Skills they've developed

⚠ Where are they still ramping?
  - What's harder than expected?
  - What skills need more development?
  - Blockers or gaps to address?

→ What's next? (1-year vision)
  - Where are they growing into?
  - New projects or responsibilities?
  - Leadership/mentoring opportunities?
  - Timeline for increased autonomy?

📋 Formal Performance Check-in:
  - 90-day success criteria met: [Yes/No]
  - Performance rating: [On track / Exceeds / Below]
  - Feedback from cross-functional team: [Summary]
  - New hire's self-assessment: [What they're proud of, what they're struggling with]

Decision:
  - [ ] Strong ramp — increase autonomy, define year-long growth
  - [ ] On-track — adjust 90-day criteria? Extended ramp planned?
  - [ ] Below track — define support plan (mentor, training, role adjustment?)

FIRST 6 MONTHS — INTEGRATION & TRAJECTORY
──────────────────────────────────────────
Month 4-6:
  - Shift 1:1s to career development focus (less logistics)
  - Assign leadership opportunity: lead small project, mentor junior person
  - Check in on: are they genuinely connected to team? Do they feel they belong?
  - 6-month calibration: are they on track for 1-year vision?

FIRST YEAR — LONG-TERM THRIVING
────────────────────────────────
Month 9-12:
  - Regular 1:1s on growth, career, development
  - 360 feedback if available
  - 1-year performance review: assess against expectations, celebrate growth
  - 2-year vision conversation: where do they want to go?

ONBOARDING BUDDY NOTES
──────────────────────
Buddy: [Name]
Role: [What they're teaching]
Focus Areas: [What systems/processes to explain]
Check-ins with manager: [Weekly sync on how ramp is going]

LISTENING TOUR SYNTHESIS
────────────────────────
[To be completed by end of Month 1]
[New hire presents to leadership: "Here's what I'm learning about our company"]

Document:
- What's working well: [Themes from interviews]
- What's broken: [Recurring frustrations]
- Opportunities: [What could we improve?]
- New hire's perspective: [What surprised you? What's different from previous companies?]

Example

ONBOARDING PLAN — Jamie Torres

Role: Lead Product Designer
Start Date: April 7, 2026
Manager: Sofia Reeves
Onboarding Buddy: Marcus (Product Manager)

BEFORE START DATE (Pre-onboarding)
──────────────────────────────────
✓ Sent welcome email with:
  - Company strategy document (public strategy and 3-year roadmap)
  - Design system overview and philosophy
  - Engineering team structure and decision-making norms
  - Slack culture guide (we use threads, respond within 4 hours business hours)
  - First day logistics: office is open 8am-6pm, parking info, lunch options nearby

✓ Set up:
  - MacBook Pro, external monitor
  - Figma, Slack, Google Workspace
  - Design system documentation
  - GitHub access (read-only, for understanding eng constraints)

✓ Sent light reading:
  - "How We Make Design Decisions" (5-page internal doc)
  - Last 3 months of design blog posts
  - Team member bios (faces + backgrounds)
  - Current design challenges (3 main friction points)

✓ Assigned Marcus as buddy:
  - Context sent: Jamie is design-systems focused, coming from bigger company, wants to move fast

FIRST WEEK — BELONGING & ORIENTATION
──────────────────────────────────────
Monday (April 7, Day 1):
  - 9am: Welcome call with Sofia (30 min)
    • "Welcome! You're going to love this team. They're hungry for better design."
    • Introduced Marcus as buddy
    • Scheduled 1:1 cadence (Tuesdays & Fridays, 30 min)
  - 10am-12pm: Pair with Marcus
    • Toured Figma workspace, design system
    • Showed current design-in-progress for upcoming feature
    • "Here's what we're stuck on — design + engineering perspective clash on modality. We need your thinking."
  - 1-3pm: Lunch with design team + one engineer (informal, no work talk, just relationships)
  - 3pm: Met 4 other team leads in quick 15-min intros

Tuesday (April 8):
  - 9am: Design team standup (observed, watched how they work)
  - 10am-12pm: Pair with Marcus again
    • Explained design documentation practices
    • Walked through 2-3 design decisions & tradeoffs
  - 2pm: 1:1 with Sofia (30 min check-in)
    • "How's day 2? Any blockers? How's the belonging feeling?"
    • Talked about week 1 experience, no surprises yet

Wed-Fri: Similar pattern
  - Daily pairing (less intense, more focused on specific systems)
  - Meetings to observe: all-hands, design critique, product planning
  - End-of-week 1:1 with Sofia
    • "You're asking great questions. The team is excited about you."

FIRST 30 DAYS — LISTENING & EARLY WINS
───────────────────────────────────────
Week 2-3: Listening Tour
  - Scheduled with: CEO (product vision), VP Engineering (constraints), 3 designers (day-to-day culture), 2 engineers (collaboration), customer success leader (user feedback)
  - Notes synthesized into themes:
    • "Everyone wants design decisions faster — we're too deliberate"
    • "Communication between design & engineering breaks down; need shared language"
    • "Our design system is outdated relative to what we're building"

Week 2: First Assignment
  - Project: Design system audit & roadmap
  - Success: "Map 5 biggest gaps between current system and what we're building"
  - Assigned by Friday, due by end of week 3
  - Sofia available for questions; Marcus checking in daily

Week 3-4: Relationship Design & Success Alignment
  - "Relationship Design" conversation with Sofia (1 hour)
    • Jamie: "I prefer async-first; I think better in writing. Can we do 1:1s weekly but lighter-touch?"
    • Sofia: "Yes. I'll also create Slack thread for quick feedback so you're not blocked."
    • Jamie: "How do you like to receive critical feedback?" Sofia: "Give it to me directly, specific, in our 1:1. Don't let it fester."

  - 90-day success vision (documented together):
    • "You've shipped design system audit + priorities; team has agreed on 3 biggest improvements"
    • "You've designed 2-3 features end-to-end; team moved fast on them"
    • "Engineering team specifically asks for your input; collaboration rhythm is smooth"
    • "You've mentored junior designer on one design project"

  - Presented design system audit to leadership (20 min)
    • Sofia invited everyone to see Jamie's work early
    • "Jamie already spotted gaps we'd been ignoring. Here's what she's recommending..."

MONTH 2-3 — OWNERSHIP & GROWTH
───────────────────────────────
Week 5-8:
  - Owned design for upcoming feature (checkout redesign)
  - Led design critiques instead of observing
  - Started meeting with customers (2-3 customer calls) to understand how they use product
  - Weekly 1:1s with Sofia focused on: "How's the checkout project going? What's hard? What's flowing?"

Week 9-12: 90-Day Preparation
  - Design system audit shipped (3-month roadmap created)
  - Checkout feature in user testing
  - Started mentoring junior designer on color system work
  - Sofia gathered feedback:
    • Marcus: "She asks hard questions and pushes back when she disagrees. Team respects that."
    • VP Engineering: "So much better collaboration. She explains the why."
    • Junior designer: "She makes me better. I learned design thinking from watching her."

90-DAY REVIEW — CALIBRATION & NEXT PHASE
──────────────────────────────────────────
Sofia 1:1 (60 min, April 30):

✓ What's gone well:
  - Shipped design system audit (team adopted priority 1 improvements)
  - Checkout redesign moving to user test (fast turnaround, high quality)
  - Mentoring junior designer (they're growing)
  - "You changed how we think about design — faster iteration, less perfectionism. Exactly what we needed."

⚠ Where still ramping:
  - Understanding our technical debt (still learning constraints)
  - Navigating when engineering pushes back (getting better, sometimes gets frustrated)
  - Capacity management (does too much, needs to learn to say no)

→ What's next? (6-month vision)
  - Lead design for 2-3 major features (own full cycle: discovery, design, iteration, ship)
  - Build out design team (if growth continues, you'd hire 1 person in 6 months)
  - Establish design + product cadence (you and product lead, weekly design strategy sync)

Performance: On-track, exceeding in vision/strategy, developing in resourcing/boundaries

FIRST 6 MONTHS — INTEGRATION & TRAJECTORY
──────────────────────────────────────────
Month 4-6:
  - Full ownership of 2-3 features (end-to-end design, from brief to ship)
  - Weekly 1:1s shift to career conversations
  - Led company design thinking workshop (team culture)
  - Hired first design team member with Sofia
  - 6-month check-in: "Are you thriving? Does this role feel right? What's your 1-year vision?"

Edge Cases

New hire isolated despite planning — Check 1:1 frequency. Are they actually talking about belonging, or just work logistics? Isolation often happens when manager skips the relationship design conversation.

Early wins feel like busywork — This signals unclear role or over-planning. Align on what actually matters in month 1. Real work, even small, beats make-work every time.

Listening tour reveals company problems — That's the point. New hires see patterns old-timers miss. Create a "state of the union" conversation where they share observations without judgment. Use it to surface blind spots.

Manager over-schedules new hire — Protect their ramp time. If calendar is full of meetings, they can't do the work to ramp. Push back on non-essential meetings; protect 20 hours/week for actual work.

New hire thriving but team culture doesn't match — Onboarding went well but they don't fit. Early conversation: "How are you really feeling about the team?" Sometimes onboarding surfaces misalignment. Better to know in month 1 than month 6.

New hire delivered early wins but then hits wall in month 2 — This is common. Month 2 is when the "real job" starts. Projects get harder. Increase 1:1 frequency. Reassess support needs. This is where learning kicks in.

90-day review shows they're below track — Have honest conversation about: role fit, pace match, support level. Either adjust role/support, or acknowledge it's not working. Waiting to month 6 makes it worse.