The Advanced Selling Podcast
Bill Caskey and Bryan Neale: B2B Sales Trainers
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
Mentioned books
May 11, 2026 • 21min
The Fear Factor in Sales
They explore how fear shows up at every stage of a sales career, from first calls to big promotions. They explain why the brain treats social risks like physical threats and how to reframe anxiety into action. Beekeeping anecdotes illustrate stepping into discomfort. They also talk about turning AI anxiety into curiosity and practical prompts to post, learn, and engage.
May 4, 2026 • 20min
The Simple Shift That Changes Every Sales Conversation
They dig into why defining the real problem matters before pitching solutions. They stress focusing on the immediate process rather than distant outcomes. They talk about accountability, owning failures, and adapting your sales approach to your life season. They highlight spotting external saboteurs early and knowing when pausing a deal is the right move.
7 snips
Apr 27, 2026 • 20min
Why Your Calendar Is Killing Your Pipeline
They diagnose how bad calendar habits and reactive weeks wreck sales pipelines. They argue lead generation needs a repeatable system, not random activity. They outline calendar blocking, simple outreach cadences that drive conversations, and leverage-based content like webinars to let buyers self-identify. They stress starting small with realistic, protected prospecting time.
7 snips
Apr 20, 2026 • 15min
Stop Being Selfish: The Sales Habit That Pays Off Later
A look at how tiny, consistent actions can snowball into massive results years later. The story of a college fundraiser turned $400 million movement anchors the idea of playing the long game. A call to stop hoarding knowledge, show up regularly on LinkedIn and reach out more often. A reminder that your unique voice and small daily habits can create unexpected impact.
Apr 9, 2026 • 6min
Why Prospects Stop Trusting You (And How to Fix It)
They explore why deals fall apart when trust is missing and why virtual interactions make trust harder. Old tactics like rehearsed niceties and pushy follow-ups are called out as trust killers. The conversation recommends using consistent content so prospects can sample your thinking and become familiar before any sales conversation. Practical encouragement to start creating content now rounds out the discussion.
Apr 2, 2026 • 4min
The Identity Shift: From Labor to Leverage
A solo breakdown of shifting from grind-based selling to scalable leverage. A practical Discover, Develop, Deploy framework for finding and using your existing assets. Real examples like webinars and case studies show how to multiply impact. A push to stop wasting effort on low-probability prospects and build an identity centered on leverage.
Mar 30, 2026 • 14min
Stop Hiding. Create Space to Be Excellent.
They argue you must leave home and seek public spaces where excellence can be seen. Stories include a chance restaurant meeting that led to opportunity and a program that pushes people to tell powerful stories onstage. They warn against wasting spotlight moments by being unprepared. Even small visible actions, like holding a door with enthusiasm, can signal excellence.
Mar 23, 2026 • 16min
Raise Your Prices Without Losing Your Clients
A listener asks how to stop competing on price and how to increase fees with existing clients. They explain why pricing is a positioning problem and why technical sellers need higher-level relationships. Practical tactics include expanding contacts inside accounts, building a visible personal brand, and calmly handling pushback when rates go up.
Mar 16, 2026 • 17min
Stop Watching the Scoreboard — Start Watching the Inputs
They contrast obsessing over scores with tracking the everyday inputs that drive performance. Stories about coaching legends frame a focus on habits and process over outcomes. The conversation highlights how small habit fade slowly erodes results and why finding joy in the work creates lasting advantage.
5 snips
Mar 5, 2026 • 5min
Find the Real Pain Behind Every Sales Conversation
Prospects often state surface problems that mask deeper issues. The conversation drills into asking questions about cause, impact and the economics behind a pain. It highlights distinguishing symptoms from root causes and guiding prospects through a discovery process. Emotional hurt and past failed attempts are explored to create clarity and readiness to act.
