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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 Real Leadership Problem with Janelle Harder
18:28
18:28
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18:28
When a leader comes to executive coach Janelle Harder with a problem employee, she knows the real issue often lies elsewhere. In this conversation, Bill sits down with Janelle, founder of Humannovate Consulting, to explore the gap between the problems leaders present and the real challenges they face. With nearly 15 years working inside Fortune 500…
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Bill answers three critical questions from listeners: What's the greatest sales lesson learned the hard way? What's the biggest challenge in the last five years? And if he could eliminate one sales practice forever, what would it be? Key Takeaways: Why pushing harder in follow-up creates resistance and kills deals How the harder you press, the less…
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Stop Forecasting, Start Planning: Your 2026 Success Blueprint
15:36
15:36
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15:36
Planning season is here, but most salespeople confuse forecasting with actual planning. In this episode, Bill shares three critical building blocks from his upcoming Personal Business Planning Workshop that will help you create a comprehensive plan for 2026—not just revenue targets, but a real roadmap for growth. Bill walks you through practical ex…
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The Expertise Trap: Why Being the Expert Isn't Enough
14:02
14:02
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14:02
Bill opens up his coaching playbook to share three real goals from new clients—and what he's going to do about them. From comfort zones to expertise, from undervaluing yourself to finding confidence, these objectives represent what 90% of B2B sales teams struggle with. Listen as Bill breaks down the first goal: how to move from being the expert to …
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5 Lessons from Front-Line B2B Professionals (And How You Can Apply It Today)
13:00
13:00
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13:00
What happens when experienced B2B sales professionals—many with engineering backgrounds—spend six months mastering consultative selling techniques? In this episode, I share the five most impactful lessons from a recent training program with high-end hydraulic and timing solutions salespeople. You'll discover why being mindful of the "okay vs. not o…
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Finding Yourself in Business with Jason Leister
24:17
24:17
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24:17
In this episode, Bill Caskey sits down with marketing expert and recovering musician Jason Leister to explore a topic that sits beneath the surface of most business conversations: the power of being yourself. Jason shares his journey from being a "straight-A sheep" who followed all the rules to discovering that the only person he hadn't tried being…
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Remembering Charlie Kirk: Lessons in Being Fearless & Empowered
7:10
7:10
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7:10
In this heartfelt tribute episode, we pause to reflect on the life and legacy of Charlie Kirk, the founder of Turning Point USA who was tragically taken from us far too soon. While this isn't a political analysis, it's a personal reflection on what we can learn from Charlie's approach to life and leadership. This episode explores the leadership les…
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How to Get in the Right Position to Close More Deals
13:39
13:39
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13:39
One of the biggest problems B2B sales professionals face? They're out of position from the moment they walk into a meeting. In this episode, Bill shares a tennis lesson that completely changed how he thinks about sales positioning, and reveals the three essential elements every salesperson needs to transform from a desperate "seller" into a trusted…
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Why Prospects Lie to You (And How to Stop It)
10:46
10:46
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10:46
Ever wonder why prospects aren't being completely honest with you? In this episode, Bill reveals the uncomfortable truth: buyers think it's okay to lie to salespeople. Drawing from 30 years in the business and insights from sales expert Terry Slattery, Bill explains why prospects withhold critical information and shares four proven strategies to in…
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Stop Cold Calling Forever: How AI Can 3X Your Sales
25:44
25:44
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25:44
Ready to transform your sales game? In this episode, Bill Caskey sits down with Jonathan Mast, founder of White Beard Strategies, to reveal how AI can revolutionize your sales process—without replacing you. If you're tired of endless cold calls, struggling to keep up with CRM updates, or feeling overwhelmed by your daily tasks, this conversation is…
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5 Unpopular Sales Takes That Get Me Banned
17:41
17:41
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17:41
Why doesn't Bill get invited to traditional sales conferences anymore? In this no-holds-barred episode, he shares five controversial takes that challenge everything the sales industry has been teaching for decades. From why persuasion is overrated to why cold calling is a symptom of failed strategy, Bill dismantles conventional sales wisdom with br…
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Turning Cold Calls Into Consulting Contracts: 5 Essential Steps
11:59
11:59
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11:59
In this episode, Bill shares a live coaching session with one of his clients - a leadership consultant who landed his first cold outreach call after just one week of working a LinkedIn strategy. Bill breaks down the exact 5-step framework he uses to help consultants and service providers turn initial prospect calls into profitable engagements. This…
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Staying Relevant After 50: Sales Success in a Changing World
19:47
19:47
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19:47
Bill Caskey tackles a topic close to home - how sales professionals over 50 can maintain and even increase their relevance in a rapidly evolving marketplace. Drawing from personal experience and client success stories, Bill shares five critical strategies that seasoned professionals must adopt to thrive. Whether you're approaching 50, already there…
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Buyer Behavior Revolution: Why Exceptional Talent Gets Average Results
16:42
16:42
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16:42
Bill explores why talented sales professionals often achieve merely average results—and it has nothing to do with work ethic, integrity, or lack of skills. Bill delves into how dramatically buyer behavior has changed and what sales organizations must do to adapt. He reveals the first five crucial shifts in buyer behavior that are transforming the s…
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Everyday Leads: How to Generate New Opportunities Without Burning Out
16:24
16:24
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16:24
Bill introduces his concept of "Everyday Leads" - a framework for consistently generating new business opportunities through leverage rather than labor. He explains why traditional cold calling burns people out and introduces five key elements you need to implement an effective lead generation system: proper market positioning, clear external probl…
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The 2X Roadmap: 10 Habits of High-Performers (Part 2)
15:34
15:34
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15:34
In this follow-up episode, Bill completes his breakdown of the 10 strategies that can double your business growth. Building on last week's fundamentals, Bill reveals five additional habits that separate top performers from the rest. These insights come directly from Bill's observations of million-dollar performers. Whether you're a sales profession…
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The 2X Roadmap: 10 Habits of High-Performers (Part 1)
12:33
12:33
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12:33
In this episode, Bill shares the first five habits that separate top sales performers from the rest. Recorded from a live client session, Bill reveals key strategies that can help you double your business growth. These actionable strategies come directly from Bill's observations of high achievers in the field. Tune in next week for Part 2, where Bi…
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Tired of complicated storytelling advice with no practical framework? In this episode, Bill shares his straightforward O-O-O-E method for business storytelling that anyone can use right away. Learn how to craft compelling stories using three key observations followed by one powerful epiphany that resonates with potential clients. Bill illustrates t…
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Questions To Transform Your Sales Process
12:59
12:59
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12:59
In this episode, Bill shares his proven method for starting new client engagements - a strategic 20-question assessment that identifies sales performance gaps and growth opportunities. Whether you're a VP of Sales, CEO, or frontline salesperson, these diagnostic questions help pinpoint exactly where your sales process needs improvement. Bill walks …
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In this episode, Bill Cakey shares 10 proven strategies that have helped his high-achieving clients (those earning $150K-$500K annually) double their revenue and increase their market impact. Bill walks through each strategy in detail, from crafting a compelling personal and corporate story to developing an economic philosophy that shifts conversat…
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The Modern Seller's Mindset: 5 Mental Shifts for Success
12:04
12:04
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12:04
In this episode, Bill shares five powerful mindset shifts that can transform your sales performance in today’s rapidly changing marketplace. Drawing from his exclusive monthly Insider group sessions, Bill reveals half of his coveted “10 Mindsets” framework that helps sales professionals, CEOs, and entrepreneurs excel at customer acquisition. He exp…
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In this episode, Bill challenges the traditional labor-dependent approach to sales growth and introduces his framework for building a sustainable sales engine. He explains why relying solely on personnel leads to inconsistent results, forecasting difficulties, and vulnerability to staffing changes. Instead, he presents a paradigm shift: “You don’t …
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Crafting Your Signature Story: A Framework for Authentic Connection
19:31
19:31
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19:31
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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The Joy of Selling: 5 Ways to Remove the Struggle from Sales
17:22
17:22
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17:22
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 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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