Our virtual retreat helped boost remote team engagement.

How To Plan The Ultimate Virtual Company Retreat


July 21, 2020

Co-authored by Trainual Chief of Staff Chelsey Krisay and Head of People Ops Sasha Robinson, co-facilitators of our 2020 virtual company retreat. 

Imagine you just rolled out a 3-day company-wide retreat in Park City, UT. One filled with train rides, river rafting, hiking, golfing, and good, old-fashioned team bonding. You even made a video to get everyone excited about it.

Then, fast forward just a mere 4 weeks, and imagine having to roll back everything in the face of a pandemic. Every. Single. Thing. #RetreatCancelled.

This is what happened to our 2020 retreat. And while we’re sure that we’re not the only ones – we won’t lie, this felt like a moment of defeat.

We had put so much time and effort into designing an incredible in-person experience. And suddenly, due to something outside of our control, we had to cancel everything and plan a virtual company retreat instead.

But having never done this before, we had no idea what we were doing. We just kept asking – how does a virtual company retreat even work?

We wanted to make sure that we were still facilitating all the bonding, collaboration, cohesion, and engagement as our initial retreat. But now, squeezed into one, long day on Zoom.

It took a lot of research and several brainstorming sessions. But we finally had an outline that balanced the need for team bonding and fun, with reflecting on the last quarter and building momentum for future projects and goals.

Here’s a glimpse at what we planned:The 2020 Trainual Virtual Retreat Agenda

Coffee with Chris

Once a month, our CEO, Chris Ronzio, hosts an informal and totally optional 30-minute coffee break over Zoom. Everyone on our team can RSVP and get to know Chris (and all the other participants) on a deeper, more personal level.

It felt only right to kick off the virtual company retreat with our July Coffee with Chris.

Plus, this gave everyone who chose to do their own thing time to catch up on work before the 3-day weekend (we made sure to schedule our retreat going into the 4th of July) or to sleep in.

State of the Union

We don’t like secrets here at Trainual. So, we wanted to set up space for Chris to speak freely and openly about the state of the company. We call this our very own State of the Union.

For example, at this one, we made sure to cover:

  • Our company financials
  • Any and all team updates
  • The latest COVID-19 responses and plans
  • Our mission, vision, and values (and our North Star Goal)
  • Our strategy for reviewing compensation and performance
  • An overview of our competitive landscape
  • A roadmap of how we plan to evolve our product
  • A break down of the “Playbook” software category

Including that we added 18 new team members.

To be completely honest, the State of the Union can feel vulnerable super vulnerable. But it’s critical for building your team’s trust.

We wanted to make sure to get it out of the way sooner rather than later, so we could get to the fun stuff.

Never Have I Ever

Since we wanted the day to be a mix of fun and business, we made sure every other session was a game of some sort, starting with the classic Never Have I Ever.

We know this game can get a little R-rated at parties, so the POPs team prepared a list of SaaS-related questions.

We asked questions like, never have I ever watched The Office at work, set the office alarm off, or participated in Sushi Wednesdays. In a lot of ways, it felt nostalgic. But it also introduced our newest hires to our pre-COVID office culture – something a lot of them are yet to experience.

Leadership Meeting Takeaways

Before a virtual company retreat was even on our radar, we had been planning to be more transparent with our team after leadership meetings. This way, everyone would feel more in the know.

And our retreat gave us the perfect opportunity to test it out.

We asked every department leader to share last quarter’s wins and misses with the rest of the team.

Plus, each department gave a sneak peek into the upcoming big initiatives, complete with metrics to measure its success! That way, we could all keep each other accountable.

2 Truths and a Lie

What’s better than playing 2 truths and a lie at your middle school sleepover? Playing it with your full-grown, adult coworkers!

And before you ask – no, we’re not joking.

We split our team into groups of 5 or so using Zoom breakout rooms. And each took our turns trying to stump our teammates with which statements were fact and which were fiction.

Matched with people who we might not interact with daily, we got a chance to share our wildest stories and really get to know each other outside of work.

(We found out that one of our coworkers watched the latest Mission Impossible movie in the same theater as Tom Cruise. Now, that doesn’t come up in an all-hands meeting.)

Fireside Chat

About a week before the retreat, we sent everyone a survey, asking them to drop any questions they want answers to.

Their submissions would be completely anonymous. That way, they could ask anything, get the answers they want, and not have to feel uncomfortable about bringing up a possibly sore-subject.

Our team asked about everything from funding to our new office plans to what’s next for the company.

Then, on the day of the retreat, we had people read off the questions for Chris (and our other team leaders) to answer on the spot. And to make sure all the answers were candid, we didn’t give anyone a heads up on what we would ask.

Theme Day & Prizes

We made out virtual retreat "Depts through the Decades" themed

Taking a page out of the high school spirit week playbook, we decided to set a theme for our virtual company retreat. We called it “Departments through the Decades!”

And we assigned each department a decade to dress up as – complete with prizes for the best team and individuals.

POPs and Finance had the ’90s, Customer Experience had the ’80s, Product and Engineering had the ’70s (mostly so the team could keep their quarantine stashes), and Marketing had the ’60s.

Best virtual company retreat decision ever!

We had the Seinfeld crew, the Fresh Prince, Jazzercise instructors, Mad Men lookalikes, and a few hippies. And scrolling through all the wigs, makeup, and costumes made it easier to stay engaged.

Virtual Escape Room

Back when we had a team of 5, we went to an escape room in Scottsdale. It was an incredible team bonding experience that required us to pull our strengths together to crack a western bank heist.

And we thought it would be fun to do this again now that we’re almost a team of 50. Plus, it gave team members who don’t typically collaborate a chance to work together.

Obviously, we couldn’t do this in-person (hence, the virtual company retreat). But we did find a really cool company that specializes in virtual escape rooms.

And although it was a bit different having a screen between us, we still had some great laughs and really got a chance to bond.

Plus, who doesn’t love a chance at bragging rights when each team shares their scores?

Some extra ideas to make it extra special

Okay, so this is the part where we talk about Zoom fatigue and how it’s a real thing – especially if the day is one long Zoom call.

But there are a few things that you can do to keep the momentum going and the energy up!

For example:

  • Keep the chat going in your video conferencing software
  • Leverage breakout rooms (seriously, breakout rooms are your virtual company retreat’s best friend)
  • Add a soundtrack! It’s crazy what some “Eye of the Tiger” will do for your video call vibes
  • End the day before 5 pm (especially if it means starting your weekend early)

Plus, we added a staycation

While the virtual company retreat was a huge success, it still wasn’t in Park City, away from our day-to-day lives.

And we really wanted to make sure our team had time to not only bond but get away from the office – even if it wasn’t all together like we planned.

So, we rolled out a new 2020 Staycation benefit, including 2 extra days of time off and a $250 vacation fund to use toward a socially distanced vacation!

Don’t get us wrong – our virtual company retreat was nowhere near perfect (we probably should have added a few more bathroom breaks), and it wasn’t at all what we initially planned. But it was a way better option than having no 2020 retreat at all.

It really gave our team a chance to connect and even take a break as a team. And while we hope that this will be our first and last virtual company retreat, we highly recommend companies host their own to take a break from the 2020 craziness and bond.

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