Colleague Connections: A Free Team Building Icebreaker for Company Retreats


Want to help employees to get to know each other better at your next company retreat? Learn more about Colleague Connections, a free team building icebreaker that is easy to set up and try anywhere.


Want to help employees to get to know each other better at your next company retreat? Learn more about Colleague Connections, a free team building icebreaker that is easy to set up and try anywhere.

This year at the Outback Team Building & Training company retreat, our leadership team created a new icebreaker for our group to try in between sessions. The icebreaker was called Colleague Connections, and it ended up being one of the highlights of the trip.

Colleague Connections is ideal for business retreats because…

  • It’s very easy to explain and requires almost no set-up
  • You can try it anywhere, anytime, with any sized group
  • It is a sure-fire way to help employees build stronger relationships
  • It’s free! Just follow the instructions below

How Colleague Connections Works

The icebreaker itself is actually quite simple: employees spend five-minute intervals one-on-one with their colleagues asking questions designed to help them learn more about each other. After every five minutes, employees switch to meet with a different colleague. By the end of the activity, every employee should have met with everyone else in the room at least once.

You can think of it like “speed dating” for building relationships on your team. While five minutes is not enough time for anyone to become best friends, it’s actually the perfect amount of time for people to explore some common areas of interest or discover something new about the person they’re speaking with.

 Here’s how you can set up Colleague Connections at your next company retreat…

  1. Figure Out the Conversation Order – The goal is for everyone to speak with everyone else in the room at least once. For the Outback Team Building & Training company retreat, we set up a simple spreadsheet and shared it with everyone so they knew who was talking to who, and who they would be talking to next.
  2. Figure Out How Much Time You Need – Colleague Connections works best at company retreats if you split it up over multiple sessions, ideally over multiple days. Try to plan it out so that employees go through no more than seven or eight conversations in a single session, otherwise they might get burned out on all of the chit-chatting.
  3. Send Out 50 Questions – You can print out the 50 questions below or email them to your colleagues. Explain that employees shouldn’t feel limited by the questions on the sheet – these are just meant to be the starting off points for their conversations.
  4. Explain the Rules – Here’s the thing: there aren’t really that many rules! The goal of the icebreaker is just to give everyone a chance to get to know each other better. As long as employees are talking to the right people when they’re supposed to be, you shouldn’t need to worry very much.
  5. Keep Things Moving – Once it’s time to start, make sure you assign someone the duty of keeping time. Around every five minutes, have this person shout out that it’s time to switch to a new conversation partner. People should catch on fast!


50 Questions for Colleague Connections

Check out the list of questions Outback Team Building & Training used when we played Colleague Connections at our company retreat. We purposely picked a variety of questions – some lighthearted, some more meaningful – to give employees the option of deciding what types of conversations they wanted to have.

  1. What is your spirit animal?
  2. What was your dream profession growing up?
  3. What is something you have always wanted to do but haven't done yet?
  4. Do you have any family traditions that you look forward to each year?
  5. Do you have a favorite song to listen to when you need your spirits lifted?
  6. What was your favorite movie as a kid and why?
  7. Would you like to be famous? In what way?
  8. What's your dream car?
  9. What is something you think is totally overrated?
  10. If I handed you a plane ticket right now to anywhere in the world, where would you go?
  11. Who in your life has inspired you most?
  12. If you weren't in this career, what could you see yourself doing?
  13. What is one thing on the very top of your bucket list?
  14. What was your favorite trip you went on?
  15. What is your favorite type of cuisine?
  16. What is the most feel-good film you’ve ever seen?
  17. If you're not from this city, why did you end up here?
  18. What is your guilty pleasure?
  19. If you could change anything about the way you were raised, what would it be?
  20. What’s the craziest thing you have ever done?
  21. If you had a million dollars - what would be the first thing you bought?
  22. What is your favorite thing about your job?
  23. What weird food combinations do you really enjoy?
  24. What is your favorite thing to do locally?
  25. What is something you are really proud of accomplishing?
  26. If you could instantly master one skill or activity what would it be? Why?
  27. What is something interesting about your family history?
  28. When you're not at work, what are your passions?
  29. What was the worst injury you ever had?
  30. What are you most passionate about in life and what motivates you?
  31. Tell me an embarrassing story about yourself.
  32. What’s an activity that you’ve never tried before, but would like to try?
  33. What type of music do you like/prefer?
  34. What was the worst job you ever had?
  35. Do you have siblings? How many? Where do you fit in the mix?
  36. What is your biggest fear?
  37. What is your secret talent?
  38. Who is the most famous person you've ever met?
  39. What's your favorite hobby?
  40. What's your favorite TV show and why?
  41. What clubs were you a member of in high school?
  42. Have you ever been in a movie, TV show, or play? What was your role?
  43. Do you speak any languages besides English? Is there a reason you learned it?
  44. What's your favorite childhood memory?
  45. What is your biggest pet peeve?
  46. When did you last cry in front of another person? By yourself?
  47. Name three things you and your partner appear to have in common
  48. What is your most treasured memory?
  49. If you could change anything about the way you were raised, what would it be?
  50. For what in your life do you feel most grateful?


The Results

Here are some of the reactions from employees who tried Colleague Connections at the Outback Team Building & Training retreat:

“It was a great way for us to discover new facts about each other that would be hard to uncover normally, even through an hour’s worth of conversation. These questions cut right to the chase. I discovered hidden skillsets some of my colleagues have, some hilarious stories that I’m not going to repeat, and had a few really in-depth conversations that helped me get to know my colleagues better.”

- Jordan Adams – Employee Engagement Consultant

“It was cool because of the questions. They helped me get to know people better, even the ones who I talk with on a regular basis. Learning about people’s favorite childhood movies, or what type of music they’re into…You really can discover some surprising things about your colleagues! For example, I learned that one person had attended the same concert as me, and so we were able to immediately bond over that. It was great.”

- Yasmine Shemesh – Jr. Marketing Copywriter

“I liked that it gave us an opportunity to talk to people we wouldn’t normally have an opportunity to talk to. We’re often just hanging out with our own departments, so it was nice that we got to mix things up a bit. It really helped me get a better idea of who people are outside of the workplace, and what they like to do in their spare time.”

- Anthony Colistro – Employee Engagement Consultant

“I liked that I got to speak with every single employee, which might not happen for weeks or months if we were left to our own devices. I gained some insights into individuals through these quick moments. And from a manager’s perspective, it was really interesting as well. Even though I feel like I know my own team quite well, I appreciated being able to use this opportunity to dig a little deeper. It challenged me to get into someone’s brain in a different manner than I normally do. And with respect to working with different departments, I think it will help us take a more collaborative approach now that we have these connections.”

- Isla Robertson – Director of Customer Experience

“It was helpful to chat with people I probably haven’t had a chance to really meet yet. There are a few new members of the team, and it was nice to be able to learn a bit more about who they are. It was also a great way to learn one or two useful nuggets of information about people so that the next time you see them in the office you can say, ‘Hey, you’re that person who is learning how to write code.’ Or, ‘You’re that person who is interested in adopting a baby. How’s that going?’ It opens the door for deeper conversations.”

- Michael Culp – Employee Engagement Consultant

Are You Planning a Company Retreat?

Download our guide, Everything You Need to Know About Planning the Ultimate Company Retreat, for more free tips and ideas. You can also get in touch with our team to learn more about the top team building activities and training programs for company retreats.

Get in Touch

Subscribe to Our Blog