Open enrollment gives you one focused 30-minute window each year to review benefits choices that are otherwise locked in for the next twelve months. The routine many people use: pull last year's claims and out-of-pocket totals first, since that number predicts next year's spend better than anything else; compare health plan options against those claims; fund the right tax-advantaged account (HSA, FSA, or Dependent Care FSA); review life and disability insurance; and finish with the easy-to-forget items — beneficiary designations, commuter benefits, voluntary coverage. Open enrollment is usually two weeks long, but most of these decisions are reversible only once a year. The specifics depend on your situation, and plan designs and figures change year to year.
Minutes 0–5: which of last year's numbers do you pull first?
The numbers to pull first are last year's total claims and total out-of-pocket, because they predict next year's spend better than an estimate made from memory. A common first step is to open your insurer's portal and find both figures for the past 12 months. Total claims show what your care actually cost before insurance; total out-of-pocket shows what came out of your own pocket after it, and the distance between the two is roughly what this year's plan was worth to you. Many people find that pair is the single most useful input to everything that follows, because the health-plan comparison and the account-funding decision both rest on it. If you're new to the company, some people estimate instead based on doctor visits, prescriptions, and any planned procedures. What your insurer reports and how far back it goes may differ.
Minutes 5–15: how do you pick the health plan?
Picking the health plan generally means comparing the HDHP and the PPO against last year's actual claims rather than against the premium alone. Many people compare the two that way because the premium is the only number the enrollment portal puts in front of you, and it is the one least likely to decide the year. The pattern people look for is a break-even: claims below the HDHP deductible generally favor the HDHP on premium savings alone, claims above the PPO deductible generally favor the PPO on predictability, and a year that landed between the two is often settled by the employer's HSA contribution. Ten minutes is usually enough once the claims figure from the previous step is in front of you. The right answer depends on the year you actually had rather than the one you expect. A break-even pattern people often look at:
- If your claims came in below the HDHP deductible, the HDHP usually wins on annual premium savings alone.
- If you exceeded the PPO deductible last year, the PPO usually wins on predictability.
- If you're in between, the employer's HSA contribution often tips it.
See our HDHP vs PPO guide for the full break-even math. Which plan fits best depends on your own claims and your family's situation.
Minutes 15–20: which tax-advantaged account do you fund?
Which account you fund is generally decided by the health plan you just picked. An HSA is available alongside an HDHP, and many people contribute up to the IRS limit if they can afford it, since the IRS treats it as the only account with a triple tax advantage and the balance generally rolls over indefinitely. An FSA pairs with most PPOs, and the common approach there runs the other way: estimate predictable spending and fund only that, because the IRS generally treats most health FSA money as use-it-or-lose-it at year-end. A Dependent Care FSA sits alongside either one, and people with kids in daycare often fund it close to the cap. The IRS sets these limits and changes them each year, and your plan's terms may differ. How each account is generally used:
- HSA (paired with HDHP): Many people contribute up to the IRS limit if they can afford it. The IRS treats the HSA as the only account that gets a triple tax advantage, and HSA balances generally roll over indefinitely (per IRS Publication 969). The annual contribution limits are set by the IRS and change each year.
- FSA (paired with most PPOs): A common approach is to estimate predictable medical spend (glasses, copays, planned procedures) and fund only that. The IRS generally treats most health FSA funds as use-it-or-lose-it at year-end, though some plans offer a limited carryover or grace period — your plan's terms may differ.
- Dependent Care FSA: For people with kids in daycare, this often saves real tax dollars. Many people fund close to the cap, which the IRS sets separately from the health FSA limit.
Minutes 20–25: what do you check on life and disability insurance?
This step is mostly about accepting what is free, checking what is cheap, and not skipping disability. Basic life cover of one to two times salary is usually free, so many people simply accept it and move on. Supplemental life is worth a look if you have dependents and no other coverage, and some people compare the group rate against a term-life quote from outside work before deciding, since a group rate is not automatically the better one. Short-term and long-term disability is the piece people most often overlook: where an employer offers a buy-up, many people find the math favors taking it, and disability is one of the most under-bought protections. Five minutes generally covers it, because these are yes-or-no elections rather than calculations. Most of them can only be changed during this window, so they are worth a minute each. What people generally review:
- Basic life (1–2× salary) is usually free, so many people accept it.
- Supplemental life is worth a look if you have dependents and no other coverage. Some people compare the group rate to a term-life quote outside work before deciding.
- Short-term and long-term disability: If your employer offers a buy-up, many people find the math favors taking it. Disability is one of the most under-bought protections.
Minutes 25–30: which "easy to forget" line items are left?
The last five minutes are for the items nobody thinks about until they matter. Beneficiary designations come first: a common step is to confirm that the 401(k), life insurance, and HSA all name the people you would expect. After a marriage, divorce, or birth this is the single most-skipped update, and open enrollment is one of the few moments in the year when you are already signed in to the systems that hold it. Commuter benefits are quick — pre-tax transit and parking, easy to add if you commute. Voluntary benefits such as legal plans, pet insurance and identity-theft cover are usually optional, and many people skip them unless they have a specific need. None of these take long, which is part of why they generally sit at the end of the list rather than the start. The items people generally check:
- Beneficiary designations: A common step is to confirm your 401(k), life insurance, and HSA beneficiaries are current. After a marriage, divorce, or birth, this is the single most-skipped update.
- Commuter benefits: Pre-tax transit and parking — easy to add.
- Voluntary benefits: Legal plans, pet insurance, identity theft — usually optional, and many people skip them unless they have a specific need.
What should you ask HR?
The questions worth asking are the ones the enrollment portal doesn't answer on its own. Whether the plan design or the networks changed this year is the first, because a plan carrying the same name as last year's is not necessarily the same plan, and a network change can quietly drop a doctor you already see. Whether the employer's HSA contribution changed is the second, since that figure sits directly inside the break-even comparison between the HDHP and the PPO. The deadline is the third, along with what happens if it passes — most plans default you to last year's choices, but not all do, and the difference matters when your circumstances have changed. Plan designs and figures change year to year, so the answers are worth getting from HR rather than from last year's packet. The questions people commonly ask:
- Are there changes to plan design or networks this year?
- Has the employer HSA contribution changed?
- What's the deadline, and what happens if I miss it? (Most plans default you to last year's choices — but not all, so it often helps to confirm yours.)
The Department of Labor maintains a plain-language summary of common benefits — DOL benefits and leave overview (affiliate link — OffbookHR may earn a commission if you buy through this link. It does not affect ranking.). For the current HSA and FSA rules and contribution limits, many people check the source directly in IRS Publication 969 (Health Savings Accounts and Other Tax-Favored Health Plans).