The Advanced Selling Podcast
by Bill Caskey and Bryan Neale: B2B Sales Trainers
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.
Episodes
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Before You Build Your 2027 Plan, Do This First...
Send us Fan Mail Most sellers spend Q4 grinding toward a number, then rush their business plan into the last two weeks of December. This episode is about breaking that cycle by getting clear before you plan. Bill and Bryan kick off with a quick follow-up to their AI episode. The message is…
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Stop Getting AI Slop: Train It on How You Sell
Send us Fan Mail If AI keeps handing you generic, forgettable output, the tool usually isn’t the problem. You never taught it who you are, who you sell to, or how you sell. In this episode, Bill and Bryan get into the AI conversation everyone’s having. Their angle is a practical one: training…
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Give Buyers an Experience, Not a Slideshow
Send us Fan Mail Telling a buyer what it's like to work with you is like showing someone your vacation photos. They'll say "oh, that's nice." They won't feel a thing. Bill just got back from two weeks out West, including Death Valley and a 98-degree "cooling" pool. Showing his family the photos...
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Sales Skill Atrophy, Part 2: The Comeback Plan
Send us Fan Mail Your sales skills didn't disappear. They atrophied. And the fix isn't picking up where you left off, because the market moved while you weren't looking. In Part 2 of their series on sales skill atrophy, Bill Caskey and Bryan Neale shift from diagnosis to repair. They start with a...
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Are Your Sales Skills Atrophying?
Send us Fan Mail What happens to your sales skills when you haven't had to use them? Muscles you don't use get weaker, and sales skills work the same way. In Episode 900, Bill and Bryan start a two-part look at skill atrophy. One team lost the lead channel it depended on and suddenly has to…
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20 Years of Selling: What's Changed (and What Hasn't)
Send us Fan Mail Twenty years ago, LinkedIn had 50 employees and cold calling ruled the day. Now AI writes your emails and nobody's picking up the phone — so what actually still works? This week Bill and Bryan mark 20 years of the Advanced Selling Podcast with a celebration episode: listener...
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20 Years In: What We'd Do Differently
Send us Fan Mail Twenty years ago, Bill and Bryan started recording a podcast every other Monday. They never missed the behavior — and that consistency turned out to matter more than talent, luck, or a growth strategy ever did. To kick off ASP's 20th anniversary celebration, Bill and Bryan share...
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How to Sell Something the Market Isn't Ready For
Send us Fan Mail Got something genuinely new to sell — and buyers keep lumping it in with every other "revolutionary" pitch they've heard this month? This one's for you. Bill and Bryan work through a real scenario: a friend building software that could transform hospital billing, but can't get…
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It's Not a Skill Problem, It's an Identity Problem
Send us Fan Mail Why do good sellers freeze up the second a conversation moves from a director-level buyer to the CFO? It's not a skills gap — it's identity. Bill Caskey and Bryan Neale break down why sellers resist doing new things, even when they know exactly what it's costing them. Bryan…
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Stop Blaming Price: Positioning Is Your Problem
Send us Fan Mail You didn't lose that deal on price. You lost it because your positioning wasn't strong enough to make you the obvious, can't-do-without-you choice. Bill and Bryan dig into a claim that gets argued in every sales meeting: is price really the reason deals slip away, or is it a...
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Lessons We've Learned From Those We've Lost
Send us Fan Mail Every person you've worked with has a story you probably never asked about — and sometimes you don't find out until it's too late. In Part 2 of their series on the people of sales, Bill and Bryan honor a handful of people who shaped their careers — a neighbor and airline pilot, a...
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The People Who Taught Us Everything We Know About Sales
Send us Fan Mail Twenty years in this business means running into a lot of characters. This week Bill and Bryan riff on the people — bosses, clients, gatekeepers, baristas — who taught them something they never forgot, whether the lesson was about sales or just about being human. You'll hear…
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Self-Scouting: The Mid-Year Sales Review Most Reps Skip
Send us Fan Mail You're six months into the year. Do you actually know what's working in your sales process — and what you quietly stopped doing back in February? Bill and Bryan borrow a trick from football coaches: self-scouting. Before the next game, coaches review their own film to find what...
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Say This, Not That: Why Precise Language in Sales Closes More Deals
Send us Fan Mail Imprecise language is quietly sabotaging your sales process — and most sellers don't even notice it happening. This week, Bill and Bryan dig into the art of precise communication and why "what they hear" matters more than "what you meant." Bryan shares a real example from his own...
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Patterns of Limitation: Part 2
Send us Fan Mail Bill and Bryan continue their series on the hidden patterns that quietly cap sales performance. Building on last episode's conversation about "drift," they dig into two more limiting patterns: fear (and why naming it is the first step toward detachment) and the belief that bigger...
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Patterns That Are Holding You Back
Send us Fan Mail Bill and Bryan dig into what they call "patterns of limitation" — the ingrained habits and mindsets that quietly cap your sales growth, often disguised as things that are already working. They explore four key patterns worth examining: the tendency to focus on the big picture…
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Why Your Spiritual Foundation Is Your Biggest Sales Asset
Send us Fan Mail Bill goes somewhere different today — and that's intentional. In this solo episode, Bill Caskey shares the first six of twelve core sales principles, each grounded in a biblical reference. From understanding your divine assignment and serving before selling, to detaching from...
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7 Lies About Sales Success
Send us Fan Mail What if the beliefs driving your sales career are built on a foundation of lies? In this solo episode, Bill Caskey breaks down seven deeply normalized lies about achievement, income, and sales success — the kind that quietly run your life if you let them. From "hustle harder to...
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How to Become the Obvious Choice (Part 2)
Send us Fan Mail Bill Caskey and Bryan Neale continue their series on how to become the Obvious Choice for your prospects and customers — not by closing harder, but by selling smarter throughout the entire process. In Part 2, they cover four powerful moves: Proactively raising problems, concerns,...
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Becoming the Obvious Choice (Part 1)
Send us Fan Mail How do you become the vendor your customers never even think to replace? In Part 1 of this short series, Bill and Bryan break down what it actually takes to become the obvious choice — not through last-minute discounts or closing tactics, but by building that clarity from the…
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The Fear Factor in Sales
Send us Fan Mail Fear shows up at every stage of a sales career — first calls, big promotions, major presentations, and yes, posting on LinkedIn. In this episode, Bill and Bryan dig into how fear works, why your brain treats a LinkedIn post like a saber-toothed tiger, and how to reframe anxiety...
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The Simple Shift That Changes Every Sales Conversation
Send us Fan Mail Are you walking into sales calls without getting clear on the actual problem you're solving? In this episode, Bill and Bryan dig into one of the most overlooked fundamentals in B2B sales: defining the real problem before pitching solutions. They explore how process focus beats...
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Why Your Calendar Is Killing Your Pipeline
Send us Fan Mail What's the #1 problem facing salespeople and customer acquisition professionals right now? Bill and Bryan each share their answer — and while they come at it from slightly different angles, both point to the same root cause: the absence of a real system. Bryan breaks down why…
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Stop Being Selfish: The Sales Habit That Pays Off Later
Send us Fan Mail Bill and Bryan are back from spring break with a powerful lesson about the long game in sales. Inspired by a 35-year-old charity event that grew into a $400 million movement, they dig into how the small actions you take — or skip — today create enormous downstream outcomes you...
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Why Prospects Stop Trusting You (And How to Fix It)
Send us Fan Mail Trust is the missing ingredient in most failed deals — and the old methods of building it (the hearty handshake, the enthusiastic follow-up email) no longer cut it. In part four of the Sales Identity Crisis series, Bill breaks down why modern buyers are slow to trust and offers a...
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The Identity Shift: From Labor to Leverage
Send us Fan Mail In this solo episode, Bill Caskey continues his series on the Sales Identity Crisis — specifically, the shift from being a laborer to becoming a leverager. If your sales approach is built on effort alone — more calls, more hours, more hustle — you're operating on an old model...
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Stop Hiding. Create Space to Be Excellent.
Send us Fan Mail Most salespeople wait for opportunity to come to them. Bill and Bryan flip that script. In this episode, they explore what it means to create a "space for excellence" — the rooms, events, and moments where you show up, lean in, and let people see what you're made of. From a…
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Raise Your Prices Without Losing Your Clients
Send us Fan Mail A listener question from William — an engineer who also sells — kicks off a focused conversation on one of the oldest problems in B2B sales: getting commoditized on price. Bill and Bryan tackle both sides of the equation: how to avoid being beaten down on price coming in, and how...
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Stop Watching the Scoreboard — Start Watching the Inputs
Send us Fan Mail We're at the end of Q1 — and Bill and Bryan use a trip to the Pacers game as a launching pad for a conversation about what actually matters when you check the scoreboard. Inspired by Bill Walsh's coaching philosophy and John Wooden's legendary process focus, this episode explores...
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Find the Real Pain Behind Every Sales Conversation
Send us Fan Mail Every prospect tells you a version of their problem — and they're almost always wrong. Not lying. Just wrong. In this solo episode, Bill Caskey breaks down why the surface problem your prospect presents is rarely the real problem, and why it's your job to uncover what's actually…
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The Best Sales Gifts Nobody Buys You
Send us Fan Mail It's Bill's birthday — and that means one thing: it's time to talk about gifts. But not the usual Amazon cards and polka dot sweaters. Bill and Bryan dig into the sales gifts worth actually giving yourself: the mindset shifts, investments, habits, and tools that compound over…
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AI as a Sales Tool, Not a Salesperson with Kayla Kurtz
Send us Fan Mail In this episode of The Advanced Selling Podcast, Bryan Neale welcomes Kayla Kurtz, VP of Sales and VP of Business Development at Forthea, for a focused conversation on how AI is reshaping modern sales. Kayla shares how aligning sales and marketing improves lead quality and...
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From Content to Conquest
Send us Fan Mail Bill and Bryan are giving you a preview of the March 6th ASP Insider session — and it's one you don't want to miss. The topic is From Content to Conquest, but this isn't a social media training. It's about what you know, what you believe, and how you package your expertise so...
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Why Collaboration Beats Closing Tactics Every Time
Send us Fan Mail What if your entire sales process—from networking to contract signing—was built on collaboration instead of persuasion? In this episode, Bill and Bryan break down what real collaboration looks like at every stage: pre-sale networking, early conversations, mid-stage resistance…
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Saving Sales Time with Smarter Routes ft. Steve Benson
Send us Fan Mail In this episode of The Advanced Selling Podcast, Bryan Neale welcomes Steve Benson, founder of Badger Maps, for a conversation on why outside sales teams are often overlooked by modern sales technology — and what happens when tools are finally built with field sellers in mind....
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Is Your Through Line Costing You Business?
Send us Fan Mail What can Charlie Puth's collaboration with Kenny G for the Super Bowl national anthem teach us about sales? More than you'd think. Bill and Bryan break down the story of how Charlie Puth persistently pursued Kenny G—not through aggressive follow-ups, but through generous…
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Be the Guide Your Customers Are Craving
Send us Fan Mail Bill Caskey explores the most important question in sales: What is your role in the buyer-seller dance? In this solo episode, Bill breaks down the Guide Model—a three-part framework that transforms how you show up with customers. Instead of selling to people who don't need what…
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Mental Health in Sales: Movement Creates Momentum
Send us Fan Mail In the final episode of our mental health in sales series, Bill and Bryan tackle a truth most sellers ignore: you can't think your way out of a slump—you have to move your way out. Drawing from Scott Galloway's "get out of the house" philosophy and real client stories, they…
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How Detachment Creates Sales Freedom
Send us Fan Mail In this solo episode, Bill breaks down why detachment might be the most important skill you're not practicing. When a client asked for help with negotiation, positioning, and value communication, Bill realized all these challenges stem from one core issue: attachment to outcomes....
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Scaling Authenticity in Sales with John Wechsler
Send us Fan Mail In this episode of The Advanced Selling Podcast, Bryan Neale is joined by John Wechsler, CEO of Spokenote, for a conversation on why authentic, personalized video is becoming a critical advantage for modern sales teams. Bryan and John discuss the difference between messaging and...
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Mental Health in Sales: Detachment, Service and Personal Agency
Send us Fan Mail In part 3 of the mental health series, Bill and Bryan tackle the achievement trap that plagues high performers: when is enough enough? They introduce six practical frameworks for managing mental health in sales, covering the first three in depth: detachment from outcomes…
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Mental Health in Sales: Confidence, Purpose and Movement
Send us Fan Mail In part 2 of our mental health series, Bill and Bryan explore what creates genuine confidence in sales and why it starts with something bigger than yourself. They discuss the "divine assignment" concept, finding meaning in your work beyond financial gain, and how physical…
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Strategic Gifting with Patricia DuChene
Send us Fan Mail In this episode of The Advanced Selling Podcast, Bryan Neale is joined by the VP of Growth and Marketing at Sendoso, Patricia DuChene, to discuss how intentional gifting can be used as a strategic tool in modern sales. Rather than treating gifts as swag or gimmicks, their...
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Mental Health in Sales: Breaking the Silence
Send us Fan Mail Bill and Bryan launch a vital series on mental health in sales—a topic that's rarely discussed but critically important. After Bill's month-long absence dealing with family tragedies, they dive into why salespeople face unique mental health challenges: quota pressure, identity…
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Building a Sales Engine Framework
Send us Fan Mail In this solo episode, Bill introduces the Complete Sales Engine Framework, focusing on the first two essential blocks: Attention and Engagement. He breaks down why most companies struggle with empty pipelines despite focusing heavily on conversion training, and shares practical...
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The 9-Block Business Planning Framework for 2026
Send us Fan Mail Bill Caskey breaks down the exact business planning framework from the recent ASP Insider workshop. If you haven't done your 2026 planning yet, this episode walks you through nine critical building blocks that will set you up for sustainable sales success. From defining your…
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The Missing Block in Your Business Plan
Send us Fan Mail Most business planning workshops start with vision statements and call quotas. But Bill argues there's a critical block missing from that equation: personal development. In this solo episode, he breaks down Block 8 from his 2026 Business Planning Strategy—the piece that asks not...
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From Thinking to Doing: Operational Disciplines That Work
Send us Fan Mail Last week, Bill and Bryan covered mental discipline—getting your head right. This week, they shift to operational discipline: the actual behaviors and systems that high performers use to win. This isn't about overhauling your entire life. It's about looking at your current...
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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...
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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,...
About this show
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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Bill Caskey and Bryan Neale: B2B Sales Trainers
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