Would You Rather: Keep Employees Happy or Let the Holidays Derail Your Team?
As the holiday season approaches, it’s easy to get swept up in the excitement of festivities, end-of-year goals, and time off. But as the calendar flips toward December, many employers may find themselves facing a common workplace dilemma: how to keep employees engaged, motivated, and loyal in the face of seasonal distractions. If you’re like me, you might be tempted to play the “Would You Rather” game in your head as you try to solve the problem.
For example, “Would you rather keep your team engaged and motivated for the rest of the year… or risk losing them during the busy season?” Not much of a choice, right? That’s exactly the point! Retaining employees, especially during the hustle and bustle of the holidays, requires more than just a ‘set it and forget it’ attitude. It requires intentionality and focus on long-term employee satisfaction. So let’s explore how playing “Would You Rather” in the workplace can help us make better decisions and stay on track to create a positive work culture — even when the holiday season has us all thinking about other things.
The “Would You Rather” of Employee Retention
Remember when you were a kid, and “Would You Rather” was a go-to game during car rides or sleepovers? You’d pose ridiculous scenarios like, “Would you rather fight one horse-sized duck or 100 duck-sized horses?” The game, in its simple format, was a fun way to weigh tough choices — or just pass the time with friends.
In the workplace, however, “Would You Rather” becomes a powerful framework to consider some of the tough decisions that come with employee retention.
For example:
Would you rather:
Prioritize your holiday season sales and risk burning out your team, or
Spend extra time supporting your employees to maintain productivity and job satisfaction?
Would you rather:
Keep pushing employees to hit aggressive year-end targets and risk losing their motivation, or
Offer meaningful incentives that show appreciation and reward effort, ensuring your team stays motivated?
We often face these types of choices at the tail end of the year, when our attention is split between holiday celebrations, end-of-year wrap-ups, and the pressure to deliver. The key is to understand that, just like in the game, the stakes are real and the choices aren’t always clear-cut. So how can we make the best decision?
Don’t Put Employee Retention on the Back Burner
As we near the holidays, it’s tempting to push employee retention to the back burner. After all, we’ve all got a thousand things to juggle, from managing holiday schedules to wrapping up year-end projects. But just like the “Would You Rather” game, when you put the decision-making on autopilot, it often leads to undesirable outcomes. Neglecting employee satisfaction during the busy season can have long-lasting effects.
Employees notice when they’re being overlooked or when their needs are ignored in favor of short-term objectives. When they feel undervalued, it’s more likely they’ll look for opportunities elsewhere. This isn’t just a concern for the new year; it’s an issue that could impact your team’s morale and performance in the present.
What You Can Do: A Balancing Act
In the spirit of playing “Would You Rather” in the workplace, here are some real decisions you can make to retain your employees during this busy season — and beyond:
Offer Flexibility Over Micromanagement
As the year winds down and employees are juggling personal obligations, consider offering more flexibility with hours or work-from-home options. For example:
Would you rather enforce strict in-office attendance through the holiday season or trust your team to manage their schedules while still meeting deadlines?
In the modern workplace, flexibility is a powerful retention tool. Employees value the ability to balance work and personal commitments, especially during the holidays. By offering flexible working arrangements, you demonstrate trust and respect for their time.
Prioritize Recognition Over Burnout
The holiday season is often a time of intense work for businesses, but it can also be a time to show appreciation. Here’s a scenario to consider:
Would you rather push your team harder to meet end-of-year targets or take a step back and recognize their hard work, boosting morale for the final stretch?
Acknowledging employees' efforts and providing positive reinforcement can have an incredible impact on retention. Simple gestures like a personalized thank-you note, a team celebration, or an end-of-year bonus can go a long way in maintaining motivation and loyalty. Remember, employees want to feel seen and valued, not just during the holidays but all year long.
Invest in Development Over Stagnation
A common trap during the holiday season is to focus only on the “now” and neglect longer-term professional development. However, employees want to feel like they’re growing in their roles. Consider this choice:
Would you rather let employee growth stagnate as you prioritize urgent holiday tasks or invest in small but meaningful development opportunities that keep your team engaged?
Even small investments in professional development — like offering virtual training courses or encouraging employees to attend industry events — can signal that you’re committed to their long-term growth and success.
Foster Team Connection Over Isolation
While the holiday season often encourages people to wind down and focus on personal life, it’s also a great opportunity to strengthen team connections. Would you rather:
Keep employees isolated as they work from home through the holidays or host virtual (or in-person) team events that build camaraderie and boost team spirit?
Organizing team-building activities, even if they’re virtual or low-key, can help employees stay connected to the broader mission of the company. It’s easy for team dynamics to weaken as people check out for the holidays, so making an effort to foster connection is critical.
Keeping Customer Service Tip-Top
As you consider your employees, it’s important to remember that their engagement and happiness directly affect your bottom line — including customer service. When your employees feel supported and appreciated, they’re more likely to go the extra mile for your customers. A disengaged or burned-out team, on the other hand, may not offer the level of service you expect.
So, as we head into the busy holiday season, remember that retaining your employees isn’t just about keeping them happy for the sake of it — it’s about ensuring your business runs smoothly and continues to deliver the best service to your customers. In this context, the “Would You Rather” game isn’t just a fun distraction; it’s a reminder to prioritize people over profits in the short-term to protect the long-term success of your business.
What Would You Rather Do?
As the holiday season ramps up, it’s easy to get distracted by all the things that need to get done. But don’t let employee retention fall to the back burner. Take a moment to play the "Would You Rather" game in your head — and be sure that you're making the decisions that prioritize your team’s satisfaction, productivity, and well-being. After all, happy employees make for happy customers, and that’s the best gift any business can give itself this holiday season.
Now, what’s your “Would You Rather” decision to ensure a great end to the year?
