The Advanced Selling Podcast

In this episode, Bryan unpacks what makes a truly effective sales playbook - and why now is the time for sales leaders to get serious about it. He shares the key components every playbook must include: a foundational philosophy, planning elements, defined processes, contingency plans, and accountability mechanisms. Bryan spotlights the Blind Zebra Sales Operating System (BZSOS), a comprehensive set of procedures, tasks and scoreboards, with 10 guiding principles that help sales teams achieve clarity, consistency, and success. He also invites sales leaders to two powerful opportunities: certification classes designed to help teams master BZSOS (ahead of Q4), and Huddle, a sales leader-only event on October 30 in Indianapolis where VPs of Sales and CROs from across the country will gather for a day of learning, motivation, and inspiration. Don't let Q4 sneak up on you. Tune in and get your playbook in order! Advanced Selling Podcast Listeners save $200 on Huddle tickets purchased in July 2025 with discount code SANTA: https://wl.seetickets.us/event/Huddle-Sales-Leadership-Summit-Connect-25/628954?afflky=HuddleSalesSummit Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

Bill and Bryan dive deep into the universal experience of self-doubt in sales and business development. Moving beyond the typical "fake it till you make it" advice, they explore how conditional self-doubt shows up in specific areas—like shooting videos, talking about money, or making cold calls—even when we're confident elsewhere. The guys reveal how even the most successful people struggle with imposter syndrome. But here's the twist: instead of fighting these insecurities, what if you embraced them? Sometimes the thing you're worst at becomes your biggest advantage—you just need to reframe it. Join our LinkedIn group: http://advancedsellingpodcast.com/linkedin ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. =================================

What if the most valuable sales asset you have is something you don't even realize you possess? In this week's episode, Bill and Bryan explore the concept of "familiarity blindness" - why we discount our own expertise and fail to see the goldmine of knowledge we're sitting on. Whether you've been in your industry for 3 years or 30, you have insights that could transform your client relationships and differentiate you from the competition. The guys challenge listeners to document the "12 things you know" that others in your field might not - and explain why sharing this knowledge is more powerful than any sales pitch. Special Challenge: Record a video sharing your top insights and tag the ASP team - you never know who's watching or where it might lead. Join our LinkedIn group and check out the Insider's program for live monthly coaching with Bill. Don't just think about it - do it: http://advancedsellingpodcast.com/linkedin ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. =================================

Bill Caskey kicks off a new 12-week series based on his book "12 Bold Moves" by tackling the first bold move: creating a sales process that genuinely benefits prospects, not just salespeople. He challenges the traditional approach of "shoving people through" a process and shares how reframing discovery as mutual understanding can dramatically improve close rates. Caskey includes a real client example of using pre-call assessments to increase closing rates from 20% to 40% while providing genuine value to prospects. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now.

In this episode, Bryan shares a powerful mindset shift to help salespeople take control of the chaos: become a student of your calendar. He breaks down how proactive calendar management (daily, weekly, monthly, and even into next year) can give you more clarity, better pipeline health, and fewer wasted hours. Bryan challenges you to look at your calendar not just for what's there, but for what's missing. What calls, activities, or planning sessions should be on there but aren't? He shares how to turn those gaps into intentional action items that move deals forward and build momentum. From pruning time-wasters to locking in future priorities, this episode is your guide to building a calendar that helps you sell. Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

It's graduation season, and Bill Caskey and Bryan Neale are sharing their top advice for new graduates entering the workforce—plus essential reminders for seasoned professionals who might need to hear these truths again. In this episode, you'll discover why understanding that life and sales naturally go up and down like an accordion can save you from unnecessary stress and help you navigate both the highs and lows with greater wisdom. Bill and Bryan explore how to build a professional network that compounds like interest and why starting early makes all the difference in your career trajectory. They discuss how to be judicious about that crucial first position and avoid toxic work environments that can shape your mindset for decades. You'll also learn a simple strategy for finding multiple mentors who can accelerate your growth, and why this approach works for both graduates and seasoned veterans alike. Whether you're a recent graduate, a parent with kids entering the workforce, or a seasoned professional looking for a reset, this episode delivers practical wisdom that can reshape how you approach career growth and life decisions. Don't forget to review the podcast and join the Advanced Selling Podcast LinkedIn group with over 13,000 members! ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrets to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

Bill and Bryan continue their deep dive into evolving buyer behavior with some eye-opening insights that challenge conventional sales wisdom. In this episode, they tackle the myth of "the decision maker." They explore how buying by committee has become the new normal and why your traditional one-to-one sales training might be preparing you for a world that no longer exists. The guys also discuss the critical importance of elevating the buyer experience beyond just data dumps, why price objections aren't as prominent as they used to be (and the generational factors behind this shift), and how successful salespeople need to paint a clear picture of transformation rather than just making promises. Whether you're struggling to navigate complex buying committees or wondering why your data-heavy presentations aren't closing deals, this episode offers strategies for adapting to today's buyer reality. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================  

In this episode, Bryan introduces a bold shift in how sales coaching should be done - by focusing on the science and mechanics of selling rather than the often subjective "art" of it. Drawing on nearly three decades of experience as a coach (and a self-proclaimed “recovering sales trainer”), Bryan proposes a more measurable, documentable, and results-driven approach to developing salespeople. Bryan explains why sales leaders should spend more time coaching what can be seen, measured, and repeated. He unpacks how role-playing, while sometimes helpful, doesn't always translate to real-world outcomes, especially for remote or digital sellers. He dives into the difference between coaching “the art” of selling (which is based on opinions) and coaching “the science” (which is grounded in data and behavior). And he makes the case that most salespeople thrive when they're held accountable to actual results, not just training exercises. If you're ready to rethink your approach to coaching - and focus on what actually moves the needle — this episode is for you. Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

Bill and Bryan explore how sales professionals need to shift their focus from traditional sales techniques to understanding modern buyer behavior. They discuss how buyers have become more self-directed in their research, the growing "trust gap" between buyers and sellers, and why transparency in the sales process is crucial for success in today's market. The guys examine why conventional manipulation tactics no longer work and offer practical strategies for adapting to how today's customers make purchasing decisions. Join the conversation and discover how studying your buyers—rather than just your sales skills—can significantly improve your closing percentages ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

Bill and Bryan Neale dive into a game-changing concept called "Everyday Leads" - a systematic approach to generating B2B leads continuously, not just when you desperately need them. The guys explore why salespeople often find themselves with empty pipelines after closing quarters strong, and how to break free from the traditional labor-intensive prospecting cycle. Bill shares insights from his work with clients on building automated webinar systems that generate warm leads, while Bryan emphasizes the power of consistent connector meetings. They also discuss the psychological barriers salespeople face when shifting from traditional cold calling to systematic lead generation, drawing parallels to fitness training and the difference between cardio and strength building. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this episode, Bryan continues exploring the Guiding Principles of the Blind Zebra Sales Operating System, picking up where he left off in Part 1. This time, he dives into the principles of intent and assertiveness — and why they're game-changers for sales conversations. He shares how locking in a clear next step can eliminate the dreaded "calendaring ping pong" and keep momentum strong. Bryan explains how intent and assertiveness create a more customer-centered experience, even if that means losing the deal when the timing, problem, or solution isn't quite right. Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

Bill and Bryan explore the enduring fundamentals of sales that have stood the test of time despite decades of technological advancement. The guys reflect on timeless skills that remain essential in today's sales landscape: the art of discovery and qualification, the importance of genuine understanding and connection, bringing authenticity and purpose to your work, and the critical role of creating and executing a solid business plan. While new technologies and methodologies constantly emerge, these core elements continue to drive sales success.  ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In part 2 of their special live episode on navigating uncertain markets, Bill Caskey and Bryan Neale continue their discussion on essential skills for sales professionals. The guys emphasize the importance of utilizing free and low-cost tools already at your disposal, from LinkedIn to ChatGPT, rather than waiting until circumstances force your hand. Bill shares a powerful strategy for commanding premium pricing by developing a customer roadmap that builds trust in your process. Meanwhile, Bryan advocates for becoming a connector who actively brings valuable people together without keeping score. Through practical examples and personal experiences, Bill and Bryan demonstrate why taking decisive action now can position you to thrive regardless of economic conditions. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this episode, Bryan dives into two of the Guiding Principles from the Blind Zebra Sales Operating System: Objectivity and Expert Persona. He challenges salespeople to view their funnel without bias - imagine betting your own money on each deal to test your objectivity. Bryan also unpacks what it means to become an expert in your customer's world (not just your own product). It's about earning trust by showing you care enough to really understand their business. Plus more tactical applications coming in the next episode, Guiding Principles: Part 2! Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

In this special live episode, Bill and Bryan discuss essential skills for sales professionals facing economic uncertainty. Rather than focusing on what you can't control, the guys break down practical strategies for maintaining your edge when markets get volatile. Learn why identifying what's in your control, maintaining pricing discipline, and understanding the true abundance of opportunities in your market are critical during challenging times. Bill and Bryan also explore how to adjust your messaging for anxious clients and why understanding AI's impact on your industry is no longer optional. Join the longest-running sales training podcast for actionable insights on taking ownership of your success regardless of market conditions. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this episode, Bill and Bryan dive into the often-overlooked world of financial conversations in sales. Moving beyond simple ROI calculators, they explore how to effectively discuss investment value with prospects through compelling storytelling rather than dry spreadsheets. The guys challenge salespeople to think beyond "break-even" mentality, understand the lifetime value of clients, and recognize the importance of time horizons in financial discussions. Bill and Bryan also share insights on why not every deal is economically beneficial for customers and how to maintain objectivity when discussing financial implications. Whether you're comfortable with numbers or not, this episode provides practical guidance on having meaningful economic conversations that drive decisions. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

Bill and Bryan follow up on their popular episode about why every salesperson should have a YouTube channel, sharing Marcus Sheridan's prediction that YouTube could soon become more important than company websites. The guys tackle common obstacles like being "intrigued but intimidated" by video creation, offering practical content ideas including customer spotlights, technical demonstrations, and answering frequently asked questions. Bill and Bryan make a compelling case that the downside is zero while the upside is potentially infinite for sales professionals willing to embrace video marketing. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this episode, Bill and Bryan discuss the importance of crafting compelling stories that connect with prospects on a deeper level. They dive into how salespeople can move beyond personal anecdotes to tell meaningful market stories and "I was where you are" narratives that resonate with customers. The guys also touch on the problem of "over-discovery" in the sales process, suggesting that modern selling should focus more on explaining value than excessive questioning. Whether you're struggling to articulate your company's story or looking to differentiate yourself in competitive situations, this episode offers practical insights to elevate your sales approach. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo episode, Bill challenges traditional sales approaches by advocating for a fundamental shift from "selling" to "guiding." He explains why old-school sales tactics create negative "karma" with prospects and offers a fresh alternative: becoming a trusted guide who provides value before asking for payment. Caskey shares personal examples of how creating helpful content has naturally attracted clients to him, eliminating the need for aggressive sales tactics. If you'd like to talk to Bill about your team, go to http://scheduleacallwithcaskey.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

In this episode, Bill and Bryan tackle the challenge of time management in sales, exploring how “time goes fast and speeds up” as quarters and years fly by. They discuss the pitfalls of short-term thinking and offer practical strategies for sales professionals to extend their planning horizons. The guys emphasize the importance of looking beyond the current week to plan months ahead, while balancing immediate tasks with future initiatives. They share insights on creating momentum for future quarters by starting projects early, even with just 20 minutes of initial work. Whether you're a sales rep or manager, this episode provides valuable guidance on navigating the accelerating pace of the sales world and setting yourself up for long-term success. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo episode, Bill explores the critical concept of believing in your own economic value as a sales professional. Drawing from his document “The 15 Profit Amplifiers” created for clients, Bill discusses how understanding the economic impact of your solution transforms your ability to communicate value to prospects. Bill examines two primary ways your solution can deliver economic value: by alleviating pain points that cost customers money or by helping them achieve aspirational goals like increased revenue and profitability. The most powerful position is when your solution accomplishes both simultaneously. Whether your customers need to save money, make more money, or improve efficiencies, this episode provides valuable insights on how to identify, internalize, and articulate your true economic value proposition.  If you'd like to talk to Bill about your team, go to http://scheduleacallwithcaskey.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

In this solo episode, Bill Caskey challenges traditional sales approaches that may be holding you back. If your closing rate is hovering around 20% or less, your approach likely needs an overhaul. Bill argues that many sales organizations are stuck in outdated paradigms, failing to adapt to modern buying processes where more stakeholders are involved and decisions take longer. Bill emphasizes that people don't buy features—they buy transformation and results. He challenges listeners to start their next sales conversation by asking prospects where they want to go, not what features they're looking for. The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

In this episode, Bill and Bryan make a compelling case for why every sales professional and business leader should have their own YouTube channel. Moving beyond traditional sales training advice, they explore the numerous benefits of creating video content, from building deeper connections with younger buyers to establishing yourself as an industry thought leader. The guys share their “3E” framework—Educate, Explain, and Edify—while addressing common hesitations and highlighting the zero-downside, all-upside nature of this strategy. Bill and Bryan challenge listeners to embrace this digital asset opportunity that can transform your business and create a lasting legacy of your professional journey. They even offer to promote listeners' YouTube channels who take action after hearing this episode. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this episode, Bill and Bryan tackle the critical topic of authentic communication in a world increasingly dominated by AI-generated content. The guys share examples of personalized communication that stands out, including a clever LinkedIn exchange between Bryan and a company that demonstrates how simple, authentic engagement can create meaningful connections. Bill and Bryan also challenge listeners to reconsider mass-produced outreach strategies and instead focus on thoughtful, personalized communication that builds rapport and opens doors.  ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo episode, Bill makes a case for why sales professionals can no longer afford to ignore YouTube as a critical business tool. He explains that in 2025, not having a YouTube channel is equivalent to not having a business card in 1985—it renders you virtually invisible to a significant portion of your potential clients. Bill addresses the changing buying behaviors of modern prospects who prefer to research, learn, and vet solutions through video content before ever speaking with a salesperson. This episode provides a straightforward roadmap for sales professionals looking to establish authority, build trust, and remain competitive in an increasingly video-driven marketplace. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

In this episode, Bryan dives into the importance of a regular CRM cleanup because let's face it, an overloaded sales pipeline is just a junk drawer of data if left unchecked. He compares it to tidying up a messy garage: if you don't clean it out, it becomes impossible to find what you actually need. Sales teams should make monthly CRM clean-outs a habit to keep their pipeline accurate, realistic, and actionable. Plus, a cleaner funnel = happier CEOs and CFOs. Tune in to learn how a streamlined CRM can create space for real opportunities to grow. Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

In this episode, Bill and Bryan tackle a critical but often overlooked aspect of the modern sales process - what to do during the time gaps between prospect meetings. Moving beyond outdated practices like sending marketing brochures, they explore innovative strategies for maintaining momentum and building deeper connections. The guys share five powerful approaches including making strategic introductions, creating customized content, developing digital resource libraries, utilizing trackable video engagement, and leveraging event invitations. Whether you're dealing with a week-long gap or longer intervals between meetings, these actionable techniques will help you maintain prospect engagement while demonstrating value and expertise in today's sales environment. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo episode, Bill explores why even experts fail to effectively communicate complex ideas, drawing from a recent experience watching an AI expert lose his audience. Through a practical framework, Bill reveals three essential components that transform complicated explanations into influential communications. He demonstrates how proper explanation isn't just about information sharing—it's about creating transformation and building trust. Bill breaks down how to build context, establish purpose, and create clear roadmaps that keep audiences engaged and drive better results. This episode is essential listening for sales professionals and leaders who need to explain complex solutions without losing their audience's attention. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

In this episode, Bill and Bryan challenge traditional sales metrics and explore the often-overlooked numbers that truly matter in today's digital sales landscape. The guys discuss crucial modern measurements like inbound lead generation through LinkedIn, the power of tracking unsolicited introductions, and the importance of understanding average days to close. They give valuable insights about price increase mathematics and volume relationships, offering listeners practical ways to improve their sales performance through better metric tracking. Whether you're a seasoned sales professional or new to the field, this episode provides actionable insights on transforming your sales approach through smarter measurement strategies. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo episode, Bill challenges the conventional wisdom of modern sales coaching by exposing why most coaching relationships fail to deliver real transformation. He argues that effective coaching isn't about protecting egos or maintaining comfort—it's about driving genuine growth through constructive confrontation and challenge. Bill presents a compelling formula for growth: discomfort multiplied by action equals real transformation. He explains why coaches who prioritize likability over effectiveness ultimately fail their clients, and why the best coaches aren't afraid to make their clients uncomfortable or risk losing them. This episode serves as a wake-up call for anyone seeking meaningful professional development, emphasizing that true breakthrough comes from embracing discomfort rather than avoiding it. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

Too many sales teams use their CRM as a record-keeping tool instead of an agent of action. In this episode, Bryan breaks down how a well-utilized CRM can drive sales efficiency, improve deal visibility, and keep your pipeline moving. He shares simple yet powerful tactics to transform your CRM from a burden into a competitive advantage. Stop logging data and start leveraging it! Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

In this episode, Bill and Bryan dive deep into a crucial sales concept: the importance of selling transformation over features. The guys explore how salespeople often focus too narrowly on short-term gains and immediate features rather than the long-term transformative impact their solutions can have on clients' businesses. Through real-world examples like Gong software and personal experiences, they demonstrate how successful sales require understanding and articulating the complete journey of customer transformation. They also give some practical advice on documenting customer success stories and shifting from a “blitz mentality” to a transformation-focused approach in sales. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this final installment of his three-part series on critical future sales skills, Bill Caskey explores the vital concept of team alignment planning. Bill explains why traditional approaches to stakeholder management are no longer sufficient in today's complex sales environment. He also reveals how AI is transforming the traditional diagnosis phase of sales, shifting the salesperson's core value to implementation expertise and team alignment. Lastly, he demonstrates why getting all stakeholders involved early, understanding potential implementation challenges, and proactively addressing resistance are crucial for sales success.  Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com  

In this episode, Bill and Bryan explore a common phenomenon in sales organizations: why middle performers often harbor resentment towards top performers.  The guys dissect the excuses commonly used to discredit high achievers' success - from territory advantages to preferential treatment. The hosts share practical advice for breaking free from this mindset, including how to leverage top performers' willingness to share their secrets of success.  Whether you're a sales leader or working to climb the ranks, this episode offers valuable perspectives on turning competitive envy into collaborative growth. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo episode, Bill tackles another critical skill for modern sales professionals - the art of clear path planning. He explains why simply knowing your destination isn't enough; you must be able to clearly map out and communicate the journey from your prospect's current reality to their desired future state. He challenges the common notion that “nobody cares about the details” and emphasizes why building buyer confidence through detailed planning is crucial in complex sales.  Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

Ever consider that the opportunities you're chasing might be right under your nose? In this episode, Bryan highlights why your best prospects aren't always new—they're already in your CRM. Learn how to turn your "Closed Lost" and "Inactive Client" lists into powerful prospecting tools to revive old connections and spark new opportunities. Key Takeaways: ✅ Use your "Closed Lost" list to re-engage prospects from 6-12 months ago—they may be ready now. ✅ Don't overlook "Inactive Clients"—reach out 1-2 years after they've stopped being customers. ✅ Past customers and prospects can return as clients or become valuable referral sources. Discover the goldmine of opportunities hiding right under your nose!   Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.  

In this episode, Bill and Bryan discuss the concept of “Quitter's Day” - the January 10th phenomenon where most people abandon their New Year's resolutions. The guys dive deep into what they call “The Big Illusion” - the false belief that conforming to others' expectations leads to fulfillment. Through personal anecdotes and the story of Brad Stevens' dramatic career shift from pharmaceutical sales to NBA coaching, they discuss the importance of staying true to your authentic self in sales and life. This episode challenges you to examine whether they're following their own path or simply meeting others' expectations, offering insights on how to align your sales career with your personal values and integrity. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo episode, Bill Caskey explores a vital but often overlooked sales skill - the ability to help prospects vividly envision their future after implementing your solution. Through a compelling case study of a leadership program for sales managers, he demonstrates how making the future tangible can transform both the sales process and deliver genuine value to prospects, whether they buy or not. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com  

In this episode, Bill and Bryan cut through the AI hype to deliver actionable advice for sales professionals just beginning their AI journey. The guys share real-world applications including prospect list generation, content creation, and sales call preparation. Whether you're AI-curious or AI-anxious, this episode provides the concrete steps and use cases you need to start leveraging AI in your sales process today. You'll discover insights about treating AI like a knowledgeable friend rather than a search engine and understand how to use AI for everything from generating targeted prospect lists to preparing for important sales calls with AI-powered research. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this insightful solo episode, Bill challenges common sales beliefs by exposing three destructive fallacies: The Activity Fallacy (believing more activity automatically equals better results), The Pressure Fallacy (assuming increased pressure leads to improved performance) The Control Fallacy (trying to micromanage prospect behavior).  Caskey explains why these mindsets can actually hinder sales success and encourages sales professionals and leaders to examine their own potentially limiting beliefs. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

In this episode of the Advanced Selling Podcast: 2 Minute Drill, Bryan shares a practical framework for maximizing your ROI at trade shows. Too often, salespeople approach these high-cost opportunities without a clear plan. Bryan breaks down his proven framework into three key phases: pre-show, at-show, and post-show. Discover how to: ✅ Set measurable goals and engage on social media before the event. ✅ Build meaningful connections by interacting with speakers and influencers during the show. ✅ Finish all follow-up tasks before your "wheels down" moment at home to outpace the competition. Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

In their first episode of 2025, Bill and Bryan discuss strategies for sales professionals returning to work after the holiday break. The guys share four powerful techniques to jumpstart the new year: reconnecting with your fundamental purpose, actively engaging with your market through in-person meetings, developing a compelling personal brand in the digital space, and strengthening your network through strategic introductions. They also emphasize the importance of getting physically out of the office and scheduling face-to-face meetings in January to counter post-holiday inertia.  Be sure to join our upcoming Insider Coaching on Customer Transformation on January 10th! Go to http://advancedsellingpodcast.com/insider to save your spot now. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this final episode of the year, Bill and Bryan share their approaches to year-end reflection. The guys discuss practical strategies including the "what worked/what didn't" analysis and Dan Sullivan's concept of "measuring backward" to appreciate your progress. Between nostalgic stories of family road trips and humorous takes on modern dishwasher dilemmas, Bill and Bryan offer actionable advice for sales professionals to evaluate their 2024 strategies and set themselves up for success. Whether you're sprinting to close year-end deals or taking time to reset, this episode provides a framework for meaningful reflection and planning. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo episode, Bill challenges sales professionals to honestly evaluate whether their sales process genuinely benefits prospects. Drawing from his book "12 Bold Moves," he explains how to transform your approach by offering valuable assessments and personalized recommendation documents to prospects—whether they buy or not. Caskey illustrates how this approach, enhanced by AI tools, can help eliminate "commission breath" and potentially double closing rates by prioritizing genuine value delivery over immediate sales. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com  

In this episode, Bill and Bryan share their predictions for the sales industry in 2025, including the accelerating impact of AI on sales roles, the death of "sticky" cold outreach tactics, the decline of legacy media, a potential resurgence of in-person sales meetings, the growing importance of personal branding, and a predicted exodus of Baby Boomer sales professionals. The guys also discuss some amusing trends they are seeing during holiday travel, and share thoughts on AI tools for Christmas shopping.  This end-of-year episode combines practical sales insights with entertaining commentary on current trends affecting sales professionals. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo episode, Bill challenges traditional sales training wisdom by proposing a revolutionary approach: using digital assets to transform the buyer-seller relationship. Through a personal case study, he demonstrates how pre-recorded video content can ease the burden on salespeople to always be "on," while simultaneously building trust with prospects before the first call. Caskey argues that this approach not only aligns with changing buyer behaviors but also helps scale business results more effectively than relying solely on traditional sales skills. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

In the final installment of their Ultra High Achievers series, Bill and Bryan explore how top performers communicate. The guys break down the distinct language patterns that set ultra-successful salespeople apart. Learn how elite performers use contextual awareness, empathetic language, strategic disagreement, and financial fluency to achieve extraordinary results. Don't miss these crucial insights on mastering the vocabulary of success. ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join now. If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo series episode, Bill Caskey shares a revealing story about witnessing poor customer service at a store he visited recently, where a salesperson failed to meet a customer at their knowledge level when discussing smartwatch options. He uses this experience to illustrate a crucial sales lesson: the importance of understanding where customers are in their journey before attempting to sell. Caskey emphasizes that improving close rates requires asking the right questions and meeting prospects where they are, rather than making assumptions about their knowledge or needs. Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com

In this solo episode, Bryan and special guest Chelsea Madden dive into the power of intent data and how sales teams can leverage it to craft smarter, more effective strategies. They discuss why intent data is a game-changer for identifying when prospects are actively researching solutions—but with a caveat: it's not a shortcut to the sale. Learn how to use intent data authentically, avoid the “big brother” vibe, and adopt a consultative approach that resonates with prospects. If you want to deepen your engagement across the decision-making process, and fish in a puddle instead of the ocean, this episode is a must-listen! Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.

In this second installment of their ultra-high achiever series, Bill and Bryan dive into the concrete actions that set exceptional performers apart from their peers. The guys explore why some people know what to do but don't take action, the power of rapid execution, and why ultra-high achievers plan in years while others plan in days. They also challenge conventional wisdom about working from home and share insights about investing in accelerated learning. Plus, they discuss an intriguing tangent about a multi-million dollar modern art piece that sparks a conversation about value and perception.  Join us on December 6th for our Personal Business Planning Workshop where we'll incorporate AI into your 2025 strategy. Insider members get 50% off! http://advancedsellingpodcast.com/insider ================================= Is it time to make a BOLD move in your business? If so, download our brand new book, "12 Bold Moves - Insider Secrete to Reinventing Yourself and Your Business." http://12boldmoves.com The Insider program is open for enrollment. If you have not checked out our small learning group, go to http://advancedsellingpodcast.com/insider to join. Be sure to join our year-end, 2025 Business Planning Session on December 6th! If you haven't already, make sure you join us in our LinkedIn group: http://advancedsellingpodcast.com/linkedin. =================================

In this solo episode, Bryan and special guest Chris Dornfield dive into the science of effective sales compensation and incentive programs. They explore why most incentive budgets fail to deliver the intended results and how a behavior-focused, data-driven approach can change that. Chris shares insights from his company, Whistle, which uses behavioral science to optimize incentive programs, showing that immediate, personalized rewards tied to specific sales activities are far more effective than traditional lump-sum payouts. You'll learn why cash remains king, how to layer individual and team-based incentives, and the benefits of automating real-time rewards to keep motivation high. If you're trying to build a dynamic rewards system that drives the right behaviors, this episode is packed with actionable advice to help you rethink your approach to motivating your sales team. Curious about certification in the Blind Zebra Sales Operating System? Learn more here. And if you haven't already, make sure you join the Advanced Selling Podcast LinkedIn group: http://advancedsellingpodcast.com/linkedin.