Open enrollment isn’t just another HR deadline. It’s where retention battles, compliance risks, and your team’s confidence in their benefits all intersect.
When you’re managing a small or mid-sized business, open enrollment season can look like a tidal wave of paperwork, confusion, and unexpected costs.
But here’s a surprise: the most successful HR leaders don’t power through on grit alone. They spot the five biggest pitfalls before things start to spiral, then set up systems and tools to turn chaos into clarity.
Ready to see where others stumble and how you can sprint ahead in 2025? Let’s dive straight into the most common (and entirely fixable) open enrollment challenges for SMBs.
Confused communication
Why do most employees breeze through open enrollment and choose the same-old plan? Just 33% of HR managers believe their teams fully understand benefits choices, and the average employee spends less than 30 minutes reviewing their options (SHRM 2024).
Panic emails right before deadlines don’t build trust or show value.
When SMBs skip timely, clear communication, team members get confused, undervalue compensation, or simply ignore updates. Working with HR employee relation service can help clarify messaging and ensure your team understands their benefits.
Start instead with a simple, step-by-step 30-day communication plan. Use plain language, visuals, and real stories. Highlight contributions, matching, and perks, not just coverage changes.
Tight deadlines
Picture open enrollment as a two-week race against the clock. Short windows push teams to scramble, especially if you don’t have dedicated HR hands or automated systems.
Disorganized plan packets, manual election tracking, and missed paperwork cause painful delays and even lead to employees losing coverage, which can trigger compliance penalties.
The smartest SMBs break up the process with a week-by-week checklist and clear deadlines. They can be things like calendar invites for every step and simple task boards for tracking.
Big Cost Jumps
If climbing health premiums and shrinking budgets keep you up at night, you’re not alone.
In 2025, health plan costs are expected to rise by 10-25%, with some renewal quotes nearly doubling (Aon, KFF).
When you can’t match Fortune 500 scale, it’s tempting to cut the benefits or pass more cost to employees. But that can hurt morale or drive turnover.
Instead, push back by pooling risk or leveraging partnerships. Professional Employer Organizations (PEOs), co-op plans, or even consulting HR business partners in Florida give smaller employers bigger buying power (NASE).
Rethink your plans.
Raise deductibles but add supplemental coverage.
Explore narrow networks.
Or open up voluntary add-ons that don’t impact your bottom line.
Tech Issues
Still relying on paper forms or spreadsheets in the age of remote and hybrid work?
Manual processes do more than slow your team, they increase costly errors and scare off employees who expect easy digital access.
Top SMBs now use mobile-friendly software like Gusto, Zenefits, or Paycor to centralize enrollment, deliver plan details, and collect elections all online.
Interactive guides, on-demand videos, and virtual open houses let employees compare options without office visits.
Overstretched HR teams
Trying to manage open enrollment with a small team or worse, solo is a recipe for missed details, unnecessary stress, and employee confusion.
When HR leaders lack benefits expertise, you are at risk of making compliance mistakes, lost savings, and increasingly frustrated employees.
Many SMBs don’t realize how much time and money partnering with a PEO or outsourced HR consultant can save (NASE).
These experts know local laws, plan options, and negotiation tricks you might miss.
Transform Open Enrollment into Opportunity
You’ve seen the same top five obstacles year after year: Confused communication. Tight deadlines. Big cost jumps. Tech headaches. Overstretched HR teams
It’s important to address them head-on with proactive planning, easy-to-follow timelines, digital tools or taking help from experts. Each step clears confusion, reduces risk, and reminds employees their benefits matter.
Don’t let 2025 enrollment sneak up and consider the support of The HR Boutique to set your team up for clarity, connection, and confidence.
