Icebreakers for Remote Teams… That Don’t Involve Trust Falls

By the time most of us here at TaxJar meet in person for the first time, we’ve chatted on Flowdock daily, spoken on video chat at least once per week (or daily if we’re on the same team), and even witnessed each other belting out our best attempt at a musical number.

At TaxJar we highly value communication, so we often feel like we know one another even if we’ve never actually met in person.

Still, I’m not going to lie when I say it can be nerve-wracking to meet your co-workers face to face for the first time.

So far we’ve been lucky with our team. (Well, lucky and strategic, but we’ll write more on our job applicant assessment process later.) Like our awesome customer happiness expert Jenn said upon meeting everyone at her first JarFest after only speaking to them on Flowdock or Zoom, “Everybody is just exactly like themselves.”

Even though we rarely find ourselves with a shortage of things to talk about, we always come to JarFest, our twice-annual team gathering, with icebreakers. Our icebreakers are all about getting to know one another more deeply than we can online.

And before you completely shut down at the word “icebreaker,” I get it. They sound super “corporate” to me, too. But structured icebreakers don’t have to be corny. And they’re a great way to make sure that everyone — even your shyest and most retiring team members — have a chance for their voices to be heard.

Here are some of the icebreakers we’ve had the most success with:

Icebreaker #1: Talk about Yourself for Five Minutes

We’ve all done the “Go around the room and tell us who you are and what you do” thing. But making someone talk about themselves and only themselves for five long minutes puts a whole new spin on the traditional intro.

I’d venture to say that the majority of people in the world are humble, hardworking folks who’ve rarely been asked to fill five consecutive minutes with facts about themselves. This exercise forces a team to go beyond the basics (hometown, education, family, work history). We all learn more about what makes each other tick. We had team members choose to talk about family or work philosophy or a hobby — all of which give insight into their personalities and what they value.

Interestingly enough, it was due to this icebreaker that we realized how much working remotely meant to our team. I never would have expected a quick icebreaker to lead us to fundamentally cementing who we are as a company, but there you have it.

Icebreaker #2: Share Two Pictures that are Important to You

We’re proud and fiercely devoted to our choice to build a totally remote company. But we can admit that, being spread out all over the country, we miss out on a few things that teams who physically work together enjoy — like learning more about your co-worker from the photos and tchotchkes they keep on their desks, or meeting their families at the holiday party.

So for this icebreaker we asked everyone to pick out two pictures that mean a lot to them. In keeping with TaxJar’s focus as a family and work/life balance oriented company, almost everyone on the team shared family pictures. The best part was that each picture was accompanied by a story that let us know a little more about what is important to each team member. (And, for our shy folks, having a picture to take all the focus was a bit easier than talking about yourself for five minutes!)

Icebreaker #3: #FirstSevenJobs

Yeah, we’ve seen your carefully curated resume and we know what career stepping stones brought you to TaxJar. But how’d you get your start in the world of work?

#FirstSevenJobs was probably our funniest ice breaker. It’s just what it sounds like — you list your first seven jobs. As it turns out, a large number of us have been working from an early age. We’ve done everything from rebuilding computers to selling Christmas trees to starting our own jewelry line. We also found out that a large ratio of our team has worked for Big Ice Cream. Who knew?

This also allowed TaxJar team members to show off their entrepreneurial sides. Almost everyone who works at TaxJar has started a business in the past. As it turns out, the skills you need to be your own boss directly correlate to being self-motivated enough to thrive on a remote team. (Think you have what it takes to thrive here, too? Check out our current TaxJar job openings.)

Icebreaker #4: Answer Leading Questions

At our most recent team get-together, JarFest 5, we found ourselves with the largest TaxJar team gathering ever. Nineteen out of twenty team members were in attendance, with almost 1/3 of us attending a JarFest for the first time. This presented the added challenge of getting to know one another within a limited time frame while also finding enough time to set goals and strategize about our next steps individually, as teams, and as a company.

In this case, we tried a “work smarter, not harder” approach by asking four leading questions:

  1. What’s your passion?
  2. What is the biggest crowd you’ve ever been in?
  3. What’s one life lesson you’ve learned?
  4. What would you do if you had a free year with unlimited resources to do anything?

Once again, we learned a lot. One of us is a popcorn connoisseur. Many of us live to be outdoors. Some of us really don’t like crowds. And guess what? Many of us who had a free year to do anything would — you’re never going to guess — start another business.

Icebreaker #5: Building Something Together

Okay, so this one isn’t the traditional icebreaker. But, to me, the fact that our team is building something together is the biggest icebreaker of all. We are all equally invested in truly changing the lives of business owners by simplifying the onerous burden of sales tax. Working with 20 people who are all pulling together toward the same goal is a beautiful thing. …And if there’s ever a lull in the conversation, we can always talk about sales tax. 😉

All of these icebreakers have been successful for us, but your remote team’s mileage may vary. Do you have a go-to icebreaker? We’d love to hear about it. We’d also love to hear about any icebreakers you’ve had success with online via Flowdock/Slack or video chat. Start the conversation in the comments!



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Jennifer Dunn

Jennifer Dunn’s passion is making tough sales tax topics simple so you can get back to doing what you do best — running your business!