The Advanced Selling Podcast

Send us Fan Mail In this episode, Bill and Bryan tackle a critical but often overlooked aspect of the modern sales process - what to do during the time gaps between prospect meetings. Moving beyond outdated practices like sending marketing brochures, they explore innovative strategies for maintaining momentum and building deeper connections. The guys share five powerful approaches including making...

Send us Fan Mail In this solo episode, Bill explores why even experts fail to effectively communicate complex ideas, drawing from a recent experience watching an AI expert lose his audience. Through a practical framework, Bill reveals three essential components that transform complicated explanations into influential communications. He demonstrates how proper explanation isn’t just about informati...

Send us Fan Mail In this episode, Bill and Bryan challenge traditional sales metrics and explore the often-overlooked numbers that truly matter in today’s digital sales landscape. The guys discuss crucial modern measurements like inbound lead generation through LinkedIn, the power of tracking unsolicited introductions, and the importance of understanding average days to close. They give valuable i...

Send us Fan Mail 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:...

Send us Fan Mail 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! Cu...

Send us Fan Mail 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 person...

Send us Fan Mail 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 salesper...

Send us Fan Mail 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 levera...

Send us Fan Mail 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 detai...

Send us Fan Mail 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...

Send us Fan Mail 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 ph...

Send us Fan Mail 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, whe...

Send us Fan Mail 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 l...

Send us Fan Mail 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 actu...

Send us Fan Mail 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 m...

Send us Fan Mail 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 strengtheni...

Send us Fan Mail 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 di...

Send us Fan Mail 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, enh...

Send us Fan Mail 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....

Send us Fan Mail 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 fir...

Send us Fan Mail 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...

Send us Fan Mail 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 a...

Send us Fan Mail 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 authenticall...

Send us Fan Mail 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...

Send us Fan Mail 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...