Authenticity Episodes

Customers can smell a script from a mile away. They know when you're fishing for answers, when you're projecting your own assumptions, and when you're telling them what you think they want to hear instead of what they need to hear. Authenticity in selling means showing up as a real human being — sharing your genuine passion for what you do, being willing to say no when it's not the right fit, and having the courage to tell the truth even when the truth kills the deal. It means your intent matches your actions. The only difference between a good salesperson and a con artist is intent, and that difference is everything. These episodes explore what it looks like to sell without pretending, to build trust by being honest instead of being polished, and to let go of the plaid jacket persona that gives our profession a bad name.
Feb. 17, 2026

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, …

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Jan. 27, 2026

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.

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Jan. 21, 2026

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") …

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Jan. 13, 2026

Pete Smith, founder of SpotLogic and veteran sales leader, discusses why enterprise sales reps are drowning in tools and still starving for insight. We discuss the "Cognitive Load" crisis in modern selling.We explore why 84% of enterprise deals stall after the first meeting and how Sales Enablement leaders can help reps stop "winging it" and start winning. From his days at NCR’s legendary "Sugar Camp" to building deal intelligence software, Pete reveals how to earn the status of a "Trusted …

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Dec. 9, 2025

Episode Summary What do selling gum in the 5th grade and playing defense in hockey have in common with high-stakes Enterprise Sales? According to Nina Iannuzzi , absolutely everything. In this episode of Thoughts on Selling ,...

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Nov. 25, 2025

Episode Summary Sales is human work. And humans run on purpose, energy, and trust. Lee Levitt sits down with Lester Sidney , a 17-year tech sales veteran and "brother from another mother," for a raw and authentic conversation...

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Nov. 4, 2025

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...

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Oct. 28, 2025

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 Agr…

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Oct. 22, 2025

Episode Summary Is your sales pitch a rehearsed monologue or a collaborative improv scene? In this episode of Thoughts on Selling , Lee Levitt sits down with Kevin Hubschmann , former enterprise rep turned comedian and founde...

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Oct. 15, 2025

Episode Summary Is sales a science or a performance art? In this episode of Thoughts on Selling , Lee Levitt sits down with Jake Isham , a filmmaker, creative director, and founder of Creative Minds Agency . Jake’s story is p...

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