The Advanced Selling Podcast: Sales Training | Leadership Coaching | B2b Sales Strategy | Prospecting Tips

In this solo episode, Bill challenges sales professionals to honestly evaluate whether their sales process genuinely benefits prospects. Drawing from his book "12 Bold Moves," he explains how to transform your approach by offering valuable assessments and personalized recommendation documents to prospects—whether they buy or not. Caskey illustrates how this approach, enhanced by AI tools, can help eliminate "commission breath" and potentially double closing rates by prioritizing genuine value delivery over immediate sales. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com  

In this episode, Bill and Bryan share their predictions for the sales industry in 2025, including the accelerating impact of AI on sales roles, the death of "sticky" cold outreach tactics, the decline of legacy media, a potential resurgence of in-person sales meetings, the growing importance of personal branding, and a predicted exodus of Baby Boomer sales professionals. The guys also discuss some amusing trends they are seeing during holiday travel, and share thoughts on AI tools for Christmas shopping.  This end-of-year episode combines practical sales insights with entertaining commentary on current trends affecting sales professionals. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now

In this solo episode, Bill challenges traditional sales training wisdom by proposing a revolutionary approach: using digital assets to transform the buyer-seller relationship. Through a personal case study, he demonstrates how pre-recorded video content can ease the burden on salespeople to always be "on," while simultaneously building trust with prospects before the first call. Caskey argues that this approach not only aligns with changing buyer behaviors but also helps scale business results more effectively than relying solely on traditional sales skills. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

In the final installment of their Ultra High Achievers series, Bill and Bryan explore how top performers communicate. The guys break down the distinct language patterns that set ultra-successful salespeople apart. Learn how elite performers use contextual awareness, empathetic language, strategic disagreement, and financial fluency to achieve extraordinary results. Don't miss these crucial insights on mastering the vocabulary of success. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo series episode, Bill Caskey shares a revealing story about witnessing poor customer service at a store he visited recently, where a salesperson failed to meet a customer at their knowledge level when discussing smartwatch options. He uses this experience to illustrate a crucial sales lesson: the importance of understanding where customers are in their journey before attempting to sell. Caskey emphasizes that improving close rates requires asking the right questions and meeting prospects where they are, rather than making assumptions about their knowledge or needs. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

In this solo episode, Bryan and special guest Chelsea Madden dive into the power of intent data and how sales teams can leverage it to craft smarter, more effective strategies. They discuss why intent data is a game-changer for identifying when prospects are actively researching solutions—but with a caveat: it’s not a shortcut to the sale. Learn how to use intent data authentically, avoid the “big brother” vibe, and adopt a consultative approach that resonates with prospects. If you want to deepen your engagement across the decision-making process, and fish in a puddle instead of the ocean, this episode is a must-listen! Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

In this second installment of their ultra-high achiever series, Bill and Bryan dive into the concrete actions that set exceptional performers apart from their peers. The guys explore why some people know what to do but don't take action, the power of rapid execution, and why ultra-high achievers plan in years while others plan in days. They also challenge conventional wisdom about working from home and share insights about investing in accelerated learning. Plus, they discuss an intriguing tangent about a multi-million dollar modern art piece that sparks a conversation about value and perception.  Join us on December 6th for our Personal Business Planning Workshop where we'll incorporate AI into your 2025 strategy. Insider members get 50% off! http://advancedsellingpodcast.com/insider ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insid

In this solo episode, Bryan and special guest Chris Dornfeld dive into the science of effective sales compensation and incentive programs. They explore why most incentive budgets fail to deliver the intended results and how a behavior-focused, data-driven approach can change that. Chris shares insights from his company, Whistle, which uses behavioral science to optimize incentive programs, showing that immediate, personalized rewards tied to specific sales activities are far more effective than traditional lump-sum payouts. You’ll learn why cash remains king, how to layer individual and team-based incentives, and the benefits of automating real-time rewards to keep motivation high. If you're trying to build a dynamic rewards system that drives the right behaviors, this episode is packed with actionable advice to help you rethink your approach to motivating your sales team. Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the

In this first episode of a three-part series, sales experts Bill and Bryan explore how ultra-high achievers think differently than even regular top performers. The guys break down the unique mental patterns that set exceptional performers apart, including their exponential thinking, extreme objectivity, total ownership mindset, and purpose-driven approach. They also reveal why these rare individuals operate on an entirely different level - and why comparing to averages never crosses their minds. This episode kicks off an in-depth look at the thinking, doing, and communication patterns of those who consistently break records and write their own rules. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider

In this solo episode, Bryan takes a thoughtful look back at his biggest takeaways from 2024. He explores the idea that sales is 90% process and 10% magic—and why most sales training only focuses on the magic. To drive exponential results, Bryan argues, great training must be paired with a powerful sales operating system. He also dives into the principle that success loves discipline. But discipline doesn’t mean rigid routines—it’s about consistently executing simple, effective processes. Bryan shares how this approach helps sales teams avoid common pitfalls and unlock greater success. Whether you’re a sales leader or an individual contributor, this episode offers fresh insights to sharpen your strategy and fuel your growth. Curious about the 90%? You can learn more about the Blind Zebra Sales Operating System here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

Bill and Bryan conclude their powerful three-part series by focusing on execution and implementation. After examining current reality and creating vivid future goals in the previous episodes, they dive into practical strategies for bridging the gap between where you are and where you want to be. Learn valuable frameworks including the Start-Stop-Continue analysis, how to leverage AI tools for planning, and discover the power of Dan Sullivan's entrepreneurial time management system with its focus, buffer, and free days. This episode provides actionable steps to turn your 2025 vision into reality while maintaining balance and clarity of thought. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join

In part two of their three-part series on goal setting mastery, Bill and Bryan dive into the importance of creating a clear and vivid vision for your sales future. The guys discuss why many salespeople struggle with setting specific goals and share practical approaches to overcoming the fear of commitment in goal-setting. They emphasize the power of visualization, from detailed income targets to ideal calendar management, and explain why your professional aspirations should be personal and aspirational rather than merely meeting company quotas. Through real-world examples and actionable insights, Bill and Bryan guide you in creating a detailed roadmap for your sales future that goes beyond simple revenue targets to encompass your ideal role, schedule, and lifestyle.  ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open

In this first episode of a three-part series, Bill and Bryan explore the importance of honest self-assessment in sales performance. They discuss why facing your "brutal facts" - from income reality to process effectiveness - is crucial for growth. The guys share insights about evaluating lead sources, analyzing revenue distribution, and understanding your true strengths and weaknesses. Drawing from Tom Bilyeu's success story and Grant Cardone's marketing strategies, Bill and Bryan offer practical frameworks for taking inventory of your current sales reality. Whether you're struggling with cold outreach or relying too heavily on a single revenue stream, this episode provides valuable guidance for end-of-year reflection and planning. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not che

In this entertaining episode, Bill Caskey speaks with content marketing veteran Erik Deckers about the plague of corporate jargon in today's business world. Deckers, owner of a content marketing agency and longtime humor columnist, shares his insights on why phrases like "let's double click on that" and "value prop" are undermining clear communication in business. The conversation explores why professionals fall into using corporate buzzwords, how it affects their message clarity, and practical ways to communicate more effectively. Whether you're guilty of "circling back" or building planes while flying them, this episode offers a refreshing take on the importance of straightforward business communication and the power of writing like you're talking to your mom. Learn more about Erik and follow his blog at http://erikdeckers.com. You can also see some of his work at https://problogservice.com/. Want to break free and soar to new heights? "12 Bold Moves" is your gateway to a fearless reinvention of self an

In this solo episode, Bryan talks with empathy consultant Liesel Mertes about the transformative power of empathy in sales. Liesel shares how the loss of her daughter Mercy led her to help companies build empathetic cultures. They explore how empathy helps salespeople understand their customers beyond the immediate problem, creating deeper, more meaningful connections. For sales leaders, fostering empathy means building trust and psychological safety within teams.  Liesel stresses that empathy is an ongoing practice, essential for driving better sales outcomes. Curious what the Blind Zebra Sales Operating System is all about? You can learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

In this solo episode, Bryan is joined by special guest Will Barron to discuss the critical role of a well-defined, systematic sales process. They stress that true sales success comes from mastering fundamentals like booking meetings and communicating value, rather than relying on quick-fix tactics or gimmicks. Will highlights the importance of a repeatable, reliable sales process backed by precise metrics—understanding how many activities lead to meetings, proposals, and closed deals. He also points out that sales training often overemphasizes product knowledge at the expense of process-driven success. Listen now for great advice on systematizing the sales process to achieve efficiency and financial freedom. Curious what the Blind Zebra Sales Operating System is all about? You can learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

In this episode, Bryan and Bill continue their conversation about the concept of authenticity in sales and the critical importance of "backstage" work. They explore how the unseen majority of a salesperson's efforts shapes their public persona and performance. The guys discuss the value of clearly defining an ideal customer profile and propose a fresh approach to objection handling through "Yellow Flag" meetings.  The conversation also touches on discovering one's noble purpose in sales and how internal work leads to more authentic and effective client interactions. This episode is a must-listen for sales professionals seeking to enhance their authenticity and effectiveness in the field. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http

In this solo episode, Bryan is joined by Zinc Partners' Matt Wittlief to dive deep into the world of Customer Relationship Management systems, focusing on how salespeople and sales leaders can leverage CRM to drive better results.  For many sales professionals, platforms like Salesforce are seen as glorified rolodexes and just another task on their to-do list. But Matt and Bryan challenge that notion and encourage a different perspective. They discuss how to make your CRM work for you by understanding the essential information that can enhance your daily workflow, prioritize your tasks, and guide your decision-making. The guys also explore the art and science of forecasting, from analyzing opportunities and deal stages to evaluating historical trends. They share practical strategies for creating reliable forecasts that empower your team and influence organizational decisions. Curious what the Blind Zebra Sales Operating System is all about? You can learn more here. And if you haven't already, make sure you jo

In this episode, Bill and Bryan discuss authenticity in sales. They explore the tension between being genuine and using learned sales tactics, questioning whether certain techniques compromise a salesperson's authenticity. The guys talk about the evolution of sales practices, the importance of unlearning outdated methods, and the need for salespeople to adapt to the present and future of selling. They challenge listeners to reconsider traditional closing techniques and instead focus on building trust through consistent, value-driven interactions. This episode offers fresh perspectives on maintaining integrity in sales while still achieving results in today's rapidly changing business landscape. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go

In this solo episode, Bryan is joined by Andy Mork, owner of Mork Productions and BrandSlap. Bryan and Andy talk about the ongoing struggle salespeople face to capture buyers' attention and stay relevant. And while they agree that short form video is one of the best ways to do that, they also remind us that the key to creating good content is authenticity. Bryan and Andy offer some great advice for getting started with video, embracing your own imperfection and what to do if you simply don't know what to say. Curious what the Blind Zebra Sales Operating System is all about? You can learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.