July 16, 2015

Ask People These Questions

Here’s a short list of fun questions I’ve found that are great for asking people, or a group of people. In general, all of them meet the following requirements: They don’t require a lot of thinking, the answers are entertaining to whomever is listening, and they reveal a lot about the person answering.

These are useful for small talk at parties, icebreakers when you’re meeting new people (or forced to interact in a group), interview style podcasts, or even formal job interviews.

###1. What’s the story behind your shoes?

Credit to Robert Yang for this one, who used this to get all of his students to introduce themselves on the first day of his class. Surprisingly, everyone had an interesting story to tell – usually revealing something about their tastes or backgrounds.

###2. Tell your favorite joke.

This one is Tina Roth Eisenberg’s: she screens all her job applicants with this question. It says a ton about the person and is a great way to make friends and get a laugh out of it.

###3. What’s the hardest time you’ve ever laughed?

This question is the most difficult on the list for most people, but it guarantees a great story if they can answer it. This is a standby of Pete Holmes’s great podcast You Made It Weird.

###4. If you were trapped in a bookstore for an hour, what section would you spend it in?

Everyone has really strong opinions about this.

###5. What are you looking forward to?

This is probably the question that meets all 3 requirements best. It also has the bonus of being great for discussion, because a lot of people default to talking about vacations and that always invites helpful contributions from fellow travelers.

###6. On a scale of 1 to 10, what are you definitely a 10 at?

The best thing about this one is that it can go either way. Lots of people end up being self-deprecating, and those answers are sometimes better. If you want, you can also ask people what they are 1s at. This one comes from an AskReddit thread.