How to Break the Ice & Start a Conversation w/ Kai Stabell

Breaking the ice is an important skill that, when done correctly, will lead to more productive, more comfortable conversations. A good ice breaker can help you make a memorable first impression and it can turn your first encounter with someone new into something wonderful — maybe even a lasting friendship.

So, how do you start a meaningful conversation with someone new and avoid embarrassments or awkward moments of silence? Where do you begin?

Kai Stabell starts to answer this question by explaining most people approach icebreakers all wrong.

“Most people don’t care when they’re breaking the ice.”

As he puts it, breaking the ice has gone from a critical part of starting a connection to a routine we all must struggle through. And is is why we end up with shallow icebreakers like, “how are you doing?” or something weather-related.

Rather than suffer through mindless icebreakers, Kai suggests we all try to break the ice by being thoroughly interested in the person we’re speaking with. And his recommendation to do this is through the use of open-ended questions using the 5W’s.

“Why are you here today?”

“What was the best part of your weekend?”

“Who have you met that you’ve found interesting?”

“When did you meet your best friend?

“Where in the world do you want to visit most?

These types of questions don’t just break the ice and give us the opportunity to learn about a person, they open up the conversation to go somewhere deeper and more interesting.

“Give people the baton to speak and it’ll open up the conversation to endless possibilities.”

If you’ve been to an Engage Over Coffee event, you’ve experienced the power of open-ended questions. What I’ve founded is that powerful open-ended questions lead to self-reflection and a moment of silence. And as Elaine Ezekiel points out, the response after the silence is where you get the best response - and your best opportunity to connect.

In addition to open-ended questions, Kai also suggested something I’ve never heard of before, and that’s to proactively wear a “conversation starter” aka something someone else will notice and most likely ask you about as a way to break the ice. Kai used to wear a knotted gun, and even though he wasn’t wearing it during the interview, I also took the conversation in a different direction just to ask him about the knotted gun. So I guess this technique works!

No matter what technique you use, Kai does give one final piece of advice:

Example of a knotted gun

Example of a knotted gun

“Don’t make the icebreakers and conversation starters about you.”

This is such sage advice and something I’ve always admired about Kai - his ability to make the conversation about those with whom he’s sharing a conversation. Having conversed with him and seen him in action, Kai makes every new interaction about the other person - every icebreaker and conversation starter is his way to learn about and get to you. That’s the goal of every great ice breaker - to help you start to know more about the individual across from you. Icebreakers don’t have to be tired small talk. They can be the beginning of a meaningful journey.

Of course, curiosity took over and I had to know Kai’s favorite icebreaker.

“‘Tell me more about yourself’ is my personal favorite icebreaker.”

And isn’t that the goal at the end of the day? To know more about someone? What better way than to genuinely break the ice and start a conversation.

- Brooke



For your next conversation starter, use one of the 5W’s instead of asking the individual about the weather or how their day is going. And remember that this is your first opportunity to learn and connect with this individual.


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