Crafting Memorable Holiday Events for Small Teams

I was at a party recently and a good friend of mine shared a story of how she spent over 4 nightmarish hours attending multiple work holiday events last year. As she told this story, people’s faces reflected back shock and horror. How could these leaders have thought this was a good use of time? This reflected back very poorly on the leader and raised the question of their decision making abilities. Unfortunately, these stories aren’t uncommon. Does this sound familiar to you?

  • A “festive” virtual meeting packed with mandatory attendees. Each is told to share what they have planned for the holidays. 30-45 boring mins pass with a mix of colleagues trying to be interesting and brief -- others stammering out long-winded answers. How does this impact employee engagement for that day? Week? Month?
  • A team holds a Secret Santa. Someone spends time coming up with a thoughtful and sweet gift. Another grabs cheap slippers and some chocolate (which they didn’t wrap). How valued or undervalued do employees feel afterwards? 
  • Two teams go out for lunch together. Payment was not pre-discussed. Surprise - one leader grabs the bill for her team. The other inexplicably does not. How could this embarrassing moment have been avoided?

In this guide, we'll explore why holiday events are strategic opportunities for leaders to create lasting memories and strengthen team bonds. We also include practical tips for organizing holiday events in virtual, hybrid, or in-person settings.

Great leaders take the time to define the primary goal of the event, whether it's relaxation, team building, celebrating achievements, or showing appreciation.

Julie Guèvremont, an HR Manager and Culture Specialist, is renowned for her extraordinary talent in orchestrating epic holiday parties. At the heart of every great company culture lies the art of bringing people together, and Julie has mastered this art.

“Having at least one member of senior leadership present at holiday events shows a deeper level of appreciation for employees. This can apply IRL or virtually."


Virtual events

“Overall I find virtual gatherings like these really tricky”, says Julie. “They have a really strong tendency to be a waste of time unless they're well thought out.” When planning workplace events, especially virtual ones, it's crucial to keep in mind both their purpose and the need for genuine enjoyment.

But how do you balance purpose and avoid forced/awkward interactions?

“This one event is burned into my memory," laughs Adam Wozniak, fellow co-founder at Clifden Consulting. “We were all remote and my team lead did a poll for virtual games suggestions. Someone suggested he (my lead) play trivia with the COO on camera. The catch - loser gets an egg cracked on their head. It was hilarious! People still remember it to this day”. Entertaining games like that are great for building camaraderie in team cultures that value fun and joviality.

For groups that are new and less familiar with each other, virtual events should be capped at 8 people to maintain a personal and engaging atmosphere. If you have to have a larger group, plan breakout room activities of 4-6 people. Keep the event under 1 hour to respect everyone's time and attention.

When leaders sought Julie's assistance in planning their holiday gatherings, she typically asked questions like:

  • What is the current health of your team?
  • What are your top 2 goals for this gathering?
  • How do your team members like to be shown appreciation?
  • If your team is spread across different time zones, what time would work best for everyone to attend?

Hybrid events

Don’t. Just don’t. No, really - don’t. It's best to choose between a 100% virtual or 100% in-person event. Hybrid events are logistically complex and may not provide the desired experience.

In-person events

General guidelines that showcase thoughtfulness and care for your team(s):

  • Select a date and time that aligns with most employees' schedules. If it's outside of work hours, consider supporting employees with transportation, like paying for taxis or providing transportation options.
  • If budget constraints limit your ability to provide transportation, ensure the event is so enjoyable that employees are willing to invest in getting there.
  • Food is a universal delight, so be sure to consider your employees' dietary preferences and restrictions when planning the menu.
  • Understand your employee demographic and consider as many points of diversity as you can when creating the experience. 
  • The senior-most leader present should say a few words to express gratitude for everyone's hard work throughout the year.
“Have at least one element of surprise that will delight your employees - it completely elevates an event.”

Lunch event: 

Take the team(s) to a nice restaurant close by so folks don’t have to make a choice between work and family priorities. If you have to host in the office, avoid hosting near everyone’s desks. Instead, find a boardroom or an open space where you can gather and some decorations wouldn’t hurt.

Consider hiring a local caterer or organizing a potluck-style meal. Move seating in a way that fosters intimacy and connection. It’s amazing how the arrangement of chairs can make a space inviting or awkward.

For a touch of fun and celebration, organize a light-hearted game like Christmas bingo with prizes for the winners. BONUS: Add a memorable twist of surprise by having some outgoing team members don inflatable costumes and host the game.

After-Work Events:

Consider ways to make it easy for your team(s) to transition from work mode to celebration mode. Get the most out of your budget by focusing on appetizers and a mix of drinks, both boozy and non-alcoholic, to help everyone unwind and mingle.

If your event goal is relaxation, make sure your venue’s atmosphere complements the preferences of your team(s). Loud, rowdy venues relax some and can stress out others. 

Consider allowing plus ones. It’s a great opportunity to meet the loved ones of your team(s) and build genuine connections.

P.S. Photobooths are always a hit!

Whether virtual, hybrid, or in-person, the key to a successful holiday event lies in thoughtful planning and the genuine spirit of celebration. Need a second set of eyes on your team's festivities this year? Grab some time with me.


"A valid option for time-strapped leaders is: don't do anything at all. Controversial, right? If you have no budget, no time and you're trying to slap something together last minute, your employees will feel it and it won't be good. Sometimes, doing nothing is better than doing something half-hearted. If your intention is to show appreciation, find a genuine way to do that in the new year".

What are your favorite holiday event ideas for small teams? Share your thoughts and experiences in the comments below!

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