The Advanced Selling Podcast

Bill Caskey and Bryan Neale: B2B Sales Trainers
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  • Marketing
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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.

  1. 1d ago ·  Video

    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 firstWhy you shouldn't test a new skill on your biggest prospectThe four skills most worth auditing: prospecting, discovery, presenting your offer with conviction, and economics conversationsWhy "price resistance" is often really justification resistance, and what a $20K buying decision taught the hosts about connecting money to valuePlus: 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

    Sales Skill Atrophy, Part 2: The Comeback Plan

  2. Sep 28 ·  Video

    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 skillsHow logic can beat your emotional reluctance to get visibleWhy a plain, honest phone call often beats a clever emailWhy systems, not tricks, rebuild atrophied skillsWhy you should "face the brutal facts" even when business is goodNext 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

    Are Your Sales Skills Atrophying?

  3. Sep 21 ·  Video

    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

    20 Years of Selling: What's Changed (and What Hasn't)

  4. Sep 15 ·  Video

    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

    20 Years In: What We'd Do Differently

  5. Aug 31 ·  Video

    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

    How to Sell Something the Market Isn't Ready For

  6. Aug 24 ·  Video

    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

    It's Not a Skill Problem, It's an Identity Problem

  7. Aug 10 ·  Video

    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 symptom of weak positioning? They walk through a real audit of lost deals — 22 gone in six months, four of them deals that should have been won — and use it to unpack what separates a vendor from a "we can't do without you" partner. You'll learn the four ingredients of unshakeable positioning: naming the beliefs your customer has to shift before your value can land, getting explicit about what you don't do, choosing whether you're a problem-solver or a destination (or both), and painting the real cost of standing still. Plus, why the best time to build this is when business is good — not when you're desperate. 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

    Stop Blaming Price: Positioning Is Your Problem

  8. Aug 3 ·  Video

    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 mentor who connected without ego, a customer who never delayed a decision, and a prospect Bryan gave up on too soon.  Each story carries a lesson you can use this week: ask people about their actual lives, don't wait to reconnect with old friends, decide fast, and don't give up on a prospect after just one or two tries. 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

    Lessons We've Learned From Those We've Lost
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About

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.

Information

  • Creator
    Bill Caskey and Bryan Neale: B2B Sales Trainers
  • Years Active
    2006 - 2026
  • Episodes
    1.1K
  • Rating
    Clean
  • Copyright
    © 2026 The Advanced Selling Podcast
  • Show Website
    The Advanced Selling Podcast

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