“Mandatory Fun,” and other serious strategies for building trust with remote teams

If you’ve ever worked remotely, you know how hard it can be to feel truly connected. How do you build relationships with people you mostly see from the shoulders up? As a manager, how do you foster trust within your team — and earn their trust in return? And — dare I ask — is it possible to achieve all of this and have some fun along the way?

These are the challenges I’ve navigated as a Manager of Technical Support at Front, managing a global team from a computer in the corner of my house. Along the way, I’ve developed a concept I call Mandatory Fun — and no, it’s not as contradictory as it sounds.

My nearest team member is 600 miles away, and the farthest is 5,000 miles away. Support is the only fully remote team at Front, and yet we’ve consistently earned the highest engagement scores in the company. Here’s how we’ve made it work — and some of our favorite Mandatory Fun event ideas to inspire your team (spoiler alert: check out the full list here!)

Step 1: Establishing relationships

The first thing to understand about building a remote team is that connection is key. In an office environment, you naturally get the chance to connect — whether it’s chatting about your favorite show or bonding over the latest office gossip. When you work remotely, you miss those casual, spontaneous interactions. 

So, how do you connect with your team when you’re not in the same physical space? The answer is simple, but it requires intention: create a space for casual connection.

Whether it’s Slack, Teams, Front, Zoom, or whatever tools your team uses, you need to encourage communication beyond just work-related messages. I’m not talking about chit-chat all day (although that can help!), but I mean spaces where your team can share moments — like posting the latest picture of their dog, asking for advice on a recipe, or sharing a funny meme. Don’t wait for someone else to start the conversation — take the initiative yourself. Crack a joke. Share something fun. Sometimes it only takes one person to break the ice, and soon everyone will feel comfortable following suit.

Another challenge in a remote environment is knowing who’s in the office at any given time. In a shared office, you can glance around and immediately spot who’s there and who’s out. Online, this is trickier unless you have a system. Encourage your team to check in and out when they log on and off — whether that’s a quick hello or a fun emoji. It’s also helpful to share a daily schedule in your main team channel, including who’s in or out for the day, and maybe even throw in a fun fact or a bad joke (I live for getting a “facepalm” emoji every time). 

These small gestures may seem insignificant, but over time they help build a sense of camaraderie, even if you’ve never met your teammates in person.

Step 2: Building trust

Okay, now you’re connected. But building trust is the next big hurdle. To manage a remote team successfully, you need to trust that your team is doing their best work. But how do you build that trust when you don’t have a constant physical presence?

First, realize that trust goes both ways. Yes, you need to trust your team, but your team also needs to trust you. They need to know that you have their back and are advocating for their best interests. This is where you, as a manager, can make a huge difference. What can you do to improve your team’s day to day? Can you remove obstacles, provide better resources, or make their job easier in some way?

Let’s take a page from Ted Lasso. Early in the show, Ted, the new coach, leaves a suggestion box for his team. Most of the “suggestions” are jokes or insults, but one mentions that the water pressure in the team’s showers is terrible. Ted takes this seriously and gets it fixed, showing the team he cares about the small things.

I try to remember to “fix the water pressure” whenever I can. A good example of this is when we worked with our product team to improve our bulk import process for contacts. Previously, this required a customer to contact support, creating a lot of manual work for our team and a longer resolution time for our customers. After highlighting this pain point, we collaborated to create a feature allowing customers to manage it on their own. It’s these “water pressure” fixes that show your team and customers you’re committed to making their experience better.

Another great way to build trust is to get into the trenches with your team. Even if it’s just for an hour or two a week, diving into the work with the shows that you’re willing to roll up your sleeves. It keeps you connected with the product and customer issues, but it also proves to your team that you’re not just a manager behind a desk.

Lastly, always assume positive intentions. Set clear expectations and goals, then give your team the space to rise to those challenges. Use tools like Front Analytics to track progress and keep a pulse on team performance, but trust that your team will deliver.

Step 3: Mandatory Fun

We’ve connected, we’ve built trust — now it’s time to have some fun. But wait, isn’t Mandatory Fun an oxymoron? It’s true that when people hear “mandatory,” they often roll their eyes and think, “Oh great, here comes a teambuilding activity.” But the magic happens when you’ve already built a strong, trusting environment. When that happens, your team will actually look forward to these activities, and they won’t feel forced.

Why is Mandatory Fun important? Because it’s a great way to let your guard down and be authentic. People respond well to authenticity, and the best way to show it is when you’re having fun. Having these moments of genuine connection helps build bonds that go beyond just work.

I’m particularly proud of our monthly Mandatory Fun events. Once a month, we take a break from our usual work and play an online game together for 30-60 minutes. We break up events by region so we still have coverage in the queue while teammates participate. We’ve done everything from Tetris and drawing games to emoji hackathons and AI-assisted survival games. We even host a quarterly cooking class where one team member shares a recipe, and we all cook together via video chat. My personal favorite? Making homemade naan.

Here are some key lessons I’ve learned over 36 events:

• What works: Choose activities that everyone can easily participate in — low-barrier, quick-to-understand games. Respect time zones and working hours; if someone can’t attend an event, let them know it’s okay. Take feedback seriously — when we did a “two truths and a lie” game, introverts told us they found it stressful to speak up, so we switched to a written version where everyone could guess who the lie was about. It worked much better and was still fun.

• What doesn’t work: Trying to force participation. If someone really doesn’t want to join, it’s okay — just make it clear that having fun is mandatory, not attendance. Don’t run the same activity repeatedly. People like variety. And of course, always plan and prepare — these are still work events, so make them worth the time away from tasks.

As a manager, it’s crucial to ensure that your team can attend these events without guilt. Can you step in and cover the queue for an hour? If not, try rotating the coverage so no one feels overwhelmed. There’s no one-size-fits-all solution, but don’t be afraid to experiment and adjust as needed.

To wrap it up, building a successful remote support team isn’t just about the work — it’s about connection, trust, and yes, a bit of fun. By creating a space for authentic relationships, demonstrating that you have your team’s best interests at heart, and adding some Mandatory Fun to the mix, you’ll create a team culture that keeps everyone excited to come to work. This work can be challenging, but when you genuinely enjoy working with your team, there’s no limit to what you can achieve.

Check out the living document of activities we’ve done at Front for inspiration to take to your team.

Support teams are evolving. Are you? Check out Front’s resources designed to help you take your support team to the next level.

• Explore a rubric to build senior support talent development beyond the queue

• Learn how to do more with less in your help center with our resident help center guru.

Check out a guide to starting a “Hop in the Support Queue” program at your company, to make support a company-wide initiative