The Advanced Selling Podcast
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.
Episodes
Twenty years ago, LinkedIn had 50 employees and cold calling ruled the day. Now AI writes your emails and nobody's picking up the phone — so what actually still works?
This week Bill and Bryan mark 20 years of the Advanced Selling Podcast with a celebration episode: listener shoutouts (including a great one from longtime listener Andy in the UK), a quick teaching on the WAG framework you can steal for your next...
Twenty 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 s...
Got 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 posi...
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 tha...
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 bee...
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 ...
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 ...
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 tha...
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 calend...
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 th...
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 recogn...
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 aft...
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...
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 guard
- Delivering a Statement of Detachment that comforts prospects and skyrockets close r...
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 ...
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-...
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...
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 &mdas...
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 showin...
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 prospec...
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