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Oooh boy. Where do I start…
So, I used to be the guy who peppered people with a billion questions.
While this approach helped get the conversation going, I quickly realized that this wasn’t optimal to build a connection. Why?
Well, a good % of people felt that I was interviewing them (vs. having a conversation where each party takes turns to ask questions). Some even felt that I was interrogating them!
In this article, I will share my favorite strategies to keep a conversation going without asking too many questions.
Now, rather than throwing a bunch of tactics at you, let’s first examine the psychology of why we ask questions and also why we might end up asking too many:
Is it normal to ask a lot of questions? Yes!
By asking questions, we show that we are interested in getting to know someone.
And, research shows that people actually like it when you ask them more questions. In a series of HBS studies, researchers analyzed over 2,000 conversations, and here’s what they found:
People who asked more questions were seen as more likable.
And it makes sense. It’s flattering to have someone else interested in you, and the level of their interest is reflected by their willingness to ask questions.
That being said, here’s when your desire to connect becomes unhelpful…
When your desire to connect hijacks the show
When you’re interested in the person — whether it’s a new friend or date — there’s a risk of your interest overpowering the conversation. Let me explain…
Because you’re so eager to get to know everything about them, you ask one question after another… and before you know it, you just spent the entire conversation interviewing them!
Connection is not a one-way street.It’s a two-way street. So here’s what you gotta do:
Take turns to share about yourself
Self-disclosure is how you help the other person learn more about you and relate to you. It’s how you build familiarity and trust with them.
For people with social anxiety though, self-disclosure is often scary. By opening up about yourself, you’re also opening yourself up to potential judgment and rejection. I’ve often had this thought…
“What if they don’t like what I’m about to share about myself?”
Because of the fear of self-disclosure, the innocuous act of asking questions can morph into a safety behavior.
But when you avoid talking about yourself, here’s what happens…
In a study, not only did socially anxious participants share less, they also reciprocated less in response to the other person’s sharing. This ultimately led to them being viewed as less likable.
That’s probably not what you want. So, here’s how to make self-disclosure less intimidating and more fun:
- Share as much as they do: According to research, people who take turns disclosing information have better relationships than those who don’t. In other words, by matching their “sharing rate”, you minimize the risk of oversharing/undersharing.
- Share relevant experiences or opinions in response to what they said. For example:
“I love city cycling — it’s such a lovely way to get to know a city.”
“Yeah. Amsterdam is the best city for cycling — have you been there?” - Use “ready-to-go” questions: While I have mixed feelings about conversation card decks — they can be crutches in social situations — a list of questions can alleviate your anxiety about what/how much to share.
Learn to accept your discomfort with silence
Speaking of safety behaviors, discomfort with silence might also lead to asking too many questions. Underneath the discomfort is the following fear…
“If I stop asking questions, they will stop talking
and there will be awkward silence…”
And that’s completely normal! In North America, there’s often a cultural belief that silence is bad. Silence can also be perceived as a sign of rejection, according to studies.
But here’s how I would reframe things:
Moments of silence don’t kill the conversation — they actually make the conversation better. For one, they help you better process your thoughts and emotions. They also give the other person space to contribute to the conversation.
As Mozart said:
“The music is not in the notes, but in the silence between.”
To better accept your anxiety with silence, I’d recommend mindfulness exercises. This article might be helpful too:
How to keep a conversation going when you don’t know what to say
Help them unpack what they just said
When the other person isn’t talking much, you might be tempted to ask one question after another, in an attempt to get the conversation going.
As you know by now, there are more helpful ways to continue the conversation.
- Paraphrase what they said. For example, “What I’m hearing is…”
- Acknowledge and validate their feelings. For example, “That sounds frustrating”
- Share your opinion on what they just said, as I mentioned earlier
In my other article, I give specific examples for each “conversation tool” – click below:
66 useful phrases to keep a conversation going (and avoid awkward silence)
Comment on the surroundings
This can be very helpful in sparking conversations since it’s a natural conversation topic. Think of your comment as an invitation to be curious together 🤩
- If you notice something interesting: “Check that out…” or “I’ve never seen this before…”
- If you notice something beautiful: “That’s so pretty!!” or “Looking at that makes me happy.”
- If something triggers a memory of yours: “That reminds me of <a specific place, person, etc.>”
If they show interest in the object or environment that you’re referring to, ask follow-up questions like:
- “What do you think that is?”
- “Where do you think that came from?”
- “How did they find/build that?”
Location-specific comments/questions as below:
- If you’re at a park
- If you’re at a grocery store
- If you’re at a cafe
- If you’re at a restaurant
- If you’re at a gym
And finally…
Build a relationship one conversation at a time
No matter how amazing your social skills are, it still takes time to deepen any relationship.
Put it another way: it’s rare to go from stranger to BFF in one conversation 🙂
Just go with the flow, and see where the conversation goes!
Related articles
- 25 useful phrases to keep a conversation going (and avoid awkward silence)
- How to keep a conversation going when you don’t know what to say
- How to start a conversation with anyone
- How to stop overthinking conversations (for socially anxious)
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