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Module 5 of 73-5 days

Onboarding for Success

Set new hires up to succeed from day one with a structured onboarding experience.

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Onboarding Is Make or Break

You invested weeks finding and closing this hire. Don't let poor onboarding waste that investment. Strong onboarding can cut ramp time in half and dramatically improve retention. Weak onboarding leaves new hires confused, unproductive, and likely to leave.

"You never get a second chance to make a first impression. Onboarding is that first impression."

Preboarding

Before their first day

Preboarding Checklist

Send signed offer and all paperwork
Order equipment (laptop, monitors, peripherals)
Set up email, Slack, and core tool accounts
Add to relevant channels and calendar invites
Assign onboarding buddy/mentor
Schedule first week of 1:1s and introductions
Send welcome package or swag

The Welcome Email

Send a warm, personal email from the hiring manager a few days before start. Express excitement, share first day logistics, and give them something to read (company docs, relevant articles). Make them feel welcomed before they even start.

Day One

Making a great first impression

Day One Schedule

9:00 AM
Welcome from manager

Coffee, casual intro, set tone for the day

9:30 AM
IT/Setup

Equipment, accounts, security training

11:00 AM
Team introductions

Quick intros with immediate team

12:00 PM
Team lunch

Social time with the team

2:00 PM
Company overview

Mission, values, product, customers

4:00 PM
First task assignment

Something small they can complete today

Day One Win

Give them one small task they can complete on day one. Could be as simple as updating their profile, making a small fix, or writing a doc. Ending day one with an accomplishment builds confidence and momentum.

First Week

Building context and connections

First Week Goals

Context Building

  • • Read key docs (strategy, product, values)
  • • Shadow team members
  • • Understand the product deeply
  • • Learn the tech stack/tools

Relationship Building

  • • 1:1s with all team members
  • • Meet key cross-functional partners
  • • Connect with onboarding buddy daily
  • • Founder/CEO chat (if small team)

The Onboarding Buddy

Assign a peer (not their manager) as an onboarding buddy for the first month:

• Daily check-ins: "How's it going? What questions do you have?"

• Answer "dumb" questions they may not ask their manager

• Share unwritten rules and cultural norms

• Help navigate tools and processes

First 30 Days

Getting to first real contributions

30-Day Milestones

Week 1

Orientation complete

All setup done, context absorbed, team met

Week 2

First small win

Completed a real task with guidance

Week 3

Independent work

Taking on tasks with less hand-holding

Week 4

Meaningful contribution

Shipped something that impacts the team/company

30-Day Check-in Questions

  • • "What's been clearer than expected? More confusing?"
  • • "Do you have everything you need to be successful?"
  • • "Is this role what you expected? Any surprises?"
  • • "What feedback do you have for improving onboarding?"

The 90-Day Plan

Setting expectations for the full ramp

30-60-90 Framework

Days 1-30: Learn

Absorb context, build relationships, complete initial projects with guidance.

Days 31-60: Contribute

Work independently, own small initiatives, start to identify improvements.

Days 61-90: Own

Fully own area, drive initiatives, operate at expected level for role.

Example 90-Day Goals (Engineer)

30 days:Ship 3 small PRs, understand codebase architecture
60 days:Lead a small feature end-to-end, participate in on-call
90 days:Own a system/service, contribute to technical decisions

Measuring Onboarding Success

Tracking and improving your process

Key Metrics

Time to Productivity

How long until they're contributing at expected level?

New Hire Retention

% still employed at 90 days, 6 months, 1 year

Onboarding NPS

Survey: "How would you rate your onboarding experience?"

90-Day Performance

Manager assessment at 90 days vs. expectations

Continuous Improvement

After every new hire, ask: "What worked? What didn't?" Update your onboarding docs and process based on feedback. The best companies iterate on onboarding just like they iterate on product.

Practice Exercise

Build your onboarding program:

  1. 1Create a preboarding checklist for your team
  2. 2Design a day-one schedule that makes a great impression
  3. 3Write a 30-60-90 day plan template for your key roles
  4. 4Set up an onboarding buddy program with clear expectations
  5. 5Create a new hire feedback survey for continuous improvement