Your Open Enrollment Checklist: What to Review in Your Employer Benefits

For most working professionals, open enrollment is a handful of screens in Workday or a similar portal, clicked through in under ten minutes once a year. That's exactly the problem. A benefits package is major component of total compensation, and it deserves more than autopilot, especially at companies like Microsoft, Amazon, Meta, and Google, where the menu of options tends to be unusually rich.

A quick note before the checklist: for specific questions about which medical plan is the best fit for you and your family, your HR benefits team is the right first stop. Many employers provide plan comparison tools, cost calculators, and specific guidance that reflect your company's exact plan designs, details a financial advisor generally won't have visibility into.

1. Start With What Changed, Not Just the Menu

Before comparing plan tiers line by line, ask what's different for you this year, income, family size, health needs, a new dependent, a spouse's new job. Let that drive the review, rather than defaulting to whatever you picked last year.

2. Medical, Dental, and Vision Elections

• Compare this year's premiums, deductibles, and out-of-pocket maximums against what you actually used last year, not just against last year's plan.

• If you're choosing between a PPO and a high-deductible health plan (HDHP), remember that only the HDHP pairs with an HSA.

• Check whether your preferred doctors and prescriptions are still in-network and on the formulary for next year.

3. HSA and FSA Re-Enrollment

• HSAs and FSAs elections typically do not roll over automatically, most employers require you to re-elect your contribution amount every year, even if you want the same amount as last year.

• If you're HSA-eligible, check that you're on track to maximize your annual contribution limit, including any employer contribution. Note that the limit depends on your coverage type: if you and your spouse are both covered under the same family HDHP plan, you share a single-family limit between you. If you each have separate individual HDHP coverage, you're each subject to the individual limit instead. HSAs are one of the few triple-tax-advantaged accounts available, so it's worth prioritizing if you're already maxing other tax-advantaged savings.

• Dependent Care FSA elections also reset annually, so it's worth revisiting if your childcare or eldercare costs have changed. Try to estimate your actual expected expenses carefully: most Dependent Care FSAs have little to no rollover allowed, and any unused funds are typically forfeited at year-end (the "use it or lose it" rule), so overestimating your contribution can cost you money just as much as underestimating it can leave you short.

4. Life and Disability Insurance

• Confirm your basic employer-paid life insurance amount, and whether supplemental coverage still matches your needs.

• Check short-term and long-term disability elections, particularly if your income has changed.

• This is the easiest time of year to update beneficiary designations, a five-minute task that's frequently overlooked for years at a time.

5. Retirement Plan / ESPP Contributions

• Revisit your 401(k) contribution rate anytime your cash flow changes (a raise, a bonus, a paid-off debt) rather than sitting at whatever percentage you chose years ago. Unlike your health plan elections, this isn't limited to open enrollment: most plans let you adjust your contribution rate at any point during the year, so there's no need to wait until next year's enrollment window if your situation changes.

• Confirm you understand your employer's match formula and are contributing enough to capture it in full; leaving match on the table is leaving compensation on the table.

• If your plan offers a Mega Backdoor Roth (common at large tech employers, including Microsoft and Amazon), confirm your after-tax contribution elections are set up correctly, this is a separate election from your standard 401(k) deferral.

• If you have an Employee Stock Purchase Plan (ESPP), review your contribution percentage alongside your broader equity concentration. This can be periodically updated when the plan allows, which is typically at set times during the year. It's worth a conversation with us if company stock has grown into a large share of your net worth.

6. Additional Perks Worth a Second Look

• Wellness stipends, backup child and elder care benefits, and Employee Assistance Programs (EAP) often go unused simply because employees forget they exist.

• Legal plans, identity theft protection, and voluntary benefits like pet or critical illness insurance are worth a quick cost-benefit look, even if you skip them most years.

A Few Company-Specific Notes

• Microsoft: known for pairing a standard 401(k) with a Mega Backdoor Roth option and an ESPP confirm current-year contribution limits on both, since they're separate elections from your base 401(k) deferral.

• Amazon: base salary tends to be a smaller share of total compensation relative to RSUs, which makes 401(k) match mechanics and HSA elections worth double-checking each year rather than assuming last year's setup still applies.

• Meta: typically offers a straightforward 401(k) match alongside a broad wellness and mental health benefit suite, worth checking whether you're using the full range of what's offered, not just the retirement plan.

• Google: known for a comprehensive benefits menu including strong family-care benefits, if your household situation changed this year, it's worth a closer look at what's newly relevant.

Exact match formulas, contribution limits, and plan menus shift from year to year and sometimes mid-year, so treat the notes above as a starting point for questions, not a substitute for checking your own employer's current portal.

A Quick Checklist Before You Submit

• Have I reviewed this year's elections against what actually changed in my life, rather than just re-selecting last year's choices?

• Am I capturing the full 401(k) match, and does my contribution rate still reflect my current income?

• Have I revisited my HSA/FSA elections and beneficiary designations, not just my medical plan?

• If I have equity compensation (RSUs, ESPP, options), have I considered how this year's elections interact with that concentration and my tax situation?

• Is there anything here worth bringing to my advisor before I submit, rather than after?

The Bottom Line

Open enrollment doesn't have to take long, but it deserves more than autopilot. A few intentional minutes reviewing your elections, especially anything tied to HSA/FSA re-enrollment, your 401(k) contribution rate, and beneficiary designations, can make a real difference over time. If anything you find raises a bigger question about how it fits your broader financial plan, we'd be glad to have that conversation. Reach out and let’s chat.

DISCLOSURES:

Investment advisory services offered through Consilio Wealth Advisors a registered investment adviser. The views expressed represent the opinion of Consilio Wealth Advisors. Information does not constitute investment, tax, or legal advice.

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