Onboarding a New Employee Checklist Is the Wrong Way to Think About It
Tired of generic advice? Here’s our opinionated, real-world onboarding a new employee checklist for making the first 90 days count. No fluff, just what works.
Dan Robin
We’ve hired a lot of people over the years. We’ve also made every onboarding mistake in the book. The awkward first day. The forgotten laptop. The new hire dropped into the deep end of a project with no life raft. It’s a familiar story.
Most companies try to solve this with a checklist. It feels productive. Send paperwork. Check. Set up email. Check. But a checklist is a tool for assembling furniture, not for welcoming a human being. It’s sterile, bureaucratic, and misses the entire point. A great onboarding experience isn't about ticking boxes; it's about starting a relationship. It's about replacing a new person's anxiety with confidence and their confusion with clarity.
The first week sends a powerful signal. A chaotic welcome says, "We're disorganized and you're an afterthought." A thoughtful one says, "We're calm, we're prepared, and we're genuinely glad you're here." This isn't just another generic list. This is our playbook, born from experience. It’s opinionated and human, because your new teammate is, too.
1. Get the Paperwork Out of the Way, Before Day One
Let's be honest, nobody gets excited about filling out forms. It’s the necessary administrative chore that stands between a new hire and their actual work. The trick is to make this process invisible. Our goal is to handle it so swiftly that it barely registers as part of their experience. This first step isn't about compliance; it's about respect for their time. Getting essentials like I-9s, W-4s, and direct deposit details handled before they walk in the door removes a major source of first-day friction.
Think of it as the opposite of a trip to the DMV. A clunky, paper-heavy process sends a terrible message about your company's efficiency. Modern tools have made this easy. E-signatures can turn what used to be an hour of signing papers into a 10-minute task they can complete from their couch a week before they start.
How we do it
We handle this with a simple, guided workflow. A week before their start date, the new hire gets a link. They can securely upload documents and fill out digital forms. This means their first day is about meeting people, not wrestling with paperwork. We set up a private channel between the new hire and HR for any questions. No intimidating processes, just a direct line for help. It’s a clean, professional first impression that says, "we've got this."
2. The Laptop and Logins Should Just Work
Nothing says "we weren't ready for you" quite like a new person showing up to an empty desk and a missing computer. It's an instant morale killer. Providing the right technology isn't a logistical task; it's a fundamental sign of respect. When someone can log in and access their tools on day one, you’re telling them their contribution is valued from the very first minute. It lets them focus on learning, not on chasing down an IT ticket.
This is a solved problem. Apple ships pre-configured MacBooks directly to remote employees' homes. GitHub uses automated scripts to grant precise access permissions. The message is clear: technology should be an enabler, not a barrier. For smaller teams, dedicated small business IT support can handle this, ensuring a smooth handoff.
How we do it
We have an automated workflow for this. The moment a new hire is confirmed, a task list is assigned to IT: order laptop, set up email, provision software licenses. The manager can see the status in real time. We use a secure, one-time-view message to share initial login details—no passwords sent over email. We also create a dedicated "IT Help" channel where the new hire can ask for help directly. It empowers them to solve minor issues without feeling like they’re bothering someone.
3. A Tour Is About People, Not Places
An office tour is more than just pointing out the kitchen and the restrooms. It’s the first real connection a new hire makes with their physical space and the people in it. A good tour transforms an unfamiliar building into their office. It reduces the first-day jitters and helps them feel like they actually belong there. It’s about providing context and facilitating those crucial first face-to-face introductions.
When this step is skipped, new people feel lost. They’re hesitant to interrupt someone to ask a basic question. We’ve found the best way to do this is to have a peer—their assigned "buddy"—give an informal tour. It feels less like a corporate procedure and more like a genuine welcome from a teammate. The goal is simple: make them feel comfortable in their new environment.
How we do it
For in-office folks, we upload an interactive office map they can pull up on their phone, with key spots tagged. For our remote team, we created a channel with short video clips—a "Day in the Life" tour from a teammate, a quick video on how to use the conference room tech. It bridges the gap between the digital and physical worlds. We also have a permanent, searchable guide with all safety procedures and emergency contacts. No paper handouts to lose.
4. Make the Handbook Accessible, Not Intimidating
Let’s face it, no one is thrilled to read an employee handbook. It’s the corporate equivalent of the terms and conditions you scroll past. But it's crucial. This is about setting clear expectations from the start, protecting both the company and the person. A well-presented handbook prevents future misunderstandings and shows you care about transparency.
The old way was to hand over a dusty binder. The better way is to make this information easy to digest. How you present your policies is just as important as the policies themselves. It's the difference between a new hire feeling informed and one feeling overwhelmed.
How we do it
We break our handbook into bite-sized digital modules. "Code of Conduct," "Benefits Overview," "Remote Work Policy"—each is a separate, digestible piece. New hires can review them at their own pace. After reading a section, they digitally sign off. This creates an automatic record for compliance, so there’s no chasing down signed papers. We also have a dedicated Q&A space where they can ask questions. It’s less intimidating than asking a manager, and the answers help build a living FAQ for everyone.
5. Give Them a Buddy, Not Just a Manager
Navigating a new company is like exploring a new city without a map. You'll figure it out eventually, but having a friendly local makes the experience infinitely better. A buddy isn't their manager; they’re the go-to for all the unwritten rules: "Where's the good coffee?" or "Is it okay to sign off at 5 PM?"
This simple step is critical for retention. A study by Microsoft found that 97% of new employees who met with their buddy at least eight times in their first 90 days felt they were productive faster. The goal isn't just to assign a name; it’s to create a real support system that helps someone feel like they belong.
How we do it
We create a private channel for the new hire and their assigned buddy for a warm introduction before day one. It becomes their space for informal questions and daily check-ins. We also have a simple "Buddy Program Guide" that outlines expectations and suggests conversation starters, like scheduling a virtual coffee. We even set up automated nudges in their channel to remind them to connect. For a deeper look, here's how to create a buddy system at work.
6. Define What Winning Looks Like
Nothing creates more anxiety than ambiguity. Showing up without knowing what success looks like is a recipe for stress. This step is about providing clarity and direction from the start. When you clearly define a role, its responsibilities, and how performance will be measured, you give someone the confidence to contribute.
This isn't micromanagement; it's alignment. The goal is to shift a new hire's energy from "What should I be doing?" to "Here's how I can make an impact." Setting explicit 30, 60, and 90-day goals gives them a clear roadmap. It provides the psychological safety they need to take initiative.
How we do it
We use a "First 90 Days" plan template. Managers customize it with specific goals for the new hire and share it directly. We also create a dedicated channel for the new hire and their manager to discuss progress. It's a space to ask for help and share small wins, making goal-setting a conversation rather than a directive. Automated reminders for 30, 60, and 90-day check-ins ensure these vital conversations always happen.
7. Provide Real Training, Not a Document Dump
Once the basics are covered, the real work begins. This is where you equip your new hire with the specific skills they need. Neglecting structured training is like handing someone the keys to a complex machine without telling them how it works. A well-planned training program shows you're invested in their growth.
The goal isn't to overwhelm them, but to build a foundation. Throwing a manual at someone doesn't work. A mix of self-paced learning and hands-on practice is far more effective. It turns the daunting task of learning a new role into a manageable, step-by-step journey.
How we do it
We create a "First 30 Days Training" workflow. It sequences tasks like watching video tutorials, reading key documents, and completing small assignments. The new hire can check things off as they go, giving them a sense of progress. All our training materials live in a centralized, searchable knowledge library. We also set up channels for specific training topics, so they can ask questions and get answers from the right expert.
8. Introduce the Culture Through Stories, Not Slogans
Beyond the org chart lies the company’s real operating system: its culture. Someone can have all the right skills, but if they don’t connect with your values and unwritten rules, they’ll always feel like an outsider. This step is about showing a new person how they fit into the bigger story.
This isn’t about posters with words like "Integrity." It’s about storytelling. Zappos famously dedicated a huge part of its onboarding to its core values, not as rules, but as the foundation for every decision. When you share your company’s origin story, its mission, and its traditions, you give people the context they need to feel a sense of purpose.
How we do it
We have a dedicated "Culture Hub" space. It includes a video from our founder sharing the origin story, our culture deck, and posts that highlight team members who exemplify our values. We also integrate our values into public recognition. Team members can give shout-outs that specifically tag a company value. This makes our values visible and celebrated every day.
9. Check In Constantly
Leaving a new person to "figure it out" is a recipe for disengagement. The first few weeks are filled with a thousand small questions. Scheduling regular check-ins isn't micromanagement; it's providing a safety net. It shows you're invested in their success. It turns onboarding from a one-time event into a continuous, supportive conversation.
This is about creating a predictable, safe space for conversation before minor issues become major frustrations. A brief, 15-minute chat at the end of each day during the first week can quickly resolve blockers and build rapport.
How we do it
We schedule recurring 1:1 check-ins: daily for the first week, then weekly for the first month. We use a shared private channel for the new hire and their manager to collaborate on an agenda. After each meeting, the manager posts a quick summary of takeaways and action items. We also send automated pulse surveys on Fridays, asking simple questions like, "What was one win and one challenge this week?" to get real-time insight. Learning how to effectively collect onboarding feedback is key to making this work.
10. Engineer Social Collisions
No one wants to be the new person eating lunch alone. A new job is more than a list of tasks; it’s joining a community. This final step is about intentionally creating opportunities for human connection. Great work is done by people who trust and understand each other.
Companies known for strong remote cultures are masters at this. GitLab uses "donut" pairings to randomly connect colleagues for virtual coffee chats. Buffer organizes informal video calls just for socializing. These aren't just perks; they are strategic investments in building a collaborative team. After the initial period, using effective tools to boost employee engagement keeps the momentum going.
How we do it
On their first day, we post a fun bio of the new hire in the main team channel, prompting everyone to welcome them. We use a channel that automatically pairs random team members for a 15-minute virtual coffee chat each week. It breaks down silos and helps new people meet colleagues they wouldn't normally interact with. We also schedule a team lunch or virtual happy hour during the first week and manage it all in one place.
10-Point New Hire Onboarding Checklist Comparison
Onboarding Activity | Implementation Complexity 🔄 | Resource Requirements ⚡ | Expected Outcomes 📊 | Ideal Use Cases & Tips 💡 | Key Advantages ⭐ |
|---|---|---|---|---|---|
Complete Paperwork and Documentation | Moderate; sequential legal checks and verifications | Low–Moderate; HR time, secure storage, e-sign tools | Compliance, accurate payroll, reduced legal risk | Every hire; send docs pre-start, use e-sign and checklist | Ensures legal compliance, payroll accuracy, IP protection |
Provide IT Equipment and Technology Setup | High; procurement, configuration, cross-team coordination | High; hardware, licenses, IT staff, shipping logistics | Day-one productivity, enforced security, fewer support tickets | On-site & remote hires; order 2–3 weeks early, test devices | Immediate productivity, consistency, security enforcement |
Conduct Office Tour and Orientation | Low–Moderate; scheduling and guided walkthrough | Low; staff time, simple materials (maps/guides) | Familiarity with facilities, safety awareness, reduced anxiety | On-site hires; 20–30 min tour, assign a buddy, provide map | Builds belonging, clarifies logistics, ensures safety |
Review Company Policies and Employee Handbook | Moderate; prepare materials and track acknowledgments | Low–Moderate; HR time, digital distribution, tracking tools | Clear expectations, legal protection, uniform standards | All hires; use digestible modules, require acknowledgment | Standardizes behavior, reduces misunderstandings and risk |
Assign a Mentor or Buddy | Moderate; matching, expectations, mentor training | Low–Moderate; mentor time, training guides, tracking | Faster integration, informal learning, higher retention | Roles with high onboarding complexity; set check-ins and duration | Accelerates learning curve and improves retention |
Establish Clear Job Expectations and Goals | Moderate; goal-setting conversations and documentation | Low; manager time, simple documentation | Clarity, measurable performance, alignment with team goals | Roles with measurable outputs; use 30/60/90 and SMART goals | Improves accountability and performance evaluation |
Provide Training and Skill Development | High; curriculum design, scheduling, delivery methods | High; trainers, platforms, materials, assessment tools | Faster competent performance, fewer errors, standardized skills | Technical/regulatory roles; mix methods, include quizzes | Raises competence, reduces rework, supports growth |
Introduce Company Culture and Values | Low–Moderate; content creation and leader involvement | Low; leadership time, presentations, media assets | Greater engagement, cultural alignment, sense of purpose | All hires; use leadership stories, examples, virtual sessions | Strengthens identity, improves motivation and fit |
Schedule Regular Check-ins and Feedback Sessions | Moderate; consistent scheduling and documentation | Moderate; manager time, meeting tools, agendas | Early issue detection, ongoing alignment, documented progress | First 90 days; follow recommended cadence, use agendas | Builds trust, improves performance, catches problems early |
Build Social Connections and Team Integration | Low–Moderate; planning events and introductions | Low; team time, small budget for activities or virtual tools | Stronger relationships, collaboration, improved engagement | Teams needing cohesion; schedule low-pressure socials, virtual options | Enhances engagement, collaboration, and informal support |
The Checklist Is Just the Beginning
So, that's our list. These are the essential steps, the scaffolding that supports a new hire as they find their footing. Following them ensures nothing critical gets missed.
But a checklist is just a tool. It can’t guarantee a great experience. Ticking boxes is the easy part. The real impact comes from the human element that no list can capture. It’s the spontaneous coffee run, the patient answer to a "silly" question, the manager who checks in not just about tasks, but about how the person is actually feeling.
The real goal isn't just to get someone productive by day 90. It's to build such a strong foundation of trust and belonging that the new hire no longer feels new. They just feel like part of the team.
From Checklist to Culture
The magic happens when this process becomes an ingrained habit. After the first three months, the formal "onboarding" might end, but the integration never does. The rhythms you establish—the regular check-ins, the open feedback, the focus on connection—shouldn't stop. They should simply become the way you work.
The checklist is the script for the first act. The rest of the story depends on the environment you've built. Did you create a space where your new hire feels comfortable asking for help? Did you connect their work to a mission they can believe in? Did you show them, through actions, that their well-being matters as much as their output?
A successful onboarding program is one that makes itself obsolete. Its principles become so deeply embedded in your culture that supporting new people is no longer a process you run, but simply who you are.
This is what we’re chasing. We’re not just trying to reduce turnover. We’re trying to build a calm, cohesive team where every person, from day one, feels seen, supported, and set up to do their best work. When you get that right, you haven't just filled a role. You've made your entire organization stronger.
Tired of juggling spreadsheets and email threads for your onboarding a new employee checklist? Pebb brings every step—from paperwork and training to team introductions and feedback—into a single, calm employee app. See how you can create an onboarding experience your new hires will actually enjoy at Pebb.
