How to Start an Interesting Conversation with Anyone

“So what do I talk about when I’m a guest at my spouse’s work party?”

I received this great question last week and couldn’t resist answering it. If you’ve ever asked yourself What do I talk about?, you’ll benefit from this post. You don’t have to be your spouse’s work party guest either. All of us need solid conversational material when connecting with others.

I spent the week digging for answers to this question and discovered a few gems along the way.

Apply these three principles to your next conversation, and see if it doesn’t turn out to be smoother and more enjoyable.

Tired of starting conversations that go nowhere? Want to know what to talk about? Find out how to start an interesting conversation with anyone!

Want to start more interesting conversations? Download these questions and conversation starters and become a better conversationalist.

1. Solicit stories.

I watched a couple of TEDx talks this week in my search to find better conversational material. The best talk I watched was by Malcom Azania.

In How to Engage in Better Small TalkMalcom’s main point was:

Ask questions that get people to tell you STORIES. Stories are the great equalizers.

It’s for this reason, he says, you should NEVER ask, “So what do you do?” While you may ask the question innocently, it rarely comes across that way. Most of the time, it just makes your conversational partner feel like you’re trying to see who’s higher on the totem pole so that you can flaunt your superiority or schmooze him.

Fortunately, Azania shared a number of questions and statements that lead to safe conversation and good stories. Here are a few of my favorites:

  • Who was your favorite teacher, and why? (Or ask other “favorite”-based questions.)
  • Tell me about a book or movie that changed you and why.
  • Tell me about the songs that remind you of your own youth and why.
  • If you could cook any meal for a guest, what would you cook, and why?
  • What’s a fear you overcame?
  • Tell me the story of one of the nicest things anyone has ever done for you.
  • Tell me about a time you discovered you were stronger than you thought you were.

2. Channel your inner journalist.

A second conversational revelation came from another TEDx talk. This one, entitled 10 Ways to Have a Better Conversationwas given by Celeste Headlee.

The main thought I took away from her presentation was this:

If you want quality conversations, ask effective OPEN-ENDED QUESTIONS.

The good news is, to be effective, your question doesn’t have to be spellbinding. It just needs to encourage the other person to talk freely.


  • Who?
  • What?
  • When?
  • Where?
  • Why?
  • How?

Admittedly, I have a hard time asking these questions. It’s so much easier for me to ask questions that lead to a “Yes” or “No”. But the results of a good inquiry are worth the effort.

Celeste also recommended that, after you ask an open-ended question, you do your best to “go with the flow”. She said that thoughts are going to enter your mind while you’re listening.

Let them go, and keep listening!

And to really get to the good stuff and show other people you’re interested in them, Michael Hyatt suggests you ask follow-up questions.

If you keep your phone in your pocket and give the other person your full attention – Hyatt and Celeste agree – this will be way easier to do. And, consequently, the two of you will have plenty of good material to talk about.

Want to start more interesting conversations? Download these questions and conversation starters and become a better conversationalist.

3. Monitor your motivation.

Finally, the third and last conversational insight I gleaned this week came from Stu McClaren’s post How to Instantly Connect with People” ft. Victoria Labalme.

In it, McClaren interviews Victoria Labalme, an expert speaker, and asks her what enables her to connect with an audience when she gives a talk.

The thought she shared that stuck out to me was this:

A lot of times our motivation is in the WRONG PLACE.

We’re nervous or worried about looking good. But when we focus on these feelings, we only get fake conversations and have trouble connecting with the people we meet.

Labalme says the next time you find yourself worrying about what people will think of you or how to come across the right way, ask yourself these questions.

  • How can I help this person?
  • Can I encourage, inspire, share, or engage with him or her?

Channel your energy into helping others and your conversations will instantly become more enjoyable and meaningful for you and your conversation partner.

What do you talk about when you want to have a great conversation?

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