20 Questions to Ignite Meaningful Conversations

The Right Questions Can Make the Difference

October 13, 2022 |

Meaningful Conversations

Powerful conversations have positively impacted my life. I long for them. While there are no guarantees, you can create an environment where meaningful discussions are more likely to occur. Great questions are a part of creating this environment.

I have a friend from college named Aaron. I remember us having meaningful talks soon after we met. They were about our hopes and our dreams. They were about our problems and worries. They were about our families. They were real. These talks started a friendship that remains strong 20 years later.

There are many benefits to meaningful conversations including…

• Tense family relationships can be restored
• Gaining empathy for, and actually liking, someone you disliked
• Insight into your strengths and potential
• Inspiration to pursue goals you never thought possible
• Getting back on the right path and focused on the right things

Meaningful conversations almost always start with a great question. I have spent significant time figuring out what questions get people to open up and talk, and here are 20 of my favorites.

“A conversation is a dialogue, not a monologue. That’s why there are so few good conversations: due to scarcity, two intelligent talkers seldom meet.” – Truman Capote

20 Great Questions

  1. What is a positive habit you would like to establish?
  2. How have you learned from a mistake? What mistake?
  3. What do you like about yourself?
  4. What would you do if you were 10 times bolder?
  5. What do you want LESS of in your life?
  6. When was a time in your life that you felt most alive? What were you doing?
  7. What ENERGIZES you? What DRAINS you?
  8. What change could you make that would make a big difference?
  9. How are you stuck (i.e not making progress)? How can you get unstuck?
  10. What stops you from doing what you really like to do?
  11. What do you want MORE of in your life?
  12. What do you wish you were great at?
  13. What do you NEED to get your life to the next level?
  14. How can people best encourage you?
  15. What are you biggest goals right now?
  16. What do you need to say “No” to more?
  17. What do you want to do that you haven’t done? 
  18. What positive difference do you want to make?
  19. How do you want to be remembered whey you’re gone?
  20. What are the toughest decisions for you to make? 

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Each of these questions is simple. Each can lead to other questions that will give you further insight into yourself and others. They are relevant to any age group. Don’t give in to the resistance many have to opening up. Ask questions anyway. People will love and respect you for your sincere interest in their lives. There’s a joy that comes only from connection. I hope you experience this joy soon.

If you felt challenged by my simple questions, go through my online coaching course Tune Up For Life. Learning about having a healthy perspective, loving yourself better, living with balance, living out your core values and life purpose, goal setting, developing healthy habits, and more.

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An Excellent Communication Game & Tool To Strengthen Your Work Team, Family, and Friendships. Includes 108 questions. Check it out!

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