Employees feel plenty of different sentiments towards the classic annual company holiday party. Some absolutely love the tradition and cannot wait to see Tracie from accounting do her signature jingle bell rock dance after four margaritas. Others find them to be an obligative chore to endure and do not enjoy dressing up, dragging along their partner, and drinking eggnog with their coworkers while juggling many other holiday events. As the workplace rapidly changes to remote/hybrid environments and culture is more important than ever, reassessing the actual holiday joy your company party brings is a necessary recalibration.
At Compass, our team works fully remote and are located all over the nation. When we had a traditional holiday party a few years ago, we realized it was difficult to connect with other team members with their partners there. Although we love our teams’ partners, we realized we needed to prioritize connecting with each other during our yearly in-person event to build relationships. Holiday parties are typically budget consuming especially with travel, so we completely revamped our annual tradition to spend quality time with each other, focus on our core values, and still have plenty of time for espresso martinis.
Two years ago, we decided to hold our annual holiday party in January in Pittsburgh since our employees’ schedules were less congested with multiple holiday events. We based the first new party off our Care core value and turned it into a two-day retreat including a spa day and we decompressed and socialized. We saw a need for self-care for our employees that year and decided a spa retreat benefited them more than flying out for a four-hour holiday party.
This year, we based the annual party around our Craft core value and held the two-day event in Fort Lauderdale, Florida. We facilitated trainings with our team to reflect on the unique craft and excellence they bring to the Compass team. One of the activities required everyone to write the specific craft and talents each person possesses on notecards to bring home. This built on the trust and reliance our team needs to work together and bring craft expertise to our clients. We still had blast by renting a boat and sailing around the Ft. Lauderdale canals and taking a party bus down to Miami for an indulgent dinner. Every year it is invigorating to help plan what core value we can develop internally at these annual events while bonding with the team.
Every team is different so every annual party must reflect their culture and core values. I have worked in team environments where having a rowdy holiday party absolutely fit that distinct culture and in-office work environment. If your party is starting to feel stale or like an obligation, ask yourself:
- Is this party a high-quality use for our budget?
- Can we do something different for the same budget that would feel more impactful for our employees?
- Can this party happen during another time of year where our employees are not burnt out by other holiday commitments?
- What workplace traditions do we want to keep, and which new traditions can we create?
If the annual party is falling flat, it may be time to revamp your annual party to better accommodate the needs of your employees and organizational goals. A full two-day retreat is not necessary for everyone but creating a more intentional yet joyous activity would distinctly improve the culture of the organization. The holidays are a merry but busy time, so do not hesitate revamp your annual party for the benefit of your distinct organizational culture.
Need direction in planning a work retreat? Contact hannah@wearecompass.com

