Welcome. I’m Chad and I’ve got a deck full of 60 really great icebreaker questions. And while I would love to just like port them through the screen and give you all of them ,that’s not going to work super well. (1) There is there is a link in the description below. If you just want a list of really awesome questions, you can access those digitally right below. And in this video, I’m going to share two techniques and ideas that we used in creating this deck of 60 really great questions over the course of 2 years and a ton of research and testing and trialing  to create your own icebreaker questions.

Blog Note: The following is an adapted and edited transcript of one of our daily YouTube tutorials. We know sometimes it is easier to scroll through written content which is why we are publishing here. Because of that, there may be typos or phrases that seem out of context. You’ll definitely be able to get the main idea. To get the full context, visit our YouTube channel hereAnd if you want to watch the video on this topic specifically, you can scroll down to the bottom of this post to access it as well. 

Because the best ice breaker questions are ones that are  perfectly custom-tailored and fitted to your context. Whether it’s a class or a meeting  or a workshop that you’re leading, whatever it is, at the end of this video, you will have 2  techniques. But I’m also going to share 5 of my favorite questions so that you can… If you don’t  want to think at all, you can just steal those and run with it the moment the video ends to make  your next meeting a little bit more connecting, a little bit more engaging. I’m Chad. Here we go.

1 to 2 Words

Technique number 1. Really great questions, ice breaker questions tend to begin with 1 of 2 words –how or what. If you’re creating your own icebreaker questions,  ask yourself do they begin with how or what. Because if a question doesn’t begin with how or what, it’s quite possible that’s going to be a closed question. “Where are you from?” -“Boston”. Done, right? Conversation over. Not a good icebreaker question because it doesn’t allow you to expand at all. If you ask questions that begin with why,  they’re not great icebreaker questions because why questions typically require people to justify or rationalize. And if you’re just trying to break the ice in a non-threatening psychologically safe kind of way, asking why questions is not a great idea. 

Ask Really GREAT Questions

Technique number 2 to ask really great icebreaker questions is really, really simple but incredibly powerful. Typically, if you look at… If you like Google ice breaker questions, you’ll get a lot of superlatives. Meaning,  questions to ask “What is your favorite ___? What is your best ___? What is your most ___?” The tool  that I would love to offer to you is to never ask an icebreaker question that is a superlative. Just put the phrase one of right before that. What is one of your favorite memories, right? Do you see how that allows people takes off the pressure to find the most compelling response.  And it allows people to just be a little bit more comfortable and answer with a thing that comes to mind. Way easier, way better free-flowing. Creates way less pause and hesitation and silence which is are not things that you necessarily want in an icebreaker kind of conversation.

Alright. Now, if  you came for questions, I’m going to share 5 with you right now. And I’m going to share the question so that you can take it write it down, screenshot it if you want it. And then immediately use it in  your next meeting class, etc to create some more meaningful connection. I’ll share the question. I’ll also share a sentence or 2 of why I like this question in particular. So, this deck of cards that I’m pulling from in particular is called We! Connect Cards. It’s a deck that my partner will  and I created. It much to our surprise. It’s being used in over 80 countries all around the world and  companies and on campuses to create conversations that matter, to skip past a small talk,  to break the ice in really great ways. You can get a free digital version of the questions on  the deck in the link in the description. Or you can pull these 5 from here. Or if you want to  have this deck mailed to you, you can check out some links in the description as well. One thing  that’s important to know about the deck is that the questions are color-coded. Green questions  tend to be fun and light. Purple questions tend to encourage some level of self-reflection.  And we included those questions to make ice breakers a little bit more introvert-friendly.  And then the last color blue cards tend to have questions that go a little bit deeper. Because I  don’t think that the best ice breaker questions are super light. Like what kind of m&m would  you be if you’re an m&m. Like that doesn’t help you actually meaningfully connect with somebody.  A question like “What is one of the most meaningful affirmations you’ve ever received?” is a much more compelling question to ask. What is one of the most meaningful affirmations you’ve ever received? That one of peace allows people to choose something that comes to their mind in that context. 

Number 2 this is a really good one. Maybe a good one to post on LinkedIn or something. What is the best worst or funniest job that you’ve ever had. Now, this is a superlative but it gives  3 options. Right? Remember, the reason I don’t like superlatives is because the person has to find the best or the worst or the funniest. Whereas this question says “Pick whichever one  you want”. And the more choice and voice that we can give people, the better the quote icebreaker   is and the less hives that it’s going to give skeptics who hear the word icebreaker or team  building. And they’re like, “I am not feeling that so much”.

Third question, “What is something  funny that has happened to you?” I love this one because it brings about a little bit of joy. I have met zero people that haven’t had something funny happen to them. In fact, I’ve met lots of people who have had lots of funny things happen to them.  When you ask them this question it creates a lot of choice in how they answer it. You know, one of my favorite characteristics of questions is that when you’re asked  any question usually has multiple answers. And I think a really great icebreaker question in order  to be non-threatening, the person has to be able to choose. “Do I want to share something light? Do I want to share something deep? Do I want to share something in the middle?” And when we give people more choice like that, it creates a much better conversation. What is something funny that has  happened to you? Next one. I like purely selfishly because I love finding out people’s answers to it.  And that is “What are people usually surprised to find out about you? The reason i like this  question “What are people surprised to find out about you?” is it’s a really safe way to bring out  some information about people that you would never otherwise learn.

Because when people are usually surprised to find out about it, it means that they’re not expecting it. And creating that novelty is really really useful in a conversation. In fact, just the other day, I was facilitating a workshop and I asked this question –What are people usually surprised to find out about you?  And just invited people to drop their answer in the chat. We were meeting over Zoom. And she said that she used to take care of elephants in a sanctuary. And this was like a corporate gathering  workshop that I was leading. And so this question brings out some really cool unexpected stuff that opens up lots of possibilities for connections. And last but not least, I think the best ice breakers also serve a purpose. This question –“What is something you’d like to  do more of?”, is a really phenomenal question because it brings out information in someone  that describes what they want to do from this point forward.

An icebreaker can also  help teleport people into the future, that’s a really useful concept. To be able to say,  “What would you like to do more of when you learn the answer to that?” Imagine if you were  the teacher of a class. And you knew every single one of your students answer to this question.  You could tailor and personalize your lessons based on what people want to do more of. That people are a little bit more connected to your lessons, your content, etc. The last tip  I’ll drop on you is really the best icebreaker questions are the ones that you don’t ask. If  you’re the leader, if you’re the facilitator, if you’re asking an icebreaker question; people are  indulging you as opposed to in a natural, organic conversation with each other. For me the best types of icebreaker conversations or the best types of icebreaker questions are the ones asked by your participants, by your students, by your employees. In any icebreaker, I usually really love to ask people to answer a question. But then invite people who are listening to follow up with that answer with their own question rooted in their own curiosity. Then it goes from this activity my boss is making me do to “Oh, this is actually kind of a cool conversation with a really great human being”. And that shift is really useful if you want to meaningfully connect people. These 2 videos are also really useful if you want to meaningfully connect people.  It was awesome hanging out with you in cyberspace. 

I’m Chad Littlefield. Have an awesome day.



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