TIN #120 - How To Unlock Trust When Networking With 3 Powerful Questions
Transform Small Talk Into Meaningful Networking
Hey everyone! It’s Greg, the Introverted Networker.
If you’re tired of surface-level small talk and want to dig deeper in your networking conversations, this one’s for you.
Today, I’ll share three questions that can transform your interactions.
These questions work whether you’re adding someone new to your network, getting to know team members, or building relationships across your organization.
This issue takes about 5 minutes to read…
Before We Get Started:
My online course, “5 Steps To Grow Your Professional Network,” is FREE for all my newsletter subscribers. Learn the process I use everyday to grow my professional network.
Each week, I post a new podcast with tips you’ll find in the weekly newsletter and bonus stories, wisdom, and motivation. The Introverted Networker podcast is like the weekly newsletter but with additional narration and thoughts from me. Be sure to listen to this week’s podcast and check out the previous episodes of the podcast on Spotify and Apple Podcasts for more networking tips and insights.
The video version of the podcast is available on my YouTube channel.
Why Better Questions Matter
Let’s be real: small talk is safe, but it rarely leads to meaningful connections.
When we only talk about the weather or weekend plans, we miss the chance to build trust and understand who someone really is.
That’s why asking better questions is so valuable.
Instead of staying surface-level, the right questions allow people to open up and share their stories, backgrounds, and values, which builds a foundation for genuine connection.
Here are three you can try out this week:
Question 1: “Where Did You Grow Up?”
Why it works: Instead of “Where are you from?”—a typical small-talk question—try asking, “Where did you grow up?”
The difference?
This question invites more storytelling.
People might tell you about different places they lived, schools they attended, or experiences that shaped them.
You’ll often learn about family, childhood, and background, which helps you see a fuller picture of the person.
Example: If someone asked me, I’d tell them about growing up in Cañon City, Colorado, and staying in the same town my whole life until I moved.
That consistency shaped me as an introvert, and it’s part of my story.
Asking someone where they grew up offers a glimpse into their life journey, making it a perfect way to go beyond small talk.
Question 2: “What’s Something Most People Don’t Know About You That You Wish They Did?”
Credit for this one goes to Sahil Bloom from The Curiosity Chronicle.
Sahil talks about a finance professional who also does stand-up comedy—a surprising fact that led to a fascinating conversation. He calls this type of question a Pattern Interrupt.
Why it works: By asking, “What’s something most people don’t know about you that you wish they did?” you give the other person permission to share something they’re proud of but don’t often get to mention.
It avoids being too personal while inviting them to reveal something meaningful.
You’d be surprised how often people are thrilled to share a hidden passion or talent that makes them unique.
Example: If someone asked me this, I’d mention that I’ve been training jiu-jitsu for the last five years.
It’s not something I bring up often, but it’s a part of who I am something most people don’t expect from me.
Or, I might mention meeting my wife on a cruise ship—a story that always surprises people and gives a fun, unexpected twist to how they see me.
Question 3: “When Was the Last Time You Cried About Something?”
This one comes from Charles Duhigg, author of The Power of Habit and Super Communicators.
In his TEDx talk, he shared this as a way to deepen conversations quickly.
Why it works: Asking about an emotional moment may sound intense, but it builds instant trust.
This question is powerful when you want a deeper connection and are willing to share vulnerably yourself.
Use this one with discretion, though—it’s best saved for moments when you’re both open to a more personal conversation.
You don’t have to ask this question with every new contact, but in the right context, it can lead to incredibly impactful conversations.
Duhigg even suggests trying it with a stranger to see how people respond!
The Goal: Building Relationships, Not Transactions
At the core, networking isn’t about collecting contacts or creating transactions; it’s about building meaningful relationships.
When we ask questions that invite real answers, we’re building a foundation of trust.
The more trust we have with someone, the more we’re likely to stay connected and help each other in the long term.
That’s what makes a network powerful—not the number of names, but the strength of the relationships.
Try It This Week
Ready to give these questions a shot?
Pick one and use it in your next conversation—whether it’s meeting someone new, catching up with a colleague, or connecting with a leader in your company.
You might be surprised at how quickly you can go beyond small talk and into something real.
And, hey, if anyone tries the “crying” question, let me know how it goes!
It’s a bold move, but sometimes those are the ones that pay off the most.
Keep connecting, and remember: always be connecting.