Podcast
The Bill Caskey Podcast: High Impact Sales Training for Sellers and Leaders
Hosted by Bill Caskey · EN
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 insights and actionable advice that will help you build your skills and think differently about the profession of selling.
Whether you're a seasoned sales professional or just starting out in your sales career, The Bill Caskey Podcast has something for you. So, join us every week as we explore the latest trends, techniques, and strategies for driving sales growth and success.
To learn more about Bill Caskey and his work, visit www.billcaskey.com or follow him on LinkedIn at https://www.linkedin.com/in/billcaskey/.
27episodes
Episodes
Newest firstAll episodes
Why Your Prospects Lie (And How to Stop It)
2w ago00:18:22Tap to summarizeYou've heard "buyers are liars." But what if the problem starts with you?In this episode, Bill Caskey breaks down five specific shifts that stop your prospects from shading the truth and create the kind of honest sales conversation where you can actually help.What You'll Learn: → Why salespeople have trained their prospects to lie → How to separate the symptom from the real problem → What high-income producers do differently to create an environment for truth → The right way to ask questions that get beneath the surface → Why your closing rate is a diagnostic tool — not just a scorecard🎟️ FREE EVENT — The Two X Leverage Code Wednesday, May 20th | 7 PM EST. Register → https://resources.billcaskey.com/may-workshop-registration12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com.Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.
Transcribe →Stop Chasing Opportunities — Let Them Find You
Apr 2900:11:48Tap to summarizeWhat if opportunities came to you instead of the other way around? In this episode, Bill Caskey breaks down the three levels of personal brand building that every sales professional and business developer needs to master. Starting with the foundational elements — your story, your values, how you show up — and moving through consistent content publishing and eventually building a platform, Bill makes the case that the future of B2B sales belongs to those who attract, not chase. Download Bill's AI Content Engine: A practical, no-excuses framework you can start on today. 🔗 Click here to get it now!Join the Insider Program: AdvancedSellingPodcast.com/insider 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com.Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.
Transcribe →The One Slide Most Salespeople Miss (And Why It Changes Everything)
Apr 2300:13:48Tap to summarizeMost salespeople build pitch decks full of features, case studies, and credentials — and then wonder why prospects push back on price. In this episode, Bill Caskey reveals the one slide nearly every deck is missing: the Extrapolation Slide. It's not complicated. It takes known quantities, plugs in real numbers, and shows your prospect exactly what's waiting for them on the other side of a "yes." Bill walks through all three columns — cost reduction, revenue growth, and profitability — and explains why this single slide shifts the conversation from budget to transformation. If you're tired of having your solutions picked apart line by line, this episode is for you.Join the Insider Program: AdvancedSellingPodcast.com/insider 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com.Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.
Transcribe →Closing the Trust Gap: Why Prospects Don't Believe You
Apr 200:16:22Tap to summarizeMost salespeople jump straight into questions, pitches, and proposals — without ever addressing the elephant in the room: your prospect doesn't trust you yet. In this episode, Bill Caskey shares a segment from a recent interview where he breaks down the "trust gap" — that invisible wall between seller and buyer that kills deals before they start. Then Bill goes deeper, offering four practical ways to close that gap fast: asking what prospects want from the meeting, laying out the process upfront, staying psychologically safe, and checking in consistently throughout. If you're tired of being treated like just another vendor in a spreadsheet, this episode is your blueprint.Join the Insider Program: AdvancedSellingPodcast.com/insider — $97/month, 🗓️ April 3rd — Live Insider Session 5 Ways to Use AI to Build Business Assets12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com.Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.
Transcribe →The Sales Success Spectrum: Where Are You — and Where Could You Be?
Mar 1800:12:21Tap to summarizeWhere are you on the Sales Success Spectrum? In this episode, Bill Caskey introduces a powerful self-assessment framework — four distinct levels of sales mastery, from the Hustler to the Master — and challenges you to honestly plot yourself on it.At 101, you're grinding on effort alone. At 401, the market comes to you, prospects arrive pre-sold, and income reaches $300K–$1M+. Most salespeople are stuck between 201 and 301 — and the path forward isn't more activity. It's systems, positioning, and personal brand.Click here to download the "Spectrum Framework" PDF.Join the Insider Program: AdvancedSellingPodcast.com/insider — $97/month, 🗓️ April 3rd — Live Insider Session 5 Ways to Use AI to Build Business Assets12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com.Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.
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Your Sales Problem Is Actually a Content Problem
Mar 1200:14:39Tap to summarizeIf your content isn't generating leads, there's a reason — and it probably isn't what you think. In this episode, Bill Caskey breaks down his 5 Laws of Content Conquest: the exact framework sales professionals and business owners need to stop spinning their wheels and start building a content engine that converts. From knowing your prospect's obsession to creating a conversion event that moves suspects to serious buyers, Bill lays out a clear path from beginner to pro. Plus: why Google's "7-hour rule" means your cold calls are losing before they start — and how content fixes that.Join the Insider Program: AdvancedSellingPodcast.com/insider — $97/month, Content Conquest session recording + live follow-up this Friday12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com.Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.
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The Future of Sales: From Training to Coaching, Performance to Warmth
Feb 1800:19:22Tap to summarizeWhat skills will salespeople need six months from now? Five years from now? Tom Batchelder returns to discuss the future of B2B sales, starting with a new concept: "screen trust"—the ability to create warmth and safety through a computer screen. Bill and Tom unpack why concise video communication is the new superpower, how AI slop makes authenticity more valuable, and why most professionals are sitting on a mountain of unused assets. The future isn't about more training—it's about coaching, leverage, and taking 100% responsibility.About Tom Batchelder: Tom is a sales coach based in Sausalito, California, known for his weekly "Tom's Tuesday Tips" videos on LinkedIn, https://linkedin.com/in/tombatchelder. He specializes in working with sales professionals, CEOs, and business owners who want to cut through the noise and get back to what actually works. Learn more at Selling180.com.12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com.Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.
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The Anxiety Epidemic in Sales: Why Going Back to Basics Beats Chasing Technology
Feb 1100:19:25Tap to summarizeWhat's really happening inside sales organizations right now? According to Tom Batchelder—sales coach, painter, and Tuesday video creator—there's an anxiety epidemic running through companies that no amount of AI or automation can solve.In this candid conversation, Bill and Tom dissect the current state of sales coaching and what salespeople are actually dealing with beneath the surface. Tom shares what he's seeing: professionals anxious about getting attention, worried about world events, and frantically searching for the next technology to save them. But the real problem? They haven't mastered the basics.Tom breaks down the difference between clients who can admit they're anxious versus those who hide behind questions about technology and pipeline. He shares his "back to basics" framework that starts with calming down and focusing on what you can control.About Tom Batchelder: Tom is a sales coach based in Sausalito, California, known for his weekly "Tom's Tuesday Tips" videos on LinkedIn, https://linkedin.com/in/tombatchelder. He specializes in working with sales professionals, CEOs, and business owners who want to cut through the noise and get back to what actually works. Learn more at Selling180.com.This is Part 1 of a two-part conversation. Next week: What does the future hold for sales coaching and training?12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com.Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.
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Stop Teaching, Start Observing: The Content Strategy That Actually Works
Feb 400:09:14Tap to summarizeMost sales professionals struggle with the same question: "What should I create content about?" The answer isn't another teaching video or step-by-step guide. It's something far simpler and more authentic.In this episode, Bill introduces the concept of "observational content"—a powerful approach that leverages what you're already seeing every day in your marketplace. Instead of positioning yourself as a teacher, you become a trusted observer who shares insights from real conversations, trends, and patterns.The key insight? You're already an observational machine. This episode shows you how to put those observations to work. Next week: Special guest Tom Batchelder joins for a conversation you won't want to miss.12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com.Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.
Transcribe →Have You Published Your Greatest Hits Yet?
Jan 2100:15:54Tap to summarizeEver wonder what to post that actually means something? In this episode, Bill breaks down the "Greatest Hits" framework - a powerful way to identify the 5-7 core beliefs that define your expertise and turn them into an endless content engine.Inspired by Dan Koe's viral article on changing your life in one day, Bill shares his own five greatest hits including sales leverage over labor, the leverage effect, qualification over closing, positioning as a guide, and achievement as divine assignment. But more importantly, he walks you through the exact 6-part framework for creating YOUR greatest hits.If you've been struggling with what to post or how to stand out, this framework will change everything. 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook.Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com.Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com.
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