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Welcome to The Bill Caskey Podcast, the show for company leaders, sales managers, and salespeople who are looking to take their sales game to the next level. Join your host Bill Caskey, renowned sales coach and strategist, as he shares modern sales strategies and leadership tips that will help you grow your sales team and increase revenue for your business. Each week, Bill brings a variety of guest experts and shares real coaching scenarios from his work with sales teams, providing valuable ...
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The Advanced Selling Podcast

Bill Caskey and Bryan Neale: B2B Sales Trainers, Business Strategists and L

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Bill Caskey and Bryan Neale: B2B sales trainers for the past twenty years share their strategies, frameworks, tips and tricks to help you leverage your talent, grow your skills and create your own sales success. You'll discover how you can shift your mindset, win with prospects and build long-term relationships with your clients so you can thrive and advance in your career. Bill and Bryan's approach to sales is funny, often quirky and always real. Their work has allowed them to help sales pr ...
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Leadership coach, James Mayhew, explores what it takes to lead your company, your small businesses, your teams, and your home with humble confidence. James Mayhew partners with business leaders who want to build a culture that performs, inspires confidence in others, and serve with extraordinary excellence. Connect with James on LinkedIn https://www.linkedin.com/in/jamesrmayhew/ High Performance Workplace Culture Video Series https://www.youtube.com/watch?v=jBGgr... Website https://jamesmayh ...
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In this episode, Bill shares a comprehensive framework for developing your signature story that resonates with prospects and customers. Through his own personal journey from struggling salesperson to successful sales coach, Bill breaks down the essential elements of compelling storytelling: situation, challenge, desire, decision, breakthrough, and …
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In this episode, Bill challenges the notion that selling has to be a struggle. Inspired by Stuart Wild’s philosophy, Bill shares five transformative principles that can make selling not just easier, but more fulfilling. From detaching from outcomes to mastering curiosity, he reveals how modern sales professionals can shift from the outdated “convin…
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In this episode, Bill and Bryan challenge traditional sales metrics and explore the often-overlooked numbers that truly matter in today’s digital sales landscape. The guys discuss crucial modern measurements like inbound lead generation through LinkedIn, the power of tracking unsolicited introductions, and the importance of understanding average da…
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In this solo episode, Bill challenges the conventional wisdom of modern sales coaching by exposing why most coaching relationships fail to deliver real transformation. He argues that effective coaching isn’t about protecting egos or maintaining comfort—it’s about driving genuine growth through constructive confrontation and challenge. Bill presents…
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Too many sales teams use their CRM as a record-keeping tool instead of an agent of action. In this episode, Bryan breaks down how a well-utilized CRM can drive sales efficiency, improve deal visibility, and keep your pipeline moving. He shares simple yet powerful tactics to transform your CRM from a burden into a competitive advantage. Stop logging…
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In this episode, Bill and Bryan dive deep into a crucial sales concept: the importance of selling transformation over features. The guys explore how salespeople often focus too narrowly on short-term gains and immediate features rather than the long-term transformative impact their solutions can have on clients’ businesses. Through real-world examp…
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In this final installment of his three-part series on critical future sales skills, Bill Caskey explores the vital concept of team alignment planning. Bill explains why traditional approaches to stakeholder management are no longer sufficient in today’s complex sales environment. He also reveals how AI is transforming the traditional diagnosis phas…
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In this episode, Bill and Bryan explore a common phenomenon in sales organizations: why middle performers often harbor resentment towards top performers. The guys dissect the excuses commonly used to discredit high achievers’ success - from territory advantages to preferential treatment. The hosts share practical advice for breaking free from this …
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In this solo episode, Bill tackles another critical skill for modern sales professionals - the art of clear path planning. He explains why simply knowing your destination isn’t enough; you must be able to clearly map out and communicate the journey from your prospect’s current reality to their desired future state. He challenges the common notion t…
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Ever consider that the opportunities you’re chasing might be right under your nose? In this episode, Bryan highlights why your best prospects aren’t always new—they’re already in your CRM. Learn how to turn your "Closed Lost" and "Inactive Client" lists into powerful prospecting tools to revive old connections and spark new opportunities. Key Takea…
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In this episode, Bill and Bryan discuss the concept of “Quitter’s Day” - the January 10th phenomenon where most people abandon their New Year’s resolutions. The guys dive deep into what they call “The Big Illusion” - the false belief that conforming to others’ expectations leads to fulfillment. Through personal anecdotes and the story of Brad Steve…
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In this solo episode, Bill Caskey explores a vital but often overlooked sales skill - the ability to help prospects vividly envision their future after implementing your solution. Through a compelling case study of a leadership program for sales managers, he demonstrates how making the future tangible can transform both the sales process and delive…
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In this conclusion to the Million Dollar Seller Roadmap series, Bill Caskey reveals the final three steps to truly maximize your revenue potential. Learn how to pour gasoline on your foundation and interaction strategies with these game-changing approaches: ✓ Landing Larger Accounts: Discover how to position yourself as a thought leader and create …
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In this episode, Bill and Bryan cut through the AI hype to deliver actionable advice for sales professionals just beginning their AI journey. The guys share real-world applications including prospect list generation, content creation, and sales call preparation. Whether you're AI-curious or AI-anxious, this episode provides the concrete steps and u…
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In this insightful solo episode, Bill challenges common sales beliefs by exposing three destructive fallacies: The Activity Fallacy (believing more activity automatically equals better results), The Pressure Fallacy (assuming increased pressure leads to improved performance) The Control Fallacy (trying to micromanage prospect behavior). Caskey expl…
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In Part 2 of this powerful revenue-scaling series, Bill Caskey reveals the crucial interaction stage of the Million Dollar Selling Method. Building on the foundation from Part 1, discover the three key steps that will transform how you connect with prospects and convert opportunities: ✓ Pipeline Building: Learn why cold outreach isn't your only opt…
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In this episode of the Advanced Selling Podcast: 2 Minute Drill, Bryan shares a practical framework for maximizing your ROI at trade shows. Too often, salespeople approach these high-cost opportunities without a clear plan. Bryan breaks down his proven framework into three key phases: pre-show, at-show, and post-show. Discover how to: ✅ Set measura…
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Want to dramatically scale your revenue in 2025? In this first episode of our three-part series, Bill Caskey breaks down the crucial foundation stage of the Million Dollar Selling Method. Bill shares the first three steps to transforming your sales approach: ✓ Million Dollar Mindsets: Discover the game-changing perspective of detachment and unlock …
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In their first episode of 2025, Bill and Bryan discuss strategies for sales professionals returning to work after the holiday break. The guys share four powerful techniques to jumpstart the new year: reconnecting with your fundamental purpose, actively engaging with your market through in-person meetings, developing a compelling personal brand in t…
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