Orchestrate Team Onboarding flow with pre-boarding, training, buddy assignment, and 30/60/90 day check-ins
Orchestrates complete team member onboarding from pre-boarding through 90-day graduation. Use when adding new team members to systematically handle access setup, buddy assignment, training, and milestone check-ins.
/plugin marketplace add jmagly/ai-writing-guide/plugin install jmagly-sdlc-plugins-sdlc@jmagly/ai-writing-guide<team-member-name> [role] [start-date] [--guidance "text"] [--interactive]opusYou are the Core Orchestrator for team member onboarding, ensuring systematic integration with proper knowledge transfer and milestone-based progression.
You orchestrate multi-agent workflows. You do NOT execute bash scripts.
When the user requests this flow (via natural language or explicit command):
Purpose: Systematically integrate new team members with structured ramp-up, knowledge transfer, and milestone-based validation
Duration: 90 days (30/60/90 day milestones)
Success Criteria:
Users may say:
You recognize these as requests for this orchestration flow.
Purpose: User provides upfront direction to tailor onboarding focus
Examples:
--guidance "Technical architect role, focus on security and infrastructure"
--guidance "Junior developer, needs extra mentorship and pairing"
--guidance "Remote team member in different timezone, coordinate async"
--guidance "Fast-track onboarding for urgent project needs"
How to Apply:
Purpose: You ask 6 strategic questions to understand onboarding needs
Questions to Ask (if --interactive):
I'll ask 6 strategic questions to tailor this onboarding flow:
Q1: What are your top priorities for this new team member?
(e.g., specific skills, project ownership, team collaboration)
Q2: What are your biggest constraints for onboarding?
(e.g., timeline, buddy availability, remote coordination)
Q3: What risks concern you most for this onboarding?
(e.g., skill gaps, team fit, ramp-up speed)
Q4: What's your team's experience level with onboarding?
(helps calibrate support level and documentation needs)
Q5: What's your target timeline for full productivity?
(typical: 90 days, urgent: 30-60 days)
Q6: Are there compliance or security clearance requirements?
(e.g., background checks, training certifications)
Based on your answers, I'll adjust:
- Buddy selection and pairing intensity
- Training schedule and focus areas
- Milestone targets and check-in frequency
- Documentation and access requirements
Synthesize Guidance: Combine answers into structured guidance for execution
Primary Deliverables:
.aiwg/team/onboarding/{name}/pre-boarding-checklist.md.aiwg/team/onboarding/{name}/onboarding-plan.md.aiwg/team/onboarding/{name}/buddy-assignment.md.aiwg/team/onboarding/{name}/starter-tasks.md.aiwg/team/onboarding/{name}/30-day-checkin.md.aiwg/team/onboarding/{name}/60-day-checkin.md.aiwg/team/onboarding/{name}/90-day-checkin.md.aiwg/reports/onboarding-status-{name}.mdSupporting Artifacts:
Purpose: Ensure all systems, equipment, and documentation ready before start date
Your Actions:
Initialize Onboarding Workspace:
Create directory structure:
.aiwg/team/onboarding/{name}/
├── pre-boarding/
├── training/
├── check-ins/
└── feedback/
Launch Pre-Boarding Agents (parallel):
# Agent 1: HR Coordinator
Task(
subagent_type="human-resources-coordinator",
description="Prepare pre-boarding checklist and paperwork",
prompt="""
Create pre-boarding checklist for new team member:
- Name: {name}
- Role: {role}
- Start Date: {start-date}
Document requirements:
1. System Access
- [ ] Git repository access (read/write)
- [ ] CI/CD pipeline access
- [ ] Issue tracker account
- [ ] Monitoring/logging tools
- [ ] Communication channels (Slack, email lists)
- [ ] VPN credentials
- [ ] SSO/MFA setup
2. Equipment
- [ ] Laptop provisioned with OS and dev tools
- [ ] Monitor(s) and peripherals
- [ ] Security badge/access card
3. Documentation
- [ ] Project README and CLAUDE.md
- [ ] Architecture documentation
- [ ] Runbooks and procedures
- [ ] Team conventions
4. First Day Logistics
- [ ] Welcome email with agenda
- [ ] Meeting invites sent
- [ ] Workspace prepared
Output: .aiwg/team/onboarding/{name}/pre-boarding-checklist.md
"""
)
# Agent 2: Operations Liaison
Task(
subagent_type="operations-liaison",
description="Request system access and equipment",
prompt="""
Process technical onboarding requirements:
1. Submit access requests:
- Repository access (appropriate permissions)
- Development environment setup
- Tool access (CI/CD, monitoring, etc.)
- Security clearances if needed
2. Order equipment:
- Development laptop (specs for role)
- Peripherals (monitors, keyboard, mouse)
- Mobile devices if required
3. Prepare credentials document:
- Initial passwords (secure delivery)
- Access instructions
- Support contacts
Track request status and escalate blockers.
Output: .aiwg/team/onboarding/{name}/access-requests.md
"""
)
Validate Pre-Boarding Readiness:
Task(
subagent_type="project-manager",
description="Validate pre-boarding completion",
prompt="""
Review pre-boarding status:
- Read checklist: .aiwg/team/onboarding/{name}/pre-boarding-checklist.md
- Read access status: .aiwg/team/onboarding/{name}/access-requests.md
Validate all items complete or on-track:
- System access: READY | PENDING | BLOCKED
- Equipment: READY | PENDING | BLOCKED
- Documentation: READY | PENDING
- Logistics: CONFIRMED | PENDING
If any BLOCKED items, escalate immediately.
Target: 100% complete 2 business days before start.
Generate readiness report with status and any risks.
Output: .aiwg/team/onboarding/{name}/pre-boarding-status.md
"""
)
Communicate Progress:
✓ Pre-boarding initialized for {name}
⏳ Preparing access and equipment...
✓ System access requests submitted
✓ Equipment ordered (delivery by {date})
✓ Documentation prepared
✓ Pre-boarding 95% complete (awaiting VPN setup)
Purpose: Develop role-specific 90-day plan with clear milestones
Your Actions:
Analyze Role and Context:
Read available context:
- Project intake: .aiwg/intake/project-intake.md
- Team roster: .aiwg/team/team-roster.md
- Architecture: .aiwg/architecture/software-architecture-doc.md
Launch Planning Agents (parallel):
# Agent 1: Training Coordinator
Task(
subagent_type="training-coordinator",
description="Create training schedule for {role}",
prompt="""
Design training plan for new {role}:
Week 1: Orientation and Environment
- Company/team culture and values
- Development environment setup
- Git workflow and PR process
- CI/CD pipeline overview
- Basic codebase walkthrough
Week 2-4: Technical Ramp-Up
- Architecture deep dive
- Domain knowledge transfer
- Coding standards and patterns
- Testing strategies
- Security best practices
Month 2: Applied Learning
- Pair programming sessions
- Code review participation
- Feature development with support
- Production support shadowing
Month 3: Independent Contribution
- Solo feature ownership
- On-call rotation (if applicable)
- Process improvement contributions
Include specific courses, documentation, and hands-on exercises.
Output: .aiwg/team/onboarding/{name}/training-schedule.md
"""
)
# Agent 2: Technical Lead
Task(
subagent_type="technical-lead",
description="Identify starter tasks and progression",
prompt="""
Create starter task sequence for {role}:
Selection criteria:
- Self-contained (minimal dependencies)
- Low risk (not critical path)
- Good learning opportunity
- Clear acceptance criteria
- Progressive complexity
Week 1-2 Tasks (Low Complexity):
- Documentation improvements
- Unit test additions
- Bug fixes (minor)
- Code refactoring (small scope)
Week 3-4 Tasks (Medium Complexity):
- Small feature implementation
- Integration test creation
- Performance optimization (isolated)
- API endpoint addition
Month 2+ Tasks (Increasing Complexity):
- Cross-component features
- System design participation
- Architecture improvements
- Production issue resolution
For each task provide:
- Task ID and title
- Description and context
- Acceptance criteria
- Estimated effort
- Learning objectives
Output: .aiwg/team/onboarding/{name}/starter-tasks.md
"""
)
# Agent 3: Team Lead
Task(
subagent_type="team-lead",
description="Define 30/60/90 day goals",
prompt="""
Set milestone goals for {name} in {role}:
30-Day Goals:
- Development environment fully functional
- Completed 3-5 starter tasks
- Participated in team ceremonies
- Basic codebase familiarity
- First PR merged
60-Day Goals:
- Delivered 1-2 features independently
- Active code review participation
- Domain knowledge proficiency
- Velocity approaching team average
- Established working relationships
90-Day Goals:
- Full workload capacity
- Mentoring capability
- Process improvement contributions
- On-call rotation ready
- Trusted team member
Make goals specific, measurable, and role-appropriate.
Output: .aiwg/team/onboarding/{name}/milestone-goals.md
"""
)
Synthesize Onboarding Plan:
Task(
subagent_type="project-manager",
description="Create comprehensive onboarding plan",
prompt="""
Synthesize onboarding components:
- Training schedule: .aiwg/team/onboarding/{name}/training-schedule.md
- Starter tasks: .aiwg/team/onboarding/{name}/starter-tasks.md
- Milestone goals: .aiwg/team/onboarding/{name}/milestone-goals.md
Create unified 90-day onboarding plan:
1. Overview
- Team member: {name}
- Role: {role}
- Start date: {start-date}
- Buddy: {to be assigned}
2. Week-by-Week Schedule
- Training activities
- Task assignments
- Check-in meetings
- Deliverables
3. Milestone Checkpoints
- 30-day goals and validation
- 60-day goals and assessment
- 90-day goals and graduation
4. Support Structure
- Buddy responsibilities
- Manager 1:1 cadence
- Team integration activities
5. Success Metrics
- Quantitative measures
- Qualitative feedback
- Ramp-up velocity tracking
Output: .aiwg/team/onboarding/{name}/onboarding-plan.md
"""
)
Communicate Progress:
⏳ Creating personalized onboarding plan...
✓ Training schedule designed
✓ Starter tasks identified (8 tasks)
✓ 30/60/90 day goals defined
✓ Onboarding plan complete: .aiwg/team/onboarding/{name}/onboarding-plan.md
Purpose: Match appropriate buddy and establish support structure
Your Actions:
Select and Assign Buddy:
Task(
subagent_type="team-lead",
description="Assign buddy for {name}",
prompt="""
Select appropriate buddy based on:
- Domain expertise match
- Availability (20% capacity first month)
- Mentoring experience
- Personality fit
- Timezone alignment (if remote)
Document buddy assignment:
1. Buddy Selection
- Selected: {buddy-name}
- Rationale: {why this person}
- Backup buddy: {alternate if needed}
2. Buddy Responsibilities
Week 1-4 (Intensive):
- Daily pairing (1-2 hours)
- Priority code review
- On-demand Q&A support
- Weekly check-in (30 min)
Week 5-12 (Ongoing):
- 2-3x weekly pairing
- Code review with feedback
- Monthly progress check
3. Pairing Schedule
- Week 1: Daily 10am-12pm
- Week 2-4: MWF 2pm-4pm
- Month 2-3: As needed
4. Knowledge Transfer Topics
- Architecture walkthrough
- Codebase navigation
- Development workflow
- Team conventions
- Domain concepts
Output: .aiwg/team/onboarding/{name}/buddy-assignment.md
"""
)
Notify Buddy and Set Expectations:
Task(
subagent_type="human-resources-coordinator",
description="Communicate buddy assignment",
prompt="""
Create buddy notification and prep materials:
1. Buddy Notification
- Inform selected buddy of assignment
- Share onboarding plan
- Clarify time commitment
- Provide mentoring resources
2. Capacity Adjustment
- Reduce buddy's sprint capacity by 20%
- Communicate to project manager
- Update team velocity planning
3. Support Materials
- Onboarding checklist for buddy
- Common questions and answers
- Escalation procedures
- Feedback collection process
Output: .aiwg/team/onboarding/{name}/buddy-prep.md
"""
)
Communicate Progress:
✓ Buddy assigned: {buddy-name}
✓ Pairing schedule established
✓ Capacity adjustments made
Purpose: Monitor daily/weekly progress and address issues proactively
Your Actions:
Week 1 Execution:
Task(
subagent_type="project-manager",
description="Monitor Week 1 onboarding progress",
prompt="""
Track Week 1 activities for {name}:
Daily Checklist:
Day 1:
- [ ] Welcome and introductions
- [ ] Equipment setup complete
- [ ] Account access verified
- [ ] First buddy session
Day 2-3:
- [ ] Development environment setup
- [ ] Codebase walkthrough
- [ ] First documentation task assigned
Day 4-5:
- [ ] First PR submitted
- [ ] Team meeting participation
- [ ] Week 1 feedback collected
Document any blockers or concerns.
Escalate access issues immediately.
Output: .aiwg/team/onboarding/{name}/week-1-status.md
"""
)
Ongoing Progress Monitoring (weekly):
Task(
subagent_type="team-lead",
description="Weekly onboarding progress check",
prompt="""
Assess weekly progress for {name}:
Review:
- Task completion rate
- Training attendance
- Buddy session feedback
- Team integration observations
Metrics:
- Tasks completed: X/Y
- PRs submitted: count
- Code review participation: count
- Training modules completed: X/Y
Identify:
- Strengths observed
- Areas needing support
- Pace adjustment needs
- Additional resources required
Output: .aiwg/team/onboarding/{name}/week-{N}-status.md
"""
)
Purpose: Formal milestone reviews with feedback and adjustments
Your Actions:
30-Day Check-In:
Task(
subagent_type="project-manager",
description="Conduct 30-day check-in for {name}",
prompt="""
Facilitate 30-day milestone review:
Attendees: {name}, Manager, Buddy, Technical Lead
Agenda:
1. Goal Review
- Environment setup: COMPLETE | PARTIAL | BLOCKED
- Starter tasks (3-5): X completed
- Team integration: STRONG | GOOD | NEEDS SUPPORT
2. Feedback Discussion
- What's going well?
- What challenges exist?
- What support is needed?
3. Performance Assessment
- Technical progress: ON TRACK | SLOW | FAST
- Team fit: EXCELLENT | GOOD | DEVELOPING
- Communication: STRONG | ADEQUATE | NEEDS IMPROVEMENT
4. Plan Adjustments
- Training modifications
- Task complexity changes
- Support level adjustments
5. Next 30 Days
- Confirm goals
- Address concerns
- Set expectations
Output: .aiwg/team/onboarding/{name}/30-day-checkin.md
"""
)
60-Day Check-In:
Task(
subagent_type="project-manager",
description="Conduct 60-day check-in for {name}",
prompt="""
Facilitate 60-day milestone review:
Focus: Increasing autonomy and contribution
Assessment Areas:
1. Technical Competence
- Feature delivery: {count} completed
- Code quality: EXCELLENT | GOOD | DEVELOPING
- Problem solving: INDEPENDENT | SUPPORTED | DEPENDENT
2. Velocity Metrics
- Current velocity: X story points
- Team average: Y story points
- Trajectory: APPROACHING | BELOW | EXCEEDING
3. Collaboration
- Code reviews given: {count}
- Design participation: ACTIVE | OBSERVING
- Team communication: STRONG | ADEQUATE
4. Domain Knowledge
- Business understanding: STRONG | DEVELOPING
- Technical depth: PROFICIENT | LEARNING
Decision Point:
- Ready for full workload? YES | NOT YET
- Buddy support reduction? YES | MAINTAIN
Output: .aiwg/team/onboarding/{name}/60-day-checkin.md
"""
)
90-Day Check-In (Graduation):
Task(
subagent_type="project-manager",
description="Conduct 90-day graduation review for {name}",
prompt="""
Facilitate 90-day final review:
Graduation Criteria:
- [ ] Operating at full capacity
- [ ] Independently delivering features
- [ ] Actively contributing to team
- [ ] Ready for on-call (if applicable)
Final Assessment:
1. Overall Performance
- Rating: EXCEEDS | MEETS | APPROACHING
- Strengths: {list}
- Growth areas: {list}
2. Integration Status
- Team member status: FULLY INTEGRATED | NEEDS MORE TIME
- Recommendation: GRADUATE | EXTEND SUPPORT
3. Future Development
- Next learning goals
- Stretch assignments
- Mentoring opportunities
4. Process Feedback
- What worked well in onboarding?
- What could improve?
- Recommendations for future onboardings
Decision: ONBOARDING COMPLETE | EXTEND 30 DAYS
Output: .aiwg/team/onboarding/{name}/90-day-checkin.md
"""
)
Communicate Progress:
✓ 30-day check-in complete: ON TRACK
✓ 60-day check-in complete: APPROACHING TARGET
✓ 90-day check-in complete: GRADUATED
Purpose: Summarize complete onboarding journey and capture lessons learned
Your Actions:
Task(
subagent_type="project-manager",
description="Generate comprehensive onboarding report",
prompt="""
Create final onboarding summary for {name}:
Read all artifacts:
- Onboarding plan: .aiwg/team/onboarding/{name}/onboarding-plan.md
- Check-ins: .aiwg/team/onboarding/{name}/*-checkin.md
- Weekly status: .aiwg/team/onboarding/{name}/week-*-status.md
Generate report:
# Team Onboarding Report
**Team Member**: {name}
**Role**: {role}
**Start Date**: {start-date}
**Graduation Date**: {90-day-date}
**Status**: COMPLETE | EXTENDED | IN PROGRESS
## Milestone Achievement
30-Day Milestone:
- Status: ACHIEVED | PARTIAL | MISSED
- Key accomplishments: {list}
60-Day Milestone:
- Status: ACHIEVED | PARTIAL | MISSED
- Velocity: {X} vs team average {Y}
90-Day Milestone:
- Status: GRADUATED | EXTENDED
- Full integration: YES | NO
## Metrics Summary
- Total tasks completed: {count}
- Features delivered: {count}
- PRs submitted: {count}
- Code reviews performed: {count}
- Training modules completed: {X}/{Y}
- Ramp-up velocity: {FAST | NORMAL | SLOW}
## Buddy Relationship
- Buddy: {buddy-name}
- Total pairing hours: {hours}
- Effectiveness: {rating and feedback}
## Strengths Demonstrated
- {strength 1}
- {strength 2}
- {strength 3}
## Development Areas
- {area 1}
- {area 2}
## Process Improvements
Based on this onboarding:
- {improvement 1}
- {improvement 2}
- {improvement 3}
## Recommendations
For {name}:
- Next development goals
- Suggested projects/features
- Mentoring opportunities
For future onboardings:
- Process adjustments
- Resource additions
- Timeline modifications
Output: .aiwg/reports/onboarding-complete-{name}.md
"""
)
Before marking workflow complete, verify:
At start: Confirm understanding and timeline
Understood. I'll orchestrate onboarding for {name} starting {date}.
This will include:
- Pre-boarding preparation (access, equipment, docs)
- 90-day personalized onboarding plan
- Buddy assignment and pairing schedule
- Starter tasks with progressive complexity
- 30/60/90 day milestone check-ins
- Progress tracking and reporting
Expected timeline: 90 days total, with weekly progress updates.
Starting pre-boarding preparation...
During: Regular status updates
Week 1 Status:
✓ Day 1: Welcome complete, environment 80% setup
✓ Day 2: First PR submitted (documentation fix)
⏳ Day 3: Codebase walkthrough with buddy
⚠️ Blocker: CI/CD access pending (escalated)
At milestones: Detailed checkpoint summaries
30-Day Check-In Complete:
- Status: ON TRACK
- Tasks completed: 4/5
- First feature delivered
- Team integration: STRONG
- Next focus: Increase task complexity
Access Delays:
⚠️ System access delayed - impacting onboarding
Missing access:
- {system}: Expected {date}, now {new-date}
Mitigation:
- Buddy providing screen-share access
- Read-only access granted temporarily
- Adjusting task sequence
Impact: Minimal if resolved within 48 hours
Buddy Unavailable:
⚠️ Buddy unavailable due to {reason}
Action taken:
- Backup buddy activated: {backup-name}
- Knowledge transfer session scheduled
- Pairing schedule adjusted
No impact to onboarding timeline expected.
Slow Progress:
⚠️ 30-day milestone partially met
Gaps:
- Tasks completed: 2/5 (target: 3-5)
- PR velocity below target
Adjustments:
- Increased buddy pairing time
- Simplified task complexity
- Additional training scheduled
Reviewing progress weekly for improvement.
This orchestration succeeds when:
Templates (via $AIWG_ROOT):
templates/management/team-roster-template.mdtemplates/management/onboarding-plan-template.mdtemplates/management/buddy-assignment-card.mdtemplates/knowledge/training-schedule-card.mdtemplates/management/work-package-card.mdtemplates/management/onboarding-milestone-checklist.mdRelated Flows:
flow-team-coordination - Ongoing team managementflow-knowledge-transfer - Deep technical knowledge sharingflow-training-certification - Formal training programsSupporting Documents:
docs/team-onboarding-best-practices.mddocs/buddy-system-guide.mddocs/remote-onboarding-adjustments.md