Onboarding Programs and Documentation

The Expensive First Impression

In the previous lesson, we explored interview design and question banks. Now let’s build on that foundation. You spent weeks finding the right candidate. Navigated scheduling nightmares, competing offers, and salary negotiations. They finally signed. Victory.

Then they show up on Monday morning and nobody knows where they’re supposed to sit. Their laptop isn’t ready. Their manager is in back-to-back meetings until 3 PM. They spend their first day reading a dusty employee handbook from 2019.

By Wednesday, they’re wondering if they made a mistake.

This scenario is devastatingly common. According to Gallup, only 12% of employees strongly agree that their organization does a great job onboarding new employees. The cost of getting it wrong is enormous – replacing an employee costs 50-200% of their annual salary, and poor onboarding is a leading cause of early turnover.

What You’ll Learn

By the end of this lesson, you’ll build preboarding sequences, first-day checklists, first-week agendas, and 30-60-90 day plans using AI. You’ll create documentation that answers the questions new hires are too embarrassed to ask.

From Interviews to Onboarding

In Lesson 4, you designed interviews that assess whether a candidate can succeed in the role. Onboarding is where you make sure they actually do. The competencies you identified during hiring now become the competencies you develop during onboarding. A great hiring process followed by terrible onboarding wastes everyone’s investment.

The Preboarding Period

Onboarding doesn’t start on day one. It starts the moment someone accepts your offer. The gap between acceptance and start date is when excitement peaks but anxiety starts growing.

What new hires worry about before starting:

• Will I actually be good at this?
• Will I fit in with the team?
• What should I wear? Where do I park? What time do I actually arrive?
• Did I make the right decision leaving my old job?

Preboarding checklist (AI prompt):

Create a preboarding communication plan for a new hire
starting in [timeframe].

Include:
- Welcome email (sent day of offer acceptance) -- warm,
  excited, practical
- Logistics email (sent 1 week before start) -- what to
  bring, where to go, parking, dress code, first-day schedule
- Team introduction email (sent to the team) -- brief bio
  of the new hire, their role, conversation starters
- IT setup checklist -- accounts, equipment, access needed
  before day one

Role: [Job Title]
Team: [Team name/size]
Company: [Brief description]

The logistics email alone prevents 80% of first-day anxiety. People can handle uncertainty about the job – they can’t handle not knowing where to park.

Quick Check

Think about your own last first day at a new job. What did you wish someone had told you before you arrived? Those are the gaps your preboarding materials need to fill.

The First Day

The first day sets the tone for the entire employment relationship. Here’s what it should accomplish:

1. The new hire feels expected and welcome (not like they’re inconveniencing people)
2. Logistics are handled (equipment works, accounts are set up, they know where things are)
3. They meet key people (their manager, their team, their onboarding buddy)
4. They leave with clarity about what the first week looks like

First-day agenda template (AI prompt):

Create a first-day agenda for a new [Job Title] joining
a [team size] team.

Include:
- Morning: Welcome, workspace setup, IT orientation
- Mid-morning: Manager 1-on-1 (role expectations,
  communication preferences, first-week goals)
- Lunch: Team welcome lunch
- Afternoon: Onboarding buddy introduction, tool
  walkthroughs, key documentation review
- End of day: Manager check-in (questions, how they're
  feeling, tomorrow's plan)

Tone: Structured but not overwhelming. Leave buffer time.
New hires absorb about 30% of what they hear on day one.

Critical detail: Assign an onboarding buddy. Not the manager – a peer who can answer the questions new hires won’t ask their boss. “Where do people actually eat lunch?” “How quickly should I respond to Slack messages?” “Is the 9 AM standup actually at 9 or more like 9:15?”

The First Week

Week one transitions from logistics to learning. The goal: by Friday, the new hire understands the landscape.

Create a first-week onboarding plan for a [Job Title].

Day-by-day schedule:
- Day 1: Welcome, setup, meet the team (covered above)
- Day 2: Deep dive on [core tool/system], shadow a team
  member on [key workflow]
- Day 3: Company overview (mission, products, customers),
  HR orientation (benefits, policies, time off)
- Day 4: Role-specific training begins -- [specific topic]
- Day 5: Manager 1-on-1 to review the week, set week-2
  goals, answer accumulated questions

Include:
- Key people to meet (name, role, why they matter)
- Essential reading/documentation to review
- One small, achievable task they can complete by Friday
- Daily check-in format with their buddy

The small win matters. Giving new hires something they can accomplish and ship in week one – even something tiny – creates confidence. Reviewing a document, updating a spreadsheet, sitting in on a client call and writing up notes. The feeling of contributing beats another day of passive learning.

The 30-60-90 Day Plan

This is the backbone of your onboarding program. It breaks the first three months into distinct phases:

Days 1-30: Learn

• Absorb company knowledge, processes, and culture
• Meet all key stakeholders
• Understand the tools and systems
• Shadow experienced team members
• Complete required training

Days 31-60: Contribute

• Start owning specific tasks with guidance
• Take on a defined project or workstream
• Build working relationships with cross-functional partners
• Identify areas for improvement (fresh eyes are valuable)

Days 61-90: Own

• Operate independently on core responsibilities
• Lead a small initiative or project
• Propose improvements based on observations
• Have a formal 90-day review with clear performance expectations going forward

AI prompt for a 30-60-90 plan:

Create a 30-60-90 day onboarding plan for a [Job Title]
on a [team description].

For each phase (30, 60, 90 days), include:
- 3-5 specific learning milestones
- 2-3 relationship milestones (who they should know and
  how well)
- 2-3 contribution milestones (what they should be
  producing/owning)
- Manager check-in format and frequency
- How to measure whether they're on track

The role primarily involves: [key responsibilities]
Key tools: [tools they need to learn]
Key stakeholders: [who they'll work with]

Quick Check

Does your organization have a standard 30-60-90 day plan? If yes, when was it last updated? If no, that’s a significant gap – new hires without clear milestones often struggle to gauge their own performance, leading to anxiety and disengagement.

Onboarding Documentation

Beyond the plan itself, new hires need reference materials they can return to. AI can help you create:

Team handbook:

Create a team handbook for the [team name] team.

Include:
- Team mission and how we fit into the company
- Team members and their roles (brief descriptions)
- How we work (communication norms, meeting cadence,
  decision-making process)
- Key tools and how we use them
- Common acronyms and terms
- Where to find things (docs, dashboards, shared drives)
- FAQ: Questions every new team member asks

Role-specific SOP (Standard Operating Procedure):

Create an SOP for [common task the new hire will do].

Include:
- When this task needs to happen
- Step-by-step process
- Tools used at each step
- Common mistakes to avoid
- Who to ask for help
- Quality checklist before considering it done

The best onboarding documentation answers the question: “If this person had to figure this out on their own, what would they need?”

Measuring Onboarding Effectiveness

How do you know if your onboarding program is working? Track these signals:

Exercise: Build a First-Week Plan

Choose a role in your organization. Create:

1. A preboarding email covering logistics (5-6 key items the new hire needs to know before day one)
2. A day-one agenda with specific times, activities, and people
3. A first-week overview with one achievable task the new hire can complete by Friday

Use the AI prompts above as starting points, then customize for your specific team and company.

Key Takeaways

• Onboarding starts at offer acceptance, not day one – preboarding reduces anxiety and early turnover
• First-day logistics matter more than strategy – equipment, workspace, and knowing where to park
• Assign an onboarding buddy (a peer, not the manager) for the questions new hires won’t ask their boss
• 30-60-90 plans break overwhelming first months into manageable learn-contribute-own phases
• Documentation should answer the question: “What would this person need to figure things out on their own?”
• Measure onboarding with retention, time to productivity, and new hire satisfaction surveys

Next lesson: the new hire is ramping up. Eventually, you’ll need to give them feedback. Let’s make sure your performance reviews are fair, specific, and actually helpful.