Remote Company Culture: Ugly Holiday Sweater Contest

We share our experiences, detail how to hold a virtual ugly sweater contest, and we share our Google Form Templates for you to use with your own team.

Kelsey Opel
SquaredAway
4 min readDec 18, 2020

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On Thursday afternoon, the Squared Away team hosted their usual all-hands meeting. This time, we included our teammate’s ugly sweaters.

We’ve seen time and time again questions about how to build an engaging and supportive remote work culture or any remote culture for that matter.

Coordination of the Event

Whenever we have an event take place, we notify the whole team. We have bi-weekly team-wide calls within Squared Away, so when we do a fun event, we make sure it takes place on a team-wide call day for the best facilitation of everyone’s schedules.

In our Company Culture: Zoom with Pets blog, we shared what we learned from doing a team-wide call where we have volunteers offering to do an intro. We learned that prep before team call day is paramount to a seamless experience for the whole team.

Google Form Entries and a Template

The team had notice of the event 1-month prior to the actual event, so they were aware it was coming and had time to prep. We sent the following update email to the Squared Away team 2-weeks prior to the event. It was accompanied by the form (shown below). Need Our Template? Head here (example below).

Email and Form Example

If you would like to enter, please fill out this form (example below) by 5:00 pm EST on Wednesday, December 16th. You will need to upload a photo of you in your sweater to allow for seamless voting.

Reminders About the Event

We reminded the team weekly starting the first week of December. We sent out an email reminder, a few Slack reminders, and an email reminder directly from the Google Form to sign up.

Ugly Sweater Contest Time!

We had a total of 11 teammates that joined the Ugly Sweater Contest along with about 10 additional teammates who joined in ugly sweaters or other holiday costumes to participate in the fun.

I had a list readily available of who we were going to have participate in the contest, so they were the first to share their holiday sweaters. Each participant took themselves off of mute, shared about their ugly sweater, then the team added comments in the chat box, or shared their thoughts. Everyone was respectful and encouraging.

Voting for the Contest

After the call was over, we shared a Google Form with photos of each participant’s ugly sweater. If the participant didn’t enter into the contest, we got a screenshot while on the team call and uploaded their photo to be entered. We had a few teammates join the team this week, so we wanted to ensure everyone who was interested was able to participate.

Below is an example of the Google Form we shared with the team over Slack, we had 10 total photos and participants.

  • We had the settings on multiple choice, limit each response to 1 entry, we removed “edit after submit” to keep it fair, and we announced the parameters (due time) for the form.
  • We sent the voting form in our team’s Slack #general channel and are emailing it to the team in a team-wide email.
  • Need our voting template? Head here.

Building Remote Culture

Our goal was to continue to support and build our team’s remote culture. We saw a lot of participation, excitement and smiles on our Ugly Sweater Team call. We hope you and your team have a safe and happy holiday season!

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

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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.