A few months ago I was having dinner in San Francisco with the organizers of the TEDx conference that I attended in Iran. We were discussing the event as well as my own talk. One of their comments was an encouragement to think about how I could take the topic of my talk to the next level.
Next level? Well … I thought the next step would be to convert the talk about “Breaking the Habit of Smalltalk” into something that can actually be used in real-life. So I created a Google Spreadsheet, went out on my social outlets and I asked all folks in my network to contribute fun/interesting/quirky questions. Soon enough, I ended up with a list of 150+ different questions that people had submitted.
Simultaneously, I was co-organizing a 260-person trip to Colombia for my fellow classmates at the GSB. As these things normally go, you have a lot of people meeting each other for the first time and just as I described in my talk, you end up with conversations that run on a path of predictable superficiality: "where you from, what did you do, etc. etc.”
So we thought we would spice it up a bit and printed 50 conversation cards – each with a fun and quirky question on it. We then distributed those cards upon arrival to make sure that everyone would have at least three conversation cards. And in our welcome announcement, we encouraged everyone to make use of them.
I’m sure that not everyone got a chance to do so, but I heard that many did and that those conversations ended up being very meaningful and memorable. I myself had the opportunity to use those cards during dinner on one of the evenings. We were four people and we ended up asking each other some of those questions. Looking back, it was pretty incredible how quickly our conversation ended up becoming very deep. From the first time undergoing Brazilian waxing to a history of suffering from eating disorders – everyone was sharing some very personal stories in an environment in which we felt heard and trusted.
Beyond the questions which do nothing more than to facilitate a conversation, the willingness to make oneself vulnerable in front of others is the real ingredient for a conversation to become meaningful. We ended the dinner with a group-hug and a wonderful dinner moment that we won’t forget again that quickly. Find below the list of 50 questions we used on this past trip!
- When was the last time you did something for the first time?
- What's your passion project these days?
- So, what's your story?
- Tell me something fun about yourself!
- What’s the strangest thing about where you grew up?
- How’d you end up in your line of work?
- Which of your scars has the most interesting story to tell?
- What was the weirdest/craziest thing you experienced abroad/while traveling?
- Once you came online, which was the longest time you have been offline since?
- Tell me something about yourself that you wouldn't mention on a first date/meet.
- Which is you favorite blog/YT channel/Instagram/Twitter/news resource right now?
- If you could solve one problem, which would it be?
- What did you buy with your first salary ever?
- What superpower would you chose if you had absolute free choice?
- What job or activity would you do in spite of having all resources in the world?
- When was the last time you were really proud of yourself?
- What is the craziest thing you have ever done in your life?
- What life experience made you grow the most?
- Describe the last time someone's actions really surprised you.
- What did you want to be when you were a child?
- Do you have any nickname(s) and what's the background story?
- What was your most embarrassing username/email address
- How did your parents values shape your career choices?
- What is the most depressed you've ever been?
- What's your best opener on Tinder?
- Would you pick a different career path if you did life over again?
- Do you think you have become any better or worse looking with time?
- What's the best date you have ever planned?
- What's the coolest gift you ever gave someone?
- How do you feel about open relationships?
- Do you think you would be hot as the opposite sex?
- What is the hardest thing about being you?
- What was your last epiphany?
- What companies align with your personal values?
- What's the hardest thing you've ever gone through?
- What experience have you had that made you a more compassionate person?
- What is the nicest compliment you have ever received?
- What's a moment you are proud of?
- Has anything magical ever happened to you?
- What was your best first kiss?
- What romantic gesture would you be really stoked about?
- Which event in history influenced you most?
- What would constitute a “perfect” day for you?
- For what in your life do you feel most grateful?
- Given the choice of anyone in the world, whom would you want as a dinner guest?
- A crystal ball can tell you the truth about yourself or your future. What would you ask?
- When did you last cry in front of another person? By yourself?
- What would be a dealbreaker when it comes to dating someone?
- What is your guilty pleasure?
- What's the most illegal thing you did and are comfortable sharing?