Best practices for remote onboarding

Best practices for remote onboarding

Guidance for centering trust, psychological safety, and a sense of community from a new hire’s first day.
Part of
Issue 15 November 2020


When I first joined a company as a developer, I felt like the biggest imposter in the world. I didn’t know what version control was, let alone what a server was or how to run code on one. I spent my nights furiously googling, terrified that I would disappoint everyone by not being a fully productive team member from day one. Since then, I’ve been on a mission to help create a positive and smooth onboarding process for as many people as I can—whether it’s their first day at a new company, or their first day as an engineer.

Fast-forward nearly a decade: Today, I’m an engineering manager at Fellow, where I designed the engineering organization’s onboarding process, and I’ve helped teams at other companies create their own, too. I’ve written before about the basics you need in onboarding (think: goals, 1:1s, and feedback loops, among other things), and I want to show you how you can build upon that foundation and make the experience great for remote engineers so they can have a strong start on their new team.

Successful onboarding isn’t about learning the codebase at light speed or pushing out new features as quickly as possible; it’s about building a foundation of relationships and psychological safety that allows your team to feel comfortable asking questions and requesting feedback so they can grow. This isn’t easy! You need to take explicit steps to foster this culture, which is hard in person and can be especially challenging when teams are remote.

Keeping that in mind, I’ve put together some strategies based on what we do at Fellow to kick-start your onboarding and help create a solid foundation for your team.

Start with thoughtful basics

Logistically, seamless remote onboarding requires thorough prep work up front so new team members are ready to work remotely right away. Along with making sure any required hardware (preinstalled with necessary software) arrives before their first day, work with new hires in advance of their start date to create a first-day (or first-week) schedule. This step is key to preventing any surprises when your new hire gets access to their new corporate calendar, and allows them to make sure personal considerations (e.g., childcare) are accounted for as they plan their workday. Sending those first-week calendar invitations to both their corporate and personal emails—or, if sending to the latter creates logistic challenges, sending the schedule itself to their personal email—will allow them time to prepare.

Joining a new team brings on a whirlwind of emotions and an overwhelming amount of information—and, combined, that’s pretty stressful. To ease the anxiety and information overload, provide new hires with a templated document that outlines the “how-to” of the team (including elements such as links to documentation, code repositories, monitoring and logging tools, and the names of the members), and a company readme with references to company handbooks or official policy documents. You should also give them a personalized checklist of clear and actionable goals for the first one, seven, 30, 60, and 90 days, so your new hire can better understand what’s expected of them, how they’re progressing, and what their early-days work is building up to.

Whatever onboarding process you create, keep in mind that feedback is a gift. Asking for feedback at the end of your remote new hire’s first week to learn what went well, what could have gone better, and what information they felt was missing is a great way to make sure that the process is continuously improving, and that you can support your team member in getting what they need from the outset. Your processes might go through dozens of subtle or even substantial iterations: There’s always something good that could be great, a company might evolve between iterations, or someone’s learning style might lend itself to new ways to present information. When possible, you might even encourage new hires to update the process themselves as they go through it: You’ll demonstrate trust and a collaborative spirit, and they’ll have an opportunity to make a meaningful impact on the team experience from day one.

Create a content list

When you join a new in-office team you usually have the opportunity to meet people at lunch, over coffee, and through spontaneous hallway conversations. Remotely, those interactions have to be initiated deliberately. What’s more, it’s easier to set up virtual coffee chats or team lunch-and-learns than it is to move the conversation beyond awkward small talk. Instead of relying on icebreakers and dreaded silence, set the team up to have real conversations right away by establishing a baseline pool of topics that everyone can discuss. One format I particularly like is a multimedia content “playlist” that the team curates together—a compilation of anything safe for work which showcases the unique personalities and interests of team members. Perhaps folks will add favorite background music for focus time, links to podcast episodes, books, blog posts, pet pictures, descriptions of their remote work setups, and so on. Sharing this in advance helps to break the ice, providing new team members a window into what others on the team are interested in or care about.

Make it fun

Onboarding isn’t just a one-week thing—it’s a process for the long haul, and it can take months before someone develops a sense of belonging at their new company. When teams are co-located, connections are built by virtue of proximity and the ability to easily strike up or join conversations. Remotely, those same interactions can be challenging because of differences in communication: Writing often takes longer than talking, and starting a call with someone can feel like an intrusion into their work time. At Fellow, we replicate some of these nonwork conversations and continuously get to know each other by participating in a “Friday Funday” Slack thread. Every week we answer questions like, “What is the most unbelievable fact about you?” with pictures. It’s an inclusive way to continue to get to know each other, while getting familiar with little ways a company’s culture and values manifest. And because it’s asynchronous, it doesn’t rely on everyone being available at the same time.

Struggle together

Even if you’ve established a healthy culture of psychological safety, remote new hires may not implicitly feel it right away. They won’t be a witness to their infallible veteran colleagues frantically debugging issues and coming to the realization that the issue was something small and obvious. Those day-to-day difficulties need to be visible so that new team members build confidence that it’s safe to ask questions and make mistakes (even if they’ve spent an hour trying to figure out why nothing works after forgetting a semicolon).

To bridge this gap, I recommend pair programming’s frustrating (yet productive) counterpart: pair struggling, in which remote new hires shadow experienced teammates, watching them debug issues and navigate challenges. By seeing which tools, services, dashboards, and channels are monitored and searched, new hires can gain helpful insights into the things they’ll need to do their jobs successfully, even as they observe that developers who have been working on the company’s codebase for a long time still have trouble sometimes. This helps build trust that the team has an atmosphere where it’s okay to fail, to not have all the answers, and to ask questions that may appear too “basic.”

Establish trust from afar

Creating mutual trust between teammates early on is critical to maintaining a productive and healthy team. Without trust, team members are less likely to share feedback with each other, may speak up less often about issues or new ideas, and may avoid solving problems collaboratively. Tobi Lütke, CEO of Shopify, has described how the company actively assesses the “trust battery” between team members, and how this container of trust only starts off half full. Instead of waiting for mission-critical projects to bring up the trust level when someone joins a team, I like to find other ways to build trust while showing new members the team is invested in their success.

For example, recently, a new remote engineer on my team was relocating from Brazil to Canada. He had a list of potential apartments to rent in Ottawa, but he didn’t know the city and wasn’t sure which spot would be the best fit. Instead of leaving his housing situation to chance, the Ottawa-based members of Fellow joined a #welcome-to-the-city Slack channel where our new teammate posted real estate listings and we shared our local knowledge to help him find a place he’d love. The sense of collective outreach gave everyone a stronger feeling of belonging. Establishing conventions that promote camaraderie and trust supports the workflow, too, by allowing team members to feel more comfortable with each other, and ultimately more comfortable asking questions and making mistakes.

Celebrate early accomplishments

Recognizing people for their work is always important, but at the start of a new job, it can give a sizable confidence boost that helps push past that first wave of imposter syndrome. When someone joins my team remotely and I see that the first ticket they’ve picked up is marked as “in progress,” I keep a close eye on recent pull requests to make sure that I notice theirs as soon as it’s created. When it pops up, I like to congratulate them in the team Slack channel with as many :tada:-style emojis as I can find. Creating a culture on the team where everyone celebrates each other’s wins, big and small, brings teammates closer together, and shows people that they are valued from day one.

Be mindful, though—as Lara Hogan points out in her article “Questions for Our First 1:1,” not everyone enjoys public praise. If you know this about your team member, sending a personal e-card is a fun but discreet substitute.

At Fellow, my team’s weekly meeting agenda includes a section dedicated to showing work in progress so that everyone is aware of what’s going on and to promote a culture of seeking feedback from peers early and often. After I’ve recognized a new hire’s work, I invite them to share it during this period, even if a change is minimal. For those comfortable with it, it’s a chance to showcase what they’ve done early on and reinforces that the team cares about their work and impact.

Build a remote buddy system

Onboarding is a time for asking as many questions as possible so new hires can get to know the company and codebase quickly. When co-located, you have the benefit of being surrounded by people available to answer questions, but when you’re remote, a lot of the social and environmental cues that help you decide who to go to with questions are gone. It can be intimidating to message someone (with whom you may never have interacted individually) out of the blue and await their answer, wondering whether they’re taking 10 minutes to respond because they’re out for a walk or because they’re annoyed and ignoring you.

Pairing new members with a buddy on the team (preferably one whose working hours line up with theirs) makes the process of figuring out who to go to with questions easier. While you might be tempted to assign the most senior developer on the team to be a buddy, assuming they’ll be more likely to have all the answers, I find that early-career and recently joined team members make particularly helpful buddies: They often have their own onboarding experience top of mind, which provides an important perspective when answering questions and filling in information gaps. Plus, helping others learn the ropes reinforces their own knowledge of the code and the team’s processes. Similar to getting recognition for that first pull request, spending time helping others grow in the early days of a new role reinforces the buddy’s notion of their impact on the team.

Outside of technical know-how, buddies play an essential role in helping new hires understand communication expectations, company social norms, and team dynamics. Ask them to help facilitate introductions to cross-functional teams, give the lowdown on Zoom etiquette, and invite their new-hire partner to social and community Slack channels that connect them to others with similar interests.

Be principled

As you build purposeful solutions to tackle the challenges of remote onboarding, remember that the core of high-performing teams is trust, psychological safety, and collaboration. Wherever your team is working from, you can make these principles part of your team’s experience from day one.

About the author

Alexandra Sunderland is an engineering manager at Fellow, a platform that enables teams to build collaborative meeting agendas, record decisions, and keep each other accountable.


Artwork by

Olivia Fields

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