Turn Small Talk into Meaningful Conversations

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Earlier this week, I was reminded of a conference where I saw two people approach the same speaker after his talk.

The first asked: "What's your best advice for success?"

The speaker gave a polite but generic answer.

Then the second person asked: "What's a belief you held strongly at the start of your career that you've completely changed your mind about?"

The speaker's eyes lit up.

What followed was a 15-minute conversation that ended with an invitation to lunch.

Same person.
Same time.
Different question.
Different outcome.

Here's what most people get wrong about connecting with others:

They think it's about:

• Finding common ground

• Making good impressions

• Sharing their own stories

• Being charismatic

There are Three Levels of Questions That Transform Conversations

1. Surface Questions (Where Most People Stay)

• "What do you do?"

• "Where are you from?"

• "How long have you been in this field?"

Polite but forgettable exchanges

2. Bridge Questions (Where Connection Begins)

• "What's the most unexpected part of your work?"

• "What brought you to this industry?"

• "What's changed most since you started?"

Genuine engagement and shared insights

3. Depth Questions (Where Real Bonds Form)

• "What's a belief about your work that most people disagree with?"

• "What's something you understand now that you wish you'd known earlier?"

• "What's a common assumption in your field that you think might be wrong?"

Memorable conversations and lasting connections

I know what you're thinking: "But won't deep questions feel forced or awkward?"

Here's how to make this natural:

1. Use the Bridge Method

• Start with a surface question

• Listen for details that intrigue you

• Ask about those specific details

• Let curiosity guide you deeper

2. Use the Follow-Up Formula

• Listen to their answer

• Find the emotion or value behind it

• Ask about that specifically

• Repeat

3. Use the Permission Bridge (When you want to go deeper):

• "Can I ask you something I'm curious about?"

• "Would you mind sharing your perspective on..."

• "I'd love to understand more about..."

I can hear you now.

But how do I actually make this work in my busy day?

Between meetings, deadlines, and daily fires to fight, the last thing you need is another complicated system to maintain.

So let's get practical.

Here are three "no-excuse" approaches that actually work:

1. The Two-Minute Warm-Up

• Before any meeting/call, write one bridge question

• Keep it on a Post-it or phone note

• Drop it in when the energy dips

• Note what sparked engagement

2. The Topic Bank System

• Create a notes file called "Questions That Work"

• After each good conversation, add the question that worked

• Tag it with the situation (sales, networking, team meetings)

• Review before similar situations

3. The Three-Question Challenge

• Start with one surface question

• Follow up with one bridge question

• End with one depth question

• Do this daily for a week

Pro Tip:

• Start with one approach, not all three

• Practice in low-stakes situations first

• Note what works in your specific context

• Build your own question bank over time

Remember: The goal isn't to interrogate—it's to investigate with genuine curiosity.

POLL

The questions you ask affect how well you connect with others.

So remember that the most memorable conversations aren't born from the stories we tell, but from the questions we ask and the space we create for others to share their truth.

Keep asking questions.

Thanks for reading. Be easy.
Girvin