The Advanced Selling Podcast - podcast cover

The Advanced Selling Podcast

Bill Caskey and Bryan Neale: B2B Sales Trainersadvancedsellingpodcast.com

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.

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Episodes

#417: How to Not Annoy Your Prospects - Michael Reynolds

Send us Fan Mail Picture it: You walk into a prospect’s office, exchange introductions and say, “So tell me about your business?” The prospect looks at you, sighs and begins to tell you the same biographical information they’ve shared with every other salesperson who has walked through their door. Has this happened to you? In today's episode, veteran sales trainers Bill Caskey and Bryan Neale interview a digital marketing agency CEO to learn more about how to not turn off your prospects before y...

Sep 12, 201629 minEp. 1

#416: Bloody Knuckle Cold Calling

Send us Fan Mail Are you in a cold-calling business? In this episode, veteran sales trainers Bill Caskey and Bryan Neale field a question from Blake in Texas that we know many listeners find challenging. How do you engage with a prospect when you’re knocking on their door? What can you do to soften the immediate feeling they have to tell you to go away? In today's episode of The Advanced Selling Podcast, Bill and Bryan share strategies for effective and efficient cold-calling. Getting right with...

Sep 05, 201618 minEp. 1

#415: Email as a Prospecting Tool

Send us Fan Mail Are you using email as a prospecting technique and struggling to get responses? In this episode, veteran sales trainers Bill Caskey and Bryan Neale take on the topic so many salespeople were never taught: how to write words that compel your reader to take action. How are you crafting emails to the C-Suite? Are you going out on a limb to reach out to people you don’t know? In today's episode of The Advanced Selling Podcast, Bill and Bryan give you techniques you can use to increa...

Aug 29, 201623 minEp. 1

#414: Elements of a Good Plan

Send us Fan Mail It's that time of the year again! We are closing in on the final half of 2016 and it's this time that gets us thinking about next year and our goals. In this episode, veteran sales trainers Bill Caskey and Bryan Neale discuss elements of a good sales or project plan and how you should look at anything you do as a project. Are you tired of the old "SMART" Goal plan? Are you wondering where to begin with you project? In today's episode of The Advanced Selling Podcast, Bill and Bry...

Aug 25, 201622 minEp. 1

#413: Mailbag Monday - Listener Questions

Send us Fan Mail Have you ever struggled to figure out the right attire for a new prospect meeting? In today's episode, veteran sales trainers Bill Caskey and Bryan Neale take two listener questions for this Mailbag Monday. Are you wondering how to get reacquainted with customers or prospects you haven’t talked to in a long time? Are you looking for tips to know if you’re dressed appropriately for a sales call? In this episode of The Advanced Selling Podcast, Bill and Bryan give you specific act...

Aug 22, 201617 minEp. 1

#412: Sales Lessons from the Olympics

Send us Fan Mail Are you staying up late every night mesmerized by the Olympics? In this episode, veteran sales trainers Bill Caskey and Bryan Neale look to lessons sales people can learn from athletes competing at the top of their game. How do you prepare yourself when something doesn’t go as planned in a sales call? How can you detach from things around you that you can’t control? In today's episode of The Advanced Selling Podcast, Bill and Bryan give you specific techniques to take your sales...

Aug 18, 201617 minEp. 1

#411: Inner Game Tips from a PGA Golfer

Send us Fan Mail What do golf pros know about sales training? You may be surprised by the overlaps in inner game principles. In this episode, veteran sales trainers Bill Caskey and Bryan Neale reflect on Donald Miller’s Storybrand podcast and an interview with Ben Crane, a PGA golf pro. Do you struggle to avoid your subconscious taking over your inner game? Are you practicing reps to help get your mind right? In today's episode of The Advanced Selling Podcast, Bill and Bryan share tips to help y...

Aug 15, 201615 minEp. 1

#410: Sales Pressure - Aspirational or Desperate?

Send us Fan Mail Are you feeling sales pressure? (Don’t worry, you’re not alone.) In this episode, veteran sales trainers Bill Caskey and Bryan Neale help managers and salespeople identify the differences between aspirational and desperate pressure. Are you stressed about sales and struggling to think objectively about your pipeline? Are you looking at the long term view or just short term wins? In today's episode of The Advanced Selling Podcast, Bill and Bryan share techniques you can use to tu...

Aug 11, 201614 minEp. 1

#409: Thoughts from a Longtime Listener

Send us Fan Mail Have you wondered what it’s like to be a fly on the wall of a recording session at The Advanced Selling Podcast? In today's episode, veteran sales trainers Bill Caskey and Bryan Neale are joined by a loyal listener who jumps into the conversation during a visit to the studio. Are you a naturally curious person? Are you looking for ways to keep growing your sales skills after decades in the business? In this episode of The Advanced Selling Podcast, Bill and Bryan talk with Paul f...

Aug 08, 201624 minEp. 1

#408: Helpful Hints for Email Excellence

Send us Fan Mail Have you gotten stuck in a back-and-forth email chain with a prospect that didn’t end well? In this episode, veteran sales trainers Bill Caskey and Bryan Neale dissect an actual listener email and break down what worked (and didn’t work) in his exchange with a potential customer. Are you reading your emails out loud before sending to check your tone? Are you out of balance with your communication style and language? In today's episode of The Advanced Selling Podcast, Bill and Br...

Aug 04, 201617 minEp. 1

#407: Sales Managers: Coaching After the Ride Along

Send us Fan Mail Calling all Sales Managers: there’s an art to coaching your team after the ride along. In this episode, veteran sales trainers Bill Caskey and Bryan Neale talk to Sales Managers with tips (and things not to do) when coaching after a ride along experience. This episode isn’t about the ride along itself— it’s about what happens when you get back in the car. What makes a really good feedback session? How do you help your team grow from the experience? In today's episode of The Adva...

Aug 01, 201613 minEp. 1

#406: Stir Your Sales Funnel

Send us Fan Mail Is your sales funnel getting stale? Are you stuck in the rut of closed-loop prospecting? In this episode, veteran sales trainers Bill Caskey and Bryan Neale share tips and techniques for stirring up your sales funnel to get better movement and momentum. Are you using a ranking system to know which prospects deserve more focus and attention? Are you activating opportunities you already have in your funnel or are you letting them sit there and stall out? In today's episode of The ...

Jul 28, 201617 minEp. 1

#405: Methods for Sales Practice

Send us Fan Mail Pro athletes, musicians and artists practice their craft daily. Do you practice your sales skills daily to get to the top of your game? In this episode, veteran sales trainers Bill Caskey and Bryan Neale give you six practical ways you can practice your sales techniques and hone your skills. Will you step up to the 10 Day Challenge? Are you part of a Power Triad? In today's episode of The Advanced Selling Podcast, Bill and Bryan share things you can begin doing today to practice...

Jul 25, 201619 minEp. 1

#404: Guaranteed Sales Success

Send us Fan Mail What if you could practically guarantee your success in sales? Would you do what it takes? In this episode, veteran sales trainers Bill Caskey and Bryan Neale give you insight into the characteristics of a successful salesperson. Do you have your goals written down? Are you willing to stay a few more minutes and make one more call at the end of the day? In today's episode of The Advanced Selling Podcast, Bill and Bryan will share a how-to list that will help you know where to fo...

Jul 21, 201621 minEp. 1

#403: Mid-Year Prospecting Checklist

Send us Fan Mail Are you feeling a mid-year sales slump? Are you looking for ways to modify your prospecting techniques for Q3-Q4? In this episode, veteran sales trainers Bill Caskey and Bryan Neale give you an assessment to grade your prospecting behaviors in the first half of the year. Are you using a true referral system to generate leads? Do you employ behavioral KPI’s (and stick to them)? In today's episode of The Advanced Selling Podcast, you will learn the elements of healthy prospecting ...

Jul 18, 201619 minEp. 1

#402: Commission Detachment

Send us Fan Mail Do you feel like you have to win every deal? In this episode, veteran sales trainers Bill Caskey and Bryan Neale explore a listener question from Lauren in St. Louis. Are you (or people on your team) motivated most by money? Do you have an unhealthy balance between your base salary and commission structure? In today's episode of The Advanced Selling Podcast, Bill and Bryan will help you identify what you’re attached to and why. You’ll be able to analyze if you are more intereste...

Jul 14, 201618 minEp. 1

#401: Talking Economics Doesn't Have To Be Scary

Send us Fan Mail Do you have trouble talking about money with your prospects? Does “budget” feel like a dirty word? In this episode of The Advanced Selling Podcast, veteran sales trainers Bill Caskey and Bryan Neale take on the tough topic of “Economics.” Using a real scenario from one of Bill’s client sessions, they will walk you through steps to help make the money conversations less intimidating (for you and for your prospects). Are you educating or persuading when you talk with a prospect? A...

Jul 11, 201616 minEp. 1

#400: Managing Millennials in Sales - Lindsay Boccardo

Send us Fan Mail Are you managing a team that includes Millennials? In the second part of our series on Millennials, veteran sales trainers Bill Caskey and Bryan Neale bring back Millennial coach and expert Lindsay Boccardo to talk with managers about how to maximize the value Millennials can bring to your team. Are you giving them feedback more than once every six months? Are you asking deeper questions to understand the real issues? Are you helping your team understand how their contribution c...

Jul 07, 201621 minEp. 1

#363: Margin: Secrets of the Pros

Send us Fan Mail Have you noticed that some sales people just seem like they “get it” more than others? In today’s episode, veteran sales trainers Bill Caskey and Bryan Neale explore what the top 5% do that make them stand out and have greater success than their peers. What are they doing differently than everyone else? Why are people afraid to ask those at the top for their advice? In this episode of The Advanced Selling Podcast, Bill and Bryan dive into ways you can up your selling game, inclu...

Jul 04, 201622 minEp. 1

#399: Millennial Salespeople - Lindsay Boccardo

Send us Fan Mail Were you born after 1982? Do you work with people who were? In this two-part series, veteran sales trainers Bill Caskey and Bryan Neale take on a topic that’s being talked about around the world— Millennials and their impact on today's workforce. They talk with Millennial coach and expert Lindsay Boccardo about ways sales people and their managers can work better together to maximize the benefits of having this generation on their team. In Part I, the conversation focuses on Mil...

Jun 30, 201623 minEp. 1

#398: Account Management Strategies

Send us Fan Mail Can account management and the principle of detachment work together? The very nature of the word “retention” may make you feel like you can’t be detached from your clients. In this episode, veteran sales trainers Bill Caskey and Bryan Neale dive into the world of account management to give you strategies to increase your success in managing accounts. Do you walk the halls and get to know people in other departments? Are you focused on just what you’re currently doing for them o...

Jun 27, 201623 minEp. 1

#397: Writing Sales/Marketing Emails

Send us Fan Mail Are you writing your own marketing/sales emails? In this episode, veteran sales trainers Bill Caskey and Bryan Neale explore a listener question that everyone needs to hear. Do you write emails to your prospects and struggle to make them feel personal? Are you sending something of value to people when they connect with you on LinkedIn? In today's episode of The Advanced Selling Podcast, Bill and Bryan dive into strategies you can use to bring valuable content to people you corre...

Jun 23, 201616 minEp. 1

#396: Attributes of High Performing Sales People

Send us Fan Mail What are the attributes of a high performing sales person? In this episode, veteran sales trainers Bill Caskey and Bryan Neale talk about developing a personal ethos that involves continuous self improvement. To what degree do you carry a commitment to bettering yourself? When things don’t go your way, do you look inward first or look around you to assess what others did wrong? In today's episode of The Advanced Selling Podcast, Bill and Bryan share questions to ask and ideas to...

Jun 20, 201622 minEp. 1

#395: Mailbag Mash-up: Thursday Edition

Send us Fan Mail Is youth helpful or harmful for salespeople? How can you best control your pieces of the sales process and let go of the rest? In this episode, veteran sales trainers Bill Caskey and Bryan Neale take two mailbag questions from listeners— Ty in Texas and Shawn in Wisconsin. Are you looking for ways to position yourself as an expert even when you’re young in age or new to your industry? What can you do to see yourself as a solution provider and help your prospects see you that way...

Jun 16, 201617 minEp. 1

#394: Keystone Habits of a Salesperson

Send us Fan Mail How do you ensure eternal sales success? In this episode, veteran sales trainers Bill Caskey and Bryan Neale use Charles Duhigg’s concept of Keystone Habits to determine what salespeople need to do to increase their success. (If you want more on this idea, check out Duhigg’s book, The Power of Habit: Why We Do What We Do in Life and Business .) Bill and Bryan share some of their own keystone habits— a blend of mental, physical and emotional strategies that you can use to improve...

Jun 13, 201619 minEp. 1

#393: Is the Sales System Broken?

Send us Fan Mail Could the sales system be broken? For both Buyers and Sellers, what if the process isn’t really working? In this episode, veteran sales trainers Bill Caskey and Bryan Neale analyze both viewpoints and consider areas where the system can be improved on both sides of the selling process. Is the Buyer too focused on paying the least amount of money, not getting the best outcome? Is the Seller in “get the deal” mentality more than they are trying to provide a helpful solution for th...

Jun 09, 201621 minEp. 1

#392: Winning Complex Enterprise Sales - Bud Suse

Send us Fan Mail How is your process similar or different to the process for winning complex enterprise sales? In this episode, veteran sales trainers Bill Caskey and Bryan Neale bring in an expert who has spent years winning big deals and teaching others how they can do it too. Bud Suse spent 12 years with IBM before moving into sales management for a start-up, spending hours in well-known sales training programs along the way. He realized that the success in large deals comes from defining a p...

Jun 06, 201618 minEp. 1

#391: Stumping Your Sales Trainer

Send us Fan Mail What happens in a training session when Bill or Bryan doesn’t have the answer? In a special episode of “Stumpology,” veteran sales trainers Bill Caskey and Bryan Neale bring their toughest client issues to each other to solve. How do you handle it when the client can’t get away from selling features/functions? How can you create the space with your sales team to be able to educate them? In today's episode of The Advanced Selling Podcast, the teachers become the students (of each...

Jun 02, 201618 minEp. 1

#390: How to Generate More Leads

Send us Fan Mail Are you looking for ways to generate more leads? (because who isn’t?) In today's episode, veteran sales trainers Bill Caskey and Bryan Neale respond to a specific request to provide four things sales people can do right now to generate leads. Have you considered hosting a marketing event for your prospects (not a sales event, a marketing event)? Are you using your current client’s words and testimonials to help you communicate what you do to your prospects? In this episode of Th...

May 30, 201617 minEp. 1

#389: Premium Pricing Revisited

Send us Fan Mail Standing out in a commoditized sales environment is tough. In today's episode, veteran sales trainers Bill Caskey and Bryan Neale explore the world of landscapers and the B2C marketplace. How do you sell a premium priced product, service or experience when everyone around you is selling for less? Are you creating a vision for your customer or having them help paint the vision with you? In today's episode of The Advanced Selling Podcast, Bill and Bryan give you specific steps to ...

May 26, 201618 minEp. 1
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