The Advanced Selling Podcast

Hosted by Bill Caskey and Bryan Neale: B2B Sales Trainers

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1134

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Oct 2026

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About the 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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60 recent

November 2, 2026Episode 90520 min

Why the “Decision Maker” Is a Myth

Send us Fan Mail If you’re still hunting for “the decision maker,” you’re chasing a buyer who doesn’t exist anymore, and the data proves it. Bill Caskey and Bryan Neale kick off a two-part series on multithreading with real numbers. Bryan’s team analyzed 169 of its own closed opportunities and found a 10% win rate when only two or three people were involved on the buyer side. With four or more people involved, the win rate jumped to 86%. Getting C-level and VP-level buyers involved moved the win rate sharply too. In this episode, you’ll learn: Why the single-decision-maker model is dead, and how sales leaders keep it alive without realizing it How to make involving more buyers part of your process instead of a favor you have to ask for Why your sales process should live on one page, showing which buyer titles are involved at each stage How to treat your process as a business asset, and why every stage needs a stated “why” The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com Get positioned for 2027 before you plan it. Join Bill live on Nov 6 in Insider: advancedsellingpodcast.com/insider

October 26, 2026Episode 90416 min

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 simple: just start. Tie an AI habit to a habit you already have, like scrolling social media, and stop assuming AI won’t touch your role. It will. Being skilled with it makes you more valuable, and “how do you use AI in sales?” is about to become a standard interview question. Then they turn to 2027. This isn’t the mechanical plan itself. It’s the pre-planning that makes the plan simple: The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

October 19, 2026Episode 90320 min

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 your AI so it works the way you do. They start with the shift from “prompting” to simply talking, out loud, in voice mode or a voice memo. Then they walk through the first five of their ten training questions every seller should answer and feed to their AI. You’ll learn: Why talking to your AI beats writing the “perfect” prompt The first five training questions: the problem you solve, your top objections, your sales philosophy, your discovery questions, and your ideal client Why real specifics (client names, companies, details) change the quality of what comes back How feeding your CRM’s closed-lost data to AI can show you where you’re really losing deals The question to ask your AI at the end that catches what you missed Plus, a 20th-anniversary shout-out from longtime listener (and fellow podcaster) Trevor L. in Cornwall, UK. The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

October 12, 2026Episode 90219 min

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 made one thing obvious: a picture of the experience is nothing like being there. In this episode, Bill and Bryan apply that to selling. Are you giving prospects a real experience of working with you, or just flipping through a slideshow? Plus: the 20th anniversary is coming up on October 26. Send Bill and Bryan a short note or audio clip about how the show has helped you. The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

October 5, 2026Episode 90126 min

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 challenge: the modern skill isn't just learning. It's learning, unlearning, and relearning fast. What worked six years ago, or even last year before AI research tools changed prospecting, may be irrelevant now. Then they get specific. You'll hear why old-school discovery, with its long list of pain questions and "what keeps you up at night," has stopped working with senior buyers, and why discovery today should look more like a private equity firm's analysis: facts, numbers, and critical thinking instead of picking at feelings. You'll learn: How to build an "atrophy correction plan": learn the modern version, practice it, then apply it in low-risk deals first Why you shouldn't test a new skill on your biggest prospect The four skills most worth auditing: prospecting, discovery, presenting your offer with conviction, and economics conversations Why "price resistance" is often really justification resistance, and what a $20K buying decision taught the hosts about connecting money to value Plus: the show is closing in on its 20th anniversary. The first episode dropped October 25, 2006. The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com Get positioned for 2027 before you plan it. Join Bill live on Nov 6 in Insider: advancedsellingpodcast.com/insider

September 28, 2026Episode 90013 min

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 create sales from scratch. Another company's reps have spent five years telling customers to get in line. Neither group is ready for what comes next. Bill and Bryan also explain why "just talk like a normal person" might be the most underrated sales advice out there. You'll learn: Why easy markets quietly weaken your team's selling skills How logic can beat your emotional reluctance to get visible Why a plain, honest phone call often beats a clever email Why systems, not tricks, rebuild atrophied skills Why you should "face the brutal facts" even when business is good Next week, Part 2 covers how to bring those skills back. The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

September 21, 2026Episode 89926 min

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 shoutouts (including a great one from longtime listener Andy in the UK), a quick teaching on the WAG framework you can steal for your next client conversation, and an honest look back at how selling has changed since 2006 — and where it's headed next. You'll learn how to run a WAG (Where We Were, Where We Are, Where We're Going) at any stage of a sales process, why 12 years of economic upswing may have quietly atrophied your team's sales skills, why personal brand matters more than ever in an AI-saturated world, and why the next real edge might be an "analog revolution" back toward live, face-to-face selling. The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

September 15, 2026Episode 89819 min

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 the first of several listener tribute clips — this one from Scott, a longtime Insider member and one of the "Globetrotters," a small accountability group that formed out of the show. Scott's story becomes the jumping-off point for a bigger conversation: why "relationship selling" is mostly a myth, and what actually creates lifelong client relationships (hint: it's not golf outings). Bill and Bryan also get honest about regrets — the choices that kept ASP niche and steady instead of chasing bigger growth, why they never built a true listener community, and the lane they might explore next. The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

August 31, 2026Episode 89720 min

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 CFOs past their skepticism. The fix isn't a better pitch — it's a completely different approach to who you target and how you position the offer. You'll learn how to sort prospects by tolerance for change (not company size), why positioning your offer as limited and selective beats "revolutionizing everything," and why acknowledging buyer skepticism up front builds more trust than any pitch could. It's the 20th anniversary of the show, and Bill and Bryan want to hear from you — send a short voice memo to listener@advancedsellingpodcast.com for their September anniversary celebration. The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com

August 24, 2026Episode 89623 min

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 shares what happened when he volunteered to try something brand-new outside of sales — nervous, uncomfortable, and more locked-in than he's felt in years. That leads into why "just say this instead" coaching doesn't work, why the block that keeps a rep out of the CFO's office (or a $400K advisor from becoming a $1M advisor) is about identity, and a simple reframe for calling on anyone above your comfort level: find what's the same before you worry about what's different. It's the 20th anniversary of the show, and Bill and Bryan want to hear from you — send a short voice memo to listener@advancedsellingpodcast.com for their September anniversary celebration. The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com