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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

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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

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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 [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/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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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 [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/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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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 [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/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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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 [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/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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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 [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/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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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, 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/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

Ready to stop competing on price? Join Bill's Insider coaching program at advancedsellingpodcast.com/insider.

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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'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]

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

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, 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.

P.S.: Watch the drone rescue clip that kicks off this conversation: https://www.tiktok.com/@foxweather/video/7650957122145930509

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