Open Enrollment Is Coming: 4 Ways to Help Your Team Actually Understand Their Benefits
Fall open enrollment is coming.
Your employees will soon be asked to make decisions about health insurance, HSAs, FSAs, life insurance, and retirement savings.
Most will not feel ready.
They may have access to good benefits. They may even have a strong 401(k) match. But if they do not understand how the benefits work, the benefits are not doing their job.
That creates a problem for your team: and for your business.
The problem: A benefits package is not useful if nobody understands it
Benefits documents are often written in technical language. Employees are expected to compare premiums, deductibles, copays, coinsurance, tax advantages, contribution limits, and investment options.
That is a lot to process.
The numbers also matter. According to KFF’s 2025 Employer Health Benefits Survey, the average annual premium for employer-sponsored family health coverage reached nearly $27,000. Workers contributed an average of $6,850 toward that cost.
The average deductible for single coverage was $1,886. At small firms, the average was higher.
Meanwhile, SHRM’s 2025 Employee Benefits Survey found that 93% of employers offer a traditional 401(k) or similar plan, and 85% of those employers offer a match.
That match can be one of the most valuable benefits your company provides.
But an employee who does not understand the match may not contribute enough to receive it.
The business cost shows up in predictable ways:
- Employees ask the same benefits questions repeatedly.
- Workers delay important decisions.
- Employees miss out on tax advantages and employer contributions.
- Financial stress follows them into the workday.
- HR teams spend hours explaining the same terms.
- Employees may leave for a company with benefits they believe are easier to understand.
A benefits package alone is not workplace financial wellness.
Education is the missing piece.
Here are four practical ways to help your team make better decisions this open enrollment season.
1. Explain benefits in plain English
Start by removing the jargon.
Do not hand employees a 60-page benefits guide and call the job finished. Give them simple explanations of the decisions they actually need to make.
For health insurance, explain:
- What the employee pays each month.
- What the deductible means.
- What happens after the deductible is met.
- How copays and coinsurance work.
- The annual out-of-pocket maximum.
- How the plan handles prescriptions and specialist visits.
- Whether the plan is compatible with an HSA.
For HSAs and FSAs, explain the differences clearly:
- HSA: The employee owns the account. The balance can roll over. The account stays with the employee if they leave.
- FSA: The account is generally funded through payroll deductions. Rules about rollover and deadlines apply.
- HRA: The employer funds the account. Rules depend on the plan design, and the balance generally does not follow the employee after they leave.
For 401(k) plans, answer the questions employees care about most:
- How much does the employer match?
- What contribution level is needed to receive the full match?
- What is the difference between traditional and Roth contributions?
- What investment choices are available?
- What happens if an employee changes jobs?
Use examples.
Instead of saying, “The plan has a $2,000 deductible and 20% coinsurance,” show what that could mean in a simple medical expense scenario.
Instead of saying, “The company matches 50% of contributions up to 6% of pay,” explain how much an employee could receive by contributing enough to qualify for the full match.
Make the decision smaller.
Employees do not need to become benefits experts. They need to understand their options well enough to make a confident choice.
2. Hold a live benefits education session before enrollment opens
Timing matters.
Do not wait until the final day of open enrollment to answer questions. By then, employees may already feel rushed, confused, or embarrassed to ask for help.
Schedule a group session before enrollment begins.
A useful session should:
- Explain the major benefits in your package.
- Highlight what changed from last year.
- Compare the available health plans.
- Explain the HSA, FSA, and 401(k) basics.
- Show employees where to enroll.
- Leave time for questions.
Keep it practical. Avoid reading the benefits guide line by line.
A 45- to 60-minute session can cover the major decisions without overwhelming people. Offer the session in person if your team works at one location. Use live video if your employees work across shifts or locations.
Recordings and written materials can help employees who cannot attend. But they should support the live session: not replace it.
Why?
Because employees ask better questions when they can talk to a real person.
They can say:
- “I have a family. Which costs should I compare?”
- “I do not understand how the deductible works.”
- “Should I use the HSA or the FSA?”
- “How much should I contribute to the 401(k)?”
- “What happens if I cannot afford a large medical bill?”
Those are not questions a benefits PDF can answer well.
This is where an employee benefits education program can help. A qualified educator can translate the details into clear next steps for your specific workforce.
3. Offer one-on-one financial coaching for personal questions
Group education helps everyone understand the basics.
It does not solve every employee’s situation.
Personal finances are personal. Employees may have different incomes, family situations, debt levels, health needs, and retirement goals.
One employee may need help choosing between a PPO and an HSA-qualified plan. Another may need help building an emergency fund before increasing 401(k) contributions. A third may be trying to pay off credit card debt while saving for retirement.
They may not want to ask those questions in front of coworkers.
That is why a financial coaching employee benefit matters.
One-on-one coaching gives employees a private place to ask questions without shame or pressure. The conversation can cover:
- Budgeting around benefit deductions.
- Understanding health plan costs.
- Choosing an HSA or FSA contribution.
- Getting the full 401(k) match.
- Organizing debt.
- Building emergency savings.
- Setting retirement goals.
- Creating a simple financial action plan.
The goal is not to tell every employee to make the same decision.
The goal is to help each employee understand the trade-offs and choose the next step that fits their situation.
Confidentiality also matters. Employees need to know that personal financial conversations stay private. Employers should receive only general participation information and anonymous themes: not individual financial details.
That trust is essential to a successful financial wellness benefit for employees.
4. Treat open enrollment as the start: not the finish
Open enrollment creates urgency. It should not be the only time employees hear about their benefits.
Benefits questions come up throughout the year:
- A new employee joins the company.
- Someone gets married or has a child.
- A worker receives a medical bill.
- An employee changes jobs within the household.
- Someone wants to increase retirement contributions.
- A worker is facing debt or financial stress.
Build a simple year-round rhythm.
Week 1: Prepare the information
Gather your current plan documents. Identify changes from last year. Create a short list of the decisions employees need to make.
Week 2: Educate your team
Hold a live group session. Explain the benefits in plain English. Share simple comparison materials.
Weeks 3–4: Support enrollment
Give employees time to review their options. Offer access to a benefits educator or financial coach for personal questions.
Weeks 5–8: Follow up
Remind employees to confirm their elections. Answer common questions. Watch for areas of confusion.
Ongoing: Reinforce the basics
Use quarterly or bi-monthly workshops to revisit benefits, budgeting, debt, savings, and retirement planning.
Measure simple outcomes:
- Workshop attendance.
- Number of employees requesting help.
- Common questions.
- 401(k) participation or match utilization, where available.
- HSA or FSA engagement.
- Employee feedback.
- Benefits questions received by HR.
You do not need a complicated dashboard.
You need enough information to see whether employees are engaging and where they still need help.
What this looks like for a small business
You do not need an enterprise benefits department to offer strong workplace financial wellness.
You need a clear process and the right support.
FundWise provides employer-provided financial education, group workshops, and real human coaching for small businesses with 5 to 100 employees. It is not a video library. It is not an app employees have to figure out alone.
FundWise connects your team with a real financial coach who can help employees understand their benefits, reduce money stress, manage debt, build savings, and plan for retirement.
The setup is designed to be simple:
- Quick consultation: Review your team, benefits, and goals.
- Group education: Bring employees together for a practical workshop.
- One-on-one coaching: Give employees private support for personal questions.
- Ongoing follow-up: Continue the education throughout the year.
FundWise also offers a low-commitment 90-Day Employee Financial Wellness Pilot. It is FREE — $0, no payment required, with no long-term commitment. It includes an employer kickoff call, an anonymous employee money-stress survey, one live group workshop, an HR summary report, and a renewal recommendation. One-on-one coaching is available separately as an optional add-on for employees who want deeper personal support.
There are no per-seat fees for the group program. Pricing is clear. The process is built for small businesses in Rapid City and the surrounding Black Hills area.
Make this open enrollment different
Your employees do not need more paperwork.
They need clarity.
They need someone to explain what a deductible means. They need help understanding whether an HSA fits their situation. They need to know how much of the 401(k) match they are leaving on the table. They need a safe place to ask questions that feel too personal for a group meeting.
That is the real purpose of workplace financial wellness.
Explain the benefits. Make the choices simple. Add human support. Follow up throughout the year.
If you want to see whether FundWise fits your team, schedule a low-pressure conversation. No pressure. No pitch deck. Just a practical conversation about what your employees need before open enrollment begins.
You can also calculate the potential cost of financial stress or review the FundWise FAQ.
Your benefits are already costing your business money.
Make sure your employees understand how to use them.