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 being the transformational partner your clients actually need. 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bol...

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 okay" dynamic transforms customer interactions, how upfront agreements and detachment create better outcomes, and the critical importance of operati...

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 in business was actually himself. The conversation digs into why we're taught to focus on what we want to do rather than who we want to be, and ho...

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 lessons we can all take from Charlie's life: his courage to engage in difficult spaces, his ability to stay on message, his mastery of media platforms...

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 guide. You'll discover why most salespeople are closing only 15-20% of their deals (hint: prospects don't know what happens after they say "yes"),...

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 inspire trustworthiness from the very first interaction. When you master these techniques, prospects stop looking for reasons NOT to work with ...

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 a game-changer. Jonathan shares his journey from skeptical observer to AI advocate, explaining how he built a seven-figure business in under two y...

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 brutal honesty. Warning: If you're deeply invested in traditional sales methods, this episode might make you uncomfortable. But if you're ready to ch...

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 episode is perfect for consultants, coaches, and service providers who want to scale beyond referrals and create a systematic approach to convert...

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, or managing team members in this age group, this episode provides actionable insights on leveraging your wisdom and experience while avoiding th...

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 sales landscape. Join Bill next week for Part 2, where he'll reveal six more critical elements affecting sales performance in today's market. Join ...

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 problem statements, understanding internal customer motivations, defining your transformation promise, and creating a repeatable workshop or maste...

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 professional, consultant, or business leader, these strategies provide a clear roadmap to elevate your performance and accelerate your business growth...

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 Bill will complete his breakdown of all 10 habits that can transform your sales approach and accelerate your business growth. 2X Strategies Dow...

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 this approach through a real coaching example with a financial professional, showing you exactly how to implement this framework in your own c...

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 through key metrics including conversion rates, sales cycle length, lead generation sources, and untapped assets that can dramatically impact rev...

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 conversations away from price. He emphasizes the importance of having visual sales processes, lead generation devices, and consistent content creation to ...

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 explores why recognizing your unique value is essential in an increasingly automated world, and why authentically sharing your experiences cre...

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 hire people to build business—you hire people to build systems that build business.” Bill is hosting a LinkedIn Live session on Friday at 8:...

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 importance. He demonstrates how vulnerability and authenticity can transform your sales approach while providing actionable steps to craft yo...