Leadership Episodes

Chris Carter — technologist, keynote speaker, and SAP ecosystem veteran — joins Lee to unpack what it actually means to use AI well in enterprise selling. From using Gemini to simulate discovery conversations to the Peloton analogy that woke up a room of Oracle salespeople, this episode is about preparation, strategy, and making your own rules. If you're firing off AI-generated emails and wondering why nobody's responding, this one's for you.

Joe Terry—former CEO of Corporate Visions and co-author of the USA Today bestseller Surrender to Lead—joins me for a conversation about what actually drives results.

We dig into the action trap (why hitting every activity metric still misses the number), the results pyramid (experiences → beliefs → actions → results), and the mindset shift that changes everything: showing up to give, not to get.

Joe shares the SHIFT framework for getting out of your own way, the four questions that make buyers stop and pay attention, and why 12 executives in the same room will give you 12 different answers to "What are our top three objectives?"

This one's for anyone tired of inspecting pipeline and ready to start coaching belief.

In this episode of Thoughts on Selling, Lee Levitt sits down with Drew Sechrist, CEO of Connect the Dots and an early Salesforce employee, to discuss the evolution of sales from the "No Software" era to the age of AI. Drew shares insights from his time working alongside Marc Benioff, emphasizing the critical role of "osmosis" in learning sales skills—a benefit he fears is being lost in today's remote-first work environment. He argues that while technology has made many aspects of sales easier, the loss of in-person mentorship and hallway conversations has made the profession harder for newcomers to master.

The conversation pivots to the future of selling in an AI-dominated world, where Drew asserts that "trust capital" is the only durable moat for sellers. As AI automates routine tasks, the human ability to build deep, high-stakes relationships becomes more valuable than ever. Drew explains how his company, Connect the Dots, is helping sellers leverage their "relationship capital" …

Carole Mahoney, author of Buyer First, shares her mission to change the negative perception of sales. We discuss the power of "cognitive behavioral" sales training, why improv is a crucial skill for modern sellers, and how a manager's mindset can statistically predict a team's success or failure.

In this episode of Thoughts on Selling, Lee Levitt sits down with Amos Balongo—a leadership expert who is in the business of "manufacturing leaders" to be exceptional communicators. We dig into the critical gap where strategy fails: when leaders rely on "Positional Authority" ("I told you to do this") rather than "Influential Leadership" that invites collaboration. Amos breaks down his framework for moving teams from simple motivation (an "outside job") to genuine inspiration (an "inside job") and finally to transformation , explaining why simplicity mobilizes teams better than complexity and how applying "Situational Leadership" prevents communication breakdowns.

Episode Summary Are you part of the 82% of leaders who feel like "Accidental Managers"? In this episode of Thoughts on Selling , Lee Levitt talks with Ben Perreau , a former music journalist turned leadership expert and founder of Parafoil . We discuss the most dangerous leap in any career: the transition from Individual Contributor (IC) to Team Leader. Ben explains why companies set new managers up to fail by promoting them for technical skills but ignoring the emotional intelligence required t...

In this episode of Thoughts on Selling, Lee Levitt sits down with ETA leader Garth Fasano to discuss the massive shift from traditional inside sales to "Agentic AI"—autonomous agents that think, adapt, and sell without fatigue. Garth explains why small businesses are adopting this technology faster than enterprises to solve the "consistency" problem, ensuring every prospect gets a "fully caffeinated" interaction even after 175 calls. We also explore the future of "Bot-to-Bot" commerce, where AI buyers negotiate with AI sellers, and how this shifts the sales function from simple execution to strategic business visibility.

Episode Summary In this episode of Thoughts on Selling , Lee Levitt sits down with Sean Gannon , founder of GTMPPL (GTM People) , to answer the "unanswerable" question: Who is Sean Gannon? We dive into a refreshing (and controversial) take on Sales Leadership : why the best managers strive to make themselves obsolete . If your team can't function without you, you aren't leading—you're hovering. From the trenches of EdTech to the nuances of Sandler Training , Sean shares candid stories about the ...

Episode Summary In this special episode of Thoughts on Selling , Lee Levitt sits down with Gerhard Gschwandtner , founder of Selling Power Magazine . Gerhard’s story is extraordinary—from growing up in Austria to creating one of the most influential media platforms in sales history. We discuss how Curiosity , Creativity , and Courage shape every career, and why the most important question isn't "What do you want to buy?" but "Who are you?" Gerhard shares lessons from giants like Zig Ziglar and M...

In this episode of Thoughts on Selling, Lee Levitt sits down with Lauren Bailey -- founder of Factor 8, #GirlsClub, and Legacy VIP -- for a raw and inspiring conversation about the "Inner Game" of leadership. Lauren shares how personal tragedy birthed her mission to help executives show up authentically, and she breaks down actionable frameworks like "The Pause Game" for coaching reps and the "3 F's" (Fears, Failures, and F-ups) for building psychological safety. From the wisdom of The Four Agreements to the tactical execution of inside sales, this is a masterclass on why perfectionism kills confidence and why true leadership is about creating space, not taking it.