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 a compelling formula for growth: discomfort multiplied by action equals real transformation. He explains why coaches who prioritize likability over e...
Feb 14, 2025•2 min
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 data and start leveraging it! Curious about certification in the Blind Zebra Sales Operating System ? Learn more here . And if you haven't already, m...
Feb 12, 2025•15 min
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 examples like Gong software and personal experiences, they demonstrate how successful sales require understanding and articulating the complete journey of ...
Feb 10, 2025•17 min•Ep. 825
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 phase of sales, shifting the salesperson’s core value to implementation expertise and team alignment. Lastly, he demonstrates why getting all stakeholders...
Feb 07, 2025•6 min
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 mindset, including how to leverage top performers’ willingness to share their secrets of success. Whether you’re a sales leader or working to climb th...
Feb 03, 2025•18 min•Ep. 824
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 that “nobody cares about the details” and emphasizes why building buyer confidence through detailed planning is crucial in complex sales. Is it time to...
Jan 31, 2025•4 min
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 Takeaways: ✅ Use your "Closed Lost" list to re-engage prospects from 6-12 months ago—they may be ready now. ✅ Don’t overlook "Inactive Clients"—reach out 1...
Jan 29, 2025•12 min
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 Stevens’ dramatic career shift from pharmaceutical sales to NBA coaching, they discuss the importance of staying true to your authentic self in sales and l...
Jan 27, 2025•21 min•Ep. 823
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 deliver genuine value to prospects, whether they buy or not. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold M...
Jan 23, 2025•6 min
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 use cases you need to start leveraging AI in your sales process today. You'll discover insights about treating AI like a knowledgeable friend rather th...
Jan 20, 2025•22 min•Ep. 822
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 explains why these mindsets can actually hinder sales success and encourages sales professionals and leaders to examine their own potentially limiting bel...
Jan 16, 2025•6 min
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 measurable goals and engage on social media before the event. ✅ Build meaningful connections by interacting with speakers and influencers during the show. ✅ ...
Jan 15, 2025•11 min
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 the digital space, and strengthening your network through strategic introductions. They also emphasize the importance of getting physically out of the ...
Jan 06, 2025•16 min•Ep. 821
In this final episode of the year, Bill and Bryan share their approaches to year-end reflection. The guys discuss practical strategies including the "what worked/what didn't" analysis and Dan Sullivan's concept of "measuring backward" to appreciate your progress. Between nostalgic stories of family road trips and humorous takes on modern dishwasher dilemmas, Bill and Bryan offer actionable advice for sales professionals to evaluate their 2024 strategies and set themselves up for success. Whether...
Dec 23, 2024•21 min•Ep. 820
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 de...
Dec 19, 2024•6 min
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 ...
Dec 16, 2024•22 min•Ep. 819
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 m...
Dec 12, 2024•6 min
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 BOL...
Dec 09, 2024•22 min•Ep. 818
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 prosp...
Dec 05, 2024•5 min
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 deep...
Dec 04, 2024•24 min
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 tange...
Dec 02, 2024•20 min•Ep. 817
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 ...
Nov 27, 2024•23 min
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....
Nov 25, 2024•22 min•Ep. 816
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 s...
Nov 20, 2024•14 min
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...
Nov 18, 2024•17 min•Ep. 815
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 aspir...
Nov 11, 2024•17 min•Ep. 814
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 practica...
Nov 04, 2024•17 min•Ep. 813
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 ...
Oct 17, 2024•18 min
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...
Oct 09, 2024•31 min
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 po...
Oct 02, 2024•35 min
