Imagine a speed dating event.

Two concentric circles of seats, set up with half the group seated on the inner circle while the folks in the outer circle move around in a clockwise direction with 5 minutes to introduce themselves and make their case.

The story goes that everyone spends their 5 minutes talking about themselves, selling their merits etc, etc.

Except one.

They ask every person they meet a single question: ‘What can I do to make you happy for the rest of your life?’

Needless to say, this person gets a thumbs up from everyone they meet.

What Makes A Great Question?

This unique, single question is a great question because it shows that the interrogator is interested in the other, not themselves.

This reminds me of a saying a good friend once shared with me – the most interesting people in the world are those who are interested in you. So true.

So, in the context of building and nourishing relationships, what makes a good ice-breaker question?

I believe there is an art and a science to this answer, both of which are captured in the following thoughts:

• • Start Small – don’t ask for too much too soon, lest you frighten people away. Chip away at the ice, don’t bring a sledgehammer to it. For example, ask fun yet interesting questions that meet people where they are at. Also, start in pairs and resist the urge to ask open, large group questions expecting one person to share in front of everyone. Kick off with simple, easy-to-answer questions and build up to those which require deeper, more reflective thought.
  • Avoid Superlatives – asking questions that seek the best, most, highest, etc are risky such as Tell us your most valuable lesson in life? Questions like these stunt interaction because some people will struggle to consider what is their ‘best’ or ‘most’ valuable lesson, so they shut down. Whereas, if you ask the question slightly differently as Tell us about one of your most valuable lessons in life? this will spark reflection about ANY lesson. This then gives the participant options, which leads me to my next point…
  • Honour Choice – this is one of my most powerful philosophical tools and must be liberally applied in all experiences which seek to break the ice. Honour people’s choices to not answer a question, or to respond in a way that makes them feel more comfortable, or respond in a particular way, etc. Using open-ended questions that are not laden with superlatives makes it so much easier for people to respond.
  • Allow Time for Reflection – unlike those (like me) who are ready to respond to a question at the drop of a hat, give your group ample time to respond. Allow some silence at the end of your question, even though the passage of time often feels 10x longer than it really is. You may also need to manage the overly-enthusiastic to give airtime to others less inclined to jump in quickly. In particular, research has shown that introverts are very eager to respond, they sometimes just need more time to reflect before they respond.

Ten of the Best Icebreaker Questions

Context matters, so it is unfair to tell you, dear reader, that THIS is the best list of questions. Not possible, there are just too many to draw on and every group is different.

More reasonably, I expect you will be inspired by the following icebreaker questions. You have my permission to adapt them based on the needs of your group, your program goals, and the change you want to make in the world.

Note the questions (generally) build in their intensity and depth.

• Describe a time that made you smile in the last 2 weeks.
• What is the strangest thing you used to believe as a child?
• What is something that amazes you?
• What was the last thing you fell in love with?
• Tell the story of one of the most adventurous things you’ve ever done?
• What do you lose track of time doing?
• What are you capable of?
• Was there a religious or spiritual background to your childhood?
• What is a simple idea you take very seriously?
• What’s something you never thought you’d be doing and, yet, here you are?

To be honest, I want to add SOOOO many more questions to this list but I need to keep it brief.

Please… beg, borrow and steal these questions and integrate them into your own programs. May they lead to lots of wonderful moments of sharing and connection.

Even better, why not add your favourite icebreaker question in the Comments below.

With thanks to Chad Littlefield whose recent YouTube video inspired me to consider what I have discovered to be great icebreaker questions. His wonderful We Connect Cards are featured in the image above.

Contributor Mark