50 Segue Questions for Software Teams

At Atomic, when we transitioned to remote work, we came up with a themed standup for every day of the week. Once a week, it’d be Segue Wednesday. There are always lots of questions to ask, but picking the right one for the week is the hard part.

I found success when questions were timed to what mattered to the crowd you were asking. For example, around Thanksgiving, a simple, “What’s your favorite Thanksgiving dish?” generated a lot of chatter. Or, when spring finally arrived in Michigan, people always had answers for, “Where do you want to travel this summer?” But there’s much more.

Below is a list of tried-and-true icebreakers to get people talking and connecting almost any time.

50 Segue Questions for Software Teams

• Who haven’t you seen in a while that you’d really like to visit?
• You get one podcast on a well-known show. What’s the title of your podcast?
• Who challenges you to be better?
• Who is someone you know who has a cool job? What do they do?
• Who would you switch places with for a day?
• If you were a condiment, what would you be, and why?
• If you had to replace your legs with the legs of an animal, what would you choose?
• What’s your key to success?
• What activity helps you relieve stress?
• What part of your daily routine do you look forward to? And/or what part do you not look forward to?
• Donut or no donut, that is the question.
• If you could go back in time and pay more attention to any class in high school or college, which one would you choose?
• If you could be in any game show, what would it be?
• Where were you born? What is an interesting fact about your hometown?
• What activity did you enjoy this summer?
• What’s your favorite sandwich and why?
• What’s your favorite Olympic sport?
• What’s your favorite breakfast cereal?
• If you could instantly become an expert in something, what would it be?
• If you had to delete all but three apps from your smartphone, which ones would you keep?
• What’s a performance you really enjoyed?
• If you’re gonna smell like a fruit for the rest of your life, what fruit would it be?
• What’s your favorite childhood vacation spot/memory?
• You get to name a craft beer, what would you call it?
• What’s your favorite spot in your house/apt/pod/cave/living accommodation?
• There are two types of people in this world. What are the two types?
• If all jobs had the same pay and hours, what job would you like to have?
• What would be your first question after waking up from being cryogenically frozen for 100 years?
• What product/service/thing would you rate a 10/10?
• What’s a show/movie/documentary that you’ve seen lately that you really enjoyed?
• If you’re never going to age, what age would you pick to be stuck at?
• What is an ideal breakfast for you?
• What’s one new thing you want to try out this week, month, or year?
• You’re going to be stranded on an island for who knows how long: what three things would you bring?
• What is something about you that most people don’t know?
• What’s one of your favorite spots in Southeast Michigan?
• What are your favorite books?
• What’s your favorite way to exercise?
• What’s the most memorable and/or ridiculous holiday gift you’ve gotten?
• What’s your favorite holiday dessert or drink?
• What’s an activity that you find rewarding?
• What’s a win for you this week?
• What’s a part-time/temp job you’ve had?
• What’s a game-changing tool/gadget/thing you bought or built?
• What’s your favorite fall/winter activity?
• What is one thing that you like about working remotely?
• On a scale of 1–10, how strict were your parents?
• You have unlimited resources and skills, but only yourself as labor. What would you build?
• Where have you always wanted to visit?
• What was your favorite class in college?
• If you could eat only one kind of food for the rest of your life, what would it be?

Now what?

Now that you’ve exhausted your list of segue questions, it’s time to rope in co-workers who can create unique icebreakers you haven’t thought of. Not only does this allow others to be engaged, but it also opens the door to hearing fresh perspectives.

This is an updated version of a post originally published April 29, 2020.