The Advanced Selling Podcast

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" ...

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 ca...

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 ac...

Send us Fan Mail Twenty years in this business means running into a lot of characters. This week Bill and Bryan riff on the people — bosses, clients, gatekeepers, baristas — who taught them something they never forgot, whether the lesson was about sales or just about being human. You'll hear about "Leisure Suit Larry," the grocery store manager who refused to acknowledge salespeople existed, and what he taught Bill about never forcing yourself on someone who doesn't want to talk. They also ta...

Send us Fan Mail You're six months into the year. Do you actually know what's working in your sales process — and what you quietly stopped doing back in February? Bill and Bryan borrow a trick from football coaches: self-scouting. Before the next game, coaches review their own film to find what their team does well (so they can do more of it) and what they do poorly (so the other team can't exploit it). Bill and Bryan apply that same exercise to your sales year — build a 20-point scorecard, g...

Send us Fan Mail Imprecise language is quietly sabotaging your sales process — and most sellers don't even notice it happening. This week, Bill and Bryan dig into the art of precise communication and why "what they hear" matters more than "what you meant." Bryan shares a real example from his own sales process: his team retired the vague word "calendars" as the last item on a sales agenda in favor of the more direct "get calendars out." They also cover why stating up front how many points you...

Send us Fan Mail Bill and Bryan continue their series on the hidden patterns that quietly cap sales performance. Building on last episode's conversation about "drift," they dig into two more limiting patterns: fear (and why naming it is the first step toward detachment) and the belief that bigger outcomes simply "aren't possible." Along the way, they tackle the either/or trap — the binary thinking that convinces salespeople they have to choose between income and time, ambition and family, mor...

Send us Fan Mail Bill and Bryan dig into what they call "patterns of limitation" — the ingrained habits and mindsets that quietly cap your sales growth, often disguised as things that are already working. They explore four key patterns worth examining: the tendency to focus on the big picture while ignoring critical details, the trap of pursuing vague or undefined problems with prospects, the danger of plateauing without recognizing it, and the gradual drift away from your core purpose and id...

Send us Fan Mail Bill goes somewhere different today — and that's intentional. In this solo episode, Bill Caskey shares the first six of twelve core sales principles, each grounded in a biblical reference. From understanding your divine assignment and serving before selling, to detaching from outcomes and deploying your unique gifts, Bill connects the spiritual underpinnings of great selling to the real-world results you're after. This isn't a tactics episode. It's a foundation episode — and ...

Send us Fan Mail What if the beliefs driving your sales career are built on a foundation of lies? In this solo episode, Bill Caskey breaks down seven deeply normalized lies about achievement, income, and sales success — the kind that quietly run your life if you let them. From "hustle harder to earn more" to "the best closer wins," these aren't fringe ideas. They're mainstream beliefs that keep good salespeople permanently busy, permanently stuck, and wondering why the results never match the...

Send us Fan Mail Bill 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...

Send us Fan Mail How 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 f...

Send us Fan Mail Fear 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 Insi...

Send us Fan Mail Are 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 I...

Send us Fan Mail What'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 instea...

Send us Fan Mail Bill 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...

Send us Fan Mail Trust 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 fin...

Send us Fan Mail In 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 th...

Send us Fan Mail Most 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....

Send us Fan Mail A 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...

Send us Fan Mail We'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 ...

Send us Fan Mail Every 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 ...

Send us Fan Mail It'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 w...

Send us Fan Mail In 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. Brya...

Send us Fan Mail Bill 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 stil...

Send us Fan Mail What 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...

Send us Fan Mail In 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...

Send us Fan Mail What 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 authent...

Send us Fan Mail Bill 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 ...

Send us Fan Mail In 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 wi...

Send us Fan Mail In 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 proc...

Send us Fan Mail In 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...

Send us Fan Mail In 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 insi...

Send us Fan Mail In 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 yo...

Send us Fan Mail In 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 decis...

Send us Fan Mail Bill 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...

Send us Fan Mail In 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 r...

Send us Fan Mail Bill Caskey breaks down the exact business planning framework from the recent ASP Insider workshop. If you haven't done your 2026 planning yet, this episode walks you through nine critical building blocks that will set you up for sustainable sales success. From defining your vision to finding the right accountability partner, Bill covers everything you need to create a plan that actually works—not just another resolution that fades by February. Bill dives deep into why most s...

Send us Fan Mail Most business planning workshops start with vision statements and call quotas. But Bill argues there's a critical block missing from that equation: personal development. In this solo episode, he breaks down Block 8 from his 2026 Business Planning Strategy—the piece that asks not just what you need to do, but who you need to become to achieve your goals sustainably. Bill covers four essential areas: AI literacy and staying current, personal branding and findability, digital ma...

Send us Fan Mail Last week, Bill and Bryan covered mental discipline—getting your head right. This week, they shift to operational discipline: the actual behaviors and systems that high performers use to win. This isn't about overhauling your entire life. It's about looking at your current operational system and asking: Is this working? If yes, keep rolling. If not, tweak and modify. Bill and Bryan break down five operational disciplines they see in top performers: committing to writing and i...

Send us Fan Mail Bill and Bryan tackle mental discipline—but not the way you'd expect. Instead of rigid rules and forced habits, they reframe discipline as the inputs that create freedom, not constraints. In this first part of a two-part series, they explore the mental shifts that separate high performers from the rest: quieting your mind, embracing possibility thinking, getting comfortable with failure, and continuously feeding your growth. You'll discover why discipline isn't about forcing ...

Send us Fan Mail In this episode of The Advanced Selling Podcast, Bryan Neale sits down with sales compensation expert Chris Goff, better known across the industry as “The Sales Comp Guy.” With deep experience in sales operations, territory optimization, and comp plan design, Chris brings a rare, holistic perspective to one of the most emotionally charged topics in sales: how sellers get paid. Together, Bryan and Chris unpack why compensation plans create so much tension, how leaders can desi...

Send us Fan Mail Part two of our macro vs. micro skills series—and this one gets tactical. Bill and Bryan dive into the small, incremental skills that most salespeople overlook but that separate pros from amateurs. These aren't the big-picture capabilities; they're the in-the-moment moves that determine whether your sales calls actually go anywhere. The guys cover the courage to stop and clarify when something's confusing, the power of numeric calendar values (no more "let's connect next week...

Send us Fan Mail Most salespeople waste their first meeting covering basics that could've been handled beforehand. Bill introduces a game-changing digital asset: the introductory video—a 5-minute pre-meeting video that positions you as a credible problem-solver before the conversation even starts. In this episode, Bill breaks down the exact structure of an effective introductory video, including the hook that grabs attention in 10 seconds, how to tell your story concisely, the three industry ...

Send us Fan Mail Bill and Bryan break down the difference between macro and micro sales skills—and why both matter more than you think. Inspired by a prospect who called out his own team for not asking clarifying questions, this episode explores the big-picture capabilities that separate average performers from top producers. They cover essential macro skills including strategic planning (with outcomes AND behaviors), reverse engineering your goals, financial literacy for sales professionals,...

Send us Fan Mail Bill Caskey follows up on last week's deep dive by sharing insights from coaching a high-performing salesperson who's hitting the limits of process-driven selling. He reveals why even the best sales process isn't enough—you must show up authentically and have the courage to disqualify prospects who aren't truly committed. Through a compelling coaching story, Caskey explains how being grounded in who you are allows you to spot the 20% that's missing in a conversati...

Send us Fan Mail In this episode of The Advanced Selling Podcast, Bryan Neale sits down with longtime friend and sales veteran Vince Beese, a fractional CRO and sales coach with over 25 years of B2B enterprise experience and five successful exits under his belt. Together, they dive deep into “Red Zone Selling:” a framework inspired by football that helps sellers stay focused, avoid complacency, and close more deals when it matters most. Vince breaks down how 80–90% of enterprise deals are won...

Send us Fan Mail Are you uncomfortable talking about money with prospects? You're not alone. In this episode, Bill and Bryan tackle one of the biggest challenges sales professionals face: bringing up price, cost, and economic conversations without the anxiety and uncertainty that usually comes with it. Whether you're dealing with technology sales, competitive situations, or demonstrating clear ROI, this episode gives you the confidence to talk about money like the professional you are. Key i...

Send us Fan Mail In this episode, Bill and Bryan continue their conversation on sales culture with actionable tactics you can implement immediately. Whether you're building team culture or your personal approach, these strategies will help you create intentional, high-performing environments. What You'll Learn: ✅ How to build customer relationship culture through strategic meetups ✅ The power of book clubs and team socialization for engagement ✅ Team brag sessions that uplif...

Send us Fan Mail Bill Caskey poses a challenging question: If you disappeared from your prospect's world tomorrow, would they feel the loss? In this introspective solo episode, he explores the "invisible dimension" of sales—the deeper level where prospects evaluate not just your skills and process, but your unique presence and purpose. Caskey shares three powerful practices for connecting with your authentic self: inventorying your unique experiences, clarifying your God-given assignmen...

Send us Fan Mail In this episode, Bryan Neale from Blind Zebra shares a tactical framework for building meaningful customer connections — one rooted in strategy, generosity, and intentional networking. He explains why great salespeople move beyond vague Ideal Customer Profiles (ICPs) to create “conquest account lists” that name specific people they want introductions to. Bryan also challenges listeners to identify at least 20 “Connectors” — the natural networkers who love making introductions...

Send us Fan Mail Bill and Bryan kick off a two-part series on sales culture by sharing what they've observed from years of working inside dozens of organizations. In this episode, they explore the difference between surface-level culture (the pictures on the wall) and the real culture you can feel in the air. Whether you lead a sales team or carry your own quota, this episode will help you see culture in tangible ways—and understand why the language you use, the people you surround yourself w...

Send us Fan Mail In part two of their AI series, Bill and Bryan get specific—sharing real examples of how they use AI in their daily sales work. Bill walks through actual ChatGPT conversations for client prep (including a memorable moment when the AI got it wrong about an ESOP), while Bryan demonstrates how he uses Claude to research prospects and create strategic talking points. You'll hear how they validate AI-generated research during sales calls, why telling clients "I did some research" ...

Send us Fan Mail In this episode, Bryan explores why the best sales leaders focus as much on connecting with their people as they do on connecting with their customers. Sales is often seen as an individual sport - everyone chasing their own numbers and commissions. But the real magic happens when leaders take time to understand each team member’s unique motivations and coach them accordingly. Bryan shares how great leaders: Build individual connections with reps instead of one-size-fits-all...

Send us Fan Mail Bill and Bryan dive into how they're actually using AI in their daily sales work—no hype, just practical applications. In part one of this two-part series, they share their number one use case: preparation for sales calls, including researching companies, understanding buyer contexts, and making discovery more efficient. You'll learn why Bill treats AI like an executive assistant, how Bryan uses it for everything from client prep to football officiating, and why you should te...

Send us Fan Mail In this episode, Bryan is joined by John Barrows to talk about the high-stakes final stage of the sales process, where deals are either won or lost. Together, they explore why so many sales teams stumble here, often resorting to last-minute discounts or high-pressure tactics driven by forecast anxiety. Bryan and John share strategies to keep control of the process, including engaging procurement early, coaching reps through nuanced situations, and avoiding the trap of reacti...

Send us Fan Mail Tired of perfecting your sales skills but struggling to get in front of the right people? Bill and Bryan tackle the universal challenge every B2B professional faces: visibility. Using a real client case study from the tax law industry, they reveal why traditional cold calling is dead and share actionable strategies to become visible where your prospects are already looking. Discover how to leverage weekly insight videos, LinkedIn article publishing (including the brilliant in...

Send us Fan Mail In this episode, Bill and Bryan debunk one of the most persistent myths in sales training - that you can create urgency in buyers through clever tactics and techniques. They explore why deals are taking longer to close in 2025, examining both macro factors (economic uncertainty, decision-making complexity) and micro factors (changed buyer behavior, technology overload). The guys discuss how traditional urgency-creating methods like pattern interrupts and pressure tactics are ...

Send us Fan Mail Bill and Bryan explore a growing trend that's reshaping the sales landscape: the rise of "accidental salespeople." These are the technical advisors, project managers, engineers, and executives who don't have "salesperson" on their business cards but find themselves increasingly vital to the buyer-seller relationship. The guys discuss why these technically-minded professionals are becoming more important than ever, especially as traditional SDR/BDR approaches burn out prospect...

Send us Fan Mail What happens when two conversational AI engineers realize they can't sell their own startup? They build an AI sparring partner to teach themselves—and accidentally create a game-changing sales training platform. We welcome the founders of Hyperbound.AI, Sai Guduguntla and Atul Raghunathan, who share their remarkable journey from technical founders struggling with sales to building a platform that's helping thousands of sales professionals practice and perfect their craft. In ...

Send us Fan Mail In this early Labor Day release, Bill and Bryan dive into expert frameworks—essential tools for positioning yourself as a knowledgeable sales professional in today's market. Bill breaks down the critical video framework every salesperson needs. Learn the three-part video structure that actually gets attention: the hook that stops the scroll in the first 5 seconds, the story that keeps them engaged, and the call-to-action that drives results. Discover why social media has shif...

Send us Fan Mail In this episode, Bryan Neale and Marcus Chan dive into the sales “red zone”—the late stage of the sales cycle where too many deals stall or fall apart. They explore how sales teams can avoid costly mistakes by addressing pricing, multi-threaded stakeholder engagement, and risk management early in the process. Marcus introduces his ADVANCE Framework, a practical tool for sales leaders to audit deals and improve forecasting accuracy. The conversation also highlights the import...

Send us Fan Mail In this episode, Bill and Bryan shift the focus from post-sale customer experience to what they call "PX 90" - the prospect experience during the sales process. After Bryan shares a fantastic customer service call with Southwest Airlines, they dive into practical ways salespeople can go above and beyond for prospects before they become customers. The guys share practical, low-cost ways to go above and beyond for prospects that will differentiate you from the competition...

Send us Fan Mail In this solo episode, Bill Caskey reveals one of his 12 Insider Secrets for reinventing yourself and your results: creating a mini book to establish yourself as an authority in your field. Bill shares the compelling story of how his own 20-page book "12 Bold Moves" generated a $40-50K client from a $20 purchase, demonstrating the incredible ROI potential of this positioning strategy. Whether you're in sales, consulting, or any service business, this episode shows you how to t...

Send us Fan Mail Bill and Bryan dive into the critical balance between heart-centered selling and process-driven approaches. Sparked by a real coaching session where a top salesperson admitted "I'm not a warm guy," the guys explore why both emotional connection and systematic process are essential for sales success. They also discuss the importance of decisiveness in both sales and business relationships, and remind listeners that sometimes the best thing you can do is walk away when a prospe...

Send us Fan Mail In this episode, Bryan dives into the Sales Leadership Hats, the roles great leaders switch between to unlock performance and keep their teams moving forward. You’ll learn how to wear: The Manager Hat – Cutting through noise with data-driven decisions that point the way forward. The Coach Hat – Sharpening skills and strategies so reps get better, not just busier. The Cheerleader Hat – Sparking motivation, restoring confidence, and helping reps break through mental roadbloc...

Send us Fan Mail Bill Caskey and Bryan Neale tackle a challenge every sales professional faces: how to properly prepare for sales calls in today's digital landscape. Sparked by recent conversations with VPs of Sales about their teams going into calls "cold," Bill and Bryan break down their proven preparation framework that combines traditional research methods with cutting-edge AI tools. The guys emphasize that your "lane" as a sales professional is widening—it's no longer just about conducti...

Send us Fan Mail In this solo episode, Bill Caskey tackles the growing trust crisis facing sales professionals today. Drawing from recent research showing declining trust in businesses and institutions, Bill explores why prospects automatically assume you're going to lie to them—and why they're probably right to feel that way. He shares four practical levers you can use to build trust and stop destroying it: stop selling and start understanding, be willing to walk away when the fit isn't ther...

Send us Fan Mail In this episode of the Advanced Selling Podcast, Bill and Bryan give listeners an exclusive preview of their upcoming Insider program session on building a "platform of authority." They explain how every sales professional needs a platform where they can share valuable insights and establish themselves as an authority figure in their field. The guys discuss what constitutes a platform (podcasts, LinkedIn, speaking engagements, client dinners, or even informal meetups) and how...

Send us Fan Mail In this episode, Bryan dives into the critical strategy of maintaining a “virtual bench” - a curated list of talented individuals you’d love to have on your sales team. Instead of scrambling to post job ads and sift through countless resumes when a rep leaves, Bryan explains how to stay ahead by proactively building and nurturing relationships with top talent. Learn why keeping your virtual bench warm with at least one touchpoint per year can give you a competitive edge and e...

Send us Fan Mail Bill and Bryan dive deep into one of the most frustrating challenges in sales and business: resistance to change, even when that change could lead to significant growth. They explore why some decision-makers are lightning-fast adopters while others sit in limbo for months, and why even high-performing salespeople resist proven strategies that could boost their results. The guys examine the psychology behind resistance, from the comfort of the status quo to the fear of admitti...

Send us Fan Mail Summer vacation mode might be costing you your year-end goals. In this episode, Bill and Bryan dive into why your current July activities are directly shaping your Q4 results - especially if you have a 60-90 day sales cycle. The guys share strategies for making your year in July instead of scrambling in the fourth quarter, including how to shorten your sales cycles (think restaurant "table turns"), create a documented back-half business plan with three-prong goal settin...

Send us Fan Mail In this episode, Bryan dives into a powerful yet often overlooked tool in the sales leader’s toolkit: the calendar inspection. He explains how regularly analyzing your team’s calendars can reveal dangerous pipeline gaps before they become full-blown problems. You’ll hear why having a clear sales playbook, with numeric goals like two connector meetings and two new logo meetings scheduled 2–3 weeks out, is essential for maintaining consistency in your sales process. Bryan brea...

Send us Fan Mail Bill and Bryan dive deep into four powerful quotes that challenge conventional sales thinking and offer fresh perspectives on growth and success. From Buckminster Fuller's wisdom on building new models to Elon Musk's insights on optimization, this episode will make you question everything you thought you knew about scaling your business. The guys also share personal stories, including Bryan's cautionary tale about comfort zones leading to business failure, and discuss practi...

Send us Fan Mail Bill and Bryan tackle the crucial mid-year evaluation every salesperson should be doing right now. With two quarters behind us and a time-compressed second half ahead (thanks to holiday season), they break down practical strategies for looking backward and forward to maximize your year-end results. Plus, Bryan shares his fascination with meter readers (yes, they still exist!), and the guys discuss why showing up authentically beats trying to be someone you're not when buildi...

Send us Fan Mail In this episode, Bryan unpacks a counterintuitive truth: the more structure your sales team has, the more freedom they gain. As markets grow more competitive and buyers become increasingly digital-savvy, a well-crafted sales playbook isn’t just helpful. It’s essential. Bryan explores how playbooks streamline the sales process, remove friction, and empower reps to focus on selling, not scrambling. He also discusses how discipline creates efficiency, how to overcome bu...

Send us Fan Mail Bill and Bryan tackle a common sales trap that costs deals and relationships: making judgments about prospects before you even sit down with them. Whether you're assuming someone can't afford your services based on company size, or writing off a "boring" CFO who might actually be your biggest champion, these snap judgments can blind you to real opportunities. The guys share real stories of misjudging billion-dollar executives and getting burned by outdated company re...

Send us Fan Mail Bill and Bryan are joined by Kevin Koharki, an accounting professor at Purdue University who specializes in teaching sales professionals how to speak the language of finance. Kevin shares his unique journey from investment banking and now helping sales teams worldwide understand how to communicate financial value to CEOs and CFOs. Learn the difference between gross margin and operating margin, why "payback period" isn't enough for most B2B sales, and how to shift con...

Send us Fan Mail In this episode, Bryan unpacks what makes a truly effective sales playbook - and why now is the time for sales leaders to get serious about it. He shares the key components every playbook must include: a foundational philosophy, planning elements, defined processes, contingency plans, and accountability mechanisms. Bryan spotlights the Blind Zebra Sales Operating System (BZSOS), a comprehensive set of procedures, tasks and scoreboards, with 10 guiding principles that ...

Send us Fan Mail Bill and Bryan dive deep into the universal experience of self-doubt in sales and business development. Moving beyond the typical "fake it till you make it" advice, they explore how conditional self-doubt shows up in specific areas—like shooting videos, talking about money, or making cold calls—even when we're confident elsewhere. The guys reveal how even the most successful people struggle with imposter syndrome. But here's the twist: instead of fighting these insec...

Send us Fan Mail What if the most valuable sales asset you have is something you don't even realize you possess? In this week's episode, Bill and Bryan explore the concept of "familiarity blindness" - why we discount our own expertise and fail to see the goldmine of knowledge we're sitting on. Whether you've been in your industry for 3 years or 30, you have insights that could transform your client relationships and differentiate you from the competition. The guys challenge listeners...

Send us Fan Mail Bill Caskey kicks off a new 12-week series based on his book "12 Bold Moves" by tackling the first bold move: creating a sales process that genuinely benefits prospects, not just salespeople. He challenges the traditional approach of "shoving people through" a process and shares how reframing discovery as mutual understanding can dramatically improve close rates. Caskey includes a real client example of using pre-call assessments to increase closing rates from 20% to ...

Send us Fan Mail In this episode, Bryan shares a powerful mindset shift to help salespeople take control of the chaos: become a student of your calendar. He breaks down how proactive calendar management (daily, weekly, monthly, and even into next year) can give you more clarity, better pipeline health, and fewer wasted hours. Bryan challenges you to look at your calendar not just for what’s there, but for what’s missing. What calls, activities, or planning sessions should be on there...

Send us Fan Mail It's graduation season, and Bill Caskey and Bryan Neale are sharing their top advice for new graduates entering the workforce—plus essential reminders for seasoned professionals who might need to hear these truths again. In this episode, you'll discover why understanding that life and sales naturally go up and down like an accordion can save you from unnecessary stress and help you navigate both the highs and lows with greater wisdom. Bill and Bryan explore how to bu...

Send us Fan Mail Bill and Bryan continue their deep dive into evolving buyer behavior with some eye-opening insights that challenge conventional sales wisdom. In this episode, they tackle the myth of "the decision maker." They explore how buying by committee has become the new normal and why your traditional one-to-one sales training might be preparing you for a world that no longer exists. The guys also discuss the critical importance of elevating the buyer experience beyond just data dumps,...

Send us Fan Mail In this episode, Bryan introduces a bold shift in how sales coaching should be done - by focusing on the science and mechanics of selling rather than the often subjective "art" of it. Drawing on nearly three decades of experience as a coach (and a self-proclaimed “recovering sales trainer”), Bryan proposes a more measurable, documentable, and results-driven approach to developing salespeople. Bryan explains why sales leaders should spend more time coaching what can b...

Send us Fan Mail Bill and Bryan explore how sales professionals need to shift their focus from traditional sales techniques to understanding modern buyer behavior. They discuss how buyers have become more self-directed in their research, the growing "trust gap" between buyers and sellers, and why transparency in the sales process is crucial for success in today's market. The guys examine why conventional manipulation tactics no longer work and offer practical strategies for adapting...

Send us Fan Mail Bill and Bryan Neale dive into a game-changing concept called "Everyday Leads" - a systematic approach to generating B2B leads continuously, not just when you desperately need them. The guys explore why salespeople often find themselves with empty pipelines after closing quarters strong, and how to break free from the traditional labor-intensive prospecting cycle. Bill shares insights from his work with clients on building automated webinar systems that generate warm...

Send us Fan Mail In this episode, Bryan continues exploring the Guiding Principles of the Blind Zebra Sales Operating System, picking up where he left off in Part 1. This time, he dives into the principles of intent and assertiveness — and why they’re game-changers for sales conversations. He shares how locking in a clear next step can eliminate the dreaded "calendaring ping pong" and keep momentum strong. Bryan explains how intent and assertiveness create a more customer-centered ex...

Send us Fan Mail Bill and Bryan explore the enduring fundamentals of sales that have stood the test of time despite decades of technological advancement. The guys reflect on timeless skills that remain essential in today's sales landscape: the art of discovery and qualification, the importance of genuine understanding and connection, bringing authenticity and purpose to your work, and the critical role of creating and executing a solid business plan. While new technologies and metho...

Send us Fan Mail In part 2 of their special live episode on navigating uncertain markets, Bill Caskey and Bryan Neale continue their discussion on essential skills for sales professionals. The guys emphasize the importance of utilizing free and low-cost tools already at your disposal, from LinkedIn to ChatGPT, rather than waiting until circumstances force your hand. Bill shares a powerful strategy for commanding premium pricing by developing a customer roadmap that builds trust in yo...

Send us Fan Mail In this episode, Bryan dives into two of the Guiding Principles from the Blind Zebra Sales Operating System: Objectivity and Expert Persona. He challenges salespeople to view their funnel without bias - imagine betting your own money on each deal to test your objectivity. Bryan also unpacks what it means to become an expert in your customer’s world (not just your own product). It’s about earning trust by showing you care enough to really understand their business. Plu...

Send us Fan Mail In this special live episode, Bill and Bryan discuss essential skills for sales professionals facing economic uncertainty. Rather than focusing on what you can't control, the guys break down practical strategies for maintaining your edge when markets get volatile. Learn why identifying what's in your control, maintaining pricing discipline, and understanding the true abundance of opportunities in your market are critical during challenging times. Bill and Bryan also...

Send us Fan Mail In this episode, Bill and Bryan dive into the often-overlooked world of financial conversations in sales. Moving beyond simple ROI calculators, they explore how to effectively discuss investment value with prospects through compelling storytelling rather than dry spreadsheets. The guys challenge salespeople to think beyond "break-even" mentality, understand the lifetime value of clients, and recognize the importance of time horizons in financial discussions. Bill and...

Send us Fan Mail Bill and Bryan follow up on their popular episode about why every salesperson should have a YouTube channel, sharing Marcus Sheridan's prediction that YouTube could soon become more important than company websites. The guys tackle common obstacles like being "intrigued but intimidated" by video creation, offering practical content ideas including customer spotlights, technical demonstrations, and answering frequently asked questions. Bill and Bryan make a compelling ...

Send us Fan Mail In this episode, Bill and Bryan discuss the importance of crafting compelling stories that connect with prospects on a deeper level. They dive into how salespeople can move beyond personal anecdotes to tell meaningful market stories and "I was where you are" narratives that resonate with customers. The guys also touch on the problem of "over-discovery" in the sales process, suggesting that modern selling should focus more on explaining value than excessive questionin...

Send us Fan Mail In this solo episode, Bill challenges traditional sales approaches by advocating for a fundamental shift from "selling" to "guiding." He explains why old-school sales tactics create negative "karma" with prospects and offers a fresh alternative: becoming a trusted guide who provides value before asking for payment. Caskey shares personal examples of how creating helpful content has naturally attracted clients to him, eliminating the need for aggressive sales tactics...

Send us Fan Mail In this episode, Bill and Bryan tackle the challenge of time management in sales, exploring how “time goes fast and speeds up” as quarters and years fly by. They discuss the pitfalls of short-term thinking and offer practical strategies for sales professionals to extend their planning horizons. The guys emphasize the importance of looking beyond the current week to plan months ahead, while balancing immediate tasks with future initiatives. They share insights on crea...

Send us Fan Mail In this solo episode, Bill explores the critical concept of believing in your own economic value as a sales professional. Drawing from his document “The 15 Profit Amplifiers” created for clients, Bill discusses how understanding the economic impact of your solution transforms your ability to communicate value to prospects. Bill examines two primary ways your solution can deliver economic value: by alleviating pain points that cost customers money or by helping them a...