Leaning in to some of the positive experiences I’ve had during isolation so far, I’ve been joyous to see the number of people connecting right now. Even in my own life, I’m spending way more time on the phone with friends and family than I had just a few short months ago. What I want to challenge you on today is to better these conversations to create deeper connections.

We all know how boring small talk is. Conversation is feeling a bit monotonous right now. I noticed most of my chat topics are around:

  • what’s happening on the news (no, thanks)
  • our experiences being home right now
  • what’s “new” in our world (most likely, nothing)

And while I definitely want to know how my friends and family are coping, I don’t want to spend the entire conversation stuck in fear mode. To be honest, I don’t want to constantly be talking about corona.

What about you? Are you tired of the same conversations yet?

The Art of Better Conversations

Last session on Embracing Human, I was delighted to have my dear friend, Victoria Cumberbatch, on episode 20 to talk about better conversations. She’s been running an incredible series on YouTube, called Anderson Street, that’s all about bringing different people together for discussion.

I was lucky enough to join the cast for a fun conversation on sex taboos.

In the episode, we dug into some of the most important aspects of having a good conversation. We both agreed that one of the pre-requisites for powerful conversation is to be a bit more self aware, being mindful of how we engage with others. But some other things are hugely important:

  • Active listening: Listen to understand, not to respond
  • Respond with questions, not statements or opinions. Being able to ask thoughtful questions will significantly expand your ability to relate to others.
  • Act with empathy: You may not understand someone’s story or opinion, but you can empathize with their experience.
  • Be open minded.

Signs of a good conversation? Walking away with a new understanding of yourself or others at the table. When you are able to question your own beliefs. A great conversation leaves you feeling truly connected.

Powerful Conversation Starters

One of my favorite events I’ve hosted here in Bali were called “Tea and Conversations” with the specific purpose of going deeper. I’d offer a series of questions throughout the night and give each person an opportunity to respond to whatever feels good.

My partner, Connor McCreesh, also did similar sessions with men, so we’ve pulled together top questions from both groups.

Some of these questions are light-hearted and fun. Other questions can help you to dig into the deeper emotions of the people you love. I’m giving you a big list to choose from.

Try one of these in your next facetime:

  1. Tell me about an amazing adventure you went on.
  2. What’s a new recipe you’ve tried recently? Worth sharing?
  3. What is something you identified yourself as as a teenager or young adult, that you’ve grown out of?
  4. Do you have a definition of the meaning of life?
  5. What is your life’s purpose?
  6. Tell me about the worst or best phase in your life.
  7. What do people often misunderstand about you?
  8. If you could change one mindset for the world, what would it be?
  9. What’s your biggest pet peeve?
  10. What’s your biggest fear? (or irrational fear?)
  11. Name a goal you want to have accomplished in 10 years.
  12. Can you share a time when you felt most alive?
  13. What was a big turning point in your life?
  14. What’s current bad habit or pattern you’d most like to change?
  15. Tell me about something that lit you up this week.
  16. If you had to choose one mindset lesson that was the biggest shift for you, what would it be?
  17. What’s one opinion you have that breaks from popular opinion?
  18. Do you have a skill you want to learn that you haven’t invested time in just yet?
  19. Can you share a story of when you were the most scared?
  20. What’s the weirdest thing that’s ever happened to you?
  21. Tell me about your favorite vacation and why you loved it.
  22. Do you have a big regret in your life?
  23. What’s something that used to be a challenge that you’ve overcome?
  24. Do you have a spirit animal? Why do you connect to that animal?
  25. Have you been attending any online events or workshops lately?
  26. Name a book that changed your life and why.
  27. Can you name a book or movie character that you relate to?
  28. What’s the most embarrassing thing you did as a kid?
  29. If you were given $5000 to invest in yourself, how would you spend it?
  30. Tell me about someone in your life that you really look up to and why.

You can get an additional list of conversation starters from the fabulous people at The Science of People. Also, I highly recommend reading Captivate by Vanessa Van Edwards if you wanna better your communication skills.

At the end of the day, think outside of the box. What kinds of questions would you love to be asked if you were being interviewed on a badass podcast? What are you actually curious to know about the people in your life?

Create safe space for people to share by showing empathy and active listening. Your goal in conversation is to get to know people better, not to have the wittiest remark.

I’d love to know, what are some conversation starters that you enjoy? Drop them in the comments below.

If you’re curious about having difficult conversations, check out this powerful interview with Speech Coach, Shulie Gibson. She shares powerful tips on communication with family.

Enjoy some powerful conversations!