『The Approval Trap: Why Being Liked Can Kill the Deal』のカバーアート

The Approval Trap: Why Being Liked Can Kill the Deal

The Approval Trap: Why Being Liked Can Kill the Deal

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概要

 In this episode of Sales & Cigars, Walter Crosby sits down with Nick Massaro of Membrane for a candid, no-BS conversation about what actually holds good salespeople back. From early sales foundations and structured training to the mindset traps that quietly derail deals, this episode digs into the space between opening and closing—the part most reps avoid and where deals are truly won or lost. Nick shares his journey into sales, the evolution of his mindset, and the hard-earned realization that being "the most liked rep" is often a sign something went wrong. Together, they unpack the dangers of approval-seeking, why discomfort is part of great selling, and how modern buyers require a different kind of leadership from sales professionals. This is a grounded, honest conversation for salespeople who want to stop getting compliments instead of contracts. Episode Highlights Why "You were the best rep" is often a kiss of deathThe difference between opening deals and advancing themHow early structure shaped Nick's sales foundationThe mindset shift required to lead buyers without controlling themWhy avoiding money conversations quietly kills dealsSelling outcomes vs. selling features—especially in complex softwareLetting go of approval to ask better questionsWhat great sales and good parenting surprisingly have in common Key Takeaways Being liked doesn't equal being effectiveThe middle of the deal—not the open or close—is where salespeople growApproval-seeking prevents tough (necessary) conversationsBuyers are in control—but salespeople must still leadDiscovery isn't about sounding smart; it's about creating clarityAuthenticity beats polish every timeProcess creates freedom, not rigidity Who Should Listen This episode is for: Salespeople who hear "we loved you" more than "we're buying"Reps who love prospecting but struggle with deal momentumSales leaders coaching mindset, not just activityAnyone selling complex or non-commodity solutionsBusiness owners trying to understand what their sales team is really up against About the Guest Nick Massaro is a sales professional at Membrane with a background spanning insurance, SaaS, and sales-as-a-service environments. Known for his authenticity and curiosity, Nick brings a thoughtful perspective on modern selling—one rooted in structure, accountability, and continuous improvement. Connect with Nick Nick Massaro on LinkedInMembrane Connect with Walter Crosby and Sales & Cigars: Website: Helix Sales DevelopmentLinkedIn: Walter CrosbyInstagram: @wcrosby248Facebook: Helix Sales Development Share Your Thoughts: We'd love to hear your feedback and experiences! Drop us a line and join the conversation on social media using #SalesAndCigars. Never Miss an Episode! Join the Sales & Cigars community by subscribing to our podcast and YouTube channel:Subscribe to the Podcast:Apple Podcasts: Subscribe on Apple PodcastsSpotify: Follow on Spotify...and wherever you listen to podcasts! Subscribe to Us on YouTube: Stay updated with our latest video content by subscribing to our YouTube channel. Hit the bell icon for notifications on new uploads! YouTube: Sales & Cigars Channel Stay in the loop: By subscribing, you'll get instant access to new episodes, insightful conversations, and bonus content designed to elevate your sales skills and more. Keep savoring those cigars and stay sharp in sales! Until next time, keep listening to Sales & Cigars—the podcast where the only smoke we blow is from cigars.
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