Talk to Me! – Questions to Spark Conversations

By May 18, 2017 Blog No Comments
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Talk to Me! – Questions to Spark Conversations

If you’ve ever been at a social gathering, in a business meeting or even on a date trying desperately to start a conversation and getting dead end, one-word responses, you know how awkward and frustrating it can be. Talking to someone shouldn’t require such heavy lifting, right? Maybe you’re not asking the right questions – or maybe the other person really doesn’t want to talk to you – either way, the situation can probably be improved. While it’s true that some people are natural conversationalists and others prefer dental work over chatting, there are some tricks to engaging dialogue.

First, why is conversation important? Because at the heart of every business are human interactions – with employees, colleagues, customers, suppliers or partners. In the workplace, research shows that having meaningful relationships leads to greater job satisfaction and better performance. Building strong bonds with customers and partners has obvious benefits. But these connections don’t happen magically – they require authentic conversations (which do not involve electronic devices!).

The best questions to spark conversations are open-ended and have no right or wrong answers. Genuine dialogue occurs when people reveal something about themselves or exchange thoughts and ideas. In other words, you typically learn something about the person you are talking with. You don’t need to discover the meaning of life or reveal someone’s most intimate secret to be successful – any new piece of information, no matter how trivial (e.g., do you have any hobbies?), can help forge a bond. And, of course, the more you know about your customers, the better you are able to deliver relevant content.

So, instead of asking “How was your day?” and hoping to illicit more than “Fine” in response, try saying “Tell me the best thing that happened to you today.” (Note: This works with uncommunicative teenagers, too!) To get you started, here is a sampling of conversation starters that can be used in a variety of situations:

  1. What’s on your bucket list?
  2. What do you like to do when you’re not working?
  3. What aspect of your job do you like the most?
  4. What was your dream job as a child?
  5. What’s your idea of a perfect day?
  6. What is the best question you’ve ever been asked?
  7. What is the best career advice you’ve ever received?
  8. What is the best personal advice you’ve ever received?
  9. What do you consider your greatest success? Why?
  10. What do you consider your biggest failure? What did it teach you?
  11. If you could go back five years in your life, what advice would you give yourself?
  12. If you wrote a book, what would the title be?
  13. If you could be any age for a week, what age would you be, and why?
  14. What is your biggest fear?
  15. If you could travel to any place in the world, where would you go?
  16. Which super power would you choose if you could only have one?
  17. What are you most proud of?
  18. What would you like to create in the world that doesn’t exist?
  19. Who is your personal hero or mentor and why?
  20. If you could teleport by blinking your eyes, where would you go right now?

Of course, this is just a sampling of conversation starters. If you’d like a more comprehensive list, by topic, see “250 Conversation Starters.” Try a few of these questions the next time you’re interviewing a potential employee, starting a meeting, having a team-building event, getting to know someone, or simply trying to get your teenager to say more than one word! Remember, the goal is not just to make small talk, but to build a meaningful connection. And, who knows where that might lead?

What’s your favorite conversation starter?


“20 Questions to Make Meaningful Connections,” by Jim Haudan Co-founder and CEO, Root. (Inc., March 17, 2017)

“What to Talk About on a Plane, at a Cocktail Party, in a Tiny Elevator with Your Boss’s Boss,” by Chris Colin and Rob Baedekerr. Chronicle Books, CA, 2014.