The Identity Shift: From Labor to Leverage

More from The Advanced Selling Podcast All episodes →

1. 

   E884 · 11 May 2026 · 21 min

   The Fear Factor in Sales

   Send us Fan Mail 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-gloom crowd is almost always wrong about new technology. The Insi...

2. 

   E883 · 4 May 2026 · 20 min

   The Simple Shift That Changes Every Sales Conversation

   Send us Fan Mail 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 sometimes the most powerful sales move you can make. The I...

3. 

   E882 · 27 Apr 2026 · 20 min

   Why Your Calendar Is Killing Your Pipeline

   Send us Fan Mail 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 instea...

4. 

   E881 · 20 Apr 2026 · 15 min

   Stop Being Selfish: The Sales Habit That Pays Off Later

   Send us Fan Mail 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...

5. 

   9 Apr 2026 · 6 min

   Why Prospects Stop Trusting You (And How to Fix It)

   Send us Fan Mail 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 fin...

6. 

   E880 · 30 Mar 2026 · 14 min

   Stop Hiding. Create Space to Be Excellent.

   Send us Fan Mail 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....

7. 

   E879 · 23 Mar 2026 · 17 min

   Raise Your Prices Without Losing Your Clients

   Send us Fan Mail 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...

8. 

   E878 · 16 Mar 2026 · 17 min

   Stop Watching the Scoreboard — Start Watching the Inputs

   Send us Fan Mail 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 ...

9. 

   5 Mar 2026 · 5 min

   Find the Real Pain Behind Every Sales Conversation

   Send us Fan Mail 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 ...

10. 

    E877 · 2 Mar 2026 · 21 min

    The Best Sales Gifts Nobody Buys You

    Send us Fan Mail 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 w...