Onboarding Plan

2. Pre-Start Preparation

Complete before the onboardee's first day:

• Access provisioning: List every system, tool, and repo they need access to. Include account names and who provisions each one.
• Equipment setup: Laptop, monitors, peripherals — ordered and configured.
• Welcome packet: Team org chart, key contacts, calendar invites for recurring meetings, links to onboarding docs.
• Buddy assignment: Assign a peer (not the manager) who is available for daily questions during the first two weeks.
• First-week calendar: Pre-schedule all Day 1-5 meetings and activities. An empty calendar on Day 1 signals disorganization.

3. Milestone-Based Progression

Structure the plan into milestones, not a flat task list. Each milestone has a clear success criterion.

Milestone 1: Orientation (Days 1-7)

Milestone 2: Guided Contribution (Days 8-30)

Milestone 3: Independent Contribution (Days 31-60)

Milestone 4: Full Ramp (Days 61-90)

4. Feedback Loops

Build feedback into the plan — don't wait for the end.

• Daily (Week 1): 15-minute buddy check-in. One question: "What's blocking you?"
• Weekly (Weeks 2-4): 30-minute 1:1 with manager. Review progress against milestones.
• Biweekly (Weeks 5-12): Standard 1:1 cadence. Shift from onboarding topics to regular work.
• Formal checkpoints: Written feedback at 30, 60, and 90 days. Both sides share what's working and what isn't.

At each checkpoint, ask the onboardee: "What's one thing about the onboarding that should change for the next person?"

Quality checklist

Before delivering the plan, verify:

• Every milestone has measurable success criteria, not just activities
• Pre-start preparation is complete — no "figure it out on Day 1" gaps
• A buddy is assigned and their responsibilities are documented
• Feedback checkpoints are scheduled at 30, 60, and 90 days
• The plan distinguishes between "do this task" and "be able to do this independently"
• Access provisioning lists specific systems, not "request access as needed"
• The 90-day completion criteria define what "fully ramped" means concretely

Common mistakes to avoid

• Task lists without success criteria. "Read the architecture docs" is a task. "Can draw the system architecture from memory and explain data flow" is a success criterion. Every activity needs a way to verify understanding.
• No buddy assignment. Managers are too busy for daily questions. A buddy at the same level provides low-friction support. Assign one explicitly and protect their time.
• Information firehose on Day 1. Spreading 8 hours of presentations across the first day guarantees nothing is retained. Limit Day 1 to setup, one key meeting, and one hands-on activity.
• No feedback until 90 days. If something is off at Week 2, waiting until Day 90 wastes everyone's time. Build in explicit checkpoints at 30 and 60 days with written feedback.
• Treating onboarding as one-size-fits-all. A senior hire needs less hand-holding on tools but more context on team dynamics and decision history. Adjust the plan to the person's level and background.