The Advanced Selling Podcast

Bill Caskey and Bryan Neale: B2B Sales Trainers
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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. 3d ago ·  Video

    Selling Above Your Contacts Without Going Around Them

    Send us Fan Mail Your day-to-day contacts love you. The problem is that your new offer needs a sign-off they can’t give, and they aren’t going to walk you into their boss’s office. This week Bill brings a real client situation to the table. A team of engineers and account managers has strong relationships with the people who run their projects. Their new service is a $100K–$300K decision that only a CRO-type executive can approve. Their contacts are guarding the moat, and the team doesn’t want to look like it’s going over anyone’s head. You’ll learn: Why thinking in “levels” quietly sabotages your language and confidenceHow to set an intention that makes executives and contacts lean in instead of bracingThe three-part video script for introducing yourself to an executive you’ve never metWhy you should copy everyone, and how “authentic bragging” about the team protects your championHow to treat your customer as a teammate so involving more people never feels like a threatThe 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

    Selling Above Your Contacts Without Going Around Them

  2. Nov 2 ·  Video

    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 itHow to make involving more buyers part of your process instead of a favor you have to ask forWhy your sales process should live on one page, showing which buyer titles are involved at each stageHow 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

    Why the “Decision Maker” Is a Myth

  3. Oct 26 ·  Video

    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

    Before You Build Your 2027 Plan, Do This First...

  4. Oct 19 ·  Video

    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” promptThe first five training questions: the problem you solve, your top objections, your sales philosophy, your discovery questions, and your ideal clientWhy real specifics (client names, companies, details) change the quality of what comes backHow feeding your CRM’s closed-lost data to AI can show you where you’re really losing dealsThe question to ask your AI at the end that catches what you missedPlus, 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

    Stop Getting AI Slop: Train It on How You Sell

  5. Oct 12 ·  Video

    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

    Give Buyers an Experience, Not a Slideshow

  6. Oct 5 ·  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

  7. 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?

  8. 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)
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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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