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

Bill Caskey
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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/.

  1. DEC 19

    The Year I Almost Lost My Drive (And How I Got It Back)

    Have you ever noticed someone isn't themselves but didn't know how to bring it up? Bill opens up about spending much of 2025 in that exact state - going through the motions, lacking motivation, and struggling with purpose after a health scare.  He shares the turning point that pulled him out: reconnecting with his core purpose and realizing achievement is fundamentally spiritual, not mechanical.  If you're ending the year feeling hollow despite hitting targets, or if you lead people who might be struggling silently, this episode offers both honesty and a path forward. 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.

    17 min
  2. The Real Leadership Problem with Janelle Harder

    DEC 10

    The Real Leadership Problem with Janelle Harder

    When a leader comes to executive coach Janelle Harder with a problem employee, she knows the real issue often lies elsewhere. In this conversation, Bill sits down with Janelle, founder of Humannovate Consulting, to explore the gap between the problems leaders present and the real challenges they face. With nearly 15 years working inside Fortune 500 companies like Cummins and major energy corporations, Janelle has seen the same leadership challenges repeat across generations and industries. The presenting problem? "This employee isn't performing." The real problem? Leaders haven't set expectations, provided resources, or even talked to their people regularly. Janelle shares the specific language and frameworks for noticing when something's wrong, asking the right questions, and creating the kind of connection that actually moves the needle. Whether you lead a sales team, manage managers, or wonder if your team thinks you're any good, this conversation will challenge how you think about leadership development and human connection in the workplace. Connect with Janelle: Humannovate Consulting - humannovateconsulting.com 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.

    18 min

  3. DEC 3

    Stop Pushing, Start Planning

    Bill answers three critical questions from listeners: What's the greatest sales lesson learned the hard way? What's the biggest challenge in the last five years? And if he could eliminate one sales practice forever, what would it be? Key Takeaways: Why pushing harder in follow-up creates resistance and kills dealsHow the harder you press, the less likely you are to closeWhy marketing has become essential for every sales professional (not just the marketing department)The power of platform building: podcast, YouTube, email series, or video contentHow 10 years of content consumption can turn into a 70% close rateThe needy email problem and what to do insteadThe 12-question content strategy that transforms cold prospects into warm leadsJoin Bill's December 5th Personal Business Planning Workshop (12-2pm ET) for just $97. Get the replay, workbook, and accountability session. Save your seat now: https://resources.billcaskey.com/2026-business-planning-workshop

    13 min
  4. Stop Forecasting, Start Planning: Your 2026 Success Blueprint

    NOV 20

    Stop Forecasting, Start Planning: Your 2026 Success Blueprint

    Planning season is here, but most salespeople confuse forecasting with actual planning. In this episode, Bill shares three critical building blocks from his upcoming Personal Business Planning Workshop that will help you create a comprehensive plan for 2026—not just revenue targets, but a real roadmap for growth. Bill walks you through practical examples, including how to create lead magnets that attract qualified prospects and position you as the expert. Whether you join his December 5th workshop or start implementing these three blocks today, you'll be ahead of the game in 2026. Join Bill's Personal Business Planning Workshop: December 5th, 12-2 PM ET Get all nine building blocks, a 12-page workbook, and a one-page planning overview for just $97. Get your ticket now!

    16 min

  5. NOV 14

    The Expertise Trap: Why Being the Expert Isn't Enough

    Bill opens up his coaching playbook to share three real goals from new clients—and what he's going to do about them. From comfort zones to expertise, from undervaluing yourself to finding confidence, these objectives represent what 90% of B2B sales teams struggle with.  Listen as Bill breaks down the first goal: how to move from being the expert to being the transformational partner your clients actually need. 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.

    14 min
  6. 5 Lessons from Front-Line B2B Professionals (And How You Can Apply It Today)

    NOV 5

    5 Lessons from Front-Line B2B Professionals (And How You Can Apply It Today)

    What happens when experienced B2B sales professionals—many with engineering backgrounds—spend six months mastering consultative selling techniques? In this episode, I share the five most impactful lessons from a recent training program with high-end hydraulic and timing solutions salespeople. You'll discover why being mindful of the "okay vs. not okay" dynamic transforms customer interactions, how upfront agreements and detachment create better outcomes, and the critical importance of operating on two levels simultaneously—being in the conversation while also observing it. Whether you're selling complex solutions or leading a sales team, these field-tested insights will help you connect more authentically with prospects and close more deals. 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.

    13 min
  7. Finding Yourself in Business with Jason Leister

    OCT 3

    Finding Yourself in Business with Jason Leister

    In this episode, Bill Caskey sits down with marketing expert and recovering musician Jason Leister to explore a topic that sits beneath the surface of most business conversations: the power of being yourself. Jason shares his journey from being a "straight-A sheep" who followed all the rules to discovering that the only person he hadn't tried being in business was actually himself. The conversation digs into why we're taught to focus on what we want to do rather than who we want to be, and how that misdirection costs us years of detours, therapy, and unfulfilled projects. If you've ever felt like you're operating at a fraction of your potential, or you're tired of being everyone except yourself, this conversation offers a refreshing perspective on building a business—and a life—that actually fits who you are. Subscribe to Jason's daily newsletter at JasonLeister.co for continued insights on becoming more fully yourself in business. 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.

    24 min
  8. Remembering Charlie Kirk: Lessons in Being Fearless & Empowered

    SEP 17

    Remembering Charlie Kirk: Lessons in Being Fearless & Empowered

    In this heartfelt tribute episode, we pause to reflect on the life and legacy of Charlie Kirk, the founder of Turning Point USA who was tragically taken from us far too soon. While this isn't a political analysis, it's a personal reflection on what we can learn from Charlie's approach to life and leadership. This episode explores the leadership lessons we can all take from Charlie's life: his courage to engage in difficult spaces, his ability to stay on message, his mastery of media platforms, and most importantly, his dedication to serving as a voice of hope for young people who felt forgotten by society. Whether you agreed with his politics or not, there's no denying Charlie Kirk's massive impact on American youth and his role as a devoted father and husband. Join us as we honor his memory and reflect on how we can better support the young people in our own lives during these challenging times. This is a one-time tribute episode from someone who admired Charlie's communication skills and dedication to youth empowerment, regardless of political affiliation.

    7 min
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4.9
out of 5
25 Ratings

About

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/.

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