The Bill Caskey Podcast: High Impact Sales Training for Sellers and Leaders

Hosted by Bill Caskey

Business Management Education

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Episodes

439

Latest episode

Oct 2026

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About the show

Welcome to The Bill Caskey Podcast, the show for company leaders, sales managers, and salespeople who are looking to take their sales game to the next level. Join your host Bill Caskey, renowned sales coach and strategist, as he shares modern sales strategies and leadership tips that will help you grow your sales team and increase revenue for your business. Each week, Bill brings a variety of guest experts and shares real coaching scenarios from his work with sales teams, providing valuable insights and actionable advice that will help you build your skills and think differently about the profession of selling. Whether you're a seasoned sales professional or just starting out in your sales career, The Bill Caskey Podcast has something for you. So, join us every week as we explore the latest trends, techniques, and strategies for driving sales growth and success. To learn more about Bill Caskey and his work, visit www.billcaskey.com or follow him on LinkedIn at https://www.linkedin.com/in/billcaskey/.

Listen to episodes

60 recent

October 21, 202611 min

What's Really Keeping You Stuck: 7 Things Holding You Back (Part 1)

Ever feel like there's more inside of you, but you're not reaching it? In Part 1 of this two-part series, Bill Caskey names the 7 things that hold sales professionals and business owners back from their potential: from labels and comparison to borrowed definitions of success. We're built for ambition. When companies and individuals come to Bill, the theme is almost always more : more sales, more revenue, more income. But before you can talk about the steps that get you there, you have to stop doing the things that keep you stuck. Next week, Part 2: the 9-step map Bill has seen work in his own life and with his clients, plus a downloadable handout. Complimentary coaching session: Bill is offering 45-minute complimentary coaching sessions for VPs of sales, sales managers, team leaders, and CEOs. There's no cost and no obligation, and he's only doing ten a month. Book yours here: https://resources.billcaskey.com/simple-team-assessment-call 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook . Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com . Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com .

October 14, 202613 min

Flip the Dynamic: 6 Elements That Get Prospects Selling to You

There's an emerging trend among high-impact, high-income sales professionals: they've stopped carrying the burden of selling. Instead, they flip the dynamic so the prospect is the one making the case for why their problem needs to be solved. In this episode, Bill Caskey lays out the six elements that make that shift possible. Get them right and you and your prospect end up on the same side of the desk, looking at the problem together, instead of on opposite sides arm wrestling. Miss these, and the dynamic flips the wrong way. You end up chasing, following up, and asking, "Would you like me to go over the proposal?" Complimentary coaching session: Bill is offering 45-minute complimentary coaching sessions for VPs of sales, sales managers, team leaders, and CEOs. There's no cost and no obligation, and he's only doing ten a month. Book yours here: https://resources.billcaskey.com/simple-team-assessment-call 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook . Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com . Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com .

September 30, 202612 min

Why People Buy (And Why They Don't): Aristotle's 3-Part Sales Argument

Have you ever wondered why you get certain deals and lose others? It's tempting to blame the market, the pricing, or a bad presentation. But Bill Caskey believes there's usually a deeper reason — and it traces all the way back to Aristotle. Aristotle said every argument has three elements. In this episode, Bill applies them to the sales conversation: Ethos — trust in the messenger. There's a massive trust deficit right now; buyers don't trust sellers. Bill explains why trying to get someone to trust you backfires, why the fastest way to build trust is to detach from the outcome , and why you should match your prospect's skepticism instead of fighting it. Plus: the one opening statement that sets the stage for the whole call — and why interrogation makes buyers freeze up. Pathos — the emotion. Every buyer comes to you with a plight. Your job is to understand the why behind the what — without spending 30 minutes digging. Logos — the logic. There has to be a logic to the decision. That's where the roadmap comes in — and where the ROI conversation happens. Bill makes the case that money is logical, not emotional , and shares what a mastermind salesperson missed when trying to sell him a $10,000 program. 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook . Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com . Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com .

September 9, 202613 min

5 Mistakes Killing Your Sales Career (And You Don't Even Know It)

After 35+ years coaching B2B sales teams, Bill Caskey has seen the same mistakes sabotage good salespeople and sales leaders over and over. In this episode, he breaks down five of them — from mistaking "sales rep" for "guide" to vaulting to the presentation before understanding the buyer — and what to do instead. 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook . Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com . Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com .

August 26, 202615 min

The 3-Part Roadmap Every Sales Leader Needs

Most sales leaders Bill works with have a quota, a target, even a forecast — but no actual map. In this episode, Bill lays out the framework he uses with every coaching client to close that gap: the 2X Roadmap. It breaks into three pillars, each with three elements underneath it. Message covers offer clarity, the customer map, and the customer journey. Marketing covers your lead magnet, your personal brand engine, and tracking the right activities. Method covers your qualification filter, pipeline discipline, and staying detached enough to negotiate from strength. Bill walks through real client examples for each one, including a CEO-level prospect who told a client "nobody else has given me this" after seeing a properly built customer roadmap. Download the 2X Roadmap PDF: https://www.dropbox.com/scl/fi/36i9wq8hiebzsu5mdhgbt/2x-RoadmapW-Foundation.pdf?rlkey=bq4xm1xeta3pzmn802v0wimbo&dl=0 Book a $97 coaching call with Bill: https://resources.billcaskey.com/simple-team-assessment-offer

August 19, 202616 min

The Deal Coaching Checklist: 5 Non-Negotiables Before You Chase Another Prospect

Got a deal that's dragging on too long? In this episode, Bill shares the Deal Coaching Checklist he uses with his 1:1 coaching clients to diagnose a live opportunity before another minute gets wasted on it — five non-negotiables to run every deal through. The five points: Be the guide, not the seller Flip the convincing — stop convincing prospects and let them convince you The stated problem is never the real problem Never propose until three boxes are checked: admitted, quantified, committed Are you detached from the outcome? Bill walks through real coaching stories — including a client chasing the biggest sale of his career — to show how attachment, weak positioning, and skipping past the real problem quietly kill deals. Plus: why "convincing" a prospect actually works against you, and the one question to ask yourself before you send another proposal. Download the free Deal Coaching Checklist: https://www.dropbox.com/scl/fi/jm7a5misqejw9v4in3cpz/DealCoachingChecklist.pdf?rlkey=pm9vg4b5p5nsljh55eafqe2hf&dl=0 Interested in 1:1 coaching with Bill? New slots are opening up soon — more details next week. 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook . Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com . Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com .

August 7, 20267 min

Stop Convincing, Start Guiding: A Playbook for Accidental Salespeople

If you're a project manager, an engineer, or anyone else who ends up on customer calls without "sales" in your title, this one's for you. Bill lays out eight principles that separate a savvy, confident communicator of value from someone who accidentally talks their way out of a deal. You'll learn why your job isn't to convince the prospect they need help — it's to create the environment where they convince themselves. You'll hear why the problem a buyer states first is almost never the real problem, why status quo should always be on the table, and why people don't actually buy your solution — they buy the roadmap to it. Whether you're an accidental salesperson yourself, or a sales leader bringing non-sales teammates into strategy calls, these eight principles will get everyone speaking the same language before the next customer conversation. 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook . Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com . Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com .

July 24, 202610 min

Stop Getting Called In on Deals You Can't Win

What if your team had to answer seven questions before they were allowed to pull you into a deal? Bill shares the exact qualification checklist he built for a high-performing rep who kept getting called in to "close the heavy" — so she only shows up on deals actually worth her time. You'll learn the seven things Bill has his client's team confirm before she'll agree to join a sales call: what the real problem is (in the prospect's own words), what it's costing them if it doesn't get solved, who actually owns the decision, what the buying process looks like, why the deal is happening now, whether the prospect is genuinely willing to invest, and what they've already tried that didn't work. This isn't just for people who get "called in" — it's a gut-check list for any frontline seller who wants to stop spending time on deals that were never going to close. 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook . Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com . Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com .

July 15, 202615 min

The Stable Center: 5 Biblical Principles for Sales Success

Most sales training starts with behavior — make more calls, say the right words, hit the number. Bill's found the opposite order works better: start on the inside (identity, mindset) and the outside takes care of itself almost effortlessly. This week he goes further than mindset. Two years ago, Bill started digging into the role faith and biblical principles play in sales achievement — not the church version, but the version that builds a stable center strong enough to hold up regardless of whether this month's number hits. He's built out 14 principles total; this episode covers the first 5, each paired with a verse and a real, practical sales application. In this episode: You Have a Divine Assignment — Jeremiah 29:11 Serve First — Mark 10:45 Be a Guide, Not a Convincer — Isaiah 30:21 Detach From Outcomes — Proverbs 16:9 Know and Deploy Your Uniqueness — Jeremiah 1:5 Part 2 — the next 5 principles — drops next week. 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook . Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com . Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com .

June 18, 20268 min

The Perfect Sales Call: 9 Elements Every Rep Needs

Most salespeople finish a call and immediately wonder: How did that go? Bill Caskey thinks that question is the wrong one — because if you have to ask, you probably didn't have a framework going in. In this episode, Bill lays out the nine elements of the perfect sales call. Not a perfect pitch. Not a perfect close. A perfect call — the kind that makes the entire process feel like less of a grind, more of a genuine conversation, and ultimately produces better results for you and your customer. 🎟️ FREE EVENT — The 2X Leverage Code Register → https://resources.billcaskey.com/2x-leverage-workshop 12 Bold Moves - Audiobook: Want to break free and soar to new heights? "12 Bold Moves" the Audiobook, is your gateway to a fearless reinvention of self and unlocking unprecedented sales success. Get your FREE copy now at http://12boldmoves.com/audiobook . Have a question for Bill or a topic you'd like him to discuss in a future episode? Email him at listener@caskeytraining.com . Schedule a Call: If you'd like to learn more about how Bill can help you or your team reach your potential, schedule a call at http://scheduleacallwithcaskey.com .