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Leaving a job? Ask these 12 questions before you go

If you’re checking out my website, there’s a decent chance you’re thinking of leaving your current job. Before you submit your final timesheet, be sure you get answers to these 12 (!) questions:


When does my health, dental, and/or vision insurance end? Does it stop on your last day of work? The last day of the same month? Maybe the end of your final pay period? Plans vary; don’t assume. You don’t want to end up with an unexpected gap in coverage, especially if you’re in the midst of treatment or have a chronic condition.

What are my health insurance continuation rights? Your employer may be subject to COBRA or, for small companies, the state’s “mini-COBRA” continuation law. (Some small employers miss this.) If you and your dependents had coverage, you probably have continuation rights, and if so, they owe you a notification ASAP about your rights and responsibilities. It’ll probably be sent to you soon after your last day. Don’t sleep on this, because there are deadlines to elect and pay for coverage. I wrote more about COBRA here, or visit the DOL’s website. (It should go without saying that if you weren’t covered, you can’t do COBRA. And, if you had a dependent who wasn’t covered, you can’t add them for coverage if you lose it because your job is ending.)

Can I keep my group term life insurance? Most group term life insurance plans require employers to notify you about continuation. This may be an important option if you don’t have other life insurance or don’t think you’ll be able to obtain other insurance (like if you have a health condition that makes underwriters think twice). If you think you might need it, be sure to ask for the details.

What about my disability insurance? This may depend on if it’s company-paid or voluntary (you’re paying the premium). Ask when the coverage ends and can you continue it.

What do I need to know about my flex spending accounts? This is a tricky area, and one often misunderstood by employers. But in general:

  • Healthcare FSA – Your full annual election amount is available for you to use while you’re still paying into your plan, and that includes through a COBRA-like continuation option they’re supposed to offer. Have you been reimbursed for more than you’ve paid in? You do NOT have to repay the difference. Ask how long you have to submit claims. If HR isn’t sure, call the flex vendor to ask.
  • Dependent care FSA – This account should only have reimbursed you for as much as you put in. If you haven’t claimed your deposits yet, find out how long you have to do it (there might be a deadline that’s before the plan year-end) and submit those daycare receipts pronto. At your next employer, you can elect the difference between the maximum annual amount and your YTD contribution in your previous employer’s plan.

Can I keep my pretax commuting benefits? That depends on how the plan was set up. Ask HR or your vendor whether the money in your account is yours to keep.

What happens to my retirement plan account? This one, you should ask even before you submit your resignation letter. Was any of your account balance subject to vesting, and if so, when are you fully vested? If you miss a vesting cut-off by even a few days, your employer generally cannot override the plan’s rules. Don’t forget about employer contributions that may have been made to your account, even if you didn’t defer any of your pay while you were working there.

Is there a deadline to take a rollover distribution? This probably depends on how much is in your account. Some plans will automatically cash out balances below a certain amount. Otherwise, you may be able to leave it in your former employer’s plan for now. However, I think it’s usually better to roll over your account into a rollover IRA that you set up on your own, or into your new employer’s qualified plan once you’re eligible. Your previous employer(s) will thank you for your prompt attention to this grown-up task. They don’t want to have to send you required plan notices long after you’ve left.

Are there any year-end bonuses, profit-sharing contributions, or vesting milestones I might forego if my last day is before December 31? Ask this one before you submit your resignation letter. Know before you go.

When is my final paycheck? You may have forgotten whether you are paid “current” or in arrears, but it will become evident on your final paycheck. Ask what your final paydate is and whether it will be direct deposit (some employers don’t direct-deposit final pay). Know that some states have laws about when final pay must be made upon involuntary termination (looking at you, DC and CA), and not all employers are savvy enough to know or care enough to comply. A quick internet search (or message to your favorite HR pro) will yield answers.

Will I receive pay for the paid time off I earned but didn’t take? Rules vary here, depending on company policy and how they make paid leave available. But confirm before you leave. Have you used more leave than you’ve accrued? Your employer might want to deduct the overage from your final paycheck. That may or may not be OK – if you signed a statement allowing it, such as what might be in an employee handbook, or if you’re paid on an hourly basis, it’s probably OK, but if you’re an exempt employee, it may not be. Your state might have guidance on this as well.

How will I receive my final pay statement? Employers are obligated, in most states, to give employees an itemized pay statement every payday, even when your net pay is direct deposited. If your pay statements were delivered electronically through the HR or payroll system, you might lose access to their system once you leave. Ask payroll to email or postal-mail all final pay statements to you.


Whew! I know that’s a lot of questions. But you’ll want to understand everything before you go, so you can make the best decisions for how to wrap things up and look ahead to a smooth transition to your next employer.

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