Team Productivity

4 Questions to Help You Plan Your Annual Team Meetup

Laura LaPrad
April 24, 2018
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Last week, 19 TeamGantt-ers descended upon Baltimore with one goal in mind: to get in some much-needed face time with our fellow coworkers.

We freed Pharaoh from his tomb. We outsmarted a serial killer. We secured a spot in a troupe of magicians—despite a ghost’s attempt to foil our audition. We even saved the world from destruction through the power of periodic tables (and had nightmares of high school chemistry along the way).

And that was just Tuesday night.  

Now that the dust has settled, we thought we’d show you how our meetups come together—and why they’re such an important part of our remote team culture. These simple questions can help you plan a meetup that keeps your team healthy and productive all year long.

Calculating ROI: Is a meetup really worth it?

Before we dig into the how, let’s take a moment to talk about the why. Here are three big benefits we get out of each and every meetup:

  • Having fun together enables team members to build trust and deepen friendships, which greases the wheels of collaboration year-round.
  • Sitting in proximity together—whether it’s around a conference table or dinner table—provides a natural forum for creative problem-solving and idea-sharing.
  • New team members integrate into the company more quickly by getting to know the people and the processes that make TeamGantt tick.

Establishing a rhythm: How often should you meet?

Every remote team works differently, so you’ll need to decide how much face time your people need to succeed. But here’s the rhythm we’ve established at TeamGantt.

Annually: The whole company

TeamGantt gets the whole company together once a year. Every other year, families are invited too. Family meetups are held in the summer months when kids are out of school, while company meetups typically happen during the school year.

Quarterly (or as needed): Individual teams

Smaller teams within the company get together more often to do strategic planning or to focus on special projects. For example, our dev team schedules quarterly meetups, while other teams gather a little less frequently throughout the year. Each team determines when and where to meet on an individual basis.

Picking a date: When’s the best time to meet?

Anytime you’ve got more than one calendar to juggle, scheduling can be tricky. That’s why it’s important to land on a date for your meetup as early as possible.

At TeamGantt, we hone in on a meetup date about 6 months out. That gives team members plenty of time to plan around it in the coming months.

We start by consulting our trusty team PTO gantt chart to find weeks with no out-of-office time booked. Once we’ve identified open week options, we take to Slack so the whole team can weigh in on what works best for them.

Structuring the week: How do you balance work and play?

At TeamGantt, we’re serious about work-life balance, and that goes for meetups too. Families sacrifice a lot to let team members be with us for a week, so we stick to a strict weekday-only agenda. Monday and Friday serve as designated travel days, enabling team members to make the most of their weekends at home.

Of course, that means Tuesday-Thursday come with jam-packed agendas. But don’t worry: We build in plenty of food and fun to balance out all the hard work that’s being done. Basically, each day revolves around three main themes: work, eat, and play (not necessarily in that order).

TeamGantt escape room outing

Here’s how last week’s meetup played out:


  • Travel day


  • Work + Eat: Office time with catered lunch
  • Eat (again): Team dinner outing
  • Play: Escape room game


  • Work + Eat: Office time with catered lunch
  • Play: Dodgeball tournament
  • Eat (again): Free night


  • Work + Eat: Office time with team lunch outing
  • Play: MarioKart tournament and/or free time
  • Eat (again): Dinner party with live music at local winery


  • Travel day

We zero in on the nitty-gritty details a week or two before the meetup. These decisions come from weeks of discussion about places to go, things to do, and food to eat. The options that come up in conversation over and over again rise to the top and secure an official place on the week’s agenda.

All together now

Let’s be honest: No matter how many tools you have to communicate and collaborate, nothing replaces good, old-fashioned face time. (How else will you ever know for sure whether Bob’s being serious or sarcastic on Slack?)

That’s why annual meetups are a TeamGantt tradition. For 3 solid days, we work together, play together, eat together, and even ride in minivans together. That’s a lot of together time—but it pays off in productivity 365 days a year.

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