cloudthinker-ai Onboarding Checklist
Phase 1: Pre-Start Preparation (Before Day 1)
Complete before the new team member arrives.
- Assign onboarding buddy: ___
- Assign manager: ___
- Order equipment (laptop, monitors, peripherals)
- Create accounts:
- Source control (GitHub / GitLab)
- CI/CD platform
- Cloud provider console
- Ticketing system
- Collaboration tools (Slack, Teams)
- Monitoring and observability platforms
- VPN / network access
- Add to relevant team channels and distribution lists
- Schedule Week 1 meetings (manager 1:1, team intro, buddy sync)
- Prepare starter task(s) in the backlog
Phase 2: Week 1 — Environment and Orientation
- Welcome meeting with manager (team mission, expectations, 30/60/90 goals)
- Team introductions and social coffee chat
- Development environment setup:
- Clone primary repositories
- Run local build and tests successfully
- Set up IDE with team-standard extensions and config
- Verify access to staging/dev environments
- Review key documentation:
- Architecture overview
- Team working agreements
- On-call expectations and runbooks
- Incident response process
- First code change: small, low-risk PR (typo fix, test addition, doc update)
- Daily check-in with onboarding buddy
Phase 3: Weeks 2-4 — Ramp-Up
- Complete starter task(s) with buddy support
- Shadow an on-call shift
- Participate in sprint ceremonies (standup, planning, retro)
- Review recent incident postmortems
- Understand deployment pipeline end-to-end
- Cross-team introduction meetings:
- Key upstream dependencies: ___
- Key downstream consumers: ___
- Platform / infrastructure team
- Complete any required compliance training
- Give feedback on onboarding experience so far
Phase 4: 30/60/90 Day Milestones
| Milestone | Target | Status |
|---|---|---|
| First PR merged | Week 1 | |
| Starter task completed | Week 2-3 | |
| Independent feature work | Week 4-6 | |
| First on-call shift | Week 6-8 | |
| Lead a small project | Week 8-12 | |
| Onboarding feedback submitted | Day 30 | |
| 1:1 check-in with skip-level manager | Day 60 | |
| Full team contributor | Day 90 |
Counter-Rationalizations
| Shortcut | Counter | Why |
|---|---|---|
| "We can skip some steps for this case" | Adapt the workflow steps, don't skip them | Skipped steps are where incidents and oversights originate |
| "The user seems to already know what to do" | Complete all workflow phases with the user | The workflow catches blind spots that experience alone misses |
| "This is a minor case, full process is overkill" | Scale the process down, don't turn it off | Minor cases become major when unstructured; the process scales, not disappears |
| "I'll fill in the details later" | Complete each section before moving on | Deferred details are forgotten; real-time capture is more accurate |
| "The template output isn't necessary" | Always produce the structured output format | Structured output enables comparison, audit trails, and handoff to other teams |
Output Format
Summary
- New hire: ___
- Team: ___
- Start date: ___
- Buddy: ___
- Manager: ___
- Current phase: ___
Action Items
- Complete all pre-start account provisioning
- Verify development environment works end-to-end
- Schedule all Week 1 meetings
- Review and update onboarding docs based on new hire feedback
- Conduct 30-day onboarding retrospective with new hire