The Top 4 Challenges of Virtual Onboarding (and How to Overcome Them)

Bringing in a new employee with zero in-person interaction poses a unique set of challenges. In this post, we explore some of the biggest, along with tips for overcoming them to deliver an engaging and thorough virtual onboarding experience.

The Top 4 Challenges of Virtual Onboarding (and How to Overcome Them)

Remote onboarding was a foreign concept to most organizations before the COVID-19 pandemic.

But between February and October of 2020, as offices shut down around the globe, the number of Google searches for the term “virtual onboarding” quadrupled.

Virtual onboarding is now — and will continue to be — commonplace, as teams around the world embrace a hybrid working model (55% of employees say they would prefer to continue working remotely even after the pandemic). And since the onboarding experience is directly related to productivity, engagement, and retention, getting it right is critical.

However, bringing in a new employee with zero in-person interaction poses a unique set of challenges. In this post, we’ll explore some of the biggest, along with tips for overcoming them to deliver an engaging and thorough virtual onboarding experience.

1. Ensuring access to equipment

More than 90% of remote employees surveyed encountered some issue with IT during virtual onboarding. Without the right equipment and access, a new hire’s first days on the job can be disheartening — not to mention a waste of time for both the employee and the organization.  

It’s relatively straightforward to establish in-house employees with tools. You likely outfit your office with computers, desks, chairs, and the like. In addition, you have a stocked closet for stationery. And if your new hire has trouble with any equipment or software, support — whether from the IT department or a peer — is easily accessible.

But remote workers who are onboarding virtually don’t have that same access, and management has limited visibility into their remote environment and won’t know what they’re missing. And a new hire may feel uncomfortable making too many “asks” if they don’t have everything they need and end up buying their own supplies — which can breed resentment and feelings of alienation.

More than 90% of remote employees surveyed encountered some issue with IT during virtual onboarding.


Here’s how employers can help:

Survey new hires about their needs: As soon as a new hire accepts the job offer, send them a comprehensive survey about their remote work arrangement and needs, and have the required equipment configured and delivered well before their start date. That way, they can test the equipment ahead of time (and reach out for help if needed) so they can hit the ground running on day one.

Provide an equipment stipend: Another option is to give remote employees some discretionary spending money so they can buy for themselves what they need to work comfortably. Or, some organizations set up a work-from-home store where remote employees can order supplies through the company — this is a great option for people who might feel uncomfortable expensing purchases early in their employment.

2. Maintaining new hire engagement

Onboarding is your chance to make a good first impression on newly acquired employees, and you don’t want that impression to be “boring.” Design your virtual onboarding process to be stimulating to keep new hires engaged and get them up to speed quickly. Here’s how:

Pre-board:Research shows that companies who use pre-boarding retain 81% of their first-year hires. Send new employees paperwork, reading material, and onboarding videos (along with the necessary equipment) prior to their start date so they can establish a level of understanding before they set foot in the virtual door. This will help new hires maintain the enthusiasm generated by the job offer and give them a head start on getting to know the company and culture.

Give new hires easy assignments they can complete to create small wins that help them feel engaged and productive.


Send a welcome package: Not only can this help cover some of the little things remote employees miss out on by not being co-located with the supply closet, but it also helps build a sense of team identity and connect them to the company culture. Pens, hats, pins, koozies, umbrellas with the company logo — it doesn’t have to be extravagant to make an impact.

Mix up onboarding tasks: Filling out HR paperwork and reading company policies are necessary, but doing so for hours on end is tiring. Instead, mix up your new hire’s virtual onboarding each day, breaking up drudgery with fun tasks like filling out a questionnaire about their favorite (or least favorite) things. Give them some easy assignments they can complete to create small wins that help them feel engaged and productive.

3. Sharing know-how

For remote employees, peer-to-peer interaction can be difficult, hindering the exchange of valuable information — both procedural and institutional A Harvard Business Review story on hybrid offices shared the experience of an IT professional who joined a new company in 2020, while its offices were closed due to the pandemic. His onboarding was all done online, with virtual check-ins and meetings held over Zoom.

“The truth is, I still do not know the system, the environment, and there is nothing my company can do,” he said. “Things that would have required me to simply turn around in my chair and ask my colleague at the neighboring desk in 10 seconds now take me several emails back and forth to understand.”

The employee hesitated to send “silly” questions to colleagues he hadn’t met, so he found it difficult to grasp the company culture and worried it would take a long time to learn what he needed to know to do his job effectively.

Invest in tools that make informal knowledge-sharing easy to relieve the burden on veteran employees.


Employers can take several steps to level this playing field between new hires that work in-house and remotely:

Make knowledge sharing effortless: Invest in tools that make informal knowledge-sharing easy so that answering new hires’ questions isn’t a burden on veteran employees. Jumping on a Zoom call and screen-sharing as you walk through new processes is disruptive and time-consuming. With knowledge-sharing software like Scribe, you can create beautiful, easy-to-follow step-by-step guides in just a few seconds and share them with a link that can be referenced again and again.

Build a company handbook: Create a comprehensive company wiki or handbook that’s accessible to — and editable by — everyone on the team. This enables new hires to self-serve information and learn at their own pace. It also empowers them to contribute to the team during their onboarding: If they encounter an obstacle, they can update the handbook to reflect their solution, which will help future employees.

Schedule onboarding chats: Set up onboarding calls between the new hire and either a manager or peer at regular intervals. Giving remote employees time dedicated to Q&A gives them the opportunity to collect their questions and ask them all at once — and not feel like they’re constantly interrupting their colleagues.
Create a dedicated Slack channel: Create a channel specifically for onboarding employees in Slack or other team-messaging software. That way, new hires can ask questions in a public forum that anyone else in the channel can answer in their own time. This also creates a living FAQ document that new hires can search when they get stuck.  

4. Creating personal connections

Sixteen percent of remote employees say isolation is the biggest challenge they face at work. Remote workers don’t have the kind of chance encounters their on-site colleagues enjoy — for example, striking up a conversation with a colleague while making coffee in the office kitchen. And employees who feel alienated are less productive and more likely to turnover.

Employers should help foster a sense of belonging among remote employees, starting with the virtual onboarding process. Here are some tips for helping remote new hires build relationships:

Assign an onboarding buddy: An onboarding buddy serves as a “go-to” resource for the new hire — a peer to show them the ropes and answer any questions they might not feel comfortable asking a manager. Onboarding buddies should reach out to the remote employee on their first day, keep regular contact throughout the early weeks of onboarding, and conduct monthly check-ins for the first several months.

Employees who feel alienated are less productive and more likely to turnover.


Have new hires create a personalized intro: A remote employee may never set foot in the office — and therefore never get to know their colleagues beyond a professional level. Without the informal interactions that can take place in an office environment, it’s more challenging to have spontaneous conversations and identify common interests. Have employees introduce themselves via video or email and share some personal information (such as a hobby, where they went to school, or a “fun fact”) that can spur a connection with their peers.

Establish extracurricular interaction: Encourage your teams to engage in online social activities — even during work hours — to create camaraderie and facilitate more meaningful relationships. Whether it’s optional virtual happy hours, regular group Zoom calls to discuss non-work topics, or one-on-one “water cooler chats,” these interactions give remote employees the same opportunity as on-site workers to connect with their colleagues on a deeper level.

Create a team of engaged, productive employees

Employee onboarding isn’t something that happens over a week or two — it’s an ongoing process that should last several months, especially for remote workers who may not interact with the rest of the team daily. So continue to check in with remote employees to seek feedback on their onboarding process and make sure they have access to the tools and information they need.

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