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How to Make Online Events Awesome

We’ve all been there.The host forgot to unmute; somebody else should be on mute, but isn’t. You can hear them sneeze in the background as...

CJ Cowan

by CJ Cowan - June 15th, 2022


We've all been there.

The host forgot to unmute; somebody else should be on mute but isn't. You can hear them sneeze in the background as you struggle to focus on your coworker's words. Suddenly, an awkward silence sweeps into the virtual room, and all you want to do is close your eyes and melt away.

The crux of remote culture is employee engagement. If your remote team isn't engaged at work, you should invest in your company culture, including through fun virtual socials. But if your remote team isn't engaged at the events themselves… Let's be honest: you deserve more than awkward, cringe, or boring.

We know precisely what can make or break a virtual experience. We've run hundreds of events for clients like Google, TD, Capco, and Wealthsimple. We've also tested several online socials, many of which didn't meet our high expectations. By sharing our virtual event planning insights and reserving only the best experiences for our clients, we help make remote work awesome.

That's why we've compiled this list of fatal flaws in virtual event planning and our best tips to eliminate them. So, are you ready to take your online socials from "Oh boy, when does this end?" to "This was so much fun"?Say goodbye to cringe transitions, awkward silences, and faceless Zoom windows. It's time to boost your remote team's engagement levels.

This Wealthsimple team finally discovered whodunit in this fun virtual murder mystery party!

What's holding you back?

"It just wasn't fun."

When an online social feels acutely uncomfortable, that's probably because the activity was a poor choice for your team. There's no one-size-fits-all for online events, and we should all stop pretending there is. Just think: if it's an activity nobody, absolutely nobody in the group was drawn to, then, of course, it'll be awkward! 

The trick here is to ensure people on your remote team have a say early on through a quick planning stand-up, Slack poll, or email vote. By providing that you and your coworkers all play some part in the decision-making, you're much more likely to choose an online event that suits your interests. This is especially important considering how your colleagues' tastes might differ from one quarter to the next, depending on how stressed they are and what's going on in their personal lives. 

Try mapping out your team's personality types, social networks, and interests in the long run. What a group of introverted coworkers prefers might differ from one or two colleagues' extroverted tastes. Likewise, you might all share a secret affinity for board games or traveling. Don't wait to get to know your colleagues better through informal coffee chats, async networking, or virtual icebreakers! Then, you'll be able to find the right online events for your team. 

"It feels like forced interaction."

To some extent, online events exist precisely to prompt meaningful interaction between your remote team members. If your virtual event sucks due to poor engagement, it could be because your coworkers don't understand the greater purpose.

At the office, "break rooms, communal kitchens, and even well-trafficked hallways help create what experts call functional inconvenience." You run into colleagues across shared spaces, and a quick hello in the hallway leads to informal chats and shared laughter. This casual interaction then leads to increased communication, collaboration, and engagement.

Your coworkers won't feel at ease in your online socials until they understand that the goal is to help them feel at ease.

If you've already run an online event recently, try sending over a super quick anonymous poll to collect feedback. Your coworkers need to know that their opinions are recognized and that they have ownership over how they spend their time. Moreover, to pave the way for more informal interaction, you can create a Slack channel or shared document where you can all compile resources on the transition to remote work and the positives of trust at work.

"Too close, too little, too soon."

Online events range from conversations fit for strangers to goofy games with great potential for awkwardness. Of course, it's not really about awkwardness but rather about trust. Online events suck when you choose activities requiring greater vulnerability than your remote team is prepared to give. This affects your remote team even more if you rarely make time for informal calls because your remote team won't have a social blueprint to frame their interactions. 

The solution? Work your way up to the more exciting online events with weekly socials. First, pick 2-3 short icebreaker activities with a low awkwardness potential. In other words, choose games and topics that require minimal trust to succeed, and ease your way into regular online events. You can always level up next week!

If you're a remote leader, get goofy first. It's a well-known fact that remote managers should model the behavior they wish to see in their workplace. If you're organizing online events to bond together as a team, then be the first to connect with others in events. Present an easygoing demeanor to signal the informal nature of your virtual social. And have fun! Cracking jokes, asking questions, and smiling openly help your remote team do the same.

"I'm never sure what to expect."

You're setting yourself up for awkwardness when you saddle your remote team with low or unclear expectations. Humans are social creatures, and they like to know what behavior they should adopt and expect from others. 

Introverts and planners enjoy envisioning what their day will look like to mentally prepare themselves for what's ahead.

If you leave your remote team in the dark as to the general vibes of your virtual event, most will show up in fight or flight mode, unsure of when to speak, what to say, and how to say it.

This is particularly true for new remote hires of young workers, who might be the reason you're organizing an online event in the first place. Nobody wants to feel penalized because they blurted out the wrong during their first week at work. 

To assuage these doubts, you can start by ensuring that the communication previous to your online social matches the general ambiance of the online event itself. For instance, if you're throwing goofy virtual icebreaker activities, you should share the planning details through equally goofy messages in a dedicated channel, thread, or message chain. 

Make sure to specify the general gist of the online event, what to bring (if anything), and how you feel about it. Sharing your emotions conveys an open and honest leadership style, which helps put people at ease.

The Fin News team was clearly 110% engaged in this online murder mystery event!

"Finally!" versus "Already?"

The wrong length, group, size, or timing can easily ruin Fantastic online events. 

Maybe you've taken a really exciting, high-impact activity and dragged it out so long that the adrenaline drained out of your team. On the flip side, perhaps you've taken an intriguing, thoughtful activity and tried to crunch it to 5 minutes, leaving your teammates confused and disappointed.

When planning for an online social, follow the recommended time and add another 20 minutes to your calendar as a buffer for explanations and small talk.

Otherwise, be sure to follow your host's instructions regarding group size. Squeezing a large group into a video call for an activity that involves lots of real-time interaction can be chaotic and absurd. As a result, quieter coworkers feel left out. 

But creating hype among four or five people during a high-energy game is equally awkward. Ultimately, timing is often a factor in poor engagement levels during online socials. Remote teams have their highs and lows, but it is too familiar for leaders to forget to check in with their coworkers to assess their well-being. 

By giving your employees a voice in planning, you can ensure the timing of your online event is just right — like a virtual 'Mandala Mindfulness' session before university finals or a crazy fun 'Musical Bingo' event after Eid al-Fitr celebrations.

Bonus — Wild Card

Many reasons for poor engagement in online events are bad planning or inexperienced hosts. Technical glitches are the perfect example of this and something to be mindful of when running your virtual social. Of course, if you ask somebody else to plan it for you, be sure they are seasoned professionals. 

Exceptional hosts are often the life of the party, breathing fresh air into the virtual room and helping to put your team at ease. They know how to create an exciting, joyful atmosphere, how much to speak, and how to encourage informal interaction.

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