4 remote onboarding challenges and their solutions

Think of your first day at an in-person job. It might have gone something like this: You showed up to your new office with some paperwork, a fresh outfit, and a hefty dose of nerves. Your manager greeted you when you arrived, a friendly IT partner had already set up your desk, and you shook hands with more people than you can remember. Maybe you even went out to lunch or to a happy hour with your team. 

Now imagine yourself onboarding remotely. You show up to your desk (or kitchen table) with a cup of home brewed coffee, your computer, and the same dose of nerves. There’s no one to greet you when you arrive. You just sit down, boot up your computer… and then what? 

Let’s find out. 

What is remote onboarding? 

Remote onboarding is the process of welcoming new virtual hires to your team and getting them up to speed. A great remote onboarding process makes new employees feel like they belong even if you can’t meet them face-to-face. During virtual onboarding, new hires learn the skills they need for their role, get to know your company culture, and connect with teammates. In addition, remote onboarding guides new hires through the process of setting up necessary tools—like their computer, email, and any other collaboration software your team uses. 

Why is remote onboarding important?

The COVID-19 pandemic has caused remote work to skyrocket in the past couple years. According to a 2021 Gallup survey, nearly half of US employees are working from home either all or part of the time. Furthermore, nine in 10 of those workers want to maintain some degree of remote work after the pandemic is over.  

While remote work gives employees more flexibility, it also presents some challenges—especially when it comes to onboarding. When new hires can’t meet their coworkers face-to-face and see them on a daily basis, it can be hard to foster a sense of belonging and check in on how new team members are doing. Remote hires also need to navigate virtual communication tools like chat, video conferencing, and project management software from day one. 

But onboarding is critical to employee success. According to research by Glassdoor, organizations with a strong onboarding program can improve employee retention by 82% and productivity by over 70%. That means we need to put extra care into our remote onboarding processes to make sure new hires are set up with the tools and information they need to succeed. Luckily, just because you’re remote doesn’t mean you can’t build a great virtual onboarding experience. All you need is a bit of extra planning and the right tools for the job. 

4 challenges of remote onboarding, plus solutions

Onboarding remote employees requires a bit of planning, but you can still set new hires up for success when they’re working from home. Here are five common challenges you might face while onboarding your virtual team, plus solutions to stop these pitfalls in their tracks. 

1. Getting set up with tech

Challenge: Remote hires have to set up new equipment on their own. 

When you start a new job in person, equipment is typically set up for you on or before your first day. You might arrive to find a desk equipped with a fully-functional computer, monitor, keyboard, and mouse—so all you have to do is show up and start working. 

For new remote employees, things are a bit different. Since they can’t visit the office in person, you have to ship any tech supplies they need—then the new hire has to unbox and set everything up on their own. That means there’s a lot more to think about on their first day. Before your new hire can start learning and meeting new people, they may have to set up a new computer and access essential systems like email, messaging, and project management tools. 

Solution: Give new hires dedicated time to set up their workstation.

With a few extra steps, you can make tech setup smooth and simple for new hires. Here’s how: 

• Make sure new employees have essential equipment before their start date. If you need to ship them tech items like a computer or phone, get the process in motion soon after the new hire accepts their offer. Ideally, send new hires a tracking link so they know when their equipment will arrive—especially if they need to be at home to sign for delivery. 

• Send first-day calendar invites to the new hire’s personal email, in addition to their work email. For remote employees, the first day is all about getting access to essential systems. This can take some time, so it’s a good idea to send invites and video conferencing links to the new hire’s personal email account. Make a point to send those invites in advance—that way, your new team member can see what their first-day schedule will look like before they officially start. 

• Schedule an IT session on day one to help new hires access essential systems. Before anything else, new employees need to access their computer and communication tools (like email, messaging, or work management software). That means a guided IT session should be the first thing on a new hire’s agenda. During this meeting, leave plenty of time to troubleshoot any issues that might come up. 

• Provide detailed written instructions. In addition to the session with IT, make sure your new team member has step-by-step notes on how to access tools like email, messaging, and project management software. That way they don’t have to worry about taking notes during their in-person IT session—if they forget something, they have a document to reference later. 

Use a new hire preparation project to coordinate and track all of the pre-work you need to do before onboarding begins. That way, you can be sure your employee is starting their first day with everything they need to succeed.

2. Building strong culture and relationships

Challenge: Remote team members often feel isolated. 

Loneliness and isolation are the largest reported concern among remote workers, according to a two-year study by Stanford professor Nicholas Bloom. This makes sense—when workers are remote, they lose little office interactions like catching up by the coffee machine or grabbing lunch with their team. Instead of sitting side-by-side with their coworkers, new hires are isolated in their homes, connected by screens, but without the day-to-day social interactions of office life. 

Solution: Schedule time for connection. 

Luckily, remote workers aren’t doomed to feel isolated. You can still help them build strong connections with their teammates and your company as a whole—all you need is a bit of extra planning. 

• Create connections before the first day. Just because your new hire hasn’t officially started doesn’t mean you can’t communicate with them. After they accept the job offer, send them a card from the team, a care package with company swag, or an email to let them know how excited you are. This can go a long way in making new hires feel like a part of the team on their first day. 

• Schedule meet-and-greets. Since your new hire won’t run into coworkers at the coffee machine or in the elevator, it’s up to you to schedule time for them to meet their colleagues. Be sure to let invitees know that this is an informal time to just get to know each other, so there’s no need to prepare anything. Generally, 30 minutes is a good length for this type of meeting. To prevent meeting overload, you can schedule group meet-and-greets with teams who aren’t core collaborators. Aim to spread these out over the new hire’s first month so they don’t have more than two intro meetings per day. 

• Schedule more frequent 1-1s during the first few weeks. During the first few weeks of onboarding, it’s a good idea to schedule more frequent 1-1 meetings with your new hire—for example, twice a week instead of once a week. This gives you time to answer questions and see how they’re adjusting to their new role. It also gives your new hire guaranteed time with you, so they don’t have to worry about when and how to communicate. 

• Assign a mentor for your new hire. Pairing your new hire with a mentor gives them someone to talk to aside from their manager. A mentor is a peer on the new hire’s team (or a cross-functional team) who meets with them regularly—typically every day or every other day during the first couple weeks. This provides a low-pressure space for new hires to bring up any issues they might be having. 

• Utilize virtual icebreakers and team-building games. It can be hard to bond over video, but a bit of structure can go a long way in encouraging new hires to open up and build relationships with their team. Set aside five minutes for an icebreaker question at the start of team meetings or schedule a separate session for longer team-building games. Don’t be afraid to get a bit silly—some of our favorite icebreakers include “If you were a potato, how would you be cooked?” and “If you were an athlete, what would your walkout song be?” 

3. Navigating virtual communication

Challenge: New hires may not know how to communicate with their team.

There’s no getting around it—communication is different when workers are remote. For many new hires, remote communication at a new company can be daunting because they can’t just stop by your desk with a question. Instead, they often have to navigate a sea of communication tools like email, messaging, video calls, and more. As a result, new hires may feel uncertain about which communication tools they should use for what. 

Solution: Share communication guidelines.

When it comes to virtual communication, a bit of clarity can go a long way. Here’s how to demystify remote collaboration: 

• Be specific about how your team communicates. Every team has their own way of communicating, so create detailed guidelines for how your team does things. Then, share these guidelines with your new hire during their first week. For example, explain what type of content you share in certain Slack channels, how you use time during team meetings, and how to reach out if you have quick questions vs. more actionable requests. You can also specify when to use asynchronous communication and when to schedule Zoom meetings to discuss things further.

• Create and share a communication plan for projects the new hire will work on. A communication plan outlines how you’ll keep stakeholders informed during projects—like how often you should communicate status updates and project details, or who needs to be informed of what. Sharing a communication plan helps your new hire learn how to communicate effectively with team members and stakeholders outside of your team. 

• Set expectations for different communication tools. It can be easy for new hires to feel like they need to respond to messages right away, but that type of pressure can feel overwhelming and lead to burnout. Instead, set clear expectations about what a reasonable response time is. This can depend on the new hire’s role and the tool they’re using—for example, a development team member may need to respond to urgent Slack messages within an hour when they’re on call, while an event coordinator may aim for a one-day response time for email messages. 

• Use project management software to simplify communication. According to our research, on average people switch between 10 apps 25 times per day to do their work. That’s a lot to manage, especially for new hires. So instead of making new members navigate a sea of communication tools, centralize collaboration with project management software. For example, Asana lets you comment directly on tasks—so you can ditch the back-and-forth email threads and see all the context you need in one place. 

4. Preventing information overload

Challenge: Remote hires can feel swamped with new information to read and learn.

It’s normal for new employees to receive lots of information when they first start. But when those new team members are remote, they’re often left to sift through everything on their own. And since remote hires can’t easily stop by your desk with questions or see for themselves how other team members collaborate, all that info can feel extra daunting. 

Solution: Provide guidelines and structure for learning new information. 

With a bit of extra structure, you can make sure your new hire doesn’t feel overwhelmed by new information. Here’s how to do it: 

• Schedule trainings to review key information. Set up an official training session to walk your new hire through important information, like how to perform job-specific duties or an overview of your team goals. A dedicated meeting gives your new team member an opportunity to ask questions as you go, just be sure not to make training sessions too long. According to a 2020 Microsoft study, video fatigue sets in at the 30-minute mark for virtual meetings—meaning it becomes much harder to focus past that point. If you need longer sessions, schedule a five-minute break every 25-30 minutes. 

• Balance training sessions with unstructured time. Instead of packing in back-to-back training sessions, space things out to give your new hire time to absorb and practice new techniques. Extra time is especially important during the first weeks of onboarding, when your new team member is totally unfamiliar with company processes. 

• Consolidate information in one central location. During unstructured time, new hires can read through project materials and company documentation. You can make it a lot easier for them to learn if you put everything in one place, and that’s where a work management tool like Asana can come in handy. When you share a project in Asana, team members can see all of the relevant tasks, documentation, and contributors—plus explore other related projects they might be interested in. So instead of trying to put together a comprehensive list of resources, you can just add them to relevant projects and let them explore at their own pace.

• Create an onboarding checklist. An onboarding checklist can help new hires see which tasks they should complete by when. For example, you could create a checklist that breaks down tasks (like trainings, 1-1 meetings, and recommended reading) into sections based on when they should be completed. A good way to do this is to create sections for day one, week one, week two, week three, and so on. If you create your checklist in Asana, it can also function as a central repository for all onboarding information. Asana lets you link relevant projects and contextual information to each task, so your new hire has all the information they need. 

Example remote onboarding checklist for new hires

Cheers to a great (virtual) start

A great remote onboarding process can set new hires up for success no matter where they’re located. With these tips, you’re empowered to face remote work challenges head-on and stop them in their tracks. All you need is a bit of extra planning, a good internet connection, and the right tools for the job.