Connecting as a Remote Team: Halloween Edition

How to build your team’s camaraderie through a remote team Halloween Costume Contest.

Kelsey Opel
SquaredAway
5 min readOct 29, 2020

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We are always looking for the next opportunity to build our company’s culture and continue to keep our remote-team camaraderie alive. Since day 1, Squared Away has been fully remote, and here we are, almost 3 years later & celebrating Halloween as a 135 person team!

Why is remote team camaraderie important?

Camaraderie is a joint sense of purpose and it is a teamwork mentality, it encompasses both relying on each-other, sharing the good and the bad as well as having good times together. Joining together with your teammates at work can result in lasting friendships, and at the very least, it can bring teams closer together resulting in overall better performance.

Everyone needs a friend, right?

We all need friendships at work, according to Harvard Business Review, “Employees report that when they have friends at work, their job is more fun, enjoyable, worthwhile, and satisfying. Gallup found that close work friendships boost employee satisfaction by 50% and people with a best friend at work are seven times more likely to engage fully in their work.”

#squaredawaylife

At Squared Away, we want to be a great place to work. Our team working well together, building relationships with eachother and relying on one another is a large part of our remote work culture that makes up #squaredawaylife

We aim to have a team-building moment every 1–2 months on our all-hands team calls. We have done a few team-pet introduction calls, “Zoomies” and felt a team-wide halloween costume contest was a natural next step.

How to Hold a Remote Halloween-Costume Contest

We are fully remote, but that doesn’t stop us from enjoying the same fun times that we would experience in an office setting. Planning is paramount, followed by effective communication of our planning.

1. Initial Planning:

  • We discussed with our Directors when we would hold the contest. We started prepping 2 weeks before the contest.
  • We identified what the reward would be. We chose a Starbucks gift card — via email, as we are located all over the world.
  • We set basic parameters — the costume had to be work-appropriate and something you can wear on a Zoom call. Kids, pets and significant others were welcome to join the costume contest.
  • What we learned from the planning: We should have done sign ups of who you plan to join as so we could effectively give each teammate a brief moment to share their costume (we did this, it was much less organized).

2. Reminders:

  • We reminded our team 1-week prior, 3 days prior, the day prior and the day of the call.
  • Slack is our preferred method of communication, so we sent Slack team-wide channel announcements and started quick conversations about who plans to join as each costume.
Our team reminder for our all-hands Zoom call (we redacted the other agenda items).

3. Team Call Day:

  • We held our usual team call, covered our agenda and the end of our agenda was the team costume contest.
  • This is where the planning would have helped — our Director of Ops, Kelsey, took a note down with each teammate that joined the call in a costume. Had we planned ahead, we would have run down the signup list and called everyone out.
  • Kelsey took a note of the names of the costumes that teammates joined as. The teammate got a moment to share what their costume was and any insipration they had.
  • Some of our teammates got quite creative and used Zoom backgrounds, included their kiddos & pets, and went all out on their makeup/costume.
From top left to bottom right: Meg as Rosie the Riveter, Sydney & her daughter as Elsa and Anna, Whitney as Rogue, Elise & her son as Rainbow Bright, Laura & her son as Bacon & Eggs, and Kelsie & her son as Moira & David (Schitt’s Creek).

4. Team Wide Voting

After the all hands call, we shared a Google Form via email, within our notes document, and on Slack with a link to vote anonymously for our team’s favorite Halloween costume. Our team had from Friday afternoon until EOD Monday to vote for their favorite costume, then we announced the winner on Tuesday via email.

We sent out a team-wide notes document that listed all of the teammates and their costumes along with the link to the Google Form (shown below). This process worked well for us because it is standard practice for the Squared Away team to send a team-wide notes document after a team call.

The Google Form layout we utilized for the team costume call voting.

Another learning moment from this process, if we had done sign ups prior to the call, we could have listed each participant’s name on the Google Form instead of there being write-in responses. This is our plan for next year’s call and we highly recommend it!

So, who won?

The 2020 Squared Away Halloween Costume Contest was won by Nicole S, she dressed up as a yellow inflatable tube man and gave us a full demo (you usually see these tubes dancing around in parking lots of car dealerships). Our runner-up was Stephanie and her Peter Pan’s Shadow costume that incorporated her son as Peter Pan.

From top left to bottom right: Sara-Director of Finance (and her daughter, Scarlett), Jordan-Director of Client Relations, Kelsey-Director of Operations, Michelle CEO & Co-Founder, Seni-Director of Client Connections & Shane-Co-Founder.

Final Thoughts

Our two takeaways are to plan accordingly (advanced signups are a great idea), remind your team as you get closer to the event & let them know if you/your leadership is dressing up, this is a team camaraderie event and you should have fun with it!

One last note, make sure you have plenty of makeup remover before you go all out on your Halloween costume.

If you’re ready to get Squared Away, visit us at GoSquaredAway.com or grab some time for a call.

Drop by our social media and say hi👋 Instagram, Twitter & Facebook.

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Kelsey Opel
SquaredAway

Startup Operator // Snowboarder // Taco connoisseur. Follow along for my journey in operations and lessons learned in this territory.