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Sales and Cigars

Sales and Cigars

著者： Walter Crosby
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概要

 How do you increase sales in your organization? Host Walter Crosby sits down with cigar in hand and has growth minded conversations proven to boost sales. Crosby sets the table by identifying areas where you can excel by first acknowledging the misunderstandings. Like every great sales person he takes time to reflect, strategize and execute. Sit back, listen in, and puff that cigar because Walter Crosby will light you up!2021 Walter Crosby マネジメント マネジメント・リーダーシップ リーダーシップ 経済学
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  • The Approval Trap: Why Being Liked Can Kill the Deal

    The Approval Trap: Why Being Liked Can Kill the Deal
    2026/02/10
    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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    43 分
  • The Hidden Yes: Selling by Removing Resistance, Not Pushing Harder

    The Hidden Yes: Selling by Removing Resistance, Not Pushing Harder
    2026/01/27

    Most sales advice focuses on one thing: motivation.

    More features. More urgency. More discounts.

    In this episode of Sales & Cigars, Walter sits down with consumer psychology expert Matt Sucha to challenge that assumption—and reveal why buyers often don't need more reasons to say yes… they need fewer reasons to say no.

    Matt breaks down the psychology behind stalled deals, hesitation, and "I'll think about it," drawing from behavioral economics, real-world case studies, and his book The Hidden Yes. If you've ever felt like your offer made sense but still didn't close, this conversation explains why.

    In This Episode:

    • Why logic doesn't close deals—feelings do

    • The biggest mistake salespeople make: over-focusing on motivation

    • How uncertainty, doubt, and fear silently kill conversions

    • Why free offers often feel less valuable to buyers

    • The difference between objective value and perceived value

    • How context can change willingness to pay—without changing price

    • A real-world insurance case study that led to a 167% conversion lift

    • Why better sales starts with asking: "Why wouldn't they buy?"

    Key Takeaways:

    • Buyers don't stall because they're unmotivated—they stall because something feels risky.

    • Removing psychological friction is often more powerful than adding incentives.

    • Context (how and when you present information) shapes value more than price itself.

    • Great sales conversations are designed—not improvised.

    Free Gift for Our Listeners!

    Click here for a free gift from Matt!

    Connect with Matt:

    • https://mindworx.net/

    • https://thehiddenyes.com/

    • LinkedIn: https://www.linkedin.com/in/matt-sucha/

    Connect with Walter Crosby and Sales & Cigars:

    Website: Helix Sales Development

    LinkedIn: Walter Crosby

    Instagram: @wcrosby248

    Facebook: 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 Podcasts

    Spotify: 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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    37 分
  • Selling Trust: Entrepreneurship, Ethics, and Disrupting a Broken System

    Selling Trust: Entrepreneurship, Ethics, and Disrupting a Broken System
    2026/01/13

    In this episode of Sales & Cigars, Walter sits down with Alan Ward, CEO of Securely.io, for a thoughtful conversation that spans entrepreneurship, sales, leadership, and the realities of disrupting long-entrenched systems.

    Alan shares how his worldview shapes the way he leads and sells, why transparency is missing in traditional payment systems, and what it takes to introduce truly revolutionary ideas into the market. From cutting a house in half at 19 years old to building a fintech platform designed to serve businesses—not extract from them—this episode is about values, conviction, and selling change the right way.

    In This Episode:

    • Why Who Not How shaped Alan's approach to leadership and business

    • The Golden Rule as a foundation for sales, culture, and decision-making

    • How worldview influences leadership and organizational behavior

    • Alan's entrepreneurial origin story and early risk-taking

    • Why businesses don't truly understand their payment costs

    • What "open banking" means—and why it's a game changer

    • Evolutionary vs. revolutionary change in technology and sales

    • Why education—not pitching—is required to sell disruptive ideas

    • Selling vision to customers, teams, investors, and boards

    • The role of trust, transparency, and alignment in long-term success

    • Celebratory cigars and the moments that make business memorable

    Key Takeaways:

    • Sales is often about helping people see what they couldn't see before

    • Transparency builds trust—hidden systems create resistance

    • Entrepreneurs are always selling, even when they don't realize it

    • Revolutionary ideas feel risky until they become obvious

    • Values-driven leadership scales better than tactics alone

    Connect with Alan:

    • LinkedIn: linkedin.com/in/alan-ward-63938020a

    • Website: Securely.io

    Connect with Walter Crosby and Sales & Cigars:

    Website: Helix Sales Development

    LinkedIn: Walter Crosby

    Instagram: @wcrosby248

    Facebook: 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 Podcasts

    Spotify: 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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    34 分
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