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Onboarding Remote Employees: Our Best Practices on How to Do It Right

Learn to avoid the most common missteps of onboarding employees who work remotely.

Andrea LaRowe

You hire a new person, and you immediately move from “finding” mode to “onboarding” mode. You have a goal: to effectively get your new hire up to speed as quickly as possible so they can begin the real work. The thing is, most companies go about this in the wrong way, and it’s costing them.

They focus on speed, not quality. In any setting, this is ineffective at best and toxic at worst. But when you’re onboarding remote employees, it’s even more important to get it right the first time.

Having onboarded hundreds of virtual employees over the past two decades, we have a well-honed set of tools and process to bring them up to speed, and ensure when they start work, they’re doing it from the right place.

In this article we’ll cover:

  • The differences and challenges of onboarding remote v. in-person employees
  • The process and tools we use in onboarding
  • Onboarding remote employees FAQ

The Differences and Challenges of Onboarding Remote Employees v. In-Person

Without even realizing it, most companies that are accustomed to onboarding people in person rely on informal and ad-hoc introductions and information sharing to get people started in their first days and weeks. Just sharing the same physical space makes it easier to get to know new coworkers, ask impromptu questions to someone next to you, and get a better sense of company culture by watching other peoples’ interactions.

In virtual onboarding, there’s no shared break room or elevator to bump into someone. Coworkers aren’t likely to stop to say hi as they pass by the new person’s desk. But at the same time, having a consistent set of “getting started” resources that someone can work through at their own pace and schedule is a real benefit. In fact, being virtual might encourage hiring managers to write down 30-, 60-, and 90-day goals, where to find work-in-progress, and background information on how things work – making things easier the next time, and hopefully lowering the number of things that need to be discovered on the fly.

But, the biggest difference in remote onboarding is still team integration.

Out of sight, out of mind. It definitely applies to new employees in a virtual work setting and can be the single biggest cost related to new hires.
Imagine you just got hired and you’re sitting in your home office, logging on to your company’s project management software, going about your normal day when you encounter something you don’t really understand. What was that acronym? Who do you go to? Can you just jump in with the rest of the team and ask without looking dumb?

For managers, how can you quickly integrate new people into the team, help them understand the rules of the road, and get them contributing to the work?

The Process of Onboarding Remote Employees and Setting Them Up for Success

Stage 1: Before they start

Good onboarding starts long before the first day by making sure everything is in place for a great first day.

At 37signals, we set up a “Welcome!” project for each person joining the company. There are to-do lists of things we need to do internally to set up accounts, systems, payroll and benefits.

There are lists of things we ask employees to do on their start date. Managers often write a welcome letter outlining goals and expectations for the first few months. We might include documents to read, or links to projects in process to get acquainted with. The whole thing becomes a great reference and sends the message that we’re excited to have them join us.

Stage 2: On Day 1

The first day makes a lasting impression. Did anyone know that Bethany was starting today? Was anyone ready to welcome her when she walked in the virtual door?

The prep in Stage 1 will make or break the first day. But if the manager and team have put some thought into it, Day 1 can be energizing for everyone. In addition to the preparation in Stage 1, a handful of virtual meet-and-greets can break the ice in a casual way.

A pre-set schedule of one-on-one meetings with their manager, a company “buddy” and welcome from human resources to handle remaining paperwork add a little structure to the day. Asking teammates to reach out via chat during the day also help create the feeling of being seen and part of the team.

Stage 3: First week, first month and beyond

At 37signals, we find that it can take 6 months or more for someone to really understand the company and their role within it. Using a thoughtfully structured onboarding process should make each week at the company feel more familiar.

Cultural norms and where to go for what usually gets handled by peers and onboarding buddies. Managers should also schedule regular check-ins to review progress toward goals and expectations for the first few months. Candid feedback on what’s going well or needs adjusting is also crucial at this stage.

How to Onboard Remote Employees Successfully (aka…What is Needed to Work Remotely)

You can find a hundred “how to onboard remote employees” lists online, all sharing similar information about culture and handbooks and moving quickly. While they’re not necessarily wrong, they’re also missing some of the most important pieces.

So, how do you do onboarding virtually then?

We already covered a specific 30-60-90 Day Plan for onboarding that has screenshots and a schedule, so we’re going to skip over that and focus on the important pieces to build within that plan.

This is our guide for onboarding remote employees based on our successes and failures over the past 20 years of working remotely.

1. Inform team and update projects

Bringing on someone new should be exciting for the whole company, so don’t keep it a secret. Each time we have a new person, we write a message in our company HQ project that lets everyone know a little about who’s coming, what we liked about them during the hiring process, and what they’ll be working on. It becomes a sort of “welcome card” for the new person to see on their first day that helps them feel like part of the company.

2. Set up an onboarding workflow

This doesn’t need to be crazy. There are remote companies out there with massive projects and fifty to-dos on their new hire’s list before they’re even allowed to begin working. That’s not necessary. What is necessary is creating some sort of workflow so they know how to get through onboarding information.

We already covered a specific 30-60-90 Day Plan for onboarding that has screenshots and a schedule, so we’re going to skip over that and focus on the important pieces to build within that plan. Using this 30-60-90 day plan template is a great way to create structure without reinventing the wheel.

Sample workflow we build in our Basecamp 30-60-90 Day Plans for onboarding remote employees
Sample workflow we build in our Basecamp 30-60-90 Day Plans for onboarding remote employees

3. Introduce the team

The very first thing for onboarding a remote employee should be familiarizing them with your existing team. Allow them to get to know everyone, talk, and meet “face to face”. This ultimately opens a door for your new hire to feel comfortable with everyone so they can ask questions when they have them.
There’s no need for corny ice-breaker games here. Unless it’s part of your existing traditions, “forced fun” usually makes virtual employees more uncomfortable than included. A handful of introductions at regularly scheduled team meetings will work just fine.

4. Have them review existing content

Learning culture is the hardest part of integrating new people. Company handbooks and required compliance trainings are usually terrible at illustrating what the norms are for communication, or what the company values. But you may have more to work with than you think. Try having new hires read what you’ve put out for customers and on social media. At 37signals, writing and creative work is a huge part of how we express what the company is about.

Try pointing them to these:

  • Internal podcast episodes or podcasts your CEO or members of the leadership team have been featured on
  • All product information and the help guides, videos, etc that go with them.
  • Any online communities your company hosts
  • Popular content: blog posts, social media, emails

5. Walk them through a day-to-day workflow

Even if your company is similar to the one your new hire previously worked at, the way you operate might not be. It’s a mistake to assume they’ll just be able to step into your day-to-day flow without guidance.

One of the best things you can do is have them shadow someone in a similar position and walk them through how a typical day goes. Of course, there will be differences. Make sure they know they can tweak and adjust their workflow to make it their own, just don’t leave them hanging. Provide that framework so they’re not clueless.

6. Check in consistently

As mentioned previously, not all new hires will ask questions when onboarding. They want to put their best face forward and look like they know what they’re doing. But you can be proactive in checking in and asking if they need anything. They’re much more likely to answer a request than to be the one bringing you a challenge.

Doing this actually sets the tone for how you communicate at your business.

7. Ask for feedback and iterate

You won’t always know what’s working and what’s not. Let’s not just assume things went well. Choose a date and create a to-do so you’re reminded to ask for feedback about the entire process once your remote employee is fully in the throes of their new job.

Make sure you ask specific questions instead of just, “any areas of improvement?” You’ll get more honest answers.

Here are some questions you can ask to improve your remote onboarding:

  • Do you feel confident that you could explain to a stranger how we operate here?
  • What made the way we do things “click” for you?
  • Who was most helpful during the onboarding process for you?
  • Were any areas confusing to you?
  • Any thoughts on what would be most helpful to new people hired in the future?

Remote onboarding can be challenging, and companies that are used to bringing people onsite might be tempted to try to use all the same processes for remote workers. A different approach, that makes more “self-serve” resources available, and gives people good introductions (to people and processes), might seem longer, but will pay off when new people get a more thorough understanding of how and why your company works the way it does.

Onboarding Remote Employees FAQs

What is remote/virtual onboarding

Remote or virtual onboarding is how you get new people started at your company, but without bringing them into an office. If your company is office-less this applies to all new hires. Or, if there’s an office, but only some people work in or near it, then you still want to equip them like part of the team, even though you won’t see them in person regularly.

What types of technologies help with remote onboarding?

There are a lot of software options available to help with onboarding new employees, from instant messaging to video conferencing. Our recommendation is something like Basecamp, where all the background information, work in progress and communication between teams happens in the same place. Plus, it’s right-sized to small businesses so that learning the tool doesn’t become a bigger task than doing the work. For more on how to do the work, check out this post: “Project Management for Remote Teams: The Best Project Management Tools & Tips”.

Is there a difference between employee orientation and employee onboarding?

Typically, employee orientation is a relatively short, one-time event. It’ll include things like signing up for benefits, maybe an overview of the company history and culture. Employee onboarding might extend as long as a few months, including background reading, a checklist of things to do or goals for the first 30, 60 and 90 days, and regular check-in’s with a new hire “buddy.” Onboarding is focused on helping new teammates learn how the company works, what they need to do, and how, as smoothly as possible.

How long should onboarding remote employees take?

At 37signals, everything we put in a “new hire project” is meant to cover about 90 days, or two cycles. This gives them enough time to get started on real work, which is the best way for them to learn the ropes and for managers to see what they’re capable of. Many people get up to speed faster, which is great, but it’s more effective to set a reasonable time than rush the process.

What should be on an onboarding checklist?

The onboarding checklist can include anything that’s important for new employees to get set up in the first few days. At 37signals, this generally includes HR paperwork, computer hardware, logins and profiles for different systems. It might also include important colleagues to meet (virtually), background material to read (like our Heartbeats and Kickoffs). Finally, you might include a set of to-do’s that are are a month or two later that are small starter projects.

What Should You Do Now?

If our onboarding process would be helpful in your business, try Basecamp for free and set up your own effective onboarding workflow using our 30-60-90 day plan template.

To learn more about Basecamp, 37signals and other best practices in project management and running a small business, sign up for our email newsletter.

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