A Gig of Conversations: Lessons from Bob Schmidgall

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

Being the Human AI Can’t Replace

Daniel Lucas, the host of Book 101 Review, invited me to be a guest on his podcast. The show’s format spends more time on the guest than on the book they review. So while I spoke about Will Guidara’s “Unreasonable Hospitality,” Daniel asked me lots of questions about AI.

If I were to summarize the interview, I’d say that Daniel dove into a timely question: What does it mean to be human in the age of AI?

For decades, I’ve worked in communications—helping corporations, entrepreneurs, and small businesses clarify their message, connect with their audience, and collaborate effectively. And today, with AI entering every corner of our lives, I see the same question surfacing again and again: Will AI replace us?

The short answer: No. But only if we choose to be fully human.

Driving AI Instead of Being Dragged by It

On the show, I used a simple analogy. AI is like a car. You can either grab the wheel and drive it, or you can be dragged behind it.

(I created the elements in the picture above with ChatGPT and built it with Canva.)

Too many people fear AI because of what they’ve seen in movies—machines taking over, robots replacing people. But AI is a tool, nothing more. And like any tool, it can either empower you or run you over, depending on how you use it.

If you want to stay in the driver’s seat, there are three keys I always come back to: Communication, Connection, and Collaboration.

The 3C Framework

  • Communication – Knowing not just what you want to say, but how to say it clearly to both people and AI.
  • Connection – Engaging authentically. People crave genuineness. They don’t want polished perfection; they want honesty, vulnerability, and someone who really listens.
  • Collaboration – Working productively with others and with AI. Collaboration is where we build things greater than ourselves.

If you master those three areas, you’ll always be more valuable than the technology around you.

The Power of Authenticity

One theme that came up repeatedly in the conversation was authenticity. It’s become a buzzword, but what it really means is this: I bring my full self, flaws and all, into the room—and I give you permission to do the same.

Our imperfections make us human. They make us trustworthy. They make us irreplaceable.

AI may simulate compassion or generate words that look empathetic, but at the end of the day, it’s mimicry. It can’t truly connect at a heart level. And when we show up with vulnerability and honesty, we offer something AI can’t touch.

Productivity Redefined

For years, productivity has been defined by speed and efficiency. But people don’t just want faster anymore—they want better. They want something that feels personal.

In the podcast, I shared how I worked with a global laboratory that reduced a 14-hour reporting process to just four minutes using AI automation. That freed up time for people to focus on relationships, innovation, and creative work. That’s the real win.

Productivity in the future won’t just be about doing more, faster. It will be about depth over speed—quality over quantity—human over machine.

Why Human Art Still Matters

Art gave us another window into the conversation. AI-generated art and music may look impressive on the surface, but true art always contains something AI can’t replicate: mistakes.

Every brushstroke, every lyric, every twist in a story carries the weight of human imperfection—and that’s what makes it resonate. AI’s attempts at mistakes feel artificial. Our mistakes, on the other hand, make our work feel genuine and alive.

Daily Practices for Staying Human

So how do we practice being more human in our work and life? I suggest three steps:

  1. Clarify – Be clear about your purpose and your message.
  2. Simplify – Speak at a level where both people and AI can follow. (Think sixth-grade clarity.)
  3. Amplify – Let your passion and purpose shine through, whether you’re speaking to one person or an audience of thousands.

If something can be done the exact same way three times in a row, hand it to AI. Then use your freed-up time for creativity, problem-solving, and relationships.

A Book Worth Reading

Toward the end of the interview, I recommended Unreasonable Hospitality by Will Guidara. His insights align perfectly with what we discussed:

  • Be fully present.
  • Take your work seriously.
  • Treat people as unique treasures.

That book, like this conversation, reminded me that no matter how advanced technology becomes, our human touch remains the deciding factor in business and in life.

A Final Thought

If there’s one takeaway from my conversation with Daniel, it’s this: lean into your humanity.

Experiment with AI. Automate repetitive tasks. Use the tools available. But never forget that what makes you irreplaceable isn’t efficiency—it’s authenticity.

AI can copy, simulate, and predict. But it cannot create wisdom. It cannot make genuine connections. It cannot replace the art, purpose, and relationships that define us.

So let’s stop asking if AI will take our jobs. Instead, let’s ask: Am I being fully human in the way I communicate, connect, and collaborate?

Because that’s the one thing AI can never replace.

Here is the full show…

Copyright 2025 by CJ Powers

A Journey Through AI and Reality – Helping Tweens Discern the Difference

As a tech-savvy person, I started exploring AI several years before most people knew it had entered our world. Maybe it was my appreciation for sci-fi that drove my play, or even my time writing computer programs back in the day, but in reality, it was my concern for a group of tweens I met who weren’t sure if they should engage or avoid AI.

Over the past few months, I’ve chatted with middle schoolers about their hopes and fears surrounding AI. As someone passionate about storytelling, I wanted to channel what I learned into a project that could both engage and empower them. That’s where my short film AI KNOWS comes in.

As I listened to tweens share their thoughts, I was struck by their mix of excitement and apprehension. Many of them see AI as an exciting tool—something that can make their lives easier, help them with homework, or even create fun videos. But there’s also an underlying fear of the unknown.

What does AI mean for their futures? Will it take away their future jobs? Will it even understand their creativity or emotion?

The AI Dilemma for the Next Generation

In AI KNOWS, Davis, the young shuttle pilot, faces a critical decision: Does he trust the AI, or does he listen to the wisdom of Jet, an older, more experienced aviation mechanic? This dilemma isn’t just fictional—it’s the same dilemma that today’s tweens face when they come across fake images, deepfake videos, or voice recordings that sound real but aren’t. Just like Davis learns, AI can’t always be trusted to make the right call.

Through AI KNOWS, I wanted to provide families with a tool to help them facilitate a meaningful conversation. I firmly believe that how we face AI and determine our use of this tool must be defined in the family, not in schools or the government. Once common ground is developed within our families, the schools and government should support the family’s decisions.

To that end, I wanted families to explore Davis’ journey from blindly trusting AI to realizing it’s not infallible. This evolution is something every family can reflect on as they navigate their own relationship with technology. I hope this film serves as a jumping-off point for parents and tweens to discuss how to approach AI with discernment in their daily lives.


So, how can teens discern the real from the fake in an AI-driven world? Here are three steps to help navigate this new reality:


1. Question the Source
Every piece of information or media comes from a source. Tweens should be taught to check who created the content and whether that source is trustworthy. Is it from a verified news outlet? Is it a brand or influencer they recognize? In AI KNOWS, Davis’ blind faith in AI prevents him from questioning the source of the information he’s receiving. Just like in the real world, AI may not always provide the full truth—sometimes even creating “hallucinations,” or false information that wasn’t intended. Tweens should be encouraged to ask, “Who’s behind this?” and whether the source is verified and reliable.

2. Use Technology to Verify
In the world of AI KNOWS, Davis learns that technology can also be used to find the truth. Just as AI can create fake content, there are tools that can help reveal it. Encourage tweens to use tools like reverse image search engines, apps to detect deepfakes, or software to analyze videos and images for inconsistencies. In the same way that Davis uses his resources to verify the AI’s integrity, kids should learn to use technology to verify what they encounter online.

3. Understand the Consequences of Fake Content
Fake content can have serious consequences. Tweens must know that misleading or altered content spreads quickly and can damage reputations, distort events, or worse, cause harm. By teaching them about the ripple effects of fake content, they can better understand the weight of their responsibility when sharing information. Like Davis realizes that his blind trust in AI led to a dangerous situation, tweens need to understand that sharing fake content can hurt people and impact society.

A Family Conversation Starter

As AI KNOWS moves from storyboard to screen, I’m excited about its potential as a tool to help families start conversations. How can we, as adults, help our kids understand that while AI can be a powerful tool, it’s essential to approach it with a discerning eye? How can we teach them the value of questioning, verifying, and understanding the consequences of what they share online?

The ultimate goal isn’t just to raise awareness about AI’s limitations, but to teach kids that AI is only a tool. Wisdom, on the other hand, is something that can be cherished, something that endures, and something that will stand the test of time. While AI can assist and enhance our lives, it cannot replace the timeless value of human experience and judgment.

I hope that AI KNOWS isn’t just a movie. I hope it’s a gateway for families to discuss what it means to navigate a world increasingly dominated by AI. It’s not about scaring our kids; it’s about equipping them with the skills they need to thrive in a digital world. By using the film as a discussion starter, families can explore the importance of being critical of the tools we use and understand how AI fits into the broader context of communication, creativity, and human wisdom.

Kids need to understand that while AI can be incredibly helpful, true guidance is provided by the wisdom passed down through generations of families. This understanding empowers them to use AI responsibly while still holding on to the wisdom that shapes their decisions, actions, and values.

Copyright © 2025 by CJ Powers