Questions for a retirement farewell: what to ask someone after a working life

Short answer: Ask the person who retires about the first day, how the work changed over the years, the people who mattered, what the job taught them and what they look forward to. Colleagues can each bring one question, family can ask about the years at home behind the job, and a few recorded answers make a better keepsake than a card.

Last updated: 3 November 2026.

A retirement farewell often ends a working life of thirty or forty years in one afternoon: a speech, a gift, a drink and a few photos. The stories behind those years, the first boss, the machine that always broke down, the colleague who became a friend, are told once at the bar and then gone.

The questions below help to keep them. Colleagues can use them at the farewell, friends at the dinner afterwards, and children or grandchildren at home, who often know surprisingly little about what their parent or grandparent did all those years.

How to ask

• Collect questions in advance. Ask each colleague to write one question on a card. Read a few aloud at the farewell, and give the rest to the person to answer later.
• Ask for moments, not achievements. What happened on that one day says more than a list of results.
• Bring old photos from work. A team photo from twenty years ago starts more stories than any speech.
• Respect how the person feels. Some people look forward to retiring, others find it hard. Ask about what was, and let them decide how much to say about what is next.
• Ask the family too. Partners and children have their own stories about the job: the late evenings, the phone calls, the company party.

How it started

1. How did you get this job, and what do you remember of the interview?
2. What do you remember of your first day?
3. Who showed you the ropes, and what did they teach you?
4. What did your workplace look like then, and what did you earn in your first year?
5. What did you think you would do with your life when you started?
6. What was the first mistake you made, and how did it end?

The work then and now

1. What did a normal working day look like in your first years?
2. What is the biggest change you saw in your work over all those years?
3. Which tool, machine or program do you remember from the early days?
4. Which part of the job did you love most, and which part will you not miss?
5. What did your job look like from the outside, and what was it really?
6. Which day at work will you never forget?

The people

1. Who was the best boss or colleague you ever had, and why?
2. Which colleague became a real friend?
3. Who made you laugh most at work?
4. Which customer, patient, pupil or client do you still think of?
5. Is there someone you would like to thank today who is not here?
6. What do you hope your colleagues will remember about you?

What it taught you

1. What is the best advice anyone gave you at work?
2. What would you tell someone who starts this job tomorrow?
3. When were you proudest of your work?
4. What did the job teach you that you use outside work too?
5. What would you do differently if you could start again?
6. What did your work mean to the people at home?

What comes next

1. What are you looking forward to most?
2. What have you always wanted to do and never had time for?
3. What will you do on the first Monday morning?
4. Which habit from work will you keep, and which one will you drop immediately?
5. Where would you like to travel, and with whom?
6. What would you like to learn now?
7. What can we, your colleagues and friends, still do for you?
8. What do you want to say to everyone here today?

Recording and keeping the answers

• Ask first. Say why you would like to record: so the stories are not lost, and so others can hear them later. If someone prefers not to be recorded, write down a few words afterwards instead.
• Use the voice recorder on your phone and put the phone on the table, not in your hand. After a few minutes people forget it is there. A voice says more than a perfect transcript.
• Write down the basics the same day: who answered, the date, the place and the names that came up. Without names and a date, a recording is hard to place ten years from now.
• Photograph the photos and objects that were passed around, and keep them with the recording.
• Keep two copies in two places, and send them to the people who were there.

A place for the answers

If you want one place for the answers, The Memory Palace is made for this: your own 3D palace with rooms you walk through, where photos, voice recordings, videos and written stories hang side by side. You can make a room for this farewell, write the questions and answers in it as stories, and hang the recordings next to the photos they are about. With a collect link, relatives or friends can add a photo, a memory or a voice recording from their browser, without an account. Colleagues who could not be there can add their memory later through the same link. A palace is private by default and you choose who gets in. It is made by a small team in Leuven, and you can start one for free.

Questions for other occasions

• St Nicholas and Sinterklaas
• Christmas dinner with grandparents
• New Year's Eve with friends
• A 70th, 80th or 90th birthday
• Your parents' wedding anniversary
• Mother's Day
• Father's Day
• A funeral or condolence visit
• Grandparents meeting the new baby
• A school or class reunion
• A road trip or holiday with old friends

Read on: a group memory book for a birthday or farewell, retirement projects: documenting a life story, how to interview older family members, the free printable sheet of twenty questions to ask your parents.