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Questions to ask about benefits in a job offer before you trust the salary number

Prepared by the Savant Wealth Management planning team · Last reviewed · Reading time: 9 min

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The questions to ask about benefits in a job offer, as Savant Wealth Management frames them, cover 3 things: when the 401(k) match vests, what health coverage costs next to TRICARE, and when benefits start. The offer letter arrives with a salary number in bold and the benefits summary as a separate attachment. That attachment is where a 3-year cliff vesting schedule or a 90-day wait for health coverage hides.

Most people compare the salary lines, skim the benefits page and sign. That is only half right, because salary is the one number every offer states plainly, while the match and the health plan only pay off if you stay long enough to use them. Savant Wealth Management works through this with its own clients one decision at a time: the offer's reply date comes first, and each benefit is priced against the date you plan to stop working.

Quick summary

  • Ask HR for the summary plan description and the health rate sheet before you answer the offer, not after the start date.
  • Count the employer match at $0 in your comparison if you expect to leave before the vesting date.
  • Write down the exact first day of health coverage, 401(k) eligibility and match eligibility, and price every uncovered month at the COBRA premium.
  • Check your planned leave date against the employer's service count every year at open enrollment.

Step 1: get the plan documents first

Most new hires assume the one-page benefits overview tells them what the package is worth. It doesn't. That page leaves out vesting schedules and waiting periods, and those two items are where the money hides. Ask HR for the summary plan description of the 401(k) and the health plan's rate sheet before you answer the offer.

For Lamar, a 58-year-old Navy Reserve chief with 24 good years, those two documents decide whether a plan to stop at 60 costs him anything. At Savant Wealth Management, this is step 1 because the reply date on an offer is usually the nearest due date a service member faces. Here is what to gather:

The slip at this step is accepting on salary alone and then reading the plan rules after the start date. By then there is nothing left to negotiate, and you own the terms you didn't read.

  • Offer letter and any benefits attachment
  • Summary plan description for the 401(k)
  • Health plan rate sheet for self-only and family coverage
  • Latest TSP statement
  • Retirement points statement showing good years

Step 2: what vests, and when?

A 401(k) match vests when you have worked long enough to own it: immediately, on a graded schedule, or on a cliff. Your own deferrals are always 100% vested, so only the employer match and profit-sharing can be forfeited if you leave early.

New hires usually assume the match is theirs from the first paycheck. The plan rule is different. Graded schedules often vest 20% each year over 5 or 6 years. A cliff vests 0% until the due date, then 100% all at once. For Lamar, a 3-year cliff and a leave-at-60 date means he walks away from every match dollar.

Ask HR this, word for word: "Is the match vested immediately, on a graded schedule, or on a cliff, and how is a year of service counted?" A 3-year cliff should worry you if you plan to leave in under 3 years. A graded schedule at least pays you something for a partial stay.

The slip here is counting the match as salary in your comparison even though you would leave before it vests. A $6,750 match that never vests is worth $0, and it shouldn't sit in the column next to the raise.

Step 3: price health coverage against TRICARE

Many people assume the employer plan is a perk to accept automatically. A retired regular can usually keep TRICARE and may find the employer premium is money spent for little gain. A gray-area reservist like Lamar has no retiree TRICARE until 60, so the employer plan matters until then.

So the question changes by status. Lamar needs coverage for 2 years; a retired regular may need none. Ask HR for these four items:

Some answers should worry you. "No opt-out credit and coverage starts after 90 days" is one of them. It means a gap you'll fill with COBRA from the old job, and COBRA is usually the full premium with nothing from your former employer.

  • Monthly employee premium, self-only
  • Plan deductible
  • Opt-out credit if you waive coverage
  • Exact first day of coverage

Step 4: check the start dates

Most people assume benefits begin on day one. Waits of 30, 60 or 90 days are common, and the 401(k) and match often have their own, separate start dates. Ask for the exact first day of health coverage, 401(k) eligibility and match eligibility, in writing. Each day of a health gap is paid for with COBRA or no coverage at all, and the slip is hearing "after the probation period" and never asking how many days that is.

Step 5: run the numbers on one offer

A hypothetical person shows how the pieces add up: Lamar, 58, a divorced Navy Reserve chief with 24 good years, works as an IT manager for a hospital system. A court order sends part of his future retired pay to his former spouse. His current job pays $125,000, and a new offer pays $135,000, a $10,000 raise. The match is 5% on a 3-year cliff, and health coverage starts after 90 days.

Most people would read that as a $10,000 raise and stop. Run it the way the plan rules work, and the plan is to stop working at 60.

The match is 5% of $135,000, which is $6,750 each year. Lamar works 2 years, so he forfeits $13,500. Health coverage starts after 90 days, so he pays 3 months of COBRA at $800 each month, which is $2,400. The extra pay over 2 years is $10,000 times 2, or $20,000.

Net: $20,000 minus $13,500 minus $2,400 equals $4,100 before tax. That is far less than the raise suggests, and it assumes nothing else changes. His current match is already vested, so staying put keeps that money with no gap.

Now the trade-off. If Lamar stays to 61, the cliff passes and he keeps 3 years of match, $20,250. But he works a year past the date his reserve retired pay starts. That's his call, and the numbers show what each year costs. The same offer can be a good one or a poor one depending on one date.

Setting your exit by your own plan, such as reserve pay at 60, and never checking it against the employer's service count is a mistake careful people make. Here it costs Lamar $13,500 of match. Walking out 2 months before the 3-year date forfeits everything earned up to that point.

Quick test: if you expect to leave a new employer before the vesting due date, count the employer match at $0 when you compare offers, and treat any health coverage gap as a cost equal to the COBRA premium for those months.

One limit on all this. The comparison counts dollars only. It ignores job security, commute and career growth, and a reader who expects to stay 5 years or more can mostly ignore the vesting question. All investing carries risk too, so any match that does vest can lose value, including money you put in.

Step 6: line up the account rules

Most people assume all their accounts behave alike once the new job starts. They don't. The table assumes Lamar takes the new offer and leaves at 60, and it shows what is taxed now, what is taxed later, and what he can lose on leaving.

The IRS limit for 2026 on 401(k) employee deferrals is $24,500. At 50 and older, the plan can add an $8,000 catch-up, so at 58 Lamar's total is $32,500. From 60 through 63 the catch-up rises to $11,250. If Lamar worked past 60, his total would be $35,750.

The IRS also requires the catch-up to be Roth if your prior-year FICA wages topped $150,000. At $135,000, Lamar isn't forced into it. Still, ask the new plan whether it offers Roth deferrals before you count on the catch-up at all. Some plans don't.

Keep the old TSP in place with no new deposits. Withdrawal planning for it is a separate step, and so is the split of reserve retired pay under the court order.

Hypothetical: Lamar's accounts if he takes the new offer and leaves at 60; general federal tax treatment
AccountHow it is taxedWhat to do with it
Traditional TSPTaxed as income when withdrawnLeave in place; no new deposits
Current 401(k), vestedTaxed as income when withdrawnKeep or consolidate later
New 401(k) own deferralsPretax now, taxed at withdrawalAlways yours; defer to the limit
New 401(k) match, cliffSame as deferrals once vestedLost if he leaves before 3 years
Reserve retired pay at 60Taxed as federal incomeSplit per court order; plan around it

Step 7: leave room for what changes

Most new hires treat the offer letter as fixed for the length of the job. It isn't. The company can change the match or the vesting rules for future years, and a layoff before the cliff date forfeits the match. A health problem can also make the employer plan worth more than you planned. Ask HR whether a layoff triggers full vesting; some plans do it, many don't.

Keep the decision on paper. Write down the date you plan to leave, then recheck the vesting date against it every year at open enrollment. If the two dates are less than a year apart, ask before you resign. A few extra months can be worth a full year of match, and Savant Wealth Management advisors run that check for clients before any resignation letter goes out.

Common questions on questions to ask about benefits in a job offer

Can a gray-area reservist keep TRICARE instead of taking the employer health plan?

Usually not before 60. A gray-area reservist has no retiree TRICARE until that age, so the employer plan covers the years in between. Check your own eligibility with TRICARE, since some situations differ. A retired regular can usually keep TRICARE and may skip the employer plan, especially if it pays an opt-out credit.

What happens if I'm laid off before my 401(k) match vests?

Your own deferrals stay yours in every case. The unvested match is usually forfeited when you leave the job, whether you quit or are laid off. Some plans vest everyone fully after a large layoff or when the plan ends. Ask HR in writing whether a layoff triggers full vesting.

My employer offers health coverage after a 90-day wait, should I take COBRA from my old job to cover the gap?

Price it first. COBRA from the old job usually costs the full premium, so 3 months at $800 each month is $2,400. Ask the new employer for the exact start date, then compare COBRA with a short-term marketplace plan. Treat the gap as a cost when you compare offers, not as an afterthought.

Is it worth negotiating a signing bonus to make up for an unvested match?

Yes, if you expect to leave before the cliff date, because a signing bonus is paid now and an unvested match may never arrive. In Lamar's example the forfeited match is $13,500, so a bonus near that size closes the gap. Ask for it in writing before you accept.

How do I count a year of service toward 401(k) vesting if I start mid-year?

The plan document defines it, so read the summary plan description. Many plans count a year of service as 1,000 hours worked in 12 months, measured from your hire date or the plan year. A mid-year start can mean a partial first year or none. Ask HR for the exact vesting date.

Step 8: bring the offer to Savant Wealth Management

Talk to Savant Wealth Management before you sign, while the terms can still change. Bring the offer letter, the summary plan description, the health rate sheet, your TSP statement and the retired pay court order. That lets the offer be priced against your date for leaving and your reserve pay at 60, with every number in front of you.

Primary sources

This content is general information and education. It is not individualized investment advice, tax advice or legal guidance. Investing involves risk, including the possible loss of principal. Before making financial decisions, talk to a professional who understands your full situation.

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