The Advanced Selling Podcast

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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 instead of architecture.

The guys walk through practical examples of what a real lead gen system looks like: calendar blocking that actually holds, consistent outreach cadences that generate 1-in-5 conversations, and leverage-based content strategies that let buyers raise their hand instead of being cold-called into a corner.

If your sales are inconsistent, your calendar is the first place to look.

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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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 — because someone out there might be suffering simply because they haven't heard from you yet.

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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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 finally reach out, they're already sold. He also challenges the habit of chasing prospects for next steps, arguing that if you're the one pushing, something went wrong earlier in the process.

🔗 Want more advanced sales training? Join ASP Insider: https://advancedsellingpodcast.com/insider

Download your complimentary copy of the 12 Bold Moves audiobook at 12BoldMoves.com/Audiobook

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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 the skills to use them, and put them to work in the market.

Most salespeople close 20–25% at best, which means they're burning 75–80% of their effort on people who will never buy — largely because they never leveraged anything in the process. Bill challenges you to identify where leverage is absent in your sales approach and start building a new identity around it.

🔗 Want more advanced sales training? Join ASP Insider: https://advancedsellingpodcast.com/insider

Download your complimentary copy of the 12 Bold Moves audiobook at 12BoldMoves.com/Audiobook

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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.

They also dig into what happens when people do get their moment in the spotlight — and blow it by reading from a notecard. And they share the story of Milo, door holder number three, who might have the best mindset in the room.

Get out. Get in the room. Be excellent when it counts.

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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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 cover why technical sellers tend to stay too low in the org chart, why your contact isn't selling your value upstairs for you, and what a price increase reaction tells you about where you actually stand with a client.

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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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 competitive advantage, and what it looks like when a salesperson truly loves what they do.

If your Q1 numbers aren't where you want them, this episode will help you look in the right places.

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 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 you help a prospect understand their own problem clearly, you earn the right to present your solution — and they become obsessed with solving it.

🔗 Want more advanced sales training? Join ASP Insider: https://advancedsellingpodcast.com/insider

Download your complimentary copy of the 12 Bold Moves audiobook at 12BoldMoves.com/Audiobook

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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 why refusing to take it is just inflated self-importance), building a personal brand by sharing real problems and solutions, becoming a generalist in the AI age, and seeing modern tools — your CRM, LinkedIn, AI — as gifts rather than burdens.

Whether it's your birthday or not, this episode is a reminder to stop waiting for your company to invest in you and start doing it yourself.

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

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. Bryan and Kayla also address the risks of inaccurate AI outputs and why positioning insights as questions, and not facts, protects credibility.

They close by exploring how buyers are using AI to research vendors and negotiate more strategically, challenging sales teams to elevate their preparation and technical depth. The episode reframes AI as a tool that sharpens execution without replacing relationship-driven selling.

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