What I Learned Onboarding 100+ Employees: Without a Plan, You're Planning to Fail
You spent three months finding the perfect candidate. Multiple interviews. Reference checks. Salary negotiations. Finally, they said yes.
And then what? Do you wing their first day? Scramble to set up their equipment? Realize on Day 3 you never assigned them any actual work?
Here's what I've learned after onboarding 100+ employees across tech startups, clean energy companies, and law firms: Without a plan, you're planning to fail.
Onboarding Doesn't Start on Day One
Most people get this wrong: Onboarding doesn't begin on an employee's first day. It begins the moment they accept the offer.
I once onboarded a senior engineer at a tech startup. Brilliant hire—exactly who we needed. But on Day 1, his laptop wasn't ready. His manager was in back-to-back meetings. No one took him to lunch. By 3pm, he was sitting alone, still waiting for access to anything.
He lasted six weeks.
Meanwhile, at a clean energy company, we onboarded a new hire whose manager sent her a welcome email two days before she started. On Day 1, her desk was set up, her equipment worked, and her manager greeted her at the door with coffee.
She's still there three years later.
The difference? A plan.
The Three Phases of Effective Onboarding
Phase 1: Pre-Start (Before Day 1)
Start planning two weeks before their start date. This is where most companies drop the ball.
Critical tasks:
Complete background check and employment agreements
Notify IT, Facilities, and the Hiring Manager with at least one week's notice
Order and test all equipment (laptop, monitor, phone, accessories)
Create system accounts (email, HRIS, Slack/Teams, performance tools)
Have their manager send a welcome email outlining Day 1 expectations
When a new hire arrives and everything is ready, they feel valued. When nothing is ready, they feel like an afterthought.
Phase 2: Day 1 (Make or Break)
Day 1 sets the tone for everything. It's about completing legal requirements AND making someone feel like they belong.
The Legal Basics:
I-9 Form completion (must verify documents by Day 3)
Payroll/HRIS setup (direct deposit, W-4, benefits enrollment)
Company policies review and signed acknowledgment
The Human Element (What Actually Matters):
The manager should:
Greet the new hire personally at start time
Give an office tour and introduce nearby team members
Conduct a 30-60 minute 1:1 covering:
Management style and communication preferences
What success looks like in the first 30/60/90 days
Immediate priorities and first assignment
"What do you need from me to be successful?"
Managers make or break onboarding—not HR.
Phase 3: The First 90 Days (Where Integration Happens)
Here's what most people miss: Employees who had structured 90-day onboarding stayed twice as long as those left to "figure it out" after Week 1.
The Cadence:
Week 1: Daily 15-minute check-ins
Weeks 2-3: 2-3 check-ins per week; assign meaningful first project
Weeks 4-8: Weekly 1:1s with increasing responsibility
The Milestones:
Day 30: What's going well? What's been challenging? Review 30-day goals.
Day 60: Progress check, specific feedback (positive and constructive), address any performance concerns early.
Day 90: Comprehensive review of all goals achieved, transition to regular performance cycle, and get their feedback on the onboarding experience.
Week 1 is about logistics. Week 4 is about competence. Week 12 is about belonging. Skip any phase, and you lose people.
The Cost of Winging It
A tech startup I worked with lost three engineers in six months—all within their first 90 days.
When I asked why, the answers were all onboarding-related:
"I never understood what success looked like."
"My manager was too busy to help me ramp."
"I felt like I was bothering people with questions."
Replacing those three engineers cost them 6+ months of recruiting time, $60K+ in recruiting fees, countless hours of lost productivity, and damaged team morale.
All preventable with a simple onboarding system.
The math is simple: Cost to replace an employee is 30-50% of their annual salary. Cost of a good onboarding system? A few hours upfront.
What You Actually Need
You don't need fancy software or weeks of planning. You need two things:
A checklist for HR covering every phase from offer to 90 days
A guide for managers with exactly what to do and when
That's it. Because onboarding isn't HR's job alone, and it's not the manager's job alone. It's both, working together, following a plan.
Ready to Stop Winging It?
I turned everything I learned into two tools:
The New Hire Onboarding Checklist – Your complete 8-phase roadmap for HR to manage every detail from offer to 90 days.
The Manager's Onboarding Guide – Everything managers need including the Day 1 playbook, check-in frameworks, and 30-60-90 day meeting guides.
Individual templates: $19.99 each
Not ready to buy? Download my free New Hire Day 1 Checklist first.
Want help customizing this for your company? Book a 90-minute customization session.
Book a customization session - $250
The bottom line: You invested months finding the right person. You sold them on your vision. You convinced them to take a chance on you.
Don't lose them in Week 1 because you didn't have a plan.
