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
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.
Mar 2, 2026 • 21min
The Best Sales Gifts Nobody Buys You
They riff on gifts salespeople should give themselves: small tools that make work easier and investments in training and coaching. They talk mindset shifts like abundance thinking and the value of true free time. They cover becoming a generalist in the AI era and building a real personal brand by sharing problems and solutions. They reframe CRMs, LinkedIn and AI as empowering tools rather than burdens.
Feb 25, 2026 • 31min
AI as a Sales Tool, Not a Salesperson with Kayla Kurtz
Kayla Kurtz, VP of Sales and Business Development at Forthea, helps companies align sales and marketing and apply AI to lead generation. She discusses starting small with AI to refine outreach, scaling personalized outbound, risks of inaccurate AI outputs, using AI to prep for calls, and how buyers use AI to research and negotiate.
Feb 24, 2026 • 20min
From Content to Conquest
A preview of a live Insider session about turning knowledge into demand. They unpack the mindset shifts that make content work and why perspective matters more than tactics. Conversation covers why stories beat data and how to shape messages around buyer dilemmas. They also explore expanding offers beyond the core to create helpful entry points.
Feb 16, 2026 • 20min
Why Collaboration Beats Closing Tactics Every Time
They argue for collaboration over persuasion throughout the sales journey. Learn how to give first during networking and co-create content to reach new audiences. Hear about inviting pushback mid-process and collaborating on proposals and timelines. Discover simple conversational moves that build trust from the start.
Feb 11, 2026 • 27min
Saving Sales Time with Smarter Routes ft. Steve Benson
Steve Benson, founder of Badger Maps and mapping-for-sales veteran, explains why field sales often get ignored by modern tech. He discusses territory design vs. spreadsheets. He breaks down smarter route planning, mobile CRM fit, and new tools like lead routing and geographic insights. Practical demos and ROI stories highlight the impact on meeting more customers and saving sales time.
Feb 10, 2026 • 19min
Is Your Through Line Costing You Business?
A quirky story about Charlie Puth and Kenny G becomes a lesson in creative, generous outreach. They explore how vivid demonstrations of value cut through noise. The hosts challenge selfish sales mindsets and argue for collaboration as the guiding through line. Practical tactics for inviting partners and teams into co-creative processes round out the conversation.
8 snips
Feb 6, 2026 • 7min
Be the Guide Your Customers Are Craving
A solo breakdown of the three-part Guide Model and why defining your role shifts buyer interactions. Discussion of identifying a customer's current reality and clarifying their ideal outcome. Framing yourself as the vehicle that moves customers from A to B and practical behaviors to act like a confident guide.
