I’ve always disliked how we respond to questions like “how are you doing” — it’s usually just “fine” or “good” or whatever. It’s rarely the truth. I’ve found that icebreakers are a great alternative way to start a meeting or get together, and spark different mood overall. I’ve seen lots of groups use these like EO, YPO, and Vistage, but they also became a popular starting point for Zoom meetings during the pandemic. Anyways - here’s a list of some of my favorite you can use. I updated these regularly, so check back for more anytime.
What do you think is easy for me, that’s difficult for other people? What do you think is difficult for me, that’s easy for other people?
If you were going to give a TED talk, for say 20-30 mins, about some thing that no one knows about you and there’s nothing related to your profession, what would it be?
How have you been complicit in creating the conditions you say you don't want?
Do you consider yourself religious, spiritual, neither, both, or other?
Tell us about your morning routine, your evening routine, or some routine you do consistently every day, and have for a long time.
Talk about one or two habits you want to develop this year, and what you’re going to do to achieve them.
What is an important belief or guiding principle you once held but have since changed?
Is there a belief that made a big difference in your life that you've outgrown?
Who are your five closest friends? Who are the five people you spend the most time with?
In order to be free, who do you need to break loyalty to?
What hassle are you trying to eliminate that’s actually an unavoidable cost of success?
What current unknowns will seem shockingly obvious a year from now?
Which of your current views would change if your incentives were different?
What truth about yourself did it take the longest to accept or acknowledge?
What truth are you still in denial about?
What is the strangest thing you believe in—or are afraid of?
Complete the sentence: I am: (one thing only—e.g., a dad, an investor).
Say the thing you feel you cannot say.
You meet your 13-year-old self but can only tell them three words—what are they?
If this were our last conversation, what would you want me to never forget?
What’s a non-essential you’re over-investing in?
What’s an essential you’re under-investing in?
How could you make it effortless—or nearly effortless—to make that trade-off?
What is your self-limiting belief?
If we met a year from now, what would we be celebrating?
If the next five years were a chapter in your life, what would the chapter be about?
What is the “No” or refusal you’ve been postponing?
What gift do you currently hold in exile?
What talent do you have that you’re not using?
If you were sure you were going to fail, what would you do anyway?
Another great one