The Advanced Selling Podcast: Sales Training | Leadership Coaching | B2b Sales Strategy | Prospecting Tips

Send 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.

Send 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 advan

Send 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

Send a textWe'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 why fixating on the score is the wrong move — and what sellers and sales leaders should be analyzing instead. Bill and Bryan dig into the slow fade of good habits, why joy in the process is the real competitive advantage, and what it looks like when a salesperson truly loves what they do.If your Q1 numbers aren't where you want them, this episode will help you look in the right places.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 ou

Send a textEvery 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 at stake. Bill walks through the questions you need to ask to get past symptoms and find the true pain: What's the cause? What happens if nothing changes? What are the economics of this problem?When you help a prospect understand their own problem clearly, you earn the right to present your solution — and they become obsessed with solving it.

Send a textIt'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 time.In this episode, you'll hear about the gift of applying abundance thinking to your sales life, why investing in yourself is the one gift no one else will buy you, the power of true free time (and why refusing to take it is just inflated self-importance), building a personal brand by sharing real problems and solutions, becoming a generalist in the AI age, and seeing modern tools — your CRM, LinkedIn, AI — as gifts rather than burdens.Whether it's your birthday or not, this episode is a reminder to stop waiting for your company to invest in you and start doing it yourself.The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insid

Send a textIn 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 eliminates the “bad lead” blame game, before diving into practical ways sellers can use AI tools like ChatGPT and Copilot to refine emails, personalize outreach, and prepare for complex conversations. Bryan and Kayla also address the risks of inaccurate AI outputs and why positioning insights as questions, and not facts, protects credibility.They close by exploring how buyers are using AI to research vendors and negotiate more strategically, challenging sales teams to elevate their preparation and technical depth. The episode reframes AI as a tool that sharpens execution without replacing relationship-driven selling.______Curious about certification in the Blind Zebra Sales Operating System? Learn more here.Turn your content into

Send a textBill 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 prospects say, "I want to know more."Before diving into the March session, Bill and Bryan walk through the perspective shifts that have to happen first — because you can know exactly what to do and still not do it. The missing ingredient is almost always how you see things.Plus, Bryan shares how the Mental Health for Salespeople series resonated far beyond the sales world — and what that buzz means for upcoming episodes.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

Send a textWhat 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, and closing deals. You'll discover why most salespeople avoid collaboration (they're afraid of conflict), how to audit your sales process for collaborative moments, and the simple phrase that sets the tone from day one. Bill shares a client story about refusing to send a proposal until they collaborated on unanswered questions—and how it built immediate trust. Whether you're stuck in transactional mode or ready to differentiate yourself completely, this episode gives you a new through line that actually works.Join the conversation: 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

Send a textIn 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.Bryan and Steve dig into the realities of territory design and route planning, calling out how many sales leaders still rely on gut feel and educated guesses when structuring territories. Steve explains how Badger Maps and Badger Align help sales teams visualize customers geographically, balance territories using real data, and create more efficient routes that lead to more meetings and measurable sales lift. They also explore why mobile-friendly CRM tools matter so much for outside sellers, and how removing friction from data entry in the field directly impacts performance.The conversation expands into Badger Maps’ broader platform, including lead routing, geographic insights, and performance tracking, before Steve shares the

Send a textWhat 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, creative demonstrations of value. He sent tracks. He added a choir. He painted the picture so vividly that Kenny G couldn't help but respond.The sales lessons are everywhere: Clean intention enables authentic persistence. Information isn't proprietary anymore, so stop withholding it. Collaboration beats competition. And most importantly, your "through line"—the underlying driver of your sales process—might be sabotaging your success.Most sales methodologies operate on a selfish through line: What do I need to say or do to get the deal? That approach creates manipulation, defensiveness, and resistance. But what if collaboration was your through line instead?Join the conversation: AdvancedSellingPodcast.

Send us a textBill 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 you offer, you become the guide that customers are craving.If you've ever wondered why buyers don't trust you or why price becomes the sticking point, this episode reveals what's really happening—and how to fix it.This is part 2 of a 2-part series on how to be a guide.

Send us a textIn 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 explore how physical action—whether it's actual exercise or the behavioral action of getting out and connecting with people—breaks the isolation cycle that feeds sales depression.Bill shares a coaching win where an engineer went from zero prospecting hours to booking two appointments just by reaching out to reconnect with old contacts. No pitch, no agenda—just human connection. Whether you're feeling stuck, isolated, or just going through the motions, this episode delivers the kick you need to stop overthinking and start moving.This is Part 4 of our Mental Health in Sales series. Find all episodes at https://vault.advancedsellingpodcast.com/mental-health-in-salesJoin the conversation: AdvancedSell

Send us a textIn 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.Discover why healthy detachment isn't about not caring—it's about being deliberate in your process without getting entangled in results. Bill explains how attachment creates fear, shortcuts, and procrastination, while detachment creates freedom and effectiveness.This is part 1 of a 2-part series. Next week: How to be the guide.

Send us a textIn 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 moments, emphasizing that when the moment matters more than the message, authenticity wins. John shares the evolution of Spokenote, from a simple sticker concept to a dynamic video platform, driven by real demand for scalable personalization. They unpack what truly differentiates Spokenote from other video tools: modular, variable video snippets that allow sellers to personalize outreach while staying efficient and fully integrated with existing CRM workflows.The conversation also tackles one of the biggest barriers to video adoption in sales: hesitation and self-consciousness. John encourages sales professionals to embrace imperfection, reminding listeners that vulnerability often increases trust and likability.__Curious

Send us a textIn 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, obsessive focus on customer problems, and personal agency. Bill addresses a high performer's legitimate concern about whether detachment actually helps or hurts quota achievement, and Bryan shares insights from John Mellencamp's conversation with Joe Rogan about success and happiness. The episode includes the concept of "measuring backwards" and explains why serving customers beats obsessing over your own numbers.Join the conversation: 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.comThe Insider program is open for enrollment. To c

Send us a textIn 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 movement directly impacts emotional health. If you struggle with walking on eggshells around buyers or feel desperate for outcomes, this episode offers practical remedies including discovering your purpose and becoming obsessed with customer problems instead of deal outcomes.Join the conversation: 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.comThe 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 i

Send us a textIn 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 conversation reframes gifting as a human-first way to build trust, strengthen relationships, and create influence.Bryan and Patricia explore why the most effective gifting focuses on people, not just decision-makers, and how timely, personalized gestures tied to real moments can open doors that traditional outreach often cannot. They also break down why active listening should be a measurable sales behavior, and how capturing personal details in the CRM enables more authentic, relevant engagement over time.The episode also looks at how gifting fits into execution — from prospecting to post-sale adoption — and why treating it as a consistent activity metric, supported by tools like Sendoso, can be a powerful tool for sales teams

Send us a textBill 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 tied to numbers, comparison traps, and the constant pursuit of an unreachable horizon.Bryan shares his panic attack story from his P&G days (confusing a cardiologist visit for what turned out to be anxiety), while Bill opens up about avoidance behaviors and the realization that mental health issues don't discriminate based on success level.This isn't about coddling—it's about real tools, tough love, and practical steps to tend to your mental health. They're inviting listeners to share what they want covered in the remaining episodes via the LinkedIn community.Join the conversation: AdvancedSellingPodcast.com/linkedinIs it time to make a BOLD move in your business? If so, download our brand

Send us a textIn 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 strategies for social media content, email campaigns, and outreach that actually lead somewhere.You'll learn how to create LinkedIn content with purpose, write emails that prospects actually want to read, make outreach meaningful (not desperate), and build engagement through webinars, assessments, and lead magnets that establish trust before the sales call even happens.=================================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.comThe Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insi