Mentor Mentee Icebreakers

Press Next card for one question a new mentor and mentee can both answer in a minute.

Which of your skills would surprise your manager?

Each of you: name one thing you can teach and one thing you want to learn.

Tell your partner about a skill you learned from someone newer than you.

In thirty seconds, tell your partner how you came to your current role.

Walk to a side of the room: talker on the left, listener on the right.

How should each meeting start: news, wins or straight to the agenda?

Each of you: one word you hope describes this pairing in six months.

Read the card out. One of you answers, then swap.

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Next step Icebreakers for the whole team

How it works

These mentor mentee icebreakers are 120 cards for a pair that has just been matched. There is a set for each side to ask and a set that settles how the two of you will work together.

Read the full guide

Six sets, in the order a pairing goes

First meeting, both answer breaks the ice. For the mentor to ask and For the mentee to ask give each side a turn. How we will work together settles how often you meet, how to reach each other and what stays between the two of you.

For a kickoff with a room of pairs

Kickoff rounds for a room of pairs gives a program lead short tasks that every pair does at once. Second and third meetings opens the meetings after the first, when the small talk has run out.

Agree before the first card that either of you may pass. A question nobody has to answer gets better answers.
No card asks about pay, age, family or health.

Questions and answers

What should a mentor and mentee talk about in a first meeting?

Each other first, goals second: What do people usually come to you for? Which of your skills would surprise your manager? Then agree how often to meet and how to reach each other, from the How we will work together set.

What are good icebreakers for mentors and mentees in a group?

Tasks that every pair does at once: introduce your partner to the pair beside you in one sentence, swap one tip that saves you ten minutes a week, or choose a name for your pair.

What questions should a mentee ask a mentor?

Ask how they work, not only what they know: How do you decide what to say no to? How do you prepare for a difficult conversation? What should I be asking you that I have not asked?

All 120 questions

First meeting, both answer 20

Are you a morning thinker or an afternoon thinker?
Coffee, tea or a walk: how do you like to meet?
Do you prefer a plan or a blank page?
Do you think out loud, or think first and then talk?
Notes on paper, notes on a screen or no notes at all?
One word for how you feel about this first meeting?
What are you working on this month, in one sentence?
What did you hope for when your match was announced?
What did you learn recently that surprised you?
What do people often get wrong about the way you work?
What do people usually come to you for?
What do you count as a week well spent?
What should I call you, and is there a name you would rather not be called?
What tells you by ten o'clock that a workday is going well?
What would make these meetings worth an hour of your month?
Which of your skills would surprise your manager?
Which piece of advice did you ignore and later come around to?
Which skill of yours is half built right now?
Which subject do colleagues say you never tire of?
Which subject would be a waste of these meetings?

Show all 120 questions (100 more)

For the mentor to ask 20

Do you want advice, questions or just a listener today?
What can I point you to: a person, a book or a tool?
What did your last project teach you?
What do you wish you understood about how this place works?
What does success in your role look like to you?
What feedback have you heard more than once?
What have you taught yourself?
What is one thing you want my honest view on?
What would you like to be able to do a year from now that you cannot do yet?
Where would you like more responsibility?
Which ambition have you kept to yourself so far?
Which choice are you turning over this month?
Which experiment at work have you been meaning to run?
Which meeting or task this month worries you a little?
Which part of your work do you put off?
Which part of your work gives you the most energy?
Which strength of yours does not get used enough?
Which task this year stretched you the furthest?
Which would help most right now: contacts, skills or confidence?
Who are you learning from at the moment?

For the mentee to ask 20

How did you find the kind of work that suits you?
How do you decide what to say no to?
How do you like to be told bad news?
How do you prepare for a difficult conversation?
How do you recover from a bad day at work?
How do you tell an urgent task from an important one?
If you began again tomorrow, what would you skip?
What did nobody tell you in your first month here?
What do you read, watch or listen to in order to keep learning?
What made you agree to be a mentor?
What should I be asking you that I have not asked?
Which decision of yours do you still second-guess?
Which early misstep are you now grateful for?
Which habit would you recommend to anyone starting out?
Which hours of your week are truly your own?
Which of your opinions about this field has shifted?
Which quality do you prize in a colleague?
Which question from a mentee made you stop and think?
Which skill has been worth the most to you over time?
Who mentored you, and what did they do well?

How we will work together 20

Email, a call or a message: how shall I reach you in between?
How blunt would you like my feedback to be?
How do you like to be reminded of something you said you would do?
How long should each meeting be?
How often shall we meet: weekly, every two weeks or monthly?
How should each meeting start: news, wins or straight to the agenda?
How should we tell each other that a meeting needs to move?
How will we know this is working after three meetings?
In person, on a call or a mix of both?
Is it fine to send a message outside working hours?
Shall we keep notes, and who keeps them?
Small talk first or business first?
What should I do if I disagree with your advice?
What should we do when one of us has nothing to bring?
What stays between the two of us?
What will each of us have done by the next meeting?
When shall we decide whether to carry on, change or stop?
Which day and time suit you least?
Which topics are off the table for you?
Who sets the agenda, and when do we share it?

Kickoff rounds for a room of pairs 20

As a pair, agree on one question to put to the whole room.
Each of you: complete the line, I pick things up fastest when...
Each of you: name one thing you can teach and one thing you want to learn.
Each of you: one word you hope describes this pairing in six months.
Each of you: the oddest task you have ever been handed at work.
Guess how your partner likes to spend a free hour, then check.
Hands up: who has been a mentor before? Who has been a mentee?
In thirty seconds, tell your partner how you came to your current role.
Introduce your partner to the pair beside you in one sentence.
Pairs: agree on the date of your first meeting before you sit down.
Pairs: find two things you both want to be better at.
Swap one tip that saves you ten minutes a week.
Tell your partner about a skill you learned from someone newer than you.
Tell your partner one thing you are proud of from the past month.
Tell your partner what you nearly did for a living instead.
Tell your partner who first showed you how to do your job.
Thumbs up, sideways or down: how do you feel about role play?
Together, write one sentence that says what a good mentor does.
Walk to a side of the room: talker on the left, listener on the right.
With your partner, choose a name for your pair.

Second and third meetings 20

From one to five, how was your week?
Is there someone I should introduce you to this month?
One word for where you are today?
What did you avoid this week?
What did you learn this week by getting it wrong?
What has surprised you since our last meeting?
What have you said no to lately?
What is taking more of your time than it should?
What is the next thing on your calendar that you are glad about?
What is the one thing you most want to leave with today?
What landed on your plate after we last spoke?
What should we do less of in these meetings?
What should we do more of in these meetings?
What went well this week that you want to repeat?
Which idea from our previous talk did you put to use?
Which of your goals has moved, and which is stuck?
Which question have you been saving for today?
Which question should I open with when we next sit down?
Who did you talk to this month that you had never talked to before?
Whose work have you admired lately, and why?

How this list was compiled: Written by the Game Night Generator editors for this page on 2026-10-03; no list was copied. 120 cards in six sets of 20 for a mentor and a mentee who have just been paired. Every card can be answered in under a minute. Each was screened against the site's clean-deck rules and against a workplace rule taken from the U.S. Equal Employment Opportunity Commission's list of protected characteristics (https://www.eeoc.gov/prohibited-employment-policiespractices, read on 2026-10-03): no card asks about race, color, religion, sex, national origin, age, disability or genetic information, and none asks about pay, family or health. A script compared every card with every other list on this site, by exact text and by shared words, and cards that repeated one elsewhere were replaced. Licence: own work