The Advanced Selling Podcast

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Latest Episodes:

Give Buyers an Experience, Not a Slideshow Oct 12, 2026

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Telling 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/insider

If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

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.com

Sales Skill Atrophy, Part 2: The Comeback Plan Oct 05, 2026

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Your 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 first
Why you shouldn't test a new skill on your biggest prospect
The four skills most worth auditing: prospecting, discovery, presenting your offer with conviction, and economics conversations
Why "price resistance" is often really justification resistance, and what a $20K buying decision taught the hosts about connecting money to value

Plus: the show is closing in on its 20th anniversary. The first episode dropped October 25, 2006.

The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

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.com

Are Your Sales Skills Atrophying? Sep 28, 2026

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What 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 skills
How logic can beat your emotional reluctance to get visible
Why a plain, honest phone call often beats a clever email
Why systems, not tricks, rebuild atrophied skills
Why you should "face the brutal facts" even when business is good

Next week, Part 2 covers how to bring those skills back.

The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

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.com

20 Years of Selling: What's Changed (and What Hasn't) Sep 21, 2026

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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 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, go to http://advancedsellingpodcast.com/insider

If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

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.com

20 Years In: What We'd Do Differently Sep 15, 2026

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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 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://advancedsellingpodcast.com/insider

If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

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.com

How to Sell Something the Market Isn't Ready For Aug 31, 2026

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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 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 listener@advancedsellingpodcast.com for their September anniversary celebration.

The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

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.com

It's Not a Skill Problem, It's an Identity Problem Aug 24, 2026

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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" 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 listener@advancedsellingpodcast.com for their September anniversary celebration.

The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

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.com

Stop Blaming Price: Positioning Is Your Problem Aug 10, 2026

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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 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 to hear from you — send a short voice memo to listener@advancedsellingpodcast.com for their September anniversary celebration.

The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

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.com

Lessons We've Learned From Those We've Lost Aug 03, 2026

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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 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 listener@advancedsellingpodcast.com for their September anniversary celebration.

The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

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.com

The People Who Taught Us Everything We Know About Sales Jul 27, 2026

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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 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 listener@advancedsellingpodcast.com for their September anniversary celebration.

The Insider program is open for enrollment. To check out our small learning group, go to http://advancedsellingpodcast.com/insider

If you haven't already, join 14,000+ other sales professionals in our LinkedIn group at advancedsellingpodcast.com/linkedin

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.com

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