The Strategic Value of Onboarding

Diane Briones

Hyper-growth can have its downsides. For one thing, even tight-knit cultures may start to fray as headcount swells. Yet many companies overlook a key tool for keeping the tapestry intact—the onboarding process.

A thoughtful onboarding process ensures that every new employee understands your company’s founding purpose, values, customer stories, and operating norms from the very first day. Done right, onboarding will set the tone for your company’s culture and help retain your best talent.

Brielle Rajkovich and Isabelle Bicaci

To help you build an onboarding process that works for your team, we interviewed Isabelle Bicaci and Brielle Rajkovich, who implemented Square’s first onboarding program. This helped the company maintain a strong culture and high employee engagement, even when the team grew from 60 to 1,300 in just under four years. After moving on from Square, Brielle and Isabelle founded the culture and people operations advisory, IBBR. In addition, Isabelle joined Eventbrite’s team to focus on international expansion. Eventbrite has also experienced high growth, while being named a best place to work for both millennials and women in 2015.

Who should own onboarding?

Brielle: In the beginning, most often the office manager owns the process. But as the company grows, the paperwork and administrative side of onboarding can balloon. If that person doesn’t have support, they might not have the bandwidth to be strategic.

Isabelle: It’s important to note that an onboarding process includes a couple separate components. The first piece is procedural onboarding, the second is orientation. Overall, onboarding begins before the new hire starts and extends well beyond their first week; at Square and Eventbrite it can last up to 90 days after the start date. Procedural elements include compliance processes like getting the person set up to legally work for your company, gathering their HR paperwork, and configuring IT permissions. Orientation, which can span the first day or first two weeks, is the feel-good part: getting them aligned with your company culture, connecting them with people and training resources, and making sure they know their way around.

Your office manager can handle the orientation part of the program, but you need someone who understands the legal aspects to oversee the larger onboarding process. Otherwise you risk audit issues down the road, whether you’re a startup of 10 people or 500 people. Rather than expecting your office manager to take on HR responsibilities, I recommend you find an HR person who can also serve as office manager.

How do you convince leadership to commit resources to onboarding?

Brielle: Company culture is a big topic right now, and onboarding lays the foundation of your culture. “Culture” is an ambiguous idea but thoughtful onboarding can help make it tangible—it’s a key opportunity for new hires to learn about your company and to align with your mission.

For instance, Square has a strong coffee culture. Some of Square’s early beta customers were coffee houses in SOMA; it’s in the company’s DNA. More than that, it speaks to a culture where you can walk up to anybody and ask them a question or talk to them—often over a coffee (or tea or hot chocolate if coffee isn’t your thing). That starts with onboarding. At Square, during the first week, new-hires met with Jack and the team during roundtables. These were great opportunities to grab a cup of coffee and casually chat with one another.

A strong onboarding process also improves retention. Research shows that people decide within the first 45 days at a new job if it’s a place they're going to stay for many years. It’s important those early days line up with what they were promised during the recruitment process. The problem is, they often don’t. The same research found that four percent of new employees leave a job after a disastrous first day and twenty-two percent of staff turnover occurs within the first 45 days of employment. (For more evidence supporting the importance of onboarding, check out this research summary.)

Isabelle: Since many people in leadership are product-minded, it helps to draw an analogy between customer and employee onboarding. Investing in first-time user experience improves retention and avoids churn within your customer base—the same applies to your employee base. Just as you have a cost per acquisition on the customer side, you have a cost per acquisition on the employee side. No one wants to invest money and resources into recruiting someone and then lose them because their early experience is not cohesive.

Why is executive buy-in important and how do you get it?

Brielle: Establishing executive buy-in from the beginning, when you’re still small, sets the tone throughout your growth. At Square, we were fortunate that our founder and CEO, Jack, was bought in from the beginning—and he still meets every single new hire on a bi-weekly basis. The executives followed his lead and now see orientation as an incredible opportunity. Their support has been integral to the success of Square’s program.

Isabelle: It’s valuable when the executive and leadership teams participate in the orientation program—but if they can’t, they at least need to allow their new hires to attend. Managers usually want new hires to start contributing immediately; executive buy-in helps convince them that onboarding is worth the initial time investment.

Brielle: Sometimes it’s easier to get executive buy-in than it is to get manager buy-in. We find managers are resistant when they don’t understand what onboarding is or why it’s important. At Square, we took time to walk managers through our onboarding program: the objectives, the outcomes, and the importance of their role in the process. To help keep the momentum going, we sent out weekly updates that included quotes from surveys and conversations with new employees. This proved the impact of the program and the importance of leaders’ involvement.

Do you recommend onboarding people in groups?

Brielle: Yes, without a doubt. Not only is it more efficient, it also creates a sense of camaraderie. We often had cohorts celebrate milestones and anniversaries together.

Isabelle: We sometimes postponed start dates so we could onboard a new hire with a group, ideally in a cohort that included similar roles or people they would work closely with. We occasionally got push-back, since everyone was eager to have their new team members start right away. To help make our case, we said, “Remember the connections you made your first day of university? Those bonds are irreplaceable. It’s the same when you are starting at a new company.”

Brielle: When we surveyed people about the experiences of going through onboarding alone versus as part of a cohort, the differences were dramatic. People who were onboarded as part of a cohort tended to have a more positive experience working at Square—and their tenure at the company was longer.

Onboarding Best Practices

Start late and be liberal with breaks

If possible, start the first day at 9:30 or 10 a.m. to give people time to settle in. Some people start at 11, but that can create awkward timing with lunch. Buffer everything with scheduled breaks. New hires are taking in a lot of information and need time to process (plus use the bathroom and, for some, have a smoke).

Make it fun

Break up the logistics and learning with “surprise and delight” moments. At Square, we had little gifts waiting at people’s desks—shirts, notebooks, books, stickers, pens—to make them feel welcome and part of the team. Or we had the office team stop in to bring cookies and say hi. Each quarter, consider hosting a new-hire social for those who joined within the last three months.

Be inviting & mindful of all personalities

At Square, we had people introduce themselves in front of the company, but only at the end of their first week. Some companies introduce new hires on day one, which can be nerve-wracking for some people. We recommend thinking carefully about how and when you put people on stage, or even on the spot.

Leverage your screen space

If you have screens around your office, they are great real estate for onboarding and culture-building. At Eventbrite we put up new hire profiles around the office so everyone knows their face and can make them feel welcome.

Provide name pronunciations

This might seem like a small thing, but providing a new hire’s name pronunciation when introducing them on office screens or over email can help the team feel comfortable introducing themselves.

Diversify your learning styles

Some people like to be spoken to, some like interactive learning, some want to get up and move around. Some like it live, some prefer video, and others want to read everything. By utilizing a range of teaching styles in your onboarding training, you’ll keep people engaged for more of the process.

Give thought to the tools you use

When we started building onboarding programs several years ago, there weren’t many off-the-shelf tools available, so we built our own to-do tool to automate emails and collect new hire preferences. We don’t recommend doing that today. First off, even if you can get dev hours to build the tool, it’s going to be hard to prioritize time for updates. And second, there are so many great, cheap products available today that integrate easily with one another. For example, check out this awesome CBInsights HR landscape tool here.

Set up email early

If you have a responsive IT team, have them set up email permissions the week before a new hire starts. That way you can pre-populate the person's calendar with onboarding events and their team can invite them to important meetings.

Be flexible!

The onboarding program should be a reflection of the company at the moment it’s in, so be prepared for it to evolve with the company. At Square, we tried to be particularly flexible about how long activities took. It’s like playing the accordion; we’d shorten it, then expand it, then shorten it again, depending on the demands of the team.

Document everything

Having as much of your process documented as possible helps create consistency, especially for remote and international onboarding. We recommend a welcome presentation of 45–60 minutes that is refreshed over time. At Square, we recorded live onboarding sessions to create a library of presentations in case a speaker was unavailable.

We also had a playbook of all the information needed to run and manage the onboarding process. That way if the onboarding lead was out sick or had limited bandwidth, they wouldn’t become a bottleneck. As important as documentation is, it’s best to start it once the process is pretty set, instead of when you’re still iterating and getting up to speed. It’s time consuming but worth the investment!

Gather feedback and iterate

You can't just sit down and create an onboarding program. You learn by doing and tweaking. It’s important to collect feedback from the people who have gone through the program, then modify it accordingly. We did surveys after a new hire’s first week, then again at 30, 60, and 90 days to see what they still remembered. If enough people don't remember specific parts of the program, consider cutting it and saving everyone the time.

Survey your team for onboarding ideas

In the beginning, crafting an onboarding process can feel overwhelming. But you already have a wealth of information in the building. Ask your teammates, "What was your onboarding experience at other companies? What were the highlights? What did you love about onboarding and what did you dislike?”

Rotate onboarding responsibilities

Being an onboarding lead is a fantastic role—but it can also be exhausting. It requires a ton of logistics and admin work, not to mention the emotional energy of shepherding people through nervous, giddy first days. To avoid burn-out, it’s good to have two or more team members who can alternate logistics and more one-on-one work. If you only have one person managing orientation, we recommend having them move to another role after a year or two.

Want More?

Download these materials:

Square's Step-by-Step Onboarding Guide

Square's Onboarding Checklist

International Onboarding with Eventbrite