• 110 questions

Icebreaker Questions for a Retirement Party

Press Next card for a question about the retiree, a first job or a free Monday.

Icebreaker Questions for a Retirement Party

Did your first job come with a uniform, a name tag, a time clock or none of them?

Read the card out, with the retiree's name in it.

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All 110 questions

Guests who have just met 20

  • Ask the person on your left: what do you two both know about the retiree?
  • Before you knew better, what did you think the retiree did all day at work?
  • Colleagues: tell the family one thing the retiree is known for at work.
  • Family and friends: what is the retiree like on a day with no work in it?
  • How do you know the retiree: work, family, next door or an old friendship?
  • If the retiree were a tool in a toolbox, which one would they be?
  • Is the retiree an early bird, a night owl or at their best after lunch?
  • What have you borrowed from the retiree and still mean to give back?
  • What is the retiree always the first person to do at a gathering?
  • What is the retiree's answer to almost any problem?
  • What would the retiree order for this whole table if it were left to them?
  • What would you call a film about the retiree's working life?
  • Where were you standing the first time you met the retiree?
  • Which one word belongs on the retiree's name tag tonight?
  • Which phrase do you always hear in the retiree's voice?
  • Which snack do you connect with the retiree?
  • Which song should play whenever the retiree walks into a room?
  • Which three words would the retiree use to sum up this party?
  • Who here has been taught something by the retiree: at work, at home or both?
  • Who here met the retiree most recently, and how did it happen?

Memories of working together 24

  • Finish the sentence: you could always count on the retiree to...
  • The retiree's finest skill: staying calm, the jokes, the memory or being early?
  • What did the retiree always notice before anyone else did?
  • What did the retiree bring in that the whole floor looked forward to?
  • What did the retiree do every single morning without fail?
  • What did the retiree fix that the rest of us had learned to live with?
  • What did the retiree insist on doing the long way, and turn out to be right about?
  • What did the retiree teach you about people instead of about the work?
  • What did the retiree tell you in passing that you have never forgotten?
  • What is in the retiree's desk drawer that belongs in a museum?
  • What is the first thing the retiree ever showed you how to do on the job?
  • What is the retiree's trademark: a mug, a pen, a greeting or a snack?
  • What should the plaque beside the retiree's old chair say?
  • What small kindness did the retiree do at work that nobody announced?
  • What will the building be missing on the retiree's first Monday away?
  • What would a new hire learn from one week beside the retiree?
  • Which hard day went better because the retiree was there?
  • Which kind of problem did everyone carry straight to the retiree?
  • Which machine, file or door only ever behaved for the retiree?
  • Which meeting moment with the retiree still makes you smile?
  • Which of the retiree's jobs will now take three people?
  • Which tradition did the retiree start that the rest of us should keep going?
  • Which workday with the retiree would you gladly live through again?
  • Write the retiree's final out-of-office message in one sentence.

First jobs and work stories 22

  • Did your first job come with a uniform, a name tag, a time clock or none of them?
  • What did you believe about work before your first week of it?
  • What did you carry to work every day and could not do without?
  • What did you eat for lunch most often in your first year of work?
  • What did your very first boss get right?
  • What do you still do at home the way an old job trained you to?
  • What hung on the wall at your first workplace?
  • What is the best thing a customer, student or client ever said to you?
  • What is the first mistake you remember making at work?
  • What is the proudest thing you ever made, fixed or finished at work?
  • What is the strangest thing you ever had to deliver, carry or look after at work?
  • What was the best seat you ever had at work, and what could you see from it?
  • What was the first thing you were trusted to do alone at work?
  • Which coworker from long ago would you most like to have lunch with?
  • Which job did you do for one summer and never again?
  • Which piece of work equipment do you still miss?
  • Which sound would put you back in an old workplace with your eyes shut?
  • Which work skill did you learn that no job asks for now?
  • Which workday do you remember only because of the weather?
  • Who showed you the ropes at your first job, and what came first?
  • Your first job's best perk: free food, good company, a short trip in or the view?
  • Your first job: on your feet, at a desk, behind a wheel or behind a counter?

For the retiree to answer 24

  • Retiree, what are you taking home from your desk?
  • Retiree, what did the people in this room teach you?
  • Retiree, what did you almost do for a living instead?
  • Retiree, what did you get better at every single year?
  • Retiree, what did you learn to stop worrying about?
  • Retiree, what do you remember about your first morning in this job?
  • Retiree, what happens to your work alarm now?
  • Retiree, what is the first thing you will do on Monday morning?
  • Retiree, what is the kindest thing a colleague ever did for you?
  • Retiree, what should the next person in your chair know by Friday?
  • Retiree, what went wrong in your first week that never went wrong again?
  • Retiree, what will you learn now that the mornings are yours?
  • Retiree, what will you miss that would surprise us?
  • Retiree, where was the best lunch near work, and what did you order?
  • Retiree, where will we find you at ten on a Tuesday morning?
  • Retiree, which day of the working week did you like best, and why?
  • Retiree, which part of the job would you come back and do just for fun?
  • Retiree, which piece of your work will still be in use long after tonight?
  • Retiree, which task will you not miss for one second?
  • Retiree, which tool changed your work the most on the day it arrived?
  • Retiree, which work habit is going to follow you home?
  • Retiree, which work story do you tell most often? Tell it once more.
  • Retiree, who do we call when the thing only you understand stops working?
  • Retiree, whose way of working did you copy, and what did you copy first?

The free Monday 20

  • A free Monday morning: sleep in, long breakfast, long walk or start a project?
  • Give the retiree a new job title for retirement.
  • Guess first: is the retiree's first plan a trip, a project, a hobby or a nap?
  • One suggestion each: what should the retiree do on their first free Monday?
  • The retiree is off on a first trip. Which one thing goes in the bag?
  • The retiree's new uniform: slippers, hiking boots, garden gloves or an apron?
  • What belongs on the retiree's list of things to try this year?
  • What is the best thing to do at ten on a weekday morning?
  • What is your one piece of advice for someone with no alarm set?
  • What is your wish for the retiree, in five words or fewer?
  • What should the retiree never agree to, now that everyone knows they have time?
  • What should the retiree teach the rest of us, now there is time?
  • What would you do with a completely free Monday?
  • What would you do with your travel time to work if you got it all back?
  • Which class would you sign up for if it met on weekday mornings?
  • Which hobby will the retiree take up first?
  • Which place nearby should the retiree finally visit on a weekday?
  • Which small daily ritual is worth starting in retirement?
  • Which weekday is the best one to have free: Monday, Wednesday or Friday?
  • Which work event should the retiree still be invited to?

How it works

These icebreaker questions for a retirement party are 110 cards to read aloud: some for guests who just met, some for colleagues, 24 for the retiree, and some any guest can answer about a first job or a free Monday.

Read the full guide

A room of colleagues and family

Guests who have just met holds 20 cards that seat a cousin beside a coworker: How do you know the retiree: work, family, next door or an old friendship? Memories of working together is for colleagues. First jobs and work stories asks every guest about their own working life, so nobody needs to have shared an office.

Give the retiree the floor

Every card in For the retiree to answer begins with the word Retiree, such as Retiree, what happens to your work alarm now? The free Monday turns to what comes next: the room suggests a hobby, a place to visit on a weekday or a new job title.

  • If a card for colleagues lands on a family table, press Next card past it.
  • With several tables, choose the Show of hands topic: its 12 cards list choices, so the whole room answers at once.
  • No card asks about age, money or health.

Questions and answers

What are good retirement party icebreakers for guests who do not know each other?

Questions about the one person everyone knows. From Guests who have just met: Where were you standing the first time you met the retiree? Which one word belongs on the retiree's name tag tonight? Family and colleagues can both answer.

Which retirement icebreakers can the retiree answer?

The 24 cards in For the retiree to answer: Retiree, which task will you not miss for one second? Retiree, what are you taking home from your desk? Retiree, where will we find you at ten on a Tuesday morning?

What is the difference between icebreaker questions and trivia for a retirement party?

Trivia has right answers and a score. These cards have neither: each asks for a memory, a guess or a wish, so every guest can answer. For a quiz with an answer key, open the retirement party trivia questions.

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