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20 Easy Questions to Jumpstart Conversations and Learn More About People

A long time ago I read a book.

Note: The book was SO great I have since forgotten its name.

In this amazing book, the author was comparing the differences between American and European protocols for social events. All jokes aside, it was actually a fascinating look at how we struggle to initiate meaningful conversations with strangers.

In this article, we'll outline how to start conversations that lead to more satisfying relationships by taking a cue from our brethren across the Atlantic. We'll also include a helpful "cheat sheet" of follow-up questions. But first, a quick cultural lesson:

3 Conversation Tips to Learn More About People

While there are always exceptions, most Americans start conversations with a question similar to the following: What do you do for a living?

The problem is that not everyone likes what they do and almost no one defines themselves by it. Of course, this wasn't always the case. For the past several decades, Americans have notoriously won the prize for "most unused vacation days" among industrialized nations.

But there is evidence things are changing – in 2016, Millennials (ages 18 to 34) officially became the largest generation in the U.S. workforce. One of the most published differences between the Millennials coming in and the Baby Boomers going out?

Millennials are less likely define themselves with a job title, and more likely to define themselves by whatever gives them a sense of purpose or enjoyment in life.

1. Quickly Build Trust

Interestingly, many Western European cultures have long held this attitude. Start a conversation with a European at a party, and he will initially avoid the topic of work entirely.

Instead, a European seeks to form a connection by asking things like:

  • Ex. How do you know (insert name of contact)?
  • Ex. What do you do (for fun)?

Once a commonality has been found, the conversation will naturally spin off into a satisfactory direction for both parties. Once a certain level of comfortability has been established, the topic of work may come up as something of secondary importance.

2. Don't Talk About Work

So, what happens if you "turn the tables" and immediately ask the European what he does for work?

  • The best-case scenario? He may feel slightly bored.
  • The worst? He may consider you downright rude!

Check out this dialogue posted by someone on Quora:

I remember getting in trouble when I met a woman from Holland and asked, “What do you do for a living?”

Her response: “Why do you care? Would you speak to me differently if I were a janitor than if I were a corporate president?”

My response: “Perhaps we have the same job. Or have friends or family in the same profession. When you meet new people, it’s typical (at least for Americans) to try to find what you have in common.”

When I shared this story at a family get together, a cousin mentioned that she had exactly the same experience. It, too, involved someone from Holland.

Obviously, following an introduction with "What do you do?" is unlikely to offend your American counterparts.

However, it just may bore them to tears, crush their soul or lead to a dead-end conversation that makes watching Toddlers In Tiaras seem like a good idea.

Which is why you should instead form a connection with the previously mentioned "How do you know so-and-so?" OR "What do you do (for fun)?"

3. Keep The Conversation Going

Once you've found common ground, and have resisted the temptation to discuss work, keep the conversation going with open-ended questions. The best conversationalists are inherently curious, highly observant and good listeners.

Whether they notice a twinkle in someone's eye when the topic of NBA basketball arises – or a change in vocal intonation that indicates a strongly held opinion – exceptional conversationalists let observational cues inform their questions. This leads to more storytelling and less one-word answers.

20 Questions to KickStart Conversations

Still not confident in your ability to lead memorable introductions? Have no fear!

Here's a list of 20 questions to put in your back pocket:

  1. What are you passionate about right now?
  2. What's the most unusual thing you've seen lately?
  3. What are you most looking forward to right now?
  4. Have you lived anywhere else but here?
  5. What do you like to do on the weekends?
  6. What's the last picture you took on your smartphone?
  7. What's the last restaurant you ate at?
  8. What's the last thing you experienced that really blew you away?
  9. What is your favorite thing about where you live?
  10. Where is the last place you traveled?
  11. If you could share a meal with anyone in the world, who would it be?
  12. What are your most commonly used emojis?
  13. If you were president, what's the first thing you would do?
  14. What is one thing you would change about your life?
  15. What was your favorite thing to do as a kid?
  16. What are your 5-year goals?
  17. What was the last thing you searched on Google?
  18. What is your favorite YouTube channel?
  19. What book has had the most impact on your life?
  20. Who are your heroes?

Converse Like a Boss

Though there are many things "Americans get right," starting conversations isn't typically one of them. Implement these twenty tips, and you'll be turning more introductions into enjoyable interactions in no time. And some of those interactions may even turn into relationships – both personal and professional!

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Written by Ashley Gwilliam / May 4, 2017

Ashley is a content writer and brand developer. After graduating with a degree in print-journalism, Ashley’s storytelling skills took her from the bizarre world of on-camera acting to the practice courts of NBA basketball players to the virtual meetings of inbound marketers. Today she specializes in building memorable brand voices online, with a focus on the travel & tourism, e-commerce and tech industries.

Articles by Ashley Gwilliam