3 questions that will inject curiosity into any conversation
Can you ask a question first — and feel curious as a result?
Hello and welcome to those who joined last week! Connection Hub has now reached 100 followers on Substack!🥳 (101 as of writing this, to be precise)
This means that I will be organizing an online connection event for you. The format is still brewing in my mind - I’ll send more details + an availability poll next week. This week is all about preparing for the Authentic Dating event I’m running on Valentine’s Day. 💘
Thinking about dating made me think about the power of questions in general. They are one of the best ways to turn around a conversation and create connection where there previously wasn’t any.
Below, I’m listing three of my go-to questions to make pretty much any conversation more meaningful. I hope you enjoy!
Asking questions to generate curiosity may seem backwards. Yet, it works. Good questions can create connection and engagement where there previously wasn’t any.
It happens to everyone. You want to get to know someone new — but have no idea what to ask. So, you keep going through your standard, autopilot repetoire. The conversation stalls, and you wonder how to inject life into it.
Or maybe it’s a loved one — a family member, partner, or dear friend. They talk about something important to them, and you want to offer the best quality of support. However, the right words just don’t come to mind. You end up listenining — but not knowing what to say to make them feel heard.
I used to face those scenarios all the time. I thought I needed a stack of clever, unusual questions up my sleeve for every occasion. With time, I learned that what’s needed is simply some genuine curiosity about that person’s experience.
If you don’t feel naturally curious, fear not. You can spark curiosity by asking three simple yet powerful questions.
Their magic lies in tying the conversation to the present moment.
A word on the present moment conversations
Most of our default ways of talking don’t encourage connection. That’s because we often speak about people, events, and ideas from different space and time. That’s perfectly fine if all you want to do is exchange information.
But if you want the conversation to feel meaningful or intimate, it won’t do the job. In this case, you need to tap into your present moment experience. What are you and the other person feeling and thinking here and now, while being together?
In Authentic Relating, this is called the “relational” level of conversation. It means that you’re including your moment-to-moment experience in what you’re talking about, and how. This encourages relational vulnerability, builds trust, and helps you understand more about the other person.
It shifts focus away from mental stories — and allows you to access the unfiltered experience.
There are intentional practices to connect on that level, such as Circling or Authentic Relating. However, they usually require creating a container — i.e. dedicating a separate space and time to do them. The reality is, not everyone is up for that.
A more casual way of dropping deeper is asking simple questions related to the topic of the unfolding conversation. Their power lies in questioning assumptions about what we think we already know. When we actively swap assumptions for curiosity, that’s where relational magic happens.
Are you ready? Let’s look at the questions.
1. “What is most alive for you right now?”
This question helps you pick the next conversation topic without the awkward “So… what should we talk about?” Instead, you gently bring your speaker’s attention to their present moment experience. You empower them to draw from what’s currently most alive/relevant/interesting to them.
This question suits many situations. I like asking it at the beginning of a catch up with a friend, to gauge where they’re at and what they want to share with me. I don’t want to assume they want to talk about their new job or struggles with their partner just because that’s top of mind for me. I want to know what’s top of mind for them.
You can also ask this question in a conversation with someone new— especially when the conversation stalls. It’s a little unusual, sure. But if the person you’re speaking to is as interested in deep connection as you are, they’ll appreciate it.
2. “What response would you most want from me?”
I love this question. It has been a game-changer for me many times — especially when someone spoke about a big challenge or question they were trying to answer. Typically, my instict was to assume that they wanted some advice or reassurance from me.
But then I though again and realized — that’s not necessarily what I want after sharing something big. So… what if I just asked what response they wanted?
It may unnatural to ask this at first. The unspoken assumption here is often that you should know the answer. Especially with friends and partners, you may think you should know how to support them already.
But my guess is, you often don’t. It can be empowering to ask — both for you and for the other person. It allows them to identify their needs and verbalize them. This, in turn, equips you to be more responsive to them.
Bonus: If this question feels confusing, you can always follow it up with options. “Would you like me to say back to you what I’m gathering? Would you like me to offer my perspective? Would you like some advice? Would you like me to share a similar experience I’ve had?”
This can help the other person feel really cared for. Being offered a clear menu of responses is a relational luxury not many people have had a chance to experience.
3. “How do you feel having shared this with me?”
Before you dismiss this question as a psychonalysis cliché (the infamous “And how does that make you feel?”), hear me out. When timed well, it can instantly transport your conversation to the deeper, relational level.
Why? Because it ties your conversation to the present moment, where most of human connection happens. This helps both parties be aware of how they’re showing up in this very relationship, right now. Did sharing this with you make them feel relieved? Proud? Rejuvenated? Understood? Self-conscious? Uneasy?
Whatever word they give you, it’s an indication of how your presence impacted them. If you wish, you can also share the impact this had on you.
Conversing on the relational level is a fascinating place to be. It allows you to touch on a particular kind of vulnerability that comes with sharing your experience as it happens. There’s no chance to rehearse or censor it — that’s what makes it raw and real.
You may think that a meaningful, honest conversation is hard to come by. But that’s only because we believe this is so.
The mindset we bring into each interaction informs its quality. Even a conversation with a stranger can be full of empathy and care. All you need is willingness to engage and try new things.
Next time you’re in a dull conversation, try one of these simple questions above. Then, watch how it transforms your conversation.
I’ll be curious to hear about your experience!