Navigating the Holiday Season With Smarter Benefits

December tends to bring out the best and worst in our schedules. Calendars get busier, inboxes pile up, and personal commitments stack higher than usual. For employees, that often means navigating burnout, travel, extra expenses, and trying to finish the year strong.

It’s also a time when the value of a good benefits plan becomes very clear. People aren’t thinking about theoretical perks right now. They’re thinking about what helps them get through the holidays intact.

That’s where your benefits strategy can either show up or fall short.

The Need for Clarity and Convenience

One of the biggest frustrations employees face in December is confusion. Questions like “Does my plan cover travel insurance?” or “Can I get that massage appointment in before my coverage resets?” come up a lot this time of year.

Making sure people know how to access their benefits and what’s available to them can go a long way. A short email reminder or FAQ document can ease stress and help people make use of what’s already in place.

The same goes for virtual care. When clinics are booked or closed for the holidays, virtual access to doctors, mental health professionals, or dietitians can be a lifeline. Not everyone remembers these options are available, especially in the rush of the season.

What Matters Right Now

Holiday priorities don’t always align with the flashiest parts of a benefits plan. At this point in the year, most people want:

  • Support for mental health, whether through therapy coverage or access to mindfulness apps
  • Flexibility around work hours or hybrid arrangements
  • Clear coverage info for travel, dependents, and time-sensitive appointments
  • Communication that cuts through the noise and helps them use their benefits
  • A sense that their employer understands this season is both full and demanding

These aren’t big asks. But they do require intention. Checking in with your team about what would help most in the final stretch of the year can show that you’re paying attention.

What’s Not Landing

There are also a few common missteps that can turn well-meaning efforts into noise.

For example, adding a new perk in December may feel rushed or out of touch if it’s not clearly communicated. Sending lengthy or jargon-heavy benefits emails might get ignored entirely. And relying on one-size-fits-all policies without room for conversation can backfire during a time when people’s needs are varied and personal.

Supporting Leaders Too

Managers and business owners feel the weight of year-end just as much, if not more. Supporting your leadership team with resources, clarity, and space to ask questions can keep things from trickling down as pressure or confusion.

Benefits conversations don’t have to be limited to renewal time. In fact, December is a great moment to check in on how your plan is really working.

A Smarter Start to 2026

What employees need in December can be a preview of what will matter most in the year ahead. If your team is asking for more flexibility, better mental health access, or clearer communication, that’s a useful signal as you look ahead to 2026 planning.

Your benefits plan should evolve alongside your business and your team. December gives you a live view of what’s working and what could be better.

What employees are prioritizing this time of year can also reveal where benefit trends are heading. We’re already seeing a shift toward more flexible models and personalized support. In past posts, we’ve explored how non-traditional benefits like housing support and pet PTO are quietly gaining traction, and how funding structures like HSAs and ASOs can offer more agility when budgets tighten.

Need help reading between the lines?

We’re here to dig into the data, look at what’s being used, and find practical ways to strengthen your plan without overcomplicating it.

Let’s build something that makes sense for right now and what’s next.

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