7 Proven Ways To Boost Remote Team Engagement


Tori Armendariz

December 29, 2020

I joined the Trainual people ops team on February 25 to help boost team engagement. And on March 11, we were told to pack our desks and work from home for a bit.

All the message said was: “Clearly, this virus is no joke, and everyone is taking steps to err on the side of caution. So, for the remainder of the week (Thurs/Fri), we’re going to institute a semi-mandatory work from home policy.”

And honestly, we weren’t really sure what this meant at the time. Or even how long this working from home thing would last. Should we plan on this being the new norm?

Almost 10 months later, and we’re still operating the same way as we were in March – by taking things a few days at a time. But, of course, we’ve gotten creative when it comes to planning team experiences and engaging our team members. Because those kinds of things don’t happen on the fly. 

Basically, we had one rule: don’t let Trainual be an added stressor. Because through the long days, late nights, early mornings, world-wide panic, toilet paper shortages, and presidential elections, our team had enough draining them. 

So, here’s 7 ways we’ve boosted remote team engagement since March (plus how you can do the same):

1. Put aside time for donuts

One of our first big initiates was actually a carry-over from our days in the office. Using a Slack integration called Donuts, we randomly pair team members up to chat about everything and anything – except work – during paid working hours.  

When I first started at Trainual, we would do this about once a month. Go to a coffee shop, grab lunch, hit happy hour, and have an opportunity to socialize with our coworkers. 

A screen shot from a recent donut.

And with everything now happening through a screen, we didn’t want to lose that personal touch. So we upped our donut frequency from once a month to once a week. 

Our whole goal was to reinforce that work doesn’t need to be all work. Meaning, our teams are allowed and encouraged to carve out breaks and get to know people that aren’t on their immediate team. 

But this cadence proved to be a bit too demanding on everyone’s schedules. So we’ve since cut donuts back to once every 2 weeks. And now, it’s a huge success!

2. Embrace virtual onboarding

Since going remote, we’ve been lucky enough to double our team size. But that also means that there is half the team who we’ve never met in person. So, to keep up with our growth, we had to radically (and quickly) change how we onboard new team members. 

From the get-go, we like to foster real relationships. And before quarantine, that happened via office talk and fun activities like company-wide cooking classes and horseback riding excursions (we’ve done both). 

But now, “get to know you” conversations don’t happen by happy accident. And casual Zoom meetings are rare, so we worked it into our remote onboarding process

For us, this means 30-minute meetings between the onboarding cohort and each individual team. We originally left these as unstructured times to get to know each other. 

But with a number of introverted employees and the tendency for the onboarding cohort to get stuck answering the same questions on repeat, that ended up being a mistake.

So when people came back saying that these conversations could be better, we listened. We now give each “meet the squad” meeting 3 unique ice breaker questions. This gives the meetings a little more focus and makes it easy to keep the conversation running.

Some sample ice breaker questions we ask new Trainual team members.

🔥 Tip: Trusted by thousands of growing small businesses, Trainual is the #1 tool for remote onboarding and training, according to G2. Try for free.

3. Plan a virtual retreat

At the start of the year, we had big plans for a summer retreat in Salt Lake City, Utah! And we were all stoked to hike, sing karaoke, summertime luge, and just travel together as a team.

But by the time it was supposed to happen (end of June), we were at the height of the pandemic. And there was no way we were going to risk our team’s health for a retreat. So we canceled the trip. 

We still wanted to have an amazing experience together. So our Head of People, Sasha Robinson, and Chief of Staff, Chelsey Krisay, pulled together a highly unique virtual retreat – in just a few weeks! 

Our virtual retreat helped boost remote team engagement.

They planned a jam-packed day filled with tons of fun activities to keep our team engaged, including: 

  • Coffee with Chris Ronzio, our CEO, to kick off the day (totally optional)
  • A “departments through the decades” theme. Meaning, each team was assigned a decade to dress up as (Prizes were handed out for best costumes!)
  • A really robust State of the Union presentation covering all things COVID and Trainual as a company
  • In-depth department presentations outlining big wins, bigger goals, and what we learned from our recent misses
  • A fireside chat to talk through all our burning Trainual questions
  • Break out sessions, complete with icebreaker games (my fave was the Nancy Drew themed virtual escape room!)

Plus, we even made the jam-packed day a really short workday to kick off a long weekend (AKA the big finale). 

Although it was no summer adventure in Utah, we’re deeming this experiment a huge winner. Everyone came back the following week, feeling recharged and reengaged after getting full transparency and a break from the usual grind.

4. Add quarterly all hands to the calendar

With our virtual retreat being such a wild success, we thought: why wait until possibly next year to do it again? (Spoiler: This was the right call!)

Trainual's Harry Potter themed town hall

So we put 2 hours aside on everyone’s calendar once a quarter to host a dialed-back version of the retreat. But with limited time, we decided to only hit the highlights. For example, at each quarterly all hands, we:

  • Hold a mini State of the Union, complete with time for questions
  • Give flash updates from all the department leads (they get about 10 minutes each) 
  • Include a few breakout rooms with icebreaker games

And we definitely pick a theme (costumes are a must). Our Q3 all hands were Harry Potter themed. And when you make costumes a must (hello, prizes), everyone gets really into the spirit. 

🔥 Tip: Whether you’re hosting a virtual retreat or a quarterly all hands, start reminding your team about the upcoming event at least 2 weeks in advance. That way, they have time to get rallied and pick up their costume. 

From one people leader to another, I highly recommend hosting your virtual retreat before implementing quarterly all hands. For starters, people will know what to expect and be excited because they had so much fun at the retreat. 

But if you choose to jump straight into quarterly all hands, you run the risk of people showing up and thinking it’s going to be a boring, extra-long Zoom meeting. That kind of starting point is hard to recover from. 

So if you’re unable to host a retreat first, pick people from each department to hype their team up for the all hands! For example, if you have a theme, have them ask who is dressing up as what, coordinate team costumes, or send songs that get people in the mood.

5. Do ding dong ditches

Even with all the virtual events, we still miss in-person celebrations. So we found a way to continue doing them on a smaller (socially distanced) scale – in the form of ding-dong ditches. 

A photo of Tori and Cindy during a recent ding dong ditch.

Every Friday, I hand-select someone who deserves a little more recognition (based on an accomplishment they had that week). I’ll grab their favorite drink and snack from the grocery store, and write a note thanking them for all their hard work. 

Then, to make sure everyone on the team can help celebrate, I document the experience. Photos and videos included. And with all my amateur directing skills, I even cut together short clips to share with the team via Slack. 

This is the kind of weekly highlight that we were hoping Donuts would be. Our team loves the videos and the ditch gifts – and a lot of people even stepped up their game to try to be next ding dong ditch. 

6. Host a virtual holiday party

Let’s be real – what would the holiday season be without a company party? We didn’t want to find out.

So, since we’ve spent most of the year getting really good at virtual fun together, we decided to (brace yourself) host a virtual holiday party! This time, with ugly sweaters instead of costumes. 

And we made it our mission to figure out how to play white elephant online. All the gifts – from a “pooping pooches” calendar to $100 Amazon gift cards – supplied by Trainual. 

We laughed, we fought, (some of us) came out victorious while others, uh, did not. But it was all in the spirit of good fun. And call me sappy, but the real prize was spending time with the team – absolutely no work involved. 

7. Offer some people ops TLC

Last but not least, we set aside time, all year long, for a little remote TLC. 

I’m not going to shy away from the fact that this was a challenging year for everyone. But here at Trainual, we genuinely care about our team. So we made sure that we had resources set aside to be there for them through it all. 

Sometimes this meant offering a bit more support, having uncomfortable conversations, or chatting through what’s not going great. And although some of these chats never led to resolution, we’re better for having them.

Our goal was to give the team a space to talk if they needed to. But we made sure not to push anyone to participate if they didn’t want to.

It was just important to us – whether people decided to use the resources or not – that our team knows we’re here for them.

The bottom line about remote team engagement

Admittedly, the biggest challenge around remote team engagement is getting people engaged in the first place. So if you want your team to thrive (even if virtual parties aren’t your thing), focus on keeping your team connected. 

Through all the challenges of this year, we made maintaining our team’s strong relationships top priority. And doing it in a fun way was a close second. 

That way, conversations, celebrations, and collaborations were still happening. And people didn’t feel alone through all this. And, if I do say so myself, our biggest 2020 win was that – even if we weren’t always perfect – our team always knew that we cared.

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