Episode 29
🎙️ “Yes, And…” isn’t just for improv. Chris Duprey reveals how it builds trust in business.
In this powerful episode of From Battle to Business, Dean Van Dyke sits down with Chris Duprey—former infantry officer, sales strategist, and communication expert—to unpack what it truly takes to lead high-performing teams through better conversations. Chris shares the four pillars of Breakthrough Conversations, the traps leaders fall into with communication, and how AI is reshaping the future of leadership without replacing the human element. If you’re a business owner, team leader, or sales pro looking to drive growth through clarity and trust, this episode delivers real tactics you can apply today.
Communication breakdown is one of the biggest silent killers in business, and Chris Duprey is here to fix that. A veteran of the 82nd Airborne, Chris has transformed battlefield leadership into boardroom breakthroughs with his Breakthrough Conversations framework. In this episode, he and Dean get honest about why most conversations fall flat, how to ask better questions, and how to lead your team without micromanaging them into submission.
They also dive into how AI tools can enhance your conversations—but only if you know how to keep the humanity intact. You’ll walk away with leadership mindset shifts and a framework to get your people unstuck.
🔑 Key Takeaways:
- The four pillars of Breakthrough Conversations: Yes, And…, Vanguarding, Question First, and Law of Three
- Why “telling” breaks trust, but asking builds it
- How “law of three” helps prevent information overload
- A quick tactic to shift from micromanaging to empowering
- How AI can amplify your message, but not replace human connection
- Communication mistakes sales leaders make without realizing
- Chris’s personal transition from combat to coaching—and what he learned the hard way
- Why most leaders avoid silence, and why they shouldn’t
- Tactical use of frameworks to have better 1-on-1s
- What it means to “trust the conversation to do the work"
🛠️ Step-by-Step Process: (Breakthrough Conversations Framework)
- Yes, And… – Build momentum by validating others before pivoting.
- Vanguarding – Name the tension or risk upfront to build trust.
- Question First – Stop defaulting to advice. Ask, don’t tell.
- Law of Three – Group ideas in threes to enhance clarity and retention.
💬 Notable Quotes:
“When people feel seen and heard, they’re more likely to move.”
“If you’re always filling the silence, you’re not letting the real conversation happen.”
“We coach conversations. Because that’s what drives everything forward.”
“AI should enhance human connection, not replace it.”
“Your job as a leader isn’t to have the answers—it’s to unlock the thinking in your team.”
📚 Resources Mentioned:
- The Question First Group – Chris’s firm that trains leaders and teams on mastering Breakthrough Conversations.
- AI Tools – Discussed in the context of enhancing communication workflows, not replacing them.
Connect with Chris Duprey at
https://www.linkedin.com/in/cduprey/
Connect with Dean Van Dyke at The Breakthrough Blueprint
https://www.instagram.com/dhvandyke27/
https://www.facebook.com/thepillarsgroup/
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