Darrin DeStasio is a sales leader, author, and Co-Founder of Horizon Five, with more than 25 years of experience helping enterprise organizations turn strategy into measurable business outcomes.

As a Transformation Principal at Horizon Five, Darrin works with leaders across Finance, HR, and Supply Chain to bridge the gap between data strategy and execution. His approach brings together technology, governance, and people to drive meaningful, lasting transformation.
Drawing on 27 years of experience with companies including Oracle, IBM, Demandware, and Alteryx, Darrin authored Sell the Hole, Not the Drill: What Top Sales Performers Do Differently. His philosophy challenges sales professionals to move beyond product features and focus on understanding customer needs, earning trust, and delivering outcomes that genuinely matter.

SHOW SUMMARY

In this episode of the Selling From the Heart Podcast, Larry Levine and Darrell Amy welcome Darrin DeStasio, author of Sell the Hole, Not the Drill, to explore what top-performing sales professionals do differently.

Darrin challenges salespeople to stop selling features and start solving problems. He explains why the best sales conversations begin with curiosity rather than persuasion, how to avoid the demo trap, and why understanding a customer's personal motivations is just as important as identifying their business challenges.

The conversation also explores the habits behind consistent sales performance. From researching prospects and asking better questions to establishing mutually agreed-upon next steps, Darrin shares practical ways to make every customer interaction more meaningful.
He also reveals how working backward from sales goals, understanding conversion rates, and building a disciplined activity plan helped him predict his own performance with remarkable accuracy.

At the heart of the conversation is a powerful reminder: “Amateurs wing it. Professionals plan.”

If you want to build stronger customer relationships, improve your sales execution, and become a trusted advisor instead of another product-focused salesperson, this episode offers a practical roadmap.

KEY TAKEAWAYS

• Sell the outcome, not the product. Customers aren't buying features. They're looking for solutions to problems that matter to them.
• Lead with curiosity instead of persuasion. Ask thoughtful questions, listen without rushing, and uncover the real business and personal motivations behind a decision.
• Preparation is a competitive advantage. Research your prospects before every conversation so you can spend more time discovering what matters and less time asking questions you should already know the answers to.
• Avoid the demo trap. Show customers only the capabilities that directly connect to their challenges and desired outcomes.

HIGHLIGHT QUOTES

ADDITIONAL RESOURCES

Explore the secrets of heart-centered leadership and thriving workplace cultures with Culture from the Heart Podcast! Nominate a visionary CEO at https://culturefromtheheart.com/Home

Get Larry's New Book: Selling Food from the Heart, https://a.co/d/07dzlMx8

Subscribe to The Selling from the Heart Podcast Youtube Channel! Stay updated with the latest episodes and leadership tips: https://www.youtube.com/c/sellingfromtheheart/

Get Your Daily Dose of Inspiration:
https://www.sellingfromtheheart.net/daily

Dr. Stephanie Duguid is a Leadership Culture Strategist, keynote speaker, author, and founder of Do Good Leadership. With three decades of experience in education, leadership, and human performance, she helps organizations strengthen communication, build trust, and create healthier workplace cultures where people feel valued and empowered to thrive.

Her work focuses on intentional leadership, emotional intelligence, and the power of relationships to shape organizational culture. Through practical strategies, Dr. Stephanie helps leaders reduce miscommunication, strengthen teams, and lead with greater clarity, authenticity, and purpose.

SHOW SUMMARY

In this episode of Selling from the Heart, Larry Levine and Darrell Amy welcome Dr. Stephanie Duguid to explore intentional communication, emotional intelligence, trust, and the habits that strengthen relationships.

Dr. Stephanie defines selling from the heart as service rather than transaction. Instead of focusing on delivering a pitch or closing a deal, sales professionals should listen closely enough to understand what the customer truly needs—and be honest about whether they can help.

She explains why genuine listening requires presence, curiosity, and the willingness to stop preparing your response while someone else is speaking. The conversation also explores how to respond rather than react when facing rejection, pressure, or difficult conversations. A pause, a breath, and greater awareness of tone and body language can change the direction of an interaction.

Ultimately, Dr. Stephanie emphasizes three practices that strengthen relationships and workplace culture: communication, connection, and consistency. When people feel heard, valued, and safe to speak honestly, trust has room to grow.

KEY TAKEAWAYS

• Listen to understand, not to respond. Genuine curiosity helps you understand what customers and colleagues actually need.
• Give people your full attention. Intentional presence means putting distractions aside and engaging with the person in front of you.
• Respond instead of reacting. Pause, breathe, and choose your words and body language deliberately when pressure rises.
• Consistency builds trust. People need to know they can count on how you communicate, especially during difficult moments.
• Communication shapes culture. Words, tone, body language, and assumptions all influence how people experience a relationship.

HIGHLIGHT QUOTES

ADDITIONAL RESOURCES

Explore the secrets of heart-centered leadership and thriving workplace cultures with Culture from the Heart Podcast! Nominate a visionary CEO at https://culturefromtheheart.com/Home

Get Larry's New Book: Selling Food from the Heart, https://a.co/d/07dzlMx8

Subscribe to The Selling from the Heart Podcast Youtube Channel! Stay updated with the latest episodes and leadership tips: https://www.youtube.com/c/sellingfromtheheart/

Get Your Daily Dose of Inspiration:
https://www.sellingfromtheheart.net/daily

Kieran Read is one of the most accomplished leaders in rugby history and the founder of Kieran Read Leadership. During his 15-year professional career, Kieran captained New Zealand’s legendary All Blacks 52 times, earned 127 international caps, won two Rugby World Cup championships, and was named World Rugby Player of the Year in 2013.

Today, Kieran helps leaders and organizations build high-performing teams through intentional leadership, trust, resilience, and accountability. Drawing from his experience leading one of the world’s most successful sports teams, he equips executives and teams with practical strategies to navigate pressure, strengthen culture, and achieve sustained excellence.

SHOW SUMMARY

In this episode of Selling from the Heart, Larry Levine and Darrell Amy welcome former All Blacks captain Kieran Read for a conversation about preparation, performance, leadership, trust, accountability, and the mindset required to consistently perform at a high level.

Drawing from his years competing at the highest level of professional rugby, Kieran explains why preparation creates the foundation for performance. Routines, habits, practice, and analysis help professionals prepare for pressure before the pressure arrives.

But performance is only part of the cycle. Kieran emphasizes the importance of reflection—looking honestly at what worked, what didn't, and identifying the critical few improvements that can elevate the next performance.

The conversation also explores the human side of high-performing teams. Talent alone isn't enough. Trust, genuine connection, communication, and care create an environment where people can challenge one another, give honest feedback, and hold each other accountable.

Finally, Kieran shares how he learned to manage pressure in real time by controlling his self-talk, staying present, and repeatedly returning his attention to the next task.

For sales professionals, the parallel is powerful: you can't control every buyer, outcome, or setback—but you can control how you prepare, how you respond, and what you do next.

KEY TAKEAWAYS

• Preparation dictates performance. Consistent habits, routines, and practice give you the best opportunity to perform when pressure arrives.
• Prepare, perform, reflect, repeat. Use every performance as information to improve how you approach the next opportunity.
• Build connection before accountability. Trust and genuine care create the foundation for honest feedback and difficult conversations.
• Focus on the critical few. Identify the two or three improvements that will make the greatest difference instead of trying to fix everything at once.
• Stay present under pressure. Don't allow a previous mistake or future outcome to steal attention from the task directly in front of you.
• Control what you can control. Your preparation, thoughts, response, and next action remain yours even when the outcome doesn't.

HIGHLIGHT QUOTES

ADDITIONAL RESOURCES

Explore the secrets of heart-centered leadership and thriving workplace cultures with Culture from the Heart Podcast! Nominate a visionary CEO at https://culturefromtheheart.com/Home

Get Larry's New Book: Selling Food from the Heart, https://a.co/d/07dzlMx8

Subscribe to The Selling from the Heart Podcast Youtube Channel! Stay updated with the latest episodes and leadership tips: https://www.youtube.com/c/sellingfromtheheart/

Get Your Daily Dose of Inspiration:
https://www.sellingfromtheheart.net/daily