Thoughtful icebreaker questions to try during your next workshop

Roman Grant
3 min readApr 19, 2020


Photo by Victoria Wendish on Unsplash

A thoughtful icebreaker question can be a powerful tool that provides a wealth of insights to a facilitator. I’ll admit that I am biased, but I love to use a good icebreaker question to kick off my workshops. And even though it can feel a little touchy-feely, I am always amazed at how groups are able to connect and build trust from learning just a little bit about each other.

Below, I will share a few of the questions that have been useful for me during workshops along with the rationale behind why I like to use the question.

Q1. If you were asked to give a 30-minute presentation on a non-work related topic, and only had 5 minutes to prepare, what would your presentation be about?

Rationale: Most people will say that they don’t like public speaking, and they couldn’t possibly talk about anything for 30 minutes. That’s a lie. People love talking about the things they are passionate about and I am always impressed by the variety of topics that come out of this icebreaker.

Q2. Think back to when you were a child, what did you want to be when you grew up and why?

Rationale: I find that this question is a great way for workshop participants to reflect on their personal journey and share it with the group. Participants will often connect over similar childhood aspirations and memories. Also, every once in a while, you’ll end up with someone who is doing the job they envisioned they would be doing as a child. This often sparks a lively conversation that will get participants to engage with each other.

Q3. What talent would you most like to have?

Rationale: I find that with executives, and/or participants who may have brought their “ego” as a +1 this question can work well to bring them back down to earth (a little bit) and indirectly admit a weakness they have.

Q4. What is the number one thing people ask you for help with?

Rationale: Similar to the talent question, this question can be used to get participants to indirectly acknowledge one of their strengths. This question works well when you have a group that is just beginning to work together.

Q5. What activity, outside of work, makes you lose track of time?

Rationale: This question can be a useful way to get participants to share their hobbies, and/or things they truly enjoy doing. As a bonus, I am always excited when there are participants who find out that they have similar hobbies or interests.

If you like these questions, or have others that have worked well for you, I’d love to hear about it below in the comments.



Roman Grant

Product Manager | Facilitator | Former Nurse | Army Vet | Always Forward!