$10

🧊 Plus Icebreakers

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I want this!

🧊 Plus Icebreakers

$10
Dan Li (Plus)
2 ratings

Here is one of the best ways to build stronger connections between remote coworkers and get to know teammates beyond their Zoom windows.


At Plus, we believe you have to build a great company - people, culture, and values - in order to build a great product. As a remote-first team, we try to be very intentional in building the right culture (and hiring the right people) to create a productive work environment.

How do we build a great remote-first team culture?

Our team has worked at both small startups and the biggest technology companies in the world. Many of our founding team members have also worked at remote-first companies like Webflow, and watched the process of scaling up a remote-first culture to hundreds of employees.

We’ve tried to take the best practices of our previous workplaces to build a great remote-first team culture, and here are the key principles of our approach:

  • Do more asynchronously - Write more documents and record more Loom videos, where possible. Only schedule meetings if we need them
  • Make norms explicit - Maintain living documents on our working norms, such as our User Guides that describe how we each work (here’s mine!)
  • Get together, sometimes - Meet in person for a full-team offsite every other quarter with optional co-working weeks in between
  • (Read more about our specific activities and documents for remote work in this post)

And… last, but not least:

  • Be deliberate about getting to know each other - In an office environment, you learn a lot about your coworkers in informal hallway conversations. In a remote world, those conversations get lost, so we intentionally design and set aside time to get to know each other better

There are a number of ways we try to make the “getting-to-know-you” process more deliberate in a remote-first world, but one of our favorites is our Plus Icebreakers™️!

When and how do we do icebreaker questions?

Every two weeks, we host an “All Team” meeting where we celebrate big wins, go through the latest company updates, and discuss important topics about the business.

This is one of the only times we have everyone at the company on a call at the same time, so while we spend most of the time on the typical “company news,” we also dedicate a big portion of our all team time (~20 min) to doing a round robin where everyone answers a fun “icebreaker” question.

This has been a fantastic way to get to know everyone on the team!

On a per person basis, we only spend a couple minutes a week on icebreakers, but this time “investment” brings the team together in a big way.

Our icebreakers have created many inside jokes, started conversations with friends and family, and most importantly… they bring our remote coworkers to life as “real people” who have lots of funny stories, weird (in a good way!) idiosyncrasies, and unique interests.

Here’s what we’ve found work well for work-style icebreakers:

  • Novel and fun - The easiest way to shut down an already slightly cheesy event at work is to ask everyone a cheesy question like “What’s your favorite ice cream flavor?”
  • Not too personal - Good icebreakers for work are different than the questions you’d ask a romantic partner (though we love the NY Times list of 36 Questions That Lead to Love )
  • Inclusive, easy to answer - We want questions where anyone can think of answers right away, not something you’d have to consider or research for a few hours
  • Controversial, but in a good way - The best questions spark some debate and have a wide range of answers but avoid sensitive or political topics
  • Reveal a bit of the person behind the screen - Fun icebreakers are like personality tests because it’s fun to hear how your answer might reveal something about your personality or views on the world

It’s hard to find great questions that fit all of these criteria, so instead of trying to come up with them yourself, we made this list for you.

Here are 8 of our Greatest Hits Icebreakers that have drummed up a lot of conversation with our team, our friends, and our families!

  1. What is the most surprising thing about being an adult?
  2. When is the last time you stayed up until past 3am?
  3. Do you have an inner monologue? Follow up: When you read, do you sound words out in your head?
  4. What is your daily average screen time on your phone? iPhone: Settings > Screen Time > See All Activity > Swipe to Last Week. Bonus question: Who do you think has the highest daily average phone time?
  5. How many years of your life would you trade (off the end of your life) for $1B in cash, today?
  6. Rank your favorite fast food restaurants: https://tiermaker.com/create/fast-food-restaurant-tier-list
  7. You have a flight at 7am. When do you wake up before the flight?
  8. Are there more wheels or doors in the world?


Get the full list of 50+ icebreakers here on Gumroad for $10! (along with free bi-weekly updates as we add new icebreakers to the list)

All proceeds from Plus Icebreakers go towards GiveDirectly! Thank you for your support! 😄

I want this!

50+ of THE BEST icebreakers to build better relationships with your remote teammates...

All proceeds from Plus Icebreakers go towards GiveDirectly!
Thank you for your support! 😄

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