Maybe it’s because I’m an introvert. Or because the way my family of origin communicated. Perhaps it’s because I’ve spent most of my professional life coaching. It’s probably a combination of nature, nurture, and life experience; I’m not really sure. The one thing I am sure of is that I can’t stand small talk.

I have a tendency to dive right into the deep stuff. For example, I ran into a friend at the grocery store today and we covered more in 10 minutes than many people cover over the course of a year. We discussed our businesses, travel plans, the fight I had with my husband on New Year’s Day, the frustration he’s having with his spouse, negotiation strategies, the politics of the grocery business, and much more.
This isn’t just because it’s one of my best friends. I go deep with everyone. In my upcoming free audio course, (sign up to learn more) I share a story about a conversation I had with a complete stranger on a plane. Before the flight finished boarding, he had told me more about his family than his colleagues knew.
These deep and meaningful conversations are built on asking questions and listening with genuine and authentic interest.
Our western culture is lonelier and more disconnected than ever. In the TED Talk, Breaking the Habit of Small Talk, Omid Scheybani covers the benefits of skipping the small talk in lieu of deeper conversations. In his talk, he quotes a study that shows that “more meaningful conversations lead to increased levels of happiness and wellbeing.” These deeper conversations help us to find meaning in our own lives. He suggests, and I agree, that one single conversation can change the trajectory of our lives. Deeper conversations also lead to intercultural understanding and building bridges.
So how can we incorporate this into our own lives?
Start by engaging people who are paid to be nice to you: your auto mechanic, the grocery store clerk, your chiropractor, etc. It’ll make it easier to build the habit if you get a positive response. Then branch out to family and friends. They’ll likely welcome the opportunity to get to know each other better. Next, start conversations people who share common interests. I’ve had tons of interesting conversations with other cyclists and hikers throughout my travels and adventures. Once you get to this level, you’ll be ready to engage anyone!
Obviously, you’ll want to be polite. Introduce yourself and break the ice. There’s no need to continue the conversation if you get the don’t talk to me vibe. The point is to learn to have meaningful conversations instead of “predictable superficiality.” There’s no need to torture yourself.
I suggest taking these questions off the table.
- What do you do?
- Where are you from?
- Do you have kids?
- What do you think of this weather?
- What did you think of that sports ball game last night?
Instead, select three questions and practice them. Make them your go-to conversation starters.
- Where is the most interesting place you’ve visited? What was special about it?
- If you could move anywhere in the world tomorrow, money not being a factor, where would you move and why?
- What did you love doing most as a child? Do you still do it?
- If you were a chef, what would be your signature dish?
- Tell me about the most interesting person you’ve had a conversation with. What important lesson did you learn from them?
- Which of your hobbies brings you the most joy?
- Who do you most admire? What quality do you most appreciate about that person?
- What is your favorite book of all time and why?
- What is your favorite holiday memory?
- What made you happiest during the last week?
Listen and learn. Share and grow. Enjoy the journey and remember … Each stranger is a friend we haven’t met yet.
Ready to start better conversations? Download this list of 124 questions and start building deeper connections.