Bob Schmidgall was one of the most incredible speakers I’ve ever heard. I admired his ability to connect with people and studied him often. One of his greatest strengths was speaking in a way that reached blue-collar, white-collar, and gold-collar workers—all at once. Each listener walked away believing Bob was speaking directly to them.
If you haven’t heard those terms, they’re general categories of labor:
- Blue Collar: Manual laborers and skilled tradespeople.
- White Collar: Office and professional workers.
- Gold Collar: Highly skilled and valued specialists, often in cutting-edge fields like AI.
When Bob made a key point, he often shared it three times. But he never sounded repetitive. Instead, each sentence was crafted for a different group. He wasn’t restating; he was expounding—layering meaning so each person heard it in a way they could relate to.
The result? Everyone left the room feeling as though his talk was written just for them. He was relatable, informative, humorous, and full of great stories. Out of the hundreds of speakers I’ve listened to, Bob remains in my top five.
At some point, I realized something important: no amount of study would turn me into Bob. But that wasn’t the point. Bob had his gift. What I needed to see was that all of us actually speak far more than he ever did. Over a lifetime, we will likely have the equivalent of a gigabyte of conversations—not just spoken words, but emails, texts, social DMs, and even old-fashioned snail mail.
Each exchange adds another “file” to our personal archive. Some are blurry images best deleted, but others are crisp, high-resolution moments worth revisiting.
And that leads to the real question: if you’re going to spend that much time talking, typing, and connecting—why not upgrade your conversations so they actually build trust, opportunity, and collaboration?
Here are five simple Conversation Upgrades I’ve found that can transform ordinary chatter into meaningful dialogue.
Upgrade 1: Curiosity Beats Cleverness
Instead of prepping stories to tell, prepare questions to ask. Dale Carnegie put it best: “You can make more friends in two months by becoming interested in other people than in two years by trying to get other people interested in you” (How to Win Friends and Influence People).
A practical way to stay curious? Think about their Family, Work, Recreation, and Dreams (the F-W-R-D framework). Ask about their kids’ hobbies, the wildest thing that happened at work this month, the new restaurant they tried, or the goal that lights them up. When you anticipate their story, you can’t help but lean in—and that anticipation is contagious.
Upgrade 2: Turn on Charisma Mode
Charisma isn’t some magic dust—it’s built from presence, warmth, and confidence. Olivia Fox Cabane (The Charisma Myth) shows how teachable this is.
- Presence: Give someone the sense that there’s nowhere else you’d rather be.
- Warmth: Try the “flooding smile”—pause, take them in, then let a genuine smile slowly spread. It feels personal, not pasted on.
- Confidence: Strong posture and a few thoughtful pauses tell the room you’re comfortable in your own skin.
When those three align, people don’t just hear your words—they feel your attention.
Upgrade 3: Add a Twist of Surprise
Boring conversations fade. Playful ones stick. Instead of standard answers, toss in a curveball:
- Instead of “I’m from Chicago,” say: “I’m from Chicago, where pizza is deep enough to need a lifeguard.”
- Instead of “I’m a consultant,” say: “I’m a consultant who’s learned more from coffee spills in boardrooms than from MBA textbooks.”
It’s not about impressing—it’s about giving others something fun to react to, like setting up the first line of an improv scene.
Upgrade 4: Ask for Feelings, Not Just Facts
Charles Duhigg’s Supercommunicators highlights a Harvard study of speed dating conversations: the people who landed second dates asked emotion-driven questions, not fact-gathering ones.
Swap:
- “Where are you from?” → “What do you love most about your hometown?”
- “What do you do?” → “What makes your work exciting—or exhausting?”
- “What did you do this weekend?” → “What was the highlight of your weekend?”
By aiming for Dreams, Elevated moments, and Passions (D-E-P), you’ll unlock stories that reveal what matters most. That’s the difference between polite small talk and real connection.
Upgrade 5: Let People Know They Landed
Everyone wants to feel heard. Psychiatrist Mark Goulston (Just Listen) says even small acknowledgments—nodding, “mm-hmms,” or paraphrasing—make a huge impact.
When someone shares, don’t just reply with “Wow, that’s crazy.” Echo a detail that mattered: “That’s hilarious—after all that effort, the IKEA shelf was upside down the whole time.”
It signals: I didn’t just hear you. I understood you. That’s the glue of collaboration.
Why These Upgrades Matter
Each “conversation upgrade” builds on the 3Cs framework that I’ve developed:
- Communication: Clearer, warmer, and more engaging.
- Connection: Deeper emotional resonance—because you’re asking what really matters.
- Collaboration: When people feel seen and valued, they bring their best ideas to the table.
Conversations aren’t background noise—they’re the raw material of relationships. And when you upgrade them, you upgrade your influence, your opportunities, and your impact.
It’s Time to Upgrade
You’ve got a gig of conversations ahead. Most people will let theirs auto-save in the background. But you? You can choose to upgrade yours—turning them into meaningful files worth archiving.
Start small: one curious question, one genuine smile, one playful twist. Then watch how fast your communication, connection, and collaboration grow.
Copyright 2025 by CJ Powers
CJ's Corner 