3 Key Challenges to Overcome During Remote Onboarding

Leks Drakos February 18, 2021

It wasn’t that long ago that I started at Process Street. I’d been through the onboarding process many times since my first job working the Wendy’s drive-thru. All processes are not equal, though, and some of these experiences left much to be desired.

Process Street did pose an entirely new experience, however: remote onboarding. I had no idea how that was even going to work. How would I know what to do? How would they know if I knew what to do? How would I meet my colleagues if I couldn’t actually, y’know, meet my colleagues?

Fortunately for me, Process Street was a remote company well before it was cool to be remote, so my onboarding was handled by experts in all things work-from-home. No lie - it was the best onboarding experience I’ve ever had.

Stick with me, and I’ll share our secrets for successfully integrating new hires into your remote team:

  • What is onboarding?
  • Why is onboarding so important?
  • The challenges of remote onboarding
  • If you build it, they will come

What is onboarding?

Onboarding, or organizational socialization, is the process through which new employees gain the knowledge, skills, and behaviors to become effective members of your organization. Any new hire coming into that environment has a steep learning curve, and the onboarding process is designed to ease that transition.

In other words, onboarding is not just about teaching the employee how to perform their role, but providing them with the best foundation to do that, and facilitating their integration with your existing team.


Why is onboarding so important?

30% of new hires quit within their first 90 days of employment. While some of these instances will involve an inexperienced or unqualified employee, in most cases the individual will have been vetted and interviewed multiple times before extended an offer.

If that employee isn’t given the support and encouragement they need during this time, it’s very likely they will quit before the end of their first 90 days. Integration into an organization doesn’t “just happen”; it needs to be nurtured.

As the person running the onboarding process, you need to be aware that you are, essentially, a liaison between the new employee and the company culture. Your role is to guide them through the customs and expectations of the organization, and also help them build bridges and connections with the rest of the team.


The challenges of remote onboarding

Remote onboarding puts a whole new twist on these challenges by adding some additional - and potentially unexpected - ones to the mix. While you may have a solid onboarding process for in-office employees, the same process won’t directly translate to the work-from-home experience.

According to Forbes, there are 5 must-have skills for remote work:

  • Strong written communication
  • Willingness to collaborate
  • Ability to focus and self-motivate
  • Excellent time management skills
  • Adaptability

I’d argue that many of these skills are necessary for any work environment - or at least any work environment where you need to interact with people. They do have a particular resonance in remote work, though, so even before you get to the onboarding phase, you should look for these qualities in your candidates.

While you should look for these qualities in your new hires, you also need to make sure they’re prepared and equipped to deal with a few additional challenges:

  • Feelings of loneliness and isolation
  • Maintaining a work/life balance
  • Tech failures

Your remote onboarding needs to prepare your new employee for these challenges, and provide the resources needed to handle them.


Combating loneliness & isolation during remote onboarding

While it may feel like it sometimes, remote work doesn’t mean working in isolation. It’s rare that I make it through an entire day without interacting with at least one teammate. It does happen, though, and those days stick out more than others.

When you work in an office, even if you’re swamped with a project and don’t have time to chat in the break room, there are still others around you. Colleagues will still pop by your office. A group of you might go out for lunch, or someone will do a coffee run and ask if you want your usual latte. Other collaborators on the project will drop off deliverables.

With each of those little interactions, there will likely be a conversation, a joke, an anecdote - something. At the very least, you get a handful of “good mornings” on the way to your desk.

Working from home, it’s very easy to slip out of the work loop completely. There are days I’ve felt like I don’t work for a company at all - that I’m out here on my own, typing away. A new remote worker may think that their current social support network will solve any potential loneliness they might feel working from home, but this isn’t necessarily true.

The average worker in an office spends a majority of their week with coworkers. If you remove the physical presence of those coworkers, that worker is now spending a majority of their week on their own.

During your remote onboarding process, you need to make sure your new hire is ready for this, and is fully aware of how they can connect with their colleagues. For example, some of the things we use at Process Street are:

  • Slack social channels: In addition to the team-specific Slack channels, we have several company-wide ones designed for more casual social interactions. For example, our #watercooler-chat has regular prompts like share your favorite gif, what new hobby have you taken up, and what fictional character would you like to meet. We even had a whole thread sharing our Spotify Year in Reviews.
  • Regular 1:1 meetings: In remote settings, it’s easy to miss issues or problems an employee may be having. Particularly during the onboarding process, though, regular check-ins are vital. Your new employee may not realize how much they’re struggling or may be embarrassed to ask for help. Remote communication needs to be a priority, and it needs to be proactive.
  • Coffee dates: We have a Slack bot that randomly matches us with colleagues - both within and outside departments - on a weekly basis to have a casual, purely social conversation. This helps us get to know colleagues we may not work with directly, learn about other aspects of the company we don’t encounter, and engage in normal coworker banter. If you know that someone recently got married, or you studied at the same university, or both have a passion for obscure French philosophers, it helps build those work relationships we rely on so much.

Is a work/life balance even possible?

Whether or not achieving a work/life balance is achievable, or merely a myth is highly contested. When working from home, though, your work life and your home life are literally intertwined and often hard to separate.

Remote onboarding for new employees - particularly those unfamiliar with remote work - needs to provide strategies for dealing with this. The first issue is the distractions.

With remote work, no one’s going to hold you accountable until that deadline is already gone. No one’s going to see you binging Netflix or playing Assassin’s Creed during work hours. In fact, there aren’t even “work hours.” There are just tasks you need to complete.

And along with those tasks are a million things waiting to distract you - pets, the Amazon delivery guy, family members who say they understand that you’re “at work” but don’t actually seem to, the lawn that needs mowing, and the bric-a-brac that needs dusting, and that picture you’ve been meaning to hang for months, and the shelf that needs to be repaired, and the -

You get the point. There’s a lot of noise when you work from home, and you need to be able to tune it out or you’ll quickly end up overrun and out of time.

The other side of the coin, though, is knowing when to disconnect, and this can be a critical obstacle. It’s one thing when you’d have to travel all the way into the office to do a work-related task; it’s a different matter entirely when your office is also your living room.

For your new remote employees, you need to emphasize the importance of disconnecting regularly. In the end, even if they’re able to maintain a nonstop work schedule for a few weeks - or even a few months - long term, it’s not sustainable. They’ll end up burnt out and crashing, falling further behind than if they’d simply taken the weekend off or not worked straight through dinner.


Tech mishaps and new apps

On the hottest day of the year, I had Zoom meetings scheduled back-to-back all day, finishing with a call with our CEO, Vinay.

Two minutes into the call, my computer called it quits. Now, this could have been a disaster. I’d only been with the company a few weeks at that point and really wanted to make a good impression on everyone. Essentially walking out of a meeting with my boss did not seem like a very good way to do that.

After five seconds of absolute panic, I recovered, installed Zoom on my phone, and reconnected to the call. We laughed about it, swapped some tech-fail stories, and went on with the meeting. No big deal.

Our team has had to work around everything from earthquakes to dodgy internet, which means we’ve all had to come up with backup plans for getting our work done when things go wrong. Part of this involves that adaptability mentioned in the Forbes article, but it also relies on good planning.

Remote onboarding cannot ignore the importance of appropriate technology - whether that’s apps or equipment. Not only do you need to make sure your new employee knows how to use any new apps or software they may be unfamiliar with, but you should also make sure:

  • They know how to access all relevant help documents and tutorials
  • Their physical equipment is reliable and functional
  • They have backup plans in case something fails

If you build it, they will come

One of our key values at Process Street is: over-communicate everything, twice.

This statement is the backbone of all our communications. It’s also the solution to a lot of the challenges of remote work.

Your remote onboarding process needs to prioritize communication. It will alleviate feelings of isolation, facilitate interactions across time zones and borders, and increase productivity. Establishing good communication practices during the first days of an employee’s time at your organization will solidify those practices as part of your company culture.

Relationships don’t just happen within remote companies. If you create communication channels, and make the effort to keep those channels open and accessible, your team will use them.