4 Ways Remote Work Makes Onboarding Difficult

Onboarding remotely creates specific challenges, but identifying those pain points means you can home in on how to address them.

Written by Junaid Warwani
Published on Nov. 13, 2020
4 Ways Remote Work Makes Onboarding Difficult
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On March 16, CommonBond had its first day as a fully remote company. That day also happened to be the first day for a new engineer on my team. I was an engineering manager at CommonBond at the time, and this engineer had signed her offer letter a month earlier. She had only met a handful of her new coworkers in person during her onsite, and nobody realized at the time that she was signing up to onboard remotely.

During the time I managed her, I spent a lot of time thinking about her onboarding process and trying to learn from her experience, especially as I started to realize that remote work might be here for longer than expected.

Six months later, I found myself in her shoes when I joined Jetty as a senior engineering manager. Here, I had to onboard remotely to a company that was transitioning to being fully remote, and where half of the engineering team had already moved out of its New York headquarters.

These two experiences have given me the opportunity to see remote onboarding from two different perspectives: that of a manager trying to onboard a new employee, and that of an employee joining a new company. These two perspectives have helped me better understand the challenges faced by remote onboarding.

Here, I have summarized my observations into four challenges specific to remote onboarding, and ways I have addressed them.


1. There Are Very Few Opportunities to Learn Through Observation

I remember when I first joined CommonBond back in 2018. Specifically, I remember my first few visits to the office kitchen. I wasn’t sure where the sugar was kept for my morning coffee, or even how the coffee machine worked. I had been given a tour of the kitchen, but it’s easy to forget those little details when you’re learning tons of new information in your first week.

I eventually found the sugar, and I slowly learned my way around the kitchen as I would go there and see others preparing their breakfasts and lunches. This kind of learning through observation happened in my day-to-day work as well, from seeing the drawings people left behind on whiteboards, hearing conversations as engineers tried to solve a bug in production, and watching the different interactions and collaboration that happened in the office.

In a remote world, opportunities to observe others at work are mostly limited to the meetings that I am explicitly invited to. Learning through observation can be a powerful tool for onboarding, and it can be hard to replicate in a remote environment. One way we have tried to address this at Jetty is by encouraging communication in shared public channels rather than direct messages, which allows new employees to watch some of the chatter between older employees without the onus of participating (unless they choose to).


2. Communication Has to Be Deliberate and Planned

This wasn’t an observation that surprised me, but its consequences were much larger than I anticipated. In an office setting, there are three types of communication: formal, informal, and through the grapevine. Formal communication includes emails and meetings — methods that are deliberate and usually planned ahead of time. In my observations, these have been minimally impacted by moving to remote onboarding.

Informal communication is direct communication that is not planned — everything from sending a Slack message to tapping your neighbor on the shoulder to ask a question. In an office environment, if I want to ask someone a question, I can decide whether I need to interrupt them at their desk, pull them away from a meeting, or send a message that they will get to eventually. That allows me to factor in how urgent my question is.

In a remote environment, my only option is to send them a message. It becomes the responsibility of the receiver to decide how long they will take to respond to my message, but they have no context on how pressing my question is — should they read the message immediately, or is it OK to look at it in 30 minutes after they finish testing their code?

Finally, there is grapevine communication. These are the things you overhear people discussing, or learn simply by sharing the same space as your colleagues. This type of communication has disappeared entirely and has led to less shared context across the team. For new employees, the lack of shared context can feel isolating. This type of communication has therefore needed to become more deliberate and planned.

One way to do this is to make a detailed roadmap of your entire team’s work so that there is a single place people go to get contextual information. Another method is to have a regular touchpoint (like a weekly meeting) for your entire team to share context. For the Jetty engineering team, for instance, we host a weekly product forum where we touch base on the features we have launched, the projects we are working on right now, and the ideas we are scoping to work on next.

Related ReadingHow We Solved Our Biggest Remote Communication Problem


3. Social Interactions Also Have to Be Deliberate and Planned

How much do you miss walking to get coffee at the nearby cafe with your teammates, or going for drinks after work to celebrate a release? These are types of interactions most people looked forward to. Compare that to the last time you tried to organize a Zoom happy hour — I can almost guarantee that there were some awkward pauses and that, as soon as one person called it a day, most of the others signed off too.

Social interaction between coworkers is healthy and necessary for a productive and positive work environment. Onboarding a remote employee also includes helping them create social bonds with their coworkers. One way to do this is to add social elements at the start or end of meetings, for example, by asking your team if they did anything interesting during the weekend at your Monday morning sync. I have found this to be somewhat effective, but often leads to the awkwardness of transitioning from social interactions to work conversations. Either the conversation is strained and therefore ineffective, or it leads to an interesting back-and-forth that someone has to interrupt in order to make sure you get through your agenda in the allotted time.

The other way to help create social bonds is to create set times for social interactions. Yes, that can mean Zoom happy hours. However, you can also tailor the interactions to the fact that everyone is remote. This can include playing online pictionary games, having a trivia night using Kahoot, or playing any of these other remote-friendly games. Happy hours via video calls can feel a lot like work meetings, and if you can avoid that, you might find more employees excited to join them.


4. You Share Less Context With the People You Don’t Directly Work With

As an engineering manager, I get to be in meetings with a wide range of people, from engineering to product to stakeholders on the business side. This is not the case for individual contributors. A month into remote onboarding the engineer onto my team at CommonBond, I was very happy with how well she was getting along with the team and able to be productive in her role. However, when I asked her about her onboarding, she told me that she found it hard to feel in tune with the broader mission of the company. She felt isolated.

What I learned from that experience is that an employee that is productive in their role is not necessarily fully onboarded. A remote environment means that they may not get to know Saul from the finance team, or Abbey from the sales team — they don’t have the opportunity to meet them in the kitchen area or the lounge. Because of this, new employees will find it harder to have a broader understanding of the company, its goals, how it operates, or what makes it tick.

All-hands meetings, where the entire company hears updates from the executive team, can be useful for getting information, but the number of attendees in these meetings means they don’t encourage a lot of interaction between employees. It can sometimes feel as though all-hands meetings might as well be recorded for you to watch on your own time.

I have found that there are other smaller group meetings that are open invite and can help new employees embed within the broader company. These include sprint demos, book clubs, social groups, and lunch and learns — lightweight ways for a new employee to gain more shared context with people they don’t work with on a daily basis.

Remote onboarding has its challenges, both for new employees and their managers. The past six months have been a chance for many companies to try their hand at it, and while there have been some pros and cons, it’s important that companies identify the specific challenges so that they can work on addressing them.

Improving remote onboarding will not only ensure that you can hire new employees effectively right now, but can also translate to a better onboarding experience in the future for both remote and office employees. And if you do have other tips to address any of these four challenges, let me know!

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