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

Send us Fan MailIf 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

Send us Fan MailTelling 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/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, dow

Send us Fan MailYour 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

Send us Fan MailWhat 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

Send us Fan MailTwenty 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,

Send us Fan MailTwenty years ago, Bill and Bryan started recording a podcast every other Monday. They never missed the behavior — and that consistency turned out to matter more than talent, luck, or a growth strategy ever did.To kick off ASP's 20th anniversary celebration, Bill and Bryan share the first of several listener tribute clips — this one from Scott, a longtime Insider member and one of the "Globetrotters," a small accountability group that formed out of the show. Scott's story becomes the jumping-off point for a bigger conversation: why "relationship selling" is mostly a myth, and what actually creates lifelong client relationships (hint: it's not golf outings).Bill and Bryan also get honest about regrets — the choices that kept ASP niche and steady instead of chasing bigger growth, why they never built a true listener community, and the lane they might explore next.The Insider program is open for enrollment. To check out our small learning group, go to http://adva

Send us Fan MailGot something genuinely new to sell — and buyers keep lumping it in with every other "revolutionary" pitch they've heard this month? This one's for you.Bill and Bryan work through a real scenario: a friend building software that could transform hospital billing, but can't get CFOs past their skepticism. The fix isn't a better pitch — it's a completely different approach to who you target and how you position the offer.You'll learn how to sort prospects by tolerance for change (not company size), why positioning your offer as limited and selective beats "revolutionizing everything," and why acknowledging buyer skepticism up front builds more trust than any pitch could.It's the 20th anniversary of the show, and Bill and Bryan want to hear from you — send a short voice memo to [email protected] for their September anniversary celebration.The Insider program is open for enrollment. To check out our small learning group, go to

Send us Fan MailWhy do good sellers freeze up the second a conversation moves from a director-level buyer to the CFO? It's not a skills gap — it's identity. Bill Caskey and Bryan Neale break down why sellers resist doing new things, even when they know exactly what it's costing them.Bryan shares what happened when he volunteered to try something brand-new outside of sales — nervous, uncomfortable, and more locked-in than he's felt in years. That leads into why "just say this instead" coaching doesn't work, why the block that keeps a rep out of the CFO's office (or a $400K advisor from becoming a $1M advisor) is about identity, and a simple reframe for calling on anyone above your comfort level: find what's the same before you worry about what's different. It's the 20th anniversary of the show, and Bill and Bryan want to hear from you — send a short voice memo to [email protected] for their September anniversary celebration.The Insider pr

Send us Fan MailYou didn't lose that deal on price. You lost it because your positioning wasn't strong enough to make you the obvious, can't-do-without-you choice.Bill and Bryan dig into a claim that gets argued in every sales meeting: is price really the reason deals slip away, or is it a symptom of weak positioning? They walk through a real audit of lost deals — 22 gone in six months, four of them deals that should have been won — and use it to unpack what separates a vendor from a "we can't do without you" partner.You'll learn the four ingredients of unshakeable positioning: naming the beliefs your customer has to shift before your value can land, getting explicit about what you don't do, choosing whether you're a problem-solver or a destination (or both), and painting the real cost of standing still. Plus, why the best time to build this is when business is good — not when you're desperate.It's the 20th anniversary of the show, and Bill and Bryan want

Send us Fan MailEvery person you've worked with has a story you probably never asked about — and sometimes you don't find out until it's too late.In Part 2 of their series on the people of sales, Bill and Bryan honor a handful of people who shaped their careers — a neighbor and airline pilot, a mentor who connected without ego, a customer who never delayed a decision, and a prospect Bryan gave up on too soon. Each story carries a lesson you can use this week: ask people about their actual lives, don't wait to reconnect with old friends, decide fast, and don't give up on a prospect after just one or two tries.It's the 20th anniversary of the show, and Bill and Bryan want to hear from you — send a short voice memo to [email protected] for their September anniversary celebration.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 profe

Send us Fan MailTwenty 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 talk about the trap of looking down on younger salespeople — and what a 20-year-old Starbucks employee named Joey reminded Bryan about assuming too much, even when the assumption seems like a compliment.It's the 20th anniversary of the show, and Bill and Bryan want to hear from you — send a short voice memo to [email protected] for their September anniversary celebration.The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodc

Send us Fan MailYou'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, grade yourself honestly, and use it to plan a strong back half.Subscribe, leave a review, and send us your "how I found the show" story to our FAN Mail at the top of the show notes for a shot at our 20th anniversary coaching event.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 ma

Send us Fan MailImprecise 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're about to make makes you easier to follow and easier to buy from, and why tired open-ended questions like "what keeps you up at night?" should be replaced with sharper, stack-ranked questions that force a real answer. Plus: details on ASP's 20th anniversary celebration and how to get your ticket to the live September event.Send us your story (audio, video, or just a note): [email protected] Insider program is open for enrollment. To che

Send us Fan MailBill 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, more and enough — and make the case for replacing it with "and." Plus, a bizarre drone-rescue story that turns into a surprisingly useful metaphor.This episode also kicks off the celebration of ASP's 20th anniversary — Bill and Bryan want to hear from you. Send in an audio or video sharing what the podcast has meant to you for a chance to attend an exclusive live coaching celebration this September.The Insider program is open for enrollment. To check out our small learning group, g

Send us Fan MailBill 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 identity as a seller.The conversation also includes a fun detour into time zones, a live phone interruption from Bill's wife, and a preview of their upcoming 20th anniversary celebration event in September — where every listener who submits a video is invited to join.This is Part 1 of a two-part series. Part 2 picks up on the concept of drift.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+

Send us Fan MailBill 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 for many listeners, it may be the most important one they hear.Part two drops in a few days on another solo episode.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 Reinventin

Send us Fan MailWhat 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 effort.Bill challenges you to audit which of these lies you're living — and gives you a framework for getting out from under them.The 7 Lies:Your performance determines your well-beingThe prospect holds your future in their handsIncome is determined by work ethicMore activity equals more resultsThe best closer winsThere's a scarcity of opportunityIf you're good enough, they'll find youThe Insider program is open for enrollment. To check out our small learning group, go to h

Send 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

Send 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, g

Send 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