ICEBREAKERS, via The Art of Noticing by Rob Walker

What would you write on a gigantic billboard? A list of conversation icebreakers from @notrobwalker's (brilliant) "Art of Noticing" newsletter. They can help you start a video meeting or get to know someone better.

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ICEBREAKERS, via The Art of Noticing by Rob Walker

What would you write on a gigantic billboard? A list of conversation icebreakers from @notrobwalker's (brilliant) Art of Noticing newsletter. They can help you start a video meeting or get to know someone better.

remotework, communication, teaching, zoom, talking

“Icebreaker of the Week” is a recurring feature of the newsletter The Art of Noticing ( Some are icebreakers I made up or experienced or found somewhere; many are submitted by TAoN readers. After many requests, I am collecting & sharing all the icebreakers here.

If you find this useful or enjoyable, consider buying a copy of the book that spawned the newsletter, The Art of Noticing: 131 Ways To Spark Creativity, Find Inspiration, And Discover Joy In The Everyday. There's a whole section of the book with exercises designed to help you converse with, listen to, and connect with others! Plus it makes a great gift :) But if that’s not your kind of thing, maybe just consider subscribing to the free newsletter spinoff of TAoN ( Either way: Thanks!

My name is Rob Walker. I appreciate your interest. → Please submit your icebreakers (whether you made them up or heard/read them somewhere), or your experiences trying these, to [email protected].

[NOTE: This is a read-only document, please do not ask for editing access! But feel free to just copy and paste the whole thing, and put it in a new document that you can edit per your needs.]

December 4, 2023, TAoN No. 149

Today’s icebreaker comes from reader Andrea Trancoso:

When have you felt touched by something larger than yourself?

An interesting question, because I think we all want to feel like we’re part of something larger. My thanks to Andrea! She’s on Instagram here.

November 7, 2023, TAoN No. 147

Today’s icebreaker comes from reader M.W.:

You’re the organizer of a music festival; pick any two music headliners, living or dead.

“I’m a trainer/instructor for restorative practices, so we do circles to build community,” M.W. explains. “For a warm-up or closing I like this prompt.” I like it, too! Fits with some of the recent music-listening posts, as well. Thanks, M.W.!

August 30, 2023, TAoN No. 142

Today’s icebreaker comes from reader Bella M.

What’s something you believe in but can’t prove?

This might be a risky question. But that’s partly why I like it!

July 18, 2023, TAoN No. 139

Today’s icebreaker comes from Preston A.

What animal would you ride into battle?

“Could be real or imagined,” this reader clarifies. I’d be tempted to add “no dragons, too obvious” but you decide! Either way: Thanks to Preston A. for the very fun contribution!

April 10, 2023, TAoN No. 132

Today’s icebreaker comes from reader Leonardo Zangrando, via the comments.

If you were a postcard, what would it depict?

I have a feeling I would be a jackalope card. Or maybe that’s wishful thinking? Anyway, Leonardo, who writes One & Ocean, had several other good ideas. My sincere thanks!

February 28, 2023, TAoN No. 129

Today’s icebreaker comes from reader Amy Herr:

We always hear about how smell is the sense most associated with memories. What is a smell that brings back a very strong memory for you?

“This icebreaker is always successful for me,” Amy adds. “It’s so fun to hear the answers!” Thank you so much, Amy!

February 13, 2023, TAoN No. 128

Today’s icebreaker comes from reader Brendan Hall:

If the story of your life is 300 pages long — what’s on page 283?

Brendan adds, in response to my query: “As for why Page 283.... yeah, ‘toward the end but not over’ is what I was going for, so you could pick any number in that range really. I also love this because it opens up even more possibilities as you remove assumptions about how a story of your life should be told. I originally found a version of this mentioned as an entrance exam question in a Rolling Stone article about college applications about 20 years ago.”

Thanks so much! Brendan is on Substack, and Twitter.

Jan 18, 2023, TAoN No. 126

Today’s icebreaker comes from reader Karlie B.:

If you were a potato, how would you be prepared?

Karlie B. offered no elaboration on this question — and what elaboration do we need? I love this kind of query. Thank you Karlie!

Nov 14, 2022, TAoN No. 122

Today’s icebreaker comes from reader Claire Mason:

If you were a beverage, what would you be?

“It doesn’t necessarily have to be something you enjoy drinking,” Claire clarifies. “But what beverage embodies you?”

A little more backstory: “I’m a big fan of your icebreakers! They remind me of a fun one I came up with at work many years ago. We had a lot of fun coming up with beverages for each other and ourselves! I was a French Earl Grey tea with milk at the time, but feel like I have evolved since then — might have to give it a rethink!”

October 17, 2022, TAoN No. 120

Today’s icebreaker comes from reader Estelle Metayer:

Describe your first car, and what it meant for you.

My first car was a Pontiac T1000, which I promptly totalled. But that car had other, happier associations, too! First cars are special objects, no doubt. People always have stories about them. So thanks for this great contribution, Estelle!

August 8, 2022, TAoN No. 117

Today’s icebreaker comes from Alex Hidalgo / @ahidalgosre on Twitter:

Using only food: Where did you grow up?

I’ll say chicken fajitas, brisket, and fried shrimp. See others’ replies here. Unfortunately I do not remember who brought this thread to my attention, but whoever it was: thank you!

June 27, 2022, TAoN No. 114

Today’s icebreaker comes from reader Elise Granata:

As a child, what was your third space – the space you felt you belonged, that wasn't home or school? What about as a teen? A young adult?

Elise adds: “This came out of me joking that the mall (more specifically, the Hot Topic t-shirt section) was my third space as a teen. This was in close competition with the pet store in the strip mall by my house that a friend and I would go to regularly after school, because we didn't have to buy anything to be there, and we struck up an odd but friendly relationship with the owner! Weird times.”

I love it. And for me the answer would probably be either the record store, or the house of a certain friend.

May 16, 2022, TAoN No. 111

Today’s icebreaker is something I overheard randomly. I was listening to an Amazing Radio DJ set from the musician Boyfriend (I'm a big fan). Mostly it’s music, but she always has a guest mid-show. This time one of the guests shared an icebreaker that her organization uses in its training process:

If you were a vending machine, what would you dispense?

For the record, Boyfriend’s guests were two representatives of Plan C, a nonprofit project focused on providing information about at-home abortion pill options. I don’t think this icebreaker has anything to do with that (perfectly admirable, in my view) mission; it’s just a fun and kinda weird icebreaker that works in any context!

April 18, 2022, TAoN No. 109

Today’s icebreaker is from reader Sofía:

If you could rule for a day, what would your first decree be?

Actually Sofia made several suggestions, including: Who would win in a fight between Batman and Terminator and why? What's your favourite cleaning product? And, Which is your favourite Spice Girl and why? All fun! Thanks so much Sofía!

February 21, 2022, TAoN No. 104

In the spirit of this issue’s newsletter roundup, I’m going to adapt an icebreaker from a recent issue of The Whippet. (Fingers crossed that The Whippet won’t mind!)

The context is an anecdote about someone who made a set of protest stickers that became really popular, so popular that the person got contacted by an official government agency — which wanted a few of the stickers to preserve for historical purposes! That’s obviously not a turn of events the maker of protest stickers would have predicted … but it’s also kinda cool?

Leading to this question:

“Please tell me about a career milestone you achieved (or you heard about someone else achieving) that is weird/unusual/you would never have thought of until it happened. Doesn’t need to be Nobel Prize level! Just a marker of success, however you define it.”

There are some entertaining answers in The Whippet’s comment section.

January 24, 2022, TAoN No. 100

​​This week’s icebreaker comes from reader Jackie Bayer:

What’s the worst advice you’ve ever been given?

That’s a fun one! And I guess no further explanation required. Thanks so much, Jackie!

January 10, 2022, TAoN No. 98

This week’s icebreaker is a bit of a special edition, as I’ll spell out below. It’s from reader Katherine: “As a trainee English teacher and dabbling writer,” she explained, “I'd love to contribute a metaphor-based icebreaker.”

What object, person, animal or situation is happiness? What about grief? Hope? (Emily Dickinson thought it was 'the thing with feathers ...') How about fear?

Katherine wrote to me a little while back about an icebreaker-related project of hers. “Frustrated by some years of dating incurious people, coupled with the annoyance of pandemic-centred conversation” and a certain “bland” NYT list of 36 questions that (allegedly) lead to love, she says, “I decided to make a massive (free) Google Sheet of interesting / provoking / lols questions.” (Some of the questions are adult, as they say.) Check out a more polished version of her project at

In her research she found the TAoN list — “I have recommended it to all my friends, and save it for a languorous coffee break read whenever possible” — and asked me if she could include some of its questions in her lineup.

Of course I said yes — with the friendly “condition” that she contribute one of her questions to the TAoN collection. And that is is exactly what she did above.

“I think [this question] can unfold conversations about personal associations, memories, and experiences without being too scary,” she continues. “And your interlocutor's willingness to go beyond the literal would tell me a lot about their levels of comfort with openness, how happy they are to think of themselves as creative and also just be really

ICEBREAKERS, via The Art of Noticing by Rob Walker
Tags Remotework, Communication, Teaching, Zoom, Talking
Type Google Doc
Published 19/04/2024, 13:27:34


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