Tested (and Fun) Ways to Cultivate Connection Across the Miles
Plus, ideas to borrow from other industries!
While many organizations have returned to office life post-COVID, others are maintaining hybrid or fully remote work models—and that means discovering that long-term remote engagement is an entirely different game. It’s not enough to replicate in-office experiences online. To truly engage remote employees, you need intention, creativity, and a human-first approach.
At The Orientation Company, we’ve been remote since day one. When COVID hit, we were lucky in the sense that we didn’t have to adapt — but we do face the daily challenge of preserving a culture that prioritizes connectedness in a decentralized environment. Over the years, we’ve discovered some great ways to build loyalty, connection, and purpose — and many of those ideas have been inspired by the people around us. Our vendors, partners, and clients have all shared insights that shaped how we do things.
Here are three simple and effective ideas for engaging remote employees, complete with real-world examples and cross-industry tips you can apply in your own workplace:
1. Communicate, Communicate, Communicate
Studies show that people need to hear something as many as seven times before it starts to sink in. That’s challenging enough with a captive audience inside an office building, and even harder when you can’t address workers face-to-face. Plus, remote employees can’t overhear hallway conversations or stop to chat at the watercooler. That means updates and transparency need to be intentional and repeatable.
What We Do at TOC:
- Our monthly internal newsletter is packed with updates, birthdays, employee spotlights, and yes—even a suitable-for-work meme.
- We use an online recognition platform that offers a social media-esque experience where team members can see and share stories of great service, problem solving, and expertise from all corners of the company.
- Team members can submit their own stories of meaningful service experiences that made an impact on them so others can learn about “a day in the life” for other roles and departments.
Tip to Borrow:
Consumer brands are masters of creating content that resonates with their target market. They keep customers engaged with timely and seasonal messaging that ties into the interests and needs of their audience. Treat your internal comms the same way—use newsletters or internal blogs to share wins, lessons, and milestones that tie individual effort to company-wide impact.
2. Spend Time Together IRL
No amount of Teams messages or Zoom trivia can replace the energy of in-person interaction. Even for remote companies, coming together matters. Sharing a meal or a laugh together in real life can accomplish in hours what a virtual event never could.
What We Do at TOC:
- Once a year, we gather the whole company for a team trip.
- We bond over shared experiences (like food tours or local adventures) and enjoy relaxing downtime.
- We always capture the memory — yes, matching t-shirts and a group photo included. #extracheeseplease
Tip to Borrow:
Nonprofits thrive on mission alignment and shared purpose. Their in-person retreats for donors or volunteers are designed to build emotional resonance. Apply the same approach: focus on connection, not KPIs. Let the trip remind your people why they chose to work here. Make your get-together feel like a reward, not a requirement.
3. Host Virtual Spirit Weeks That Build (and Preserve) Culture
In remote work, it’s easy to assume disengaged employees simply aren’t interested. But often, they’re just waiting for something accessible, low-pressure, and fun. A team Spirit Week gives everyone—from extroverts to quiet contributors—a structured way to step up, celebrate, and be celebrated.
What We Do at TOC:
- Each summer we host a virtual Spirit Week with daily themes like “Favorite Team Jersey Day” or “TOC Team Member Twins” (where two team members dress alike or impersonate one another’s signature look.) The results are nothing short of hilarious.
- Each day is focused on one of our core values—team members use our recognition platform to give shout-outs tied to the value of the day. We tie the day’s value to the day’s dress up theme. For example, Twin Day would be tied to our core value of Harmony.
- Participation is completely optional, but we consistently see high engagement and it gives us an extra boost of energy heading into Q4, our busiest season of the year!
Why It Works:
These “all-skate” moments of connection are about more than having fun — they’re like cultural glue. For newer employees especially, Spirit Week offers a crash course on how a company’s values are actually lived, not just posted on the website. When they see kindness, collaboration, and reliability celebrated by their peers, they learn what “how we do things here” really means.
Tip to Borrow:
Think like an industry event planner: don’t just throw a party—design an experience. One that invites people in, makes it easy and comfortable to join, and reflects your brand’s personality. The payoff? Stronger culture, increased alignment with core values, and a culture of care that is preserved as your workforce grows.
Final Thought: Driving Engagement is a Discipline, Not a Checklist
The most important lesson we’ve learned? Tactics are no substitute for true substance. Regardless of how much or little you do in the way of remote workforce engagement, the age-old adage is true that it’s about quality over quantity. It’s how you talk to each other, how you celebrate, how you show up when someone is struggling. For remote workers, it’s especially vital to feel seen, valued, and part of something bigger than themselves.
Whether you’re fully remote or juggling a hybrid mix (with half your team in the office and the other half in sweatpants), investing time and energy in employee engagement is not just for fun — it’s to give your workforce the chance to develop a sense of true belonging. Because the real goal isn’t just to keep your remote team engaged — it’s to make sure no one ever feels like they’re working alone.