Addressing Loneliness In Remote Onboarding

I’ve onboarded remote hires across time zones, continents, and cultures. And here’s what I’ve learned: Remote onboarding doesn’t ⭐fail⭐ because of location. It fails because of assumptions. Assuming someone will “just speak up.” Assuming they’ll know what success looks like. Assuming they feel like they belong. Without hallway chats or shadowing, remote employees miss all the informal context that makes onboarding feel human—not just functional. Here’s how I’ve made it work: 💬 Over-communicate expectations and priorities 🎥 Use video, even for 15-minute check-ins 📅 Create a rhythm of connection—1:1s, team intros, buddy syncs ☕ Encourage informal conversations (yes, even virtual coffee chats) Remote doesn’t have to mean disconnected. In fact, with the right systems, it can feel even more inclusive. It took me many years of learning the hard way to build this out. And I’d like to share it with you, no strings attached. (see link in comments) That’s why I built these practices right in our Manager Onboarding Kit—to help leaders support their teams with intention, no matter where they are.

Starting a new job while remote can suck. Imagine your first day: You get your laptop and login info. Set up all the software and benefits. Lovely HR folks onboard you but it’s all going through the process. You don’t actually meet your teammates though or learn about your work until later. That would feel kinda lonely, eh? 😔 Imagine a different first day: 👋Your manager posted an intro message in the company new hires channel (at Slack, we call this #yay). 📮People from different teams message you offering to chat or welcoming you to the company! ☕️You have virtual coffee invites already. I joined Slack in April 2020. Remote. Didn’t meet anyone IRL for over a year! Yet, I felt welcome and included because Slack’s leadership is very intentional about curating the culture (David Ard Robby Kwok would directly welcome people!) People from across the company DMed me. To my slack colleagues reading this, this might feel obvious. However, a lot of companies are still figuring out hybrid culture - across time zones, cultures and borders 🌎🌏🌍 Today, I try to carry on the torch. Every Monday, I message the new hires in our #yay channel. On lighter weeks, I do 15 min coffee chats. For the ones in NYC, we coordinate office days. We might be in completely different parts of the company and never work together, but that’s also an opportunity to learn something new. It might be just one message or meeting for you, but it can make a HUGE difference in someone’s onboarding experience. So, carry the torch - go make someone’s first day amazing 🔥

We set out to teach coaching—and accidentally built a lifeline. "It's more effective than training." (This knocked me off my axis.) Here's how we got there. The challenge: Managers crave support—and every org I know is trying to meet that need. The idea: Bring people together for open, lightly facilitated, peer-to-peer discussions. This is exactly what we built into the pilot: • Small cohorts (5-6 people leaders, mixed divisions & levels) • Open, often unprompted discussion ("What's on your mind today?") • Light facilitation + skill application ("This is values-based coaching.") The goal: Help managers practice coaching, apply other skills, and create a space for vulnerable conversations. The inspiration: The T-group model used in Stanford University's "Touchy Feely" class—applied in a remote-first work environment. The results: When asked about what managers enjoyed most about the 8-week pilot, every participant referenced the feeling of community as their top takeaway. They learned to coach—but just as powerfully, they realized they weren’t alone. Across functions and levels, the same challenges kept showing up. For a remote-first company, that kind of connection isn’t just a nice-to-have—it’s a lifeline. According to Gallup, loneliness and disconnection are crushing the global workforce right now. This is one way we’re fighting back. Now we're planning how to scale Coaching Circles so that all our leaders can build relationships, sharpen coaching skills, and feel less alone in their work. More to come as we build this out here at Fleetio. And if you’re experimenting with something similar, I’d love to swap notes! ——— ALSO—The quote in this graphic is a statement that emerged during a session. When folks REALIZE a concept, it's far more powerful than a trainer making a statement or listing text on a slide. #LeadershipDevelopment #PeopleManagers #CoachingCulture #RemoteWork #EmployeeExperience