20 Questions to Enhance Conversations ~ Moving from Yes to Yes And

20 Questions to Enhance Conversations ~ Moving from Yes to Yes And

There are some people who Yes, and some who Yes And.

When we share something about ourselves with others, some people respond just by saying, “Cool”, or “Great”, or “That’s interesting.” They offer some form of acknowledgement. That’s the Yes of Yes And.

And then there are those who offer an acknowledgment, AND then ask a question that further explores what we shared. They say, for instance, “Wow, that’s fascinating (Yes). What was that like for you? (And)”

We love it when people show genuine interest in us.

Whether it is simply a check in to see how our doctor’s appointment went, or a series of questions, it feels good when people are genuinely interested in us. It feels like the person cares about us and our experience, and that we matter to them. We feel heard and appreciated. We feel met! And it gives us the opportunity to share even more about ourselves and our life. The more we share, the more they learn about us and our experience, which then gives them other things to be curious about.

Curiosity is a sign others are listening and engaged.

In the attitude of curiosity, we bring our ears and heart fully into the conversation. We cannot be curious if we are not listening to what they have to say. When we don’t listen, we are more inclined to turn the conversation back on ourselves. To stay in curiosity, we have to temporarily suspend our own agenda to follow the other person’s lead.

Curiosity allows you to release the need to know or be smart.

With curiosity, we don’t have to be an expert in the other person’s life to engage in the conversation. I don’t have to be knowledgeable or smart. I can have a wonderful conversation with a financial planner, shaman, or news anchor without knowing anything about their field of expertise just by asking a series of questions. The only prerequisite is that I am keenly interested!

I am personally fascinated about people and their lives. I love to learn, and I am curious about the human journey and the choices people make. So curiosity is not hard for me. Rather it is something I deeply enjoy!

Despite being a gift, curiosity is not as widely practiced as it could be.

How many times a day do you share something with someone and all they offer you is a Yes (or worse yet, a No!)? I am not saying that you always need to And. There are some things that are better left at Yes. But I can guess that there are some conversations you have had recently where you would have loved a bit more curiosity from the other person.

Recently my mom shared with me how her cruise was. I must have asked her about forty questions!

  • What kinds of activities were on the ship?
  • Did you meet anyone interesting?
  • What was the food like?
  • Who was at your table?
  • Etc, etc.

And of course, after each answer, I asked a follow-up question.

Mom: “Oh we had a nice couple at our table from the US.”
Me: “Where in the US were they from?”
Mom: “From New York.”
Me: “What sorts of things did you talk about with them?”

And so on, and so on.

After I got home, my mom told how much she appreciated the curiosity I exuded. It meant a lot to her to have her experience heard and valued.

Begin looking for opportunities to bring more curiosity into your conversations.

Curiosity is a muscle that needs to be used. Because we don’t use it that often, we miss out on travelling many wonderful directions in our conversations.

I encourage you to begin actively looking for things to be curious about in another, and ways you can travel in their world. Each thing that you are curious about is a door to a limitless pathway that leads into a person’s heart and life. The more pathways you travel down, the more you will discover, and the deeper you will connect to the other person and enhance your relationship.

20 Questions to Enhance Conversations ~ Moving from Yes to Yes And
  1. What is your favorite thing about that?
  2. What is that like for you?
  3. What did you learn about yourself? About life?
  4. What did they say?
  5. How do you feel about that?
  6. How does that resonate for you?
  7. What will you miss most?
  8. What part are you most excited about?
  9. What will it feel like to finally have that out of your way?
  10. What will it mean to you to accomplish that?
  11. What are you hoping to discover?
  12. What are you hoping to get out of that experience?
  13. What drew you to that decision?
  14. What compelled you to go there?
  15. What challenges do you see yourself facing?
  16. What does your heart say?
  17. Who did you meet?
  18. Who did you go with?
  19. What did you talk about?
  20. What did you eat?

Don’t forget that after each answer you can then ask a follow-up question.

Person A: “I had fish and chips.”
Person B: “How did it taste?”
Person A: “Pretty good. Better than I thought it would be.”
Person B: “Did you order dessert as well?”
Person A: “Yes, I had the apple pie.”
Person B: “Oh! Did you get it heated with ice cream?!!”

Some may be surprised by your curiosity if they are accustomed to more Yes than Yes And from you. But I can assure you over time they will learn to enjoy and appreciate it. And if modelled enough, they may feel compelled to offer some back to you.

The best way to ask for what we want is to model it ourselves!

Enjoy playing with the child-like attitude of curiosity! Enjoy playing with Yes, and And! 🙂

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Check out Vince’s book: Let the Fire Burn ~ Nurturing the Creative Spirit of Children, A Children’s Book for Adults

Posted in Most Popular, Relationships, Communication and tagged , , , , .


  1. Wow, that’s a powerful perspective on how to deepen our connection with each other and ourselves. I love how clear you are on this and how easy you make it to digest and to apply in our own individual lives. I also love how openly you share your own experiences, you painted more than one smile on my face. Thank you for showering us with another piece of your brilliance! I am a fan! 🙂

  2. Really enjoyed this article Vince! I speak often to client’s about curiosity and the power of acknowledgement, which I also see you addressing here. I will be sharing this with a client and my Toastmasters group. Thanks!

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