The Advanced Selling Podcast - podcast cover

The Advanced Selling Podcast

Bill Caskey and Bryan Neale: B2B Sales Trainersadvancedsellingpodcast.com

Bill Caskey and Bryan Neale deliver practical, no-nonsense sales training through their signature blend of humor, real-world insights, and actionable frameworks. Each episode tackles the challenges you face daily: prospecting, overcoming buyer resistance, pricing strategies, cold calling, deal coaching, and building long-term client relationships.


Whether you're a sales professional, manager, or leader, you'll discover how to shift your mindset, leverage your natural talents, and create sustainable sales success. From mastering sales communication and handling RFPs to understanding buyer psychology and effective positioning, Bill and Bryan cover everything that actually works in modern B2B sales.

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Episodes

The Mental Game: Building Discipline That Actually Works

Send us Fan Mail Bill and Bryan tackle mental discipline—but not the way you'd expect. Instead of rigid rules and forced habits, they reframe discipline as the inputs that create freedom, not constraints. In this first part of a two-part series, they explore the mental shifts that separate high performers from the rest: quieting your mind, embracing possibility thinking, getting comfortable with failure, and continuously feeding your growth. You'll discover why discipline isn't about forcing you...

Nov 24, 202520 minEp. 865

Sales Compensation with Chris Goff

Send us Fan Mail In this episode of The Advanced Selling Podcast , Bryan Neale sits down with sales compensation expert Chris Goff, better known across the industry as “ The Sales Comp Guy. ” With deep experience in sales operations, territory optimization, and comp plan design, Chris brings a rare, holistic perspective to one of the most emotionally charged topics in sales: how sellers get paid. Together, Bryan and Chris unpack why compensation plans create so much tension, how leaders can desi...

Nov 19, 202524 min

Micro Mastery: Small Skills That Create Big Results

Send us Fan Mail Part two of our macro vs. micro skills series—and this one gets tactical. Bill and Bryan dive into the small, incremental skills that most salespeople overlook but that separate pros from amateurs. These aren't the big-picture capabilities; they're the in-the-moment moves that determine whether your sales calls actually go anywhere. The guys cover the courage to stop and clarify when something's confusing, the power of numeric calendar values (no more "let's connect next week"),...

Nov 17, 202518 minEp. 864

Your Most Powerful Pre-Meeting Asset

Send us Fan Mail Most salespeople waste their first meeting covering basics that could've been handled beforehand. Bill introduces a game-changing digital asset: the introductory video—a 5-minute pre-meeting video that positions you as a credible problem-solver before the conversation even starts. In this episode, Bill breaks down the exact structure of an effective introductory video, including the hook that grabs attention in 10 seconds, how to tell your story concisely, the three industry hea...

Nov 13, 20255 min

Macro vs. Micro: Sales Skills That Actually Matter

Send us Fan Mail Bill and Bryan break down the difference between macro and micro sales skills—and why both matter more than you think. Inspired by a prospect who called out his own team for not asking clarifying questions, this episode explores the big-picture capabilities that separate average performers from top producers. They cover essential macro skills including strategic planning (with outcomes AND behaviors), reverse engineering your goals, financial literacy for sales professionals, ex...

Nov 10, 202518 minEp. 863

Beyond Process: The Courage to Walk Away

Send us Fan Mail Bill Caskey follows up on last week's deep dive by sharing insights from coaching a high-performing salesperson who's hitting the limits of process-driven selling. He reveals why even the best sales process isn't enough—you must show up authentically and have the courage to disqualify prospects who aren't truly committed. Through a compelling coaching story, Caskey explains how being grounded in who you are allows you to spot the 20% that's missing in a conversation and walk awa...

Nov 07, 20257 min

Vince Beese: Red Zone

Send us Fan Mail In this episode of The Advanced Selling Podcast , Bryan Neale sits down with longtime friend and sales veteran Vince Beese , a fractional CRO and sales coach with over 25 years of B2B enterprise experience and five successful exits under his belt. Together, they dive deep into “Red Zone Selling:” a framework inspired by football that helps sellers stay focused, avoid complacency, and close more deals when it matters most. Vince breaks down how 80–90% of enterprise deals are won ...

Nov 05, 202522 min

"Let's Talk Money" 5 Scenarios Sales Reps Struggle With

Send us Fan Mail Are you uncomfortable talking about money with prospects? You're not alone. In this episode, Bill and Bryan tackle one of the biggest challenges sales professionals face: bringing up price, cost, and economic conversations without the anxiety and uncertainty that usually comes with it. Whether you're dealing with technology sales, competitive situations, or demonstrating clear ROI, this episode gives you the confidence to talk about money like the professional you are. Key insig...

Nov 03, 202517 minEp. 862

Building a Winning Sales Culture (Part 2)

Send us Fan Mail In this episode, Bill and Bryan continue their conversation on sales culture with actionable tactics you can implement immediately. Whether you're building team culture or your personal approach, these strategies will help you create intentional, high-performing environments. What You'll Learn: ✅ How to build customer relationship culture through strategic meetups ✅ The power of book clubs and team socialization for engagement ✅ Team brag sessions that uplift everyone (not just ...

Oct 27, 202516 minEp. 861

The Invisible Dimension of Sales

Send us Fan Mail Bill Caskey poses a challenging question: If you disappeared from your prospect's world tomorrow, would they feel the loss? In this introspective solo episode, he explores the "invisible dimension" of sales—the deeper level where prospects evaluate not just your skills and process, but your unique presence and purpose. Caskey shares three powerful practices for connecting with your authentic self: inventorying your unique experiences, clarifying your God-given assignment, and ma...

Oct 23, 20255 min

Connect With Customers

Send us Fan Mail In this episode, Bryan Neale from Blind Zebra shares a tactical framework for building meaningful customer connections — one rooted in strategy, generosity, and intentional networking. He explains why great salespeople move beyond vague Ideal Customer Profiles (ICPs) to create “ conquest account lists ” that name specific people they want introductions to. Bryan also challenges listeners to identify at least 20 “Connectors” — the natural networkers who love making introductions ...

Oct 22, 202514 min

What Sales Culture Really Is (And Why It Matters)

Send us Fan Mail Bill and Bryan kick off a two-part series on sales culture by sharing what they've observed from years of working inside dozens of organizations. In this episode, they explore the difference between surface-level culture (the pictures on the wall) and the real culture you can feel in the air. Whether you lead a sales team or carry your own quota, this episode will help you see culture in tangible ways—and understand why the language you use, the people you surround yourself with...

Oct 20, 202516 minEp. 860

AI in Sales (Part 2): Pre-Call Research and Content Creation

Send us Fan Mail In part two of their AI series, Bill and Bryan get specific—sharing real examples of how they use AI in their daily sales work. Bill walks through actual ChatGPT conversations for client prep (including a memorable moment when the AI got it wrong about an ESOP), while Bryan demonstrates how he uses Claude to research prospects and create strategic talking points. You'll hear how they validate AI-generated research during sales calls, why telling clients "I did some research" act...

Oct 13, 202518 min

Connect With Your Team

Send us Fan Mail In this episode, Bryan explores why the best sales leaders focus as much on connecting with their people as they do on connecting with their customers. Sales is often seen as an individual sport - everyone chasing their own numbers and commissions. But the real magic happens when leaders take time to understand each team member’s unique motivations and coach them accordingly. Bryan shares how great leaders: Build individual connections with reps instead of one-size-fits-all coac...

Oct 08, 202515 min

AI in Sales (Part 1): Practical Uses for Prep, Research, and Productivity

Send us Fan Mail Bill and Bryan dive into how they're actually using AI in their daily sales work—no hype, just practical applications. In part one of this two-part series, they share their number one use case: preparation for sales calls, including researching companies, understanding buyer contexts, and making discovery more efficient. You'll learn why Bill treats AI like an executive assistant, how Bryan uses it for everything from client prep to football officiating, and why you should tell ...

Oct 06, 202519 minEp. 858

Stop Discounting - Closing Strategies with John Barrows

Send us Fan Mail In this episode, Bryan is joined by John Barrows to talk about the high-stakes final stage of the sales process, where deals are either won or lost. Together, they explore why so many sales teams stumble here, often resorting to last-minute discounts or high-pressure tactics driven by forecast anxiety. Bryan and John share strategies to keep control of the process, including engaging procurement early, coaching reps through nuanced situations, and avoiding the trap of reactive d...

Sep 24, 202530 min

Stop Being the Best-Kept Secret: How to Get Found by Your Ideal Clients

Send us Fan Mail Tired of perfecting your sales skills but struggling to get in front of the right people? Bill and Bryan tackle the universal challenge every B2B professional faces: visibility. Using a real client case study from the tax law industry, they reveal why traditional cold calling is dead and share actionable strategies to become visible where your prospects are already looking. Discover how to leverage weekly insight videos, LinkedIn article publishing (including the brilliant inter...

Sep 22, 202518 minEp. 857

The Myth of Creating Buyer Urgency

Send us Fan Mail In this episode, Bill and Bryan debunk one of the most persistent myths in sales training - that you can create urgency in buyers through clever tactics and techniques. They explore why deals are taking longer to close in 2025, examining both macro factors (economic uncertainty, decision-making complexity) and micro factors (changed buyer behavior, technology overload). The guys discuss how traditional urgency-creating methods like pattern interrupts and pressure tactics are not...

Sep 15, 202517 minEp. 856

The Rise of Accidental Salespeople

Send us Fan Mail Bill and Bryan explore a growing trend that's reshaping the sales landscape: the rise of "accidental salespeople." These are the technical advisors, project managers, engineers, and executives who don't have "salesperson" on their business cards but find themselves increasingly vital to the buyer-seller relationship. The guys discuss why these technically-minded professionals are becoming more important than ever, especially as traditional SDR/BDR approaches burn out prospects w...

Sep 08, 202519 minEp. 855

AI Role-Playing Revolution with Hyperbound.ai

Send us Fan Mail What happens when two conversational AI engineers realize they can't sell their own startup? They build an AI sparring partner to teach themselves—and accidentally create a game-changing sales training platform. We welcome the founders of Hyperbound.AI , Sai Guduguntla and Atul Raghunathan, who share their remarkable journey from technical founders struggling with sales to building a platform that's helping thousands of sales professionals practice and perfect their craft. In ju...

Sep 02, 202524 minEp. 854

Expert Frameworks: The Video Hook That Stops the Scroll

Send us Fan Mail In this early Labor Day release, Bill and Bryan dive into expert frameworks—essential tools for positioning yourself as a knowledgeable sales professional in today's market. Bill breaks down the critical video framework every salesperson needs. Learn the three-part video structure that actually gets attention: the hook that stops the scroll in the first 5 seconds, the story that keeps them engaged, and the call-to-action that drives results. Discover why social media has shifted...

Aug 29, 202519 minEp. 853

Winning in the Red Zone with Marcus Chan

Send us Fan Mail In this episode, Bryan Neale and Marcus Chan dive into the sales “red zone”—the late stage of the sales cycle where too many deals stall or fall apart. They explore how sales teams can avoid costly mistakes by addressing pricing, multi-threaded stakeholder engagement, and risk management early in the process. Marcus introduces his ADVANCE Framework, a practical tool for sales leaders to audit deals and improve forecasting accuracy. The conversation also highlights the importance...

Aug 27, 202535 min

The Prospect Experience Revolution: Small Actions, Big Impact

Send us Fan Mail In this episode, Bill and Bryan shift the focus from post-sale customer experience to what they call "PX 90" - the prospect experience during the sales process. After Bryan shares a fantastic customer service call with Southwest Airlines, they dive into practical ways salespeople can go above and beyond for prospects before they become customers. The guys share practical, low-cost ways to go above and beyond for prospects that will differentiate you from the competition and elev...

Aug 25, 202522 minEp. 852

How 30 Pages Can Separate You from Every Competitor

Send us Fan Mail In this solo episode, Bill Caskey reveals one of his 12 Insider Secrets for reinventing yourself and your results: creating a mini book to establish yourself as an authority in your field. Bill shares the compelling story of how his own 20-page book "12 Bold Moves" generated a $40-50K client from a $20 purchase, demonstrating the incredible ROI potential of this positioning strategy. Whether you're in sales, consulting, or any service business, this episode shows you how to tran...

Aug 21, 20255 min

Heart vs. Process: Why Both Matter in Sales Success

Send us Fan Mail Bill and Bryan dive into the critical balance between heart-centered selling and process-driven approaches. Sparked by a real coaching session where a top salesperson admitted "I'm not a warm guy," the guys explore why both emotional connection and systematic process are essential for sales success. They also discuss the importance of decisiveness in both sales and business relationships, and remind listeners that sometimes the best thing you can do is walk away when a prospect ...

Aug 18, 202515 minEp. 851

Sales Leadership Hats

Send us Fan Mail In this episode, Bryan dives into the Sales Leadership Hats, the roles great leaders switch between to unlock performance and keep their teams moving forward. You’ll learn how to wear: The Manager Hat – Cutting through noise with data-driven decisions that point the way forward. The Coach Hat – Sharpening skills and strategies so reps get better, not just busier. The Cheerleader Hat – Sparking motivation, restoring confidence, and helping reps break through mental roadblocks. Br...

Aug 13, 202512 min

Sales Call Prep in the AI Era: Why Research is Non-Negotiable

Send us Fan Mail Bill Caskey and Bryan Neale tackle a challenge every sales professional faces: how to properly prepare for sales calls in today's digital landscape. Sparked by recent conversations with VPs of Sales about their teams going into calls "cold," Bill and Bryan break down their proven preparation framework that combines traditional research methods with cutting-edge AI tools. The guys emphasize that your "lane" as a sales professional is widening—it's no longer just about conducting ...

Aug 11, 202517 minEp. 850

The Trust Crisis: 4 Levers to Build Credibility

Send us Fan Mail In this solo episode, Bill Caskey tackles the growing trust crisis facing sales professionals today. Drawing from recent research showing declining trust in businesses and institutions, Bill explores why prospects automatically assume you're going to lie to them—and why they're probably right to feel that way. He shares four practical levers you can use to build trust and stop destroying it: stop selling and start understanding, be willing to walk away when the fit isn't there, ...

Aug 08, 20255 min

Building Your Platform of Authority

Send us Fan Mail In this episode of the Advanced Selling Podcast, Bill and Bryan give listeners an exclusive preview of their upcoming Insider program session on building a "platform of authority." They explain how every sales professional needs a platform where they can share valuable insights and establish themselves as an authority figure in their field. The guys discuss what constitutes a platform (podcasts, LinkedIn, speaking engagements, client dinners, or even informal meetups) and how au...

Aug 04, 202520 minEp. 849

Build Your Virtual Bench

Send us Fan Mail In this episode, Bryan dives into the critical strategy of maintaining a “virtual bench” - a curated list of talented individuals you’d love to have on your sales team. Instead of scrambling to post job ads and sift through countless resumes when a rep leaves, Bryan explains how to stay ahead by proactively building and nurturing relationships with top talent. Learn why keeping your virtual bench warm with at least one touchpoint per year can give you a competitive edge and ensu...

Jul 30, 202511 min
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