Podcast
The Advanced Selling Podcast
Hosted by Bill Caskey and Bryan Neale: B2B Sales Trainers · EN
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.
24episodes
Episodes
Newest firstAll episodes
How to Become the Obvious Choice (Part 2)
1w ago00:19:34Tap to summarizeSend us Fan MailBill 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, and objections so you're never caught off guardDelivering a Statement of Detachment that comforts prospects and skyrockets close ratesSetting a go/no-go instead of asking for the businessWarming cold audiences with pre-meeting video pagesThe Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insiderIf you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin📌 TIMESTAMPS 0:00 – Intro: 20 years of podcasting & ASP listener meetup in London 2:15 – Life observation: car alarms and bathroom fans (things that don't work) 6:50 – Part 2: How to become the Obvious Choice 7:37 – Tactic 1: Proactively surface problems and objections 10:08 – Tactic 2: The Statement of Detachment (22% → 45%+ close rate) 13:08 – Tactic 3: End precisely — the go/no-go and stating your desire 15:20 – Tactic 4: Warming up cold audiences with a pre-bid video page 18:22 – Insider promo: June 5th — How to build a conversion event#SalesTraining #B2BSales #AdvancedSellingPodcast #SalesProcess #ObviousChoice #Detachment #Prospecting #SalesStrategy #Closing #BillCaskey #BryanNeale
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Becoming the Obvious Choice (Part 1)
2w ago00:21:03Tap to summarizeSend us Fan MailHow 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 very first interaction.They cover three foundational moves: filtering your pipeline through the right lens (are they an obvious fit for you?), getting pristine on your message including who you're not for, and articulating a clear payoff — not just ROI, but the tangible transformation clients can expect at different stages of the relationship. Plus, they discuss the power of multi-threading — bringing multiple people into the conversation on both sides — and why the obvious choice is often the one that does the most work before the final decision is ever made.If you're tired of scrambling at the close, this episode is your reset.The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insiderIf you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedinIs 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
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The Fear Factor in Sales
3w ago00:21:25Tap to summarizeSend us Fan MailFear 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 into something useful. Plus: what beekeeping taught Bryan about walking into uncomfortable situations, and why the doom-and-gloom crowd is almost always wrong about new technology.The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insiderIf you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedinIs 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
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The Simple Shift That Changes Every Sales Conversation
May 400:19:38Tap to summarizeSend us Fan MailAre 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 outcome obsession, why accountability starts with you (not the market or the prospect), and how knowing when not to move forward is sometimes the most powerful sales move you can make.The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insiderIf you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedinIs 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
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Why Your Calendar Is Killing Your Pipeline
Apr 2700:19:38Tap to summarizeSend us Fan MailWhat'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 time misallocation kills pipelines, and Bill makes the case that lead generation is the core issue most companies struggle to solve — not because of effort, but because they're relying on activity instead of architecture.The guys walk through practical examples of what a real lead gen system looks like: calendar blocking that actually holds, consistent outreach cadences that generate 1-in-5 conversations, and leverage-based content strategies that let buyers raise their hand instead of being cold-called into a corner.If your sales are inconsistent, your calendar is the first place to look.The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insiderIf you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedinIs 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
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Stop Being Selfish: The Sales Habit That Pays Off Later
Apr 2000:15:25Tap to summarizeSend us Fan MailBill 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 can't predict. They challenge sellers to stop making excuses, stop being selfish with their knowledge, and start showing up consistently — on LinkedIn, in the field, and with their prospects — because someone out there might be suffering simply because they haven't heard from you yet.The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insiderIf you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedinIs 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
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Why Prospects Stop Trusting You (And How to Fix It)
Apr 900:05:38Tap to summarizeSend us Fan MailTrust 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 counterintuitive fix: create content.Bill shares how consistent content — podcasts, video, written pieces — lets prospects sample your thinking long before a sales conversation begins. When they finally reach out, they're already sold. He also challenges the habit of chasing prospects for next steps, arguing that if you're the one pushing, something went wrong earlier in the process.🔗 Want more advanced sales training? Join ASP Insider: https://advancedsellingpodcast.com/insiderDownload your complimentary copy of the 12 Bold Moves audiobook at 12BoldMoves.com/Audiobook
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The Identity Shift: From Labor to Leverage
Apr 200:04:28Tap to summarizeSend us Fan MailIn 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 that's nearly impossible to scale. Bill breaks down a better framework: Discover, Develop, Deploy. Find the assets you already have (client success stories, your personal story, your expertise), build the skills to use them, and put them to work in the market.Most salespeople close 20–25% at best, which means they're burning 75–80% of their effort on people who will never buy — largely because they never leveraged anything in the process. Bill challenges you to identify where leverage is absent in your sales approach and start building a new identity around it.🔗 Want more advanced sales training? Join ASP Insider: https://advancedsellingpodcast.com/insiderDownload your complimentary copy of the 12 Bold Moves audiobook at 12BoldMoves.com/Audiobook
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Stop Hiding. Create Space to Be Excellent.
Mar 3000:13:41Tap to summarizeSend us Fan MailMost 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 chance encounter at a restaurant to a woman coaching a thousand people to share their stories on stage, the lesson is clear: you can't demonstrate excellence from your couch, your car, or your home office.They also dig into what happens when people do get their moment in the spotlight — and blow it by reading from a notecard. And they share the story of Milo, door holder number three, who might have the best mindset in the room.Get out. Get in the room. Be excellent when it counts.The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insiderIf you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedinIs 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
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Raise Your Prices Without Losing Your Clients
Mar 2300:15:57Tap to summarizeSend us Fan MailA 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 to successfully raise prices with clients you've already got. Their answer isn't a negotiation tactic — it's a positioning problem. And the fix starts long before the price conversation happens.They cover why technical sellers tend to stay too low in the org chart, why your contact isn't selling your value upstairs for you, and what a price increase reaction tells you about where you actually stand with a client.The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insiderIf you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedinIs 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
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