5 Questions to Ask HR Before Your Last Day at Work
Here's the short answer. Before your last day, ask HR five things. When your final paycheck lands and what it includes. When your health insurance ends and how COBRA works. How to move your 401(k) and any vested stock. What the company's reference and re-hire policy is. Which HR documents to download while your access is still open.
Most people wait until the exit interview to ask HR anything, and by then half of these answers arrive too late to act on.
Your final week is the last chance to get clean answers. Once your email closes and your login stops working, you become a former employee, and former employees get slower replies, boilerplate responses, and sometimes no response at all.
Book fifteen minutes with your HR partner for the middle of your final week. Not the last day. Not the day before. Bring the five questions below.
1. When exactly will my final paycheck land, and what will it include?
The company almost always has an answer to this, but it is rarely volunteered. Ask for the date. Ask for the dollar figure if they can share it. You want to know whether it includes:
- Unused PTO paid out at your regular rate
- Any earned commissions, bonuses, or profit-sharing
- Outstanding expense reimbursements
- Vesting milestones that fall inside your notice window
The rules vary by state and by company policy. In some states unused PTO is automatically paid; in others it depends on your handbook. If your last day is close to a bonus date or a stock vest, ask HR explicitly whether the payout carries over. A difference of two days can be a difference of several thousand dollars.
Also confirm the delivery method. If you are switching banks, or your direct deposit points at an account you plan to close, make sure the final payment lands somewhere you can still reach after your work email shuts off.
2. When does my health insurance end, and how does COBRA actually work?
Some plans end the day you walk out. Some run to the last day of the month. A few extend for thirty days. Ask HR for the exact end date in writing.
Then ask about COBRA continuation. Most employers of twenty or more people must offer it under federal law. Your employer will send a formal COBRA election notice. Ask HR when to expect it and where it will arrive, mailing address or email. If you are moving, update your address now.
Compare that end date to when your new employer's benefits begin. If there is a gap, decide before your last day whether you will bridge it with COBRA, a spouse's plan, a marketplace plan, or nothing. Do the math on the COBRA premium. It is often two to five times what you paid as an employee, because the employer's share is now yours.
Ask the same question about dental, vision, and life insurance separately. They sometimes end on different dates.
3. What are the deadlines to move my 401(k) and vested stock?
The 401(k) doesn't disappear the day you leave, but the decision doesn't wait either. You have three main options: leave it in the old plan (usually allowed if the balance is over a threshold), roll it into your new employer's 401(k), or roll it into an IRA. Ask HR who the plan administrator is and how to start a rollover.
Stock is more urgent. Most companies give you a fixed window, commonly ninety days from your last day, to exercise vested stock options. Miss the window, and the options expire. Ask HR:
- What is my exercise window and when does it start?
- Which options are vested as of my last day?
- Which restricted stock units will vest during my notice period, and when do they settle?
- Who is my point of contact at the plan administrator after I leave?
If the company was recently valued or is likely to be acquired, this call is worth more than most conversations you will have all year. Get the answers in writing.
4. What is the company's reference and re-hire policy?
Most companies have a written policy about references. Some allow managers to give personal references. Some route everything through HR, who will confirm only your dates of employment and title. You need to know which.
The verbal reference from your manager is a separate conversation. See our piece on asking your boss for a reference before you leave for the script. But the HR-level answer sets the default. If HR only confirms dates and title, future employers who call the main line will get exactly that, and you'll want to steer them toward your manager's cell instead.
While you are on the topic, ask whether the company has a re-hire policy. Some companies actively invite alumni back. Some have a cool-off period. A few will not re-hire, though this is rare in most industries. Knowing where you stand is worth thirty seconds.
5. Which HR documents can I download before my access ends?
Once your login stops working, the HR portal locks you out of your own history. Download everything you might need before that happens. Ask HR:
- Where are my old pay stubs and W-2s stored, and can I download them before Friday?
- Do I have access to old performance reviews?
- Where is my signed employment agreement and any amendments?
- Where are my benefits enrollment records?
Pay stubs and W-2s are the most commonly missed. You need them for mortgage applications, background checks, and future tax filings. Some employers keep them accessible to alumni through a separate ADP or Workday login. Some don't. Ask now, and pair the answer with the wider what-to-take-home checklist.
The five questions HR handles. There's a sixth that's on you.
HR closes out the paperwork. HR does not close out the relationships. That part is yours. And it is easy to underrate until the last day arrives and you realize the final paycheck was the small problem. The harder one is that you never wrote to the senior PM you worked with on the summer launch, or the cross-functional partner who quietly saved the project in Q2.
Before the HR meeting, pull up your work calendar. The last twelve months of meetings hold the honest record of who you actually worked with, the names your memory over-writes and under-writes in weeks like this. It Was Great Working With You reads a calendar export in about three minutes and returns your goodbye list, sorted by how often you actually met.
The point is not another checklist. The point is that the calendar knows things about your working year that you do not, and the reason people regret their last week is almost never the paperwork.
How to actually run the HR meeting
Keep it short. Bring the five questions written down. Take notes. You will forget half of what HR says by Friday if you don't.
If HR is remote or overbooked, ask for the answers in email. Framed politely, most HR partners are happy to send them, because putting the answers in writing protects them too. A one-sentence request is fine: "Before my last day, could you send me the final-paycheck date, benefits end date, COBRA process, 401(k) rollover steps, and reference policy?"
Do not use the meeting to relitigate your notice period, negotiate severance, or grieve the departure. Different meetings, different people. This one is admin.
What most people get wrong
Two mistakes come up over and over.
The first is waiting until the exit interview to ask any of this. The exit interview is HR's meeting, not yours; it runs on their agenda. By the time you get to your five questions, they have twenty minutes left and boilerplate answers ready. Ask before then. If you are unclear on how the exit interview itself will go, our exit interview tips piece covers the separate conversation.
The second is treating HR as if they know everything. HR closes out one lane. They do not track your relationships, your open commitments to specific coworkers, or the people you owe a real thank-you to. That falls off if you don't build the list yourself. Two hours before the HR meeting is a fine time to open itwasgreatworkingwithyou.com and get the list back.
The HR conversation is a fifteen-minute problem with clean answers. The goodbye list is a two-hour problem with real weight. Do both, in that order, and the last week feels honest instead of scrambled.
Further reading: The people you'll forget to say goodbye to when you leave your job.
