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Inspiration

Deep Conversations December

How to Go Beyond Small Talk and Have Deeper Conversations

December is here, which means it's time for my favorite holiday song: 'tis the season to make small talk, fa-la-la-la-la, la-la-la-la...


Seriously though, December is chock full of holiday parties, and holiday parties are chock full of small talk, be it with your coworkers, bosses, vague acquaintances, or your not-quite-senile uncle.

That said, you don't need to settle for sharing the same elevator pitch about your life over and over and over again. You can mix things up by asking questions that move the conversation away from "how's business?" and "how much snow do you think we'll get this year?" and closer to, "who are you as a person and what might I learn from you?"

So this December, for our final monthly challenge of the year, we're challenging you to have deeper conversations. This is not a post denouncing small talk, but simply a challenge to have more conversations that dive deeper once the initial pleasantries are completed.

The challenge itself is simple: Have four "deep" conversations by the end of the month with four different people. Bonus points if you make them happen with people you're meeting for the first time!

For the sake of this challenge, "deep" conversations will be defined as any conversation that helps you understand a person and why they think/behave the way they do. So the depth comes not from the topic itself, but from the level on which you are engaging with someone. Meaning you could have very superficial conversation about politics, religion, or morality, and a very deep one about superhero movies.

For example, asking, "Which democratic nominee would you like to see win the primary?" does not necessarily mean you'll be having a deep conversation To qualify as helping you understand the person you're talking with and why they think/behave the way you do, this question absolutely needs to be accompanied by why and dive into how this person evaluates candidates. If the person doesn't care much about politics, it's unlikely that this question will lead to a deep conversation. So first, you need to do some work to figure out what this person cares about. Alternatively, asking someone who's just finished raving to you about the latest Avengers film why they love superhero movies could potentially lead to a very deep conversation.

Some General Tips

  • Ask exploratory questions to uncover interests
  • Then ask follow-up questions that start with why
  • Use active listening

While you can make up questions on the fly by following the tips above, you can also keep some "interesting" questions in your back pocket. Here are some of our favorites (keep in mind, all of them should be accompanied by why):

  • What's the scariest thing you've ever done?
  • What do you miss about being a kid?
  • What's your proudest accomplishment?
  • What do you like the least about yourself? The most?
  • If you had to live in a different country, which would you choose?
  • If you were on a crashing plane and knew you had about 60 seconds to live, what would you do?
  • What's your earliest memory?
  • If you won the lottery tomorrow and got 10 million dollars (post tax ;)), what would you do?
  • What three things bring you the most joy?
  • What do you think are your greatest strengths at work?
  • If you could have any job in the world, which would you choose?
  • What's the number one thing you'd like to achieve next year?
  • Would you rather die suddenly in your sleep or be told you have a year to live?
  • If you could change one thing about the world/society to make it better, what would you change?
  • Would you rather never be able to watch TV again or never be able to read books again?
  • Would you like to be extremely famous?
  • Would you rather never be able to use the internet again or never be able to go outside again?
  • How do you react when someone says something that offends you? Do you confront them?
  • Do you think happiness is the point of life? If not, what is?
  • In what environment do you feel most at ease? Where do you think you 'belong'?
  • Which three words do you think your family would use to describe you?
  • What's something about you that most people don't know or perceive?
  • Who knows you the best in the world?
  • What are 5 things you hope someone says in your eulogy when you die? How do you want to be remembered?

Now get conversing! And let us know what other questions you love to ask to spark interesting conversations in the comments.

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