Questions to Ask Someone Who Is Retiring

The questions

Open any question to see why it works.

1. 1

   When is your last day, and how does that date feel now that it is close?

   Start here because the answer tells you which conversation you are in. Someone who chose the date will talk about the date. Someone pushed out by a restructure, a buyout, or their own health will answer about something else, and that is your signal to drop the celebration framing.

2. 2

   How long have you been doing this work?

   Most people round the number and then correct themselves, which is where the useful detail arrives: the year they started, the job title that no longer exists, the building they worked in first. Follow the correction rather than the number.

3. 3

   What did the job look like when you started?

   This gets you the concrete texture that general career questions never reach: paper, phones, hours, dress codes, who was allowed to speak in meetings. It is also the easiest question for a private person to answer at length, because it is about the work and not about them.

4. 4

   What do you remember about your first day?

   First days are stored as scenes rather than summaries, so you tend to get names and small humiliations instead of a rehearsed answer. If someone says they remember nothing, ask who showed them where to sit.

5. 5

   What has changed most since then, and was it for the better?

   The second half keeps this from becoming a complaint about technology. People near the end of a career usually have a nuanced view here, and the things they say improved are often the ones you would not guess, like safety rules or who gets hired.

6. 6

   Who taught you the most, and what did they teach you?

   Retiring people are often the last person who remembers someone who mattered inside the organisation. A name and a lesson is the part of this conversation most worth writing down, because it usually disappears with them.

7. 7

   What are you proudest of that would never show up on a résumé?

   The résumé version is the promotion or the big project. This question reliably produces something else: a person they hired, a bad decision they blocked, a stretch where they held things together. Expect a pause before the answer, and do not fill it.

8. 8

   Is there a piece of work you would want your name on?

   Useful if you are writing a speech or a card, because it tells you what to mention and, by omission, what not to. If they name something small and specific over something famous, use their version.

9. 9

   What will you actually miss? Not the job, the daily small things.

   Ask it in two parts like this, because the first answer is almost always the abstract one about the people. The specific answers are better and stranger: a commute podcast, a particular chair, a Thursday routine, knowing what everyone is going to say.

10. 10

    What will you be glad to be rid of?

    This gives permission to be honest and usually loosens the whole conversation. It also tells anyone still in the job which parts of it were always miserable rather than just miserable this year.

11. 11

    What is the first thing you are doing the Monday after?

    Nearly everyone has an answer to the first week. The interesting information is the tone: an elaborate plan can mean the same anxiety as no plan at all. Both are worth noting if you plan to check on them later.

12. 12

    What does an ordinary Tuesday look like six months from now?

    This is the question the first week hides. The people who struggle in retirement are usually the ones with a great holiday planned and nothing after it. A vague answer here is not a problem to solve on the spot, just a reason to call in the spring.

13. 13

    Is this a full stop, or are you keeping a hand in somewhere?

    Part-time work, consulting, board seats, and volunteering all change what retirement means practically and financially. Ask it neutrally, since some people feel they should be fully stopping and some feel they should not be stopping at all.

14. 14

    Is there anything about it you are nervous about?

    Often the answer is money, health, or a spouse who is not retiring, and none of those come up unprompted at a leaving party. Ask this one privately, not in a group, and be ready to let it stay a short answer.

15. 15

    What do you want people here to keep doing after you go, and what should they stop?

    Leaving is the only moment when someone can say the second half out loud. The answers tend to be specific and slightly overdue: a meeting that should die, a check nobody else runs, a customer everyone avoids.

16. 16

    Is there anything only you know how to do?

    Long-serving people carry undocumented knowledge, and they usually underestimate how much. Push past the first no by naming things: who calls you when the system breaks, who asks about the old contracts, what happens every December.

17. 17

    How do you want to stay in touch, and how often is too often?

    Worth asking explicitly, because the default is enthusiastic promises followed by nothing. Some retirees want a standing lunch, some want to be left alone for a year. Getting the preference now saves both sides guessing.

18. 18

    What would you tell whoever takes this job next?

    Framing it as advice to a successor rather than advice in general produces practical answers: who to trust, which rule is real and which is folklore, what takes longer than it looks. This one is worth writing down verbatim.

19. 19

    What would you tell yourself at twenty-five, knowing how it went?

    Expect a cliché first. The second answer, if you wait, is usually about something they gave up for the job and would not give up again. Do not argue with it or reassure them out of it.

20. 20

    When you look back at the whole thing, what do you want it to have added up to?

    This is the closing question because it needs the rest of the conversation behind it. Some people answer about work, some about the people they raised or trained, and a few refuse the question entirely, which is also an answer.