Eight steps to help get you through the Open Enrollment jungle at work

(This article appeared in Kiplinger on November 3, 2025)

Wondering how to survive open enrollment this year? Arm yourself with these tools to cut through the process and get the best workplace benefits for you.

Open enrollment is an important time for employees to review and select benefits and those decisions can have a lasting impact on your financial future. According to the U.S. Bureau of Labor Statistics, the average employee benefits package accounts for 29.7% of total compensation for private industry workers and 38.4% of total compensation for state and local government workers.

But when the average employee has to choose from more than a dozen benefits it is easy to become fatigued while working through the open enrollment process. The steps that follow will help keep you on track.

1. Review your current benefits 

Start by evaluating your existing benefits. Consider what worked well in the past year and what didn’t. Look at your health-care usage, out-of-pocket costs and any changes in your circumstances — such as marriage, the birth of a child or new health needs — that may influence your choices. Try to judge how much the upcoming year’s expenses may look like this year’s.

A tool that may help is “start, stop, continue.” Try to decide what benefits were missing this year that you would like to start in the new year, what benefits were not used that you might stop and what benefits were helpful that you want to continue. This exercise can help you group your benefits by category.

2. Attend informational sessions and read materials

Keep an eye out for emails and other communications that offer enrollment support. Your employer offers these resources because they want you to get the most out of your benefits. Use your human resource team to help you manage your decision-making. Consider talking to HR with your partner, if applicable, to help your family get the most out of your benefits.

3. Compare plans carefully

When selecting, compare plan premiums, deductibles, copayments, coverage networks and prescription drug benefits. Use available online tools or calculators to estimate your annual costs based on anticipated health-care needs.

Try not to get overwhelmed. Start by thinking about how well this year’s plan served you and your family. The complexity of plan comparisons makes relying on your HR team especially important. Start by telling them what you liked and did not like about this year’s plan.

4. Consider flexible spending and health savings accounts

Flexible spending accounts (FSAs) and health savings accounts (HSAs) offer tax advantages for medical and dependent care expenses. Review contribution limits and eligible expenses for each account and decide how much you should set aside for the coming year. Remember that FSAs typically have a “use it or lose it” rule, so plan your contributions carefully. 

And don’t let the acronyms confuse you. Perhaps think of your FSA as your “fast” account that generally has to be spent in the year it is funded and think of your HSA as your potential “hold” account which can be saved, if not needed, year-over-year and even invested subject to certain conditions.

5. Evaluate supplemental benefits

Beyond core health insurance, many employers provide added benefits such as life insurance, disability coverage, legal assistance, and wellness programs. Assess your need for these supplemental benefits and consider increasing coverage to suit your needs.

Benefits you have to pay for are a bit like subscriptions for services, such as streaming. Individually they may not seem expensive, but when combined they can be expensive.

6. Plan for retirement

Open enrollment is a great time to review your retirement savings strategy. Check your contribution rates to your workplace savings plan if you have one. A best practice to consider is to at least contribute enough to get the maximum company match. Another is to increase your contributions steadily to at least 10%.

Other questions to consider include whether to use a pre-tax contribution or a Roth contribution, if offered. The former allows money to be contributed pretax and comes out as taxable income when withdrawn, while the Roth is made up of after-tax contributions and comes out as tax-free when withdrawn, subject to certain conditions. Although company contributions will most likely be taxable when withdrawn, having tax-free Roth dollars in retirement may still be beneficial.

7. Understand deadlines and take action

Be aware of open enrollment start and end dates, and submit your selections before the deadline. Late submissions may result in missed coverage or defaulting to less optimal plans.

Because benefits decisions may impact your take home pay it is best to complete the forms with your partner. Completing the process early and sleeping on your decisions before final submission is another good idea.

8. Seek advice if needed

If you’re unsure about which options are best for you and your family, consider consulting with benefits specialists or financial advisors. They can help you understand complex plan terms and make choices that align with your goals. This is particularly true if you have special circumstances, such as a family member with a chronic condition.

A final note on AI

Open enrollment season is your annual opportunity to tailor your benefits to meet your evolving needs. By reviewing your current coverage, attending informational sessions, comparing options and acting early, you can ensure you’re maximizing the value of your employee benefits.

You could also try using AI for guidance, whether by uploading plan documents to a chatbot and asking it to summarize them, or simply by asking it questions. AI isn’t foolproof, however, so be sure to verify any information you’ve been given with your HR team.