For the past few years, instead of creating solutions, I have set intentions in different areas of my life. It’s not a goal at all. These are some kind of gentle reminder of myself about how I want to show up, whether it’s work, relationships, health, etc. This year, under the “Relationship” category, I wrote: Ask better questions and practice deeper listening. Because when it comes to learning how to continue a conversation, it’s not always intuitive.
I realized that being truly connected to people I love means creating conversations that are important, listened, and cared for. And to do that, we exist, ask good questions and listen. Please listen to it.
So, if you’ve ever wanted to scramble to fill in the troublesome silence or ask for more meaningful follow-ups, this guide is for you. Let’s dive in.
A practical guide: how to keep the conversation going
1. Start by actually listening
We all went through the moments in the middle of the story when we realised that others weren’t really listening. Or maybe you were that person – diss, your mind is moving forward.
Secret secret that keeps conversation flowing naturally? Please ask first.
When you really tune, you naturally pick up details worth exploring. Conversations stop feeling like performance, and start to feel like connection.
2. Please ask more questions
Research from Harvard Business Review After a one-sided conversation, we confirm what many of us felt.
The good news is that you don’t have to be a veteran interviewer to become a great conversationalist. Start by asking more. The act of curiosity opens the door to unexpected stories, shared memories, and meaningful connections.
Some ideas to get you started:
- Please tell me how you lived [their city]. What do you like about it?
- Have you found any hobbies during the pandemic?
- What is the best vacation you’ve ever been and why?
- Who was your first celebrity crash? Do you think they influenced your type?
- What was the first book you remember that you loved? Do you still like it?
3. I’m leaning towards follow-up questions
If you want to know how to keep the conversation going with ease, this is your magical move.
Follow-up questions indicate that you are really involved. And they open the door for a deeper, more meaningful answer. It’s an easy way to turn casual chat into something special.
Try these:
- What tells you that?
- How did that feel?
- What does that mean?
Even young children notice when you ask for thoughtful follow-ups. I’ve seen it in my own relationship with Henry – he knows I care when I ask him to elaborate. And that’s not different from adults either.
bonus: Here’s how to upgrade your daily questions to Connect Builder:
- how was your day ? What was the best?
- How about mom? ? Have you kept her busy lately?
- Could you help me realize that it’s a little better?
- What motivated you to do/say it?
- How does it manifest in your daily life?
4. Ask open-ended questions
Closed-end questions that can be answered quickly with a yes or no tend to stop conversations on the track. Open-ended questions, on the other hand, are invited to reflect and share stories and become a little vulnerable.
Interviewing tastemakers or inviting guests will have the best conversations happen when people ask questions that are open in unexpected ways.
Some to put in your back pocket:
- What’s your favorite thing that happened since we last caught up?
- What do you think? [a recent event, book, or film]?
- What memorable opportunity encounters you had?
- Tell us about your last great meal – what made it so special?
5. Resist the impulse to interrupt
Well, guilty. I tend to get very excited when it comes to people saying they’re jumping in before they finish. However, interruptions can cause you to unintentionally turn into a conversation, leaving it where it heads, or making others feel rushed.
One of the best ways to improve your conversation is to get used to a little silence. Let people finish their thoughts. Pause before responding. As the proverb says“Try to understand more than you can understand.”
The power of good questions
If we need to further prove how transformed this is, Modern love Essay on how Mutual vulnerabilities build intimacy. The authors state that one important pattern in deep relationships is “lasting, escalating, mutual, and personal self-disclosure.”
The famous 36 question study promoted intimacy among strangers, but it is evidence that thoughtful questions can unleash connections in minutes.
Final Thoughts
The best conversations are completely unscripted. They are based on genuine curiosity, presence and willingness to go a little deeper.
By listening carefully, asking more (and better) questions and leaning on those open-ended moments, you naturally learn to continue the conversation – whether you’re on a date, catching up with a friend or having a small talk at an event.
Your Turn: What is your favorite question to ask people you’re getting to know? I want to hear it.
This post was last updated on April 22, 2025 to include new insights.
Source: Camille Styles – camillestyles.com
