![]() What do you like the least about yourself? The most?.What's the scariest thing you've ever done?.Here are some of our favorites (keep in mind, all of them should be accompanied by why): 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. Then ask follow-up questions that start with why.Ask exploratory questions to uncover interests.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. ![]() So first, you need to do some work to figure out what this person cares about. If the person doesn't care much about politics, it's unlikely that this question will lead to a deep conversation. Meaning you could have very superficial conversation about politics, religion, or morality, and a very deep one about superhero movies.įor 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. So the depth comes not from the topic itself, but from the level on which you are engaging with someone. Bonus points if you make them happen with people you're meeting for the first time!įor 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. The challenge itself is simple: Have four "deep" conversations by the end of the month with four different people. 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. So this December, for our final monthly challenge of the year, we're challenging you to have deeper conversations. 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?" That said, you don't need to settle for sharing the same elevator pitch about your life over and over and over again. 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. ![]() 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.
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