Selling From the Heart Podcast

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
The goal is to solve somebody else's problem that matters to them.

Care enough to ask better questions, listen long enough to uncover the real challenge, and only recommend something if it truly creates value to them, not to you.

Amateurs wing it. Professionals plan.

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
We’ve got two ears and one mouth, so we can listen twice as much as we speak.

Culture really stems from the way that you communicate with one another.

How do you communicate when you’re stressed? How do you communicate when you’re under pressure?

I don’t listen to respond. I don’t listen to react.

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
Our preparation dictates what our performance is gonna be.

You can't have a great performance without the preparation.

Preparation is about habits, it's routines.

Feedback's tough to take... but it's the key for us to grow and to get better.

Prepare, then you perform, then you reflect.
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

Simon Severino is the Founder and CEO of Strategy Sprints, where he helps B2B founders and business leaders accelerate sales, increase profitability, and build companies that can scale without burning out their teams.
Over the past two decades, Simon has helped clients generate more than $2 billion in additional revenue by simplifying strategy and focusing on disciplined execution. He is the creator of the Strategy Sprints® Method and author of Strategy Sprints: 12 Ways to Accelerate Growth for an Agile Business.
Simon is also a TEDx speaker, Forbes contributor, and host of the Strategy Sprints Podcast. His work focuses on helping leaders simplify complexity, strengthen sales processes, and create sustainable growth by concentrating on the actions that generate the greatest impact.
SHOW SUMMARY
In this episode of Selling From the Heart, Larry Levine and Darrell Amy welcome Simon Severino for a conversation about preparation, process, trust, simplification, and selling in the age of AI.
Simon defines selling as helping another person make progress. But helping someone make progress requires more than good intentions. Sales professionals need to understand the buyer's world, prepare deeply, and bring a process that can confidently guide the conversation forward. Without preparation, sellers can become reactive, overly focused on closing, and more concerned with their own pipeline than the customer's progress.
The conversation also explores why trust may become the key differentiator in the age of AI. Technology can increasingly support research, strategy, and analysis, but buyers still need trusted people who can help them execute, navigate resistance, and make meaningful change.
Simon also warns sales organizations against using AI to accelerate processes they have never clearly defined. Before automating, teams should document how they prospect, follow up, close, onboard, activate, upsell, and serve customers. Otherwise, as Simon puts it, “the AI will only scale chaos.”
Finally, Simon challenges sales professionals to simplify their offers and rethink high-volume outreach. Instead of sending hundreds of generic messages, focus on fewer prospects, understand what is relevant to them, and create communication that is thoughtful, distinctive, and human.
The message is simple: prepare better, simplify the process, build trust, and use technology to strengthen—not replace—the human side of selling.
KEY TAKEAWAYS
Selling means helping people make progress. Keep the buyer’s desired outcome at the center of every conversation.
Preparation and process build trust. Understanding the buyer’s world and following a clear process helps you guide the conversation with confidence and relevance.
Trust will differentiate you in the age of AI. Technology can support research, strategy, and analysis, but buyers still need trusted people who can help them execute and create change.
Don’t use AI to scale chaos. Simplify and document what already works before trying to automate or accelerate your sales process.
Simplify what you sell. Focus on the central problem you solve and communicate one clear outcome instead of overwhelming buyers with products, features, and options.
Send fewer, better messages. Replace generic volume with deeper preparation, relevance, personality, and communication that demonstrates you understand the person you’re trying to reach.

HIGHLIGHT QUOTES
Trust will be the key differentiator in the age of AI.

If you stick to one process, you are more in service actually, in the service of the other person making progress.

What you want is AI. What you need is writing down the process first.

Instead of sending 200 things, let’s send 20 this week, but let’s go deeper.

Send less messages, but make them more interesting, make them stand out, make them about who you are and what you can do for them.
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

Rashmi Airan is a globally recognized keynote speaker, transformation expert, and former attorney whose story of resilience, accountability, and reinvention has inspired leaders and organizations around the world.
A graduate of Columbia Law School, Rashmi built a successful career as an attorney, Wall Street investment banker, entrepreneur, and business leader before a series of decisions resulted in a federal prison sentence.
Today, Rashmi uses that experience to help leaders navigate pressure, uncertainty, and ethical challenges with greater clarity and integrity. Through her Rise Through It™ framework, she helps individuals and teams strengthen resilience, self-awareness, trust, and values-driven leadership.
SHOW SUMMARY
In this episode of Selling from the Heart, Larry Levine and Darrell Amy welcome Rashmi Airan for a powerful conversation about ethical drift, achievement, pressure, and the decisions sales professionals make when the stakes are high.
Rashmi shares how her identity became tied to achievement and how financial uncertainty and the pressure to succeed influenced decisions that eventually changed the course of her life.
She explains how fear can disguise itself as ambition, urgency, creativity, or aggressive problem-solving—making it easier to rationalize decisions that no longer align with our values.
Rashmi introduces her Clarity Loop, four questions designed to create space between pressure and action: What am I feeling? What story am I telling myself? What matters most? What choice can I own later?
Ultimately, this episode challenges sales professionals to pursue performance without sacrificing alignment, integrity, or the ability to look back and own the decisions they made.
KEY TAKEAWAYS
Integrity rarely collapses—it drifts. Small compromises can gradually move us away from our values.
Pressure can disguise fear as ambition. What looks like urgency or aggressive problem-solving may be driven by something deeper.
Create space between pressure and action. A brief pause can change the trajectory of a high-stakes decision.
Use the Clarity Loop. Ask: What am I feeling? What story am I telling myself? What matters most? What choice can I own later?
Move from performance to alignment. Results matter, but they shouldn't determine which values you're willing to compromise.
Practice moral humility. Recognize that anyone can drift under the right circumstances.
Make disagreement safe. Healthy cultures need people who are willing and able to challenge decisions without fear of punishment.

HIGHLIGHT QUOTES
We all have an inner voice. We all have a moral compass.

We need people to disagree with us.

If we’re acting out of alignment with who we are or what we believe, that’s where the bad decisions happen.

Integrity rarely collapses, it drifts.

What choice can I own later?
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