professional asking thoughtful questions in conversation

Part 2: It’s Not What You Say — It’s What You Ask 

Apr 24, 2026

If you’ve ever prepared for a networking event, a client dinner, or even a team meeting and thought: 

“What will I say?” 

You’re not alone. 

Most professionals approach conversations like they’re about to deliver a short speech. We mentally rehearse introductions, talking points, and clever lines. We worry about sounding intelligent, interesting, or impressive. 

But here’s the ironic truth. 

Most people in the room are thinking about the exact same thing – worrying about themselves. 

In fact, psychologists call this the Spotlight Effect — the tendency to dramatically overestimate how much other people are paying attention to us. 

According to research published in the Journal of Personality and Social Psychology, people believe they’re being watched and evaluated far more than they actually are. So, if everyone is worried about themselves, why don’t we actually lean into that instead of trying to turn the spotlight on ourselves. The way we do that: prepare incredible questions (focus on them) vs. preparing great speeches (focus on me).  

Because in relationship-building conversations, it’s not what you say that creates connection. 

It’s what you ask. 

Why Questions Are So Powerful 

Harvard Business Review conducted a fascinating study using speed-dating scenarios to examine conversational dynamics (what better way to study quick connection conversations than speed dating?!?). 

Participants were randomly assigned different instructions — some were told to ask many questions; others were not given any instructions for how to engage in the speed dating rounds. 

The results were clear. 

The people who asked lots of questions were consistently rated as more likable by their conversation partners and they learned significantly more about the other person. 

Think about that. 

Simply asking more questions made people more likable

But there’s another reason curiosity works so well. 

Research from Princeton University shows that talking about oneself activates the brain’s reward system (if you missed it, read more about the reward state in last month’s post here). In other words, when people talk about their own experiences, ideas, and stories, the brain releases the same pleasurable responses associated with rewards. 

People literally enjoy the interaction more. 

So, when you ask thoughtful questions, two things happen simultaneously: 

  1. The other person feels valued and heard. 
  1. Their brain experiences the interaction as rewarding. 

Which means curiosity does something incredibly powerful in conversations. 

It changes how people experience you. 


From Self-Focus to Status 

Conversations without questions fail because they unintentionally signal one thing: 

“This person is focused on themselves.” 

When someone prepares “speeches” (dominates the conversation, pivots everything back to their own experiences, or asks shallow autopilot questions) the other person quickly disengages. 

But curiosity flips that dynamic. 

When you ask thoughtful questions, the conversation signal changes to something very different: 

“My perspective matters.” 

In other words, their status rises in the conversation because their perspective is valued

When someone feels their status is raised, they naturally become more open, engaged, and willing to connect. 

This is why great leaders, great sales professionals, and great networkers all share a common skill: 

They ask better questions than everyone else in the room. 


Speeches vs. Questions 

So now, when preparing for a conversation, instead of asking yourself: 

“What will I say?” 

The more powerful question is: 

“What will I ask?” 

The moment you shift from speech mode to curiosity mode, the pressure disappears. 

You no longer have to carry the conversation. 

Instead, you become the guide. 

And the best guides ask great questions. 


The Five Types of Powerful Questions 

Not all questions create the same kind of conversation. Some questions shut dialogue down quickly, while others open the door to deeper insight. 

There are five types of questions that consistently produce stronger conversations. 

1. Closed Questions 

These gather quick information. 

Examples: 

  • “How long have you worked here?” 
  • “Have you always worked in this field?” 

Closed questions are useful for getting basic context quickly. 

2. Open-Ended Questions 

These invite the other person to share more detail. 

Examples: 

  • “What are some of the challenges your team is facing right now?” 
  • “What do you enjoy most about the work you’re doing?” 

Open questions encourage conversation rather than short answers. 

3. Clarifying Questions 

These show that you’re truly listening because you base the question on something they said.  

Examples: 

  • “You mentioned working in product development — what product do you focus on specifically?” 
  • “You said the transition was challenging — what made that period difficult?” 

Clarifying questions deepen the conversation and demonstrate active listening. 

4. Comparison Questions 

These invite concrete reflection:. 

Comparison Examples: 

  • “Between the two approaches, which one worked better?” 
  • “You’ve worked in both environments — how were they different?” 

They give the person you are talking to a narrowed focus to the conversation but gives them the chance to share their compare and contrasting opinion. 

5. Evaluation Questions  

This allows you to go first by sharing your thoughts. Then, ask the person to evaluate what you shared.   

Evaluation Examples: 

  • “We have found that AI has impacted customers in X, Y, and Z ways. What would you say is different or the same about that from your own experience?”  
  • “I am planning to visit Florence and Rome on my upcoming trip to Italy, what would you change or add about that from your recent trip?” 

This gives the listener a safe starting point to respond because you shared first and invited them to share their thoughts on the topic.  


Stop Small Talk. Start Smart Talk. 

Small talk isn’t inherently bad. 

But most small talk fails because it does four things: 

  • It’s predictable, so the brain tunes out. 
  • It’s shallow, so trust doesn’t develop. 
  • It signals conversational autopilot. 
  • It wastes the opening minutes of a conversation when attention is highest. 

Let me give you an example. 

“How was your weekend?” – classic small talk. 

Questions like this almost always produce the same answer. 

“Good” or “Fine.” 

And then the conversation stalls. 

(insert awkward silence)  

Smart talk, on the other hand, is simply small talk powered by curiosity

So instead of “How was your weekend?” 

Try – “What was the best part of your weekend?” 

Now the brain has something interesting to process. 

The answer becomes a story instead of a one-word response. 

Change your “how” questions into “what” questions and observe the difference in the conversation.  


Curiosity as an Executive Power Skill 

Many professionals assume influence comes from having the best ideas, the most expertise, or the most impressive résumé. 

But influences come from building the strongest relationships – and leaders who do that share a different trait. 

They are relentlessly curious. 

Curiosity signals: 

“I’m interested in you.” 

It communicates presence. 

It communicates respect. 

And most importantly, it communicates that the conversation isn’t just about you. 

Curiosity transforms networking from an awkward 3 minutes to a powerful connection. 



Stay Tuned for Part 3 

Curiosity might open the door to connection. 

But strong networks are not built on a single conversation. 

In the final part of this series, we’ll explore the best practices that turn a first conversation into a lasting professional relationship — including how to make outreach meaningful, how to ask for advice the right way, and how to follow up so you stay memorable. 

Because great networking isn’t just about starting conversations. 

It’s about building relationships that actually last. 

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