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Why Remote Team Employee Engagement Can’t Wait Until January—Especially in December

Thought Leadership /

By Toby Longhurst 

Being with a virtual staffing company that services different industries worldwide, I know for a fact that December looks different for every business. 

For e-commerce, logistics, and digital services teams, it’s all hands on deck due to peak volume, tight deadlines, and round-the-clock coordination across time zones. 

For others, it’s a window to reflect, reset, and prepare for the year ahead. 

But I’ve noticed one truth holds across industries: December is the best chance to reinforce connection before the new year resets priorities. And for remote teams—especially those spread across different parts of the world (like in the case of Cloudstaff – the Philippines, Colombia, India, Kenya), this moment matters more than most realize. 

As someone who oversees global employee experience, I’ve seen how this month makes or breaks momentum. It’s not just about morale—it’s about trust, retention, and cultural continuity across borders. 

Why December Engagement Is Non-Negotiable 

High performers need recognition when it’s earned—not months later. If your team is powering through peak season, delaying appreciation feels tone-deaf. 

For teams in planning mode, December sets the emotional foundation for the coming year’s execution. A team that feels aligned and valued now will ramp faster in Q1. 

And for global teams, holidays aren’t universal. Thoughtful engagement acknowledges that—whether someone is shipping orders on Christmas Eve or observing a quiet family tradition. This isn’t just empathy; it’s operational intelligence. 

For instance, at Cloudstaff, we act on this through intentional recognition. This year, we’re opening December with our Hub Awards Night, where we honor our Philippines-based teams whose behind-the-scenes work keeps our global delivery running smoothly. Throughout the month, we’re organizing small dinner parties and treats for those working during the holidays—moments made more meaningful when our CEO joins them, not from a stage, but at the table. 

Then comes CS Roar—a celebration that has grown into one of the largest gatherings for a remote workforce anywhere. Tens of thousands of Cloudstaffers, families, and partners will come together at the Philippine Arena, the world’s largest indoor arena. It’s not just a party. It’s a deliberate expression of community, gratitude, and shared momentum—built year after year because we’ve seen how it strengthens retention, connection, and pride across borders.  

Move Beyond One-Size-Fits-All “Fun” 

The goal isn’t more meetings—it’s meaningful moments. 

  • Spotlight peer-to-peer wins in team channels (e.g., “Shout-out to Maria in Bogotá for handling 3x ticket volume!”) 
  • Offer flexible, low-pressure ways to connect—optional trivia, gratitude boards, or regional mini-celebrations 
  • Anchor activities in your team’s values—not just calendar dates 
  • For peak-season teams: practical care (e.g., meal vouchers, coverage for time off or ,a special celebration in January) often means more than virtual parties 

The Bottom Line 

Engagement in December isn’t about festivity—it’s about intention. 

Whether your team is scaling support for Black Friday fallout, Christmas demand, or finalizing 2026 resourcing plans, this is the month to ask: “How do we make people feel seen—right now?” 

Because the teams that carry momentum into the new year aren’t just well-resourced. They’re well-connected. 

About the Author
Toby Longhurst is the Director of CSX (Cloudstaff Experience) at Cloudstaff, where he is dedicated to crafting engaging experiences for the global workforce. With a background in journalism and editing, and extensive experience in communications management, Toby has played a central role in connecting Australian, New Zealand, and US businesses with dedicated teams in the Philippines. Prior to his current role, he served as General Manager at Vertical Internet Media and DeskStaff.pro, and worked as an editor and journalist at QNews Magazine. He is a graduate of The University of Queensland and is passionate about building positive workplace culture and strengthening cross-border business relationships. 

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