I’ve hired well over 500 people throughout my career.

Before running my own business, onboarding a new hire was whatever awkward process the big Fortune 500 company laid out. New hires fumbled through the process, doing their best to stay excited about what they had just signed up for.

When I started running my first company, I noticed the difference it made when we invested heavily in onboarding a new hire.

They weren’t just bought in - they made an impact within the business sooner.

By looking at onboarding differently, we realized we could use this process to help increase success rates instead of just dumping information on them.

Two things were important to me: One, we could reduce the dreaded six-month hiring process, and two, our new hires weren’t easily lured by competitors.

This meant we needed to look at onboarding differently. It needed to be viewed through the new hire’s lens.

Today we'll walk through how to build an onboarding machine to accelerate how quickly a new hire makes an impact.

Let’s dive in.

Employees are Customers

If you believe in your employees, invest heavily in them. Otherwise, don’t hire them. Your biggest returns will come from increasing their odds of success - just as you would with a customer.

Customer onboarding is intentional, ensuring a smooth experience. We anticipate customers questions and fears. Done well, your customers will stay longer, buy more, and support you with word-of-mouth referrals.

When applied to your employees, the same intentional approach has powerful results.

New jobs are always stressful. Great employees want to do well from the very start but it's likely they'll fail if you ask them to start on Day 1 without context.

When I think about creating an onboarding machine, my goal is to accelerate the time for a new employee to make an impact in the company. Instead of it being a six-month process, I plan for six weeks.

To do that, I focus on four areas:

1. Over-Communicate What To Expect

2. Accelerate Relationship Building

3. Increase Mastery of Business & Job

4. Outline Clear Expectations: The First 90 Days

Throughout this process, I keep information succinct.

I look for areas where I can show genuine excitement about them joining our company, but more importantly, I look for opportunities to build trust.

I want to make it painless to succeed in a challenging role.

To do that, I need to trust they are the right fit for the role, and in turn, I need to make sure I do everything I can to help them feel like a valuable part of the team in the shortest amount of time.

Over-Communicate What To Expect

Once an offer is accepted, onboarding begins.

I use the window between the offer being accepted and their first day to help them prepare for their new role. Through an email drip campaign, I slowly share company information while building excitement for their first day.

Here’s a high-level outline of what our onboarding email drip campaign looks like for someone starting four weeks from accepting an offer.

• Day 0: Welcome To The Team

• Day 1: Sign New Employee Forms Digitally

• Day 7: Meet The Team & Onboarding Schedule

• Day 14: What To Expect Your First Week

• Day 18: Scheduled Lunch Dates With Your Peers

• Day 20: Set up Gmail, Notion, and Slack so they can start to “observe” before their first day

• Day 24: Individual Intros To Peers

• Day 27: Your First Day

One thing to note here is that these aren’t emails dumping information on them. The info should be relevant to them and in small bites.

Basically, we're trying to help them feel like they already work here by giving them a clear idea of what to expect.

Outline Clear Expectations: The First 90 Days

The goal here is to give new hires a roadmap so they know they’re on the right track to mastering their job and creating an impact within the business. Don’t write a novel, or overcomplicate this. Keep it short and to the point.

It should be a clear and concise outline of what is expected during the first 90 days. This should outline what you expect them to master and the outcomes you want them to achieve. They should be attainable and realistic.

Now work backward from that outline. What do you need to do or provide so that they can reach those outcomes? How deep do they need to understand the customer service process? Or the history of digital ad experiments that the company has done?

Here’s an example of one for a junior role that helped us nail partnerships at the beginning of one of my previous companies.

Accelerate Relationship Building

This is one of the easiest ways to help a new hire integrate quickly into the team. Building trust with the team takes time, but you can accelerate it with these simple tactics.

Schedule Lunches With Peers

Rather than being left to a new hire’s social skills, we schedule a lunch with a new peer they’ll be working with each day for the first week. These are 1:1 lunches intended to give them an opportunity to bond on a personal level.

Schedule Daily Check-Ins With You

Because my title as CEO naturally makes people feel intimidated, it’s critical I build trust with anyone who reports to me early in the relationship. I schedule 30 minutes each day during the first two weeks to have a casual Q&A session together. This is their time to ask me about what they’re learning during their onboarding while getting to know me more personally.

Assign a Mentor For Navigating The Company Culture

Give them a mentor to talk to, someone who can help them navigate the ins and outs of the company.

Ideally, they should be approachable and accessible, so they can ask dumb questions and get clarification on company processes without being judged.

The goal is to help them feel more at ease while they're getting to know the company culture.

Increase Mastery Of Their Job

This phase starts on their first day. It’s where a new hire will start to dive into the meat of the business, and their role.

2 Weeks: Who’s Our Customer, What We Do, and How We Work

We always start with who our customer is. It’s easier to understand why we exist and what we do if they understand the customer. We’ll then move into a few other topics:

• Mission & market: Where we fit, what we're doing, and why we're doing it

• Product: What we've built, how it works, who uses it.

• Building a brand: Why and how we'll do this

• Speed, Cadence & Working at a Fast Growth Startup

• How We Work: Communicating As A Team

• Building Mini Machines: Why and how we depend on systems to run our business

• Your first 90 days: What you'll achieve, learn, and be expected to run with

2 Weeks: Shadowing

We implement shadowing whenever possible as it increases the understanding of a new hire’s role exponentially. As an example, a new Chief of Staff would join me in every internal/external meeting, have access to all of my emails, etc.

2 Weeks: Doing

By now the new hire has context on the business, how the team works, and the history of their role. They’ll now start to do their job with me offering feedback over the next two weeks. This will fine-tune how they do their job, with the intent to fly without me within two weeks.

They'll get to fly, but with guardrails. Guardrails give me peace of mind that they won't break anything critical.

We make an agreement that they’ll get 51% of the vote, but I can veto anything that doesn’t align with our values or business goals.

They’re empowered to make decisions without me as long as there are no surprises. If anything isn’t going as planned they agree to come to me as soon as possible to figure out another path.

⚫️ Putting It All Together

While anyone can hire talent, retaining them is tough. An onboarding machine gives you an unfair advantage in the market simply by giving new hires a way to integrate into the business faster. You’ll retain top talent longer, attracting more talent.

Think about what it’s like to be a new employee at your company. Is it overwhelming? Or is it easy to learn about the business and acclimate? What can you do to increase a new hire’s success?