The Lost Art of Dialogue:
How to Have Conversations That Actually Matter

The Cafe Clash That Opened My Mind

I met him at the local cafe I hang out most mornings.

Young guy, full of ideas, well-read, politically charged, and more than a little fired up about changing the world.

We started talking over coffee.

At first, I thought, This should be fun.

We didn’t agree on much.

Politically, philosophically, even spiritually, we were polar opposites.

But I love that kind of tension.

That push-and-pull that challenges my thinking.

Keeps me sharp.

Makes me question what I know and why I know it.

But something felt off.

Over the next couple of chats, I noticed something strange.

No matter what I said, he would counter with something he had "researched."

• His logic.
• His facts.
• His certainty.

He wasn't sharing ideas—he was broadcasting them.

I wasn’t part of the conversation; I was the audience to his TED Talk.

It reminded me of a coworker I used to talk with before I retired.

He was deeply religious, and every conversation felt like he was correcting my worldview.

He wasn't trying to understand me—he was trying to fix me.

After one particularly heavy exchange, I went home feeling drained.

Not from the topic, but from the one-sided nature of it.

That Monday, I told him how I felt.

To his credit, he listened.

Apologized.

Said he’d be more aware.

And that’s when I realized:

It doesn’t matter what you believe if the other person doesn’t feel heard.

So I started coaching myself on how to be a better communicator.

I dove back into the classics—Nonviolent Communication, Verbal Judo, Never Split the Difference.

I wanted to master the art of conversation—not just the ability to talk, but the power to connect.

Here’s what I learned.

The 7 Levels of Conversation

Hard Truth: Most people aren’t having conversations.

They’re defending their egos.

They’re not talking with you.

They’re talking at you.

And then waiting their turn to talk again.

The secret?

You can’t control how others show up.

But you can control how you respond.

Once you understand the 7 levels of conversation, you can meet people where they are and elevate the dialogue—one step at a time.

Level 1: Verbal Combat (Win-Lose Battle)

• Tone: Aggressive, dismissive, righteous
• Goal: Win, dominate, prove a point
• Signs: Interruptions, sarcasm, loaded questions
• Your Move:
  • ​Use tactical empathy: "Sounds like this is really important to you."
  • Mirror. Label. Let them exhaust their energy.
  • Redirect instead of resist.

Level 2: Parallel Monologues (Talking At, Not With)

• Tone: Disconnected, defensive
• Goal: Get your point across
• Signs: Long-winded rants, zero questions
• Your Move:
  • Ask a calibrated question: "How do you see that playing out over time?"
  • Use NVC: "What are you hoping changes because of this?"

Level 3: Argument Framing (Debate Mode)

• Tone: Strategic, sharp, analytical
• Goal: Convince through logic
• Signs: Facts vs. facts, stats vs. stats
• Your Move:
  • ​Steelman their position: "So you’re saying X because you care about Y, right?"
  • Ask: "What would have to be true for you to change your mind?"

Level 4: Informational Exchange (Polite Surface Talk)

• Tone: Neutral, polite
• Goal: Share without friction
• Signs: Safe topics, small talk, mild opinions
• Your Move:
  • Use "Yes, and..." to build and pivot
  • Spot curiosity cues and go deeper

Level 5: Exploratory Dialogue (Curious Connection)

• Tone: Open, curious, respectful
• Goal: Understand
• Signs: New ideas, metaphors, moments of pause
• Your Move:
  • Use "I’m wondering..." to unpack assumptions
  • Highlight shared values: "Sounds like we both want to protect others."

Level 6: Collaborative Sensemaking (Shared Truth Building)

• Tone: Co-creative, trusting
• Goal: Combine insights
• Signs: Pattern recognition, mutual exploration
• Your Move:
  • Ask meta-questions: "What’s the idea underneath both our views?"
  • Use frameworks to map the landscape

Level 7: Transformational Conversation (Identity-Level Shift)

• Tone: Vulnerable, profound
• Goal: Change at the soul level
• Signs: Emotional resonance, identity shifts, silence
• Your Move:
  • Slow the pace. Let silence do the work.
  • Ask: "What story have you been telling yourself about this?"
  • "If this belief turned out to be incomplete, what would that mean for you?"

Pro Tip:

You can’t skip levels.

Trying to force a deep, transformational conversation when someone’s stuck in Level 2 will backfire.

Your job is to sense the level and elevate it one step at a time.

Putting It On the Mat

I was talking to the young man at the cafe again last week.

This time, it was different.

He had clearly reflected on our last conversation.

He asked more questions.

Gave more space.

Even said, "That’s interesting… I hadn’t thought of it that way."

We weren’t trying to win.

We weren’t trying to convert each other.

We were exploring.

It felt like rolling on the BJJ mat with a higher belt who doesn’t smash you, but flows with you.

• Tests you.
• Guides you.
• Challenges you.

And because of that, you learn.

That’s what real conversation can feel like.

But here’s the part that matters most:

I didn’t wait for him to change.

I changed first.

I chose to approach our conversations like a black belt:

• Calm under pressure
• Centered in my values
• Focused on understanding before responding

Every time I did that, the quality of the interaction changed.

So here’s your challenge for the week:

Sharpen Your Conversational Game

Each day, reflect on one conversation and ask yourself:

1. What level was it?
2. What signals did I miss?
3. What move could I use next time to elevate it?

And once a week, aim for a Level 5 or higher conversation.

Don’t just talk.

Connect.

Don’t just respond.

Listen.

Don’t just defend.

Explore.

That’s what warriors do.

That’s how leaders grow.

That’s how badasses move through the world—unshaken, open, and deadly precise.

Now go put it on the mat.

P.S. If you found this content helpful, I have a favor to ask.

Actually two of them, a selfish one and a not-so-selfish one.

First the selfish one, if this was helpful to you, forward it to someone you think it might help. That helps me to grow my reach.

Now the not-selfish one, the one thing I learned on the mat and on the job was that the most successful leaders were not the ones who knew the most but were the ones who applied and taught the most.

So, if you want to be a better leader, do two things, take immediate action on what you learned today AND share it with someone else. You'll look badass, I promise you.

Also, if you have any questions, comments or suggestions, hit me up, reply to this email and let me know what's going on and how I can help you to be a better warrior, leader, and badass.

Thank you, I appreciate you being here in The Daily Dojo, you can learn more at CharlesDoublet.com​