PODCAST · business
WINNING AT SELLING
by Bill Hellkamp
Welcome to the Winning at Selling Podcast. Your hosts Bill Hellkamp and Scott "Professor Plum."This podcast is dedicated to the overall success in the sales channel. From the CEO to the front line salespeople, every role must be aligned, trained and committed, every day to achieve the desired outcome. This is not done without a commitment to ongoing career development in learning market-relevant techniques, overcoming conceptual barriers, applying proactive and productive behaviors and projecting a positive attitude.Whether you are defending first place in the market or dedicated to fighting for first place, each episode will deliver proven advice you can apply that day to improve your sales results.
Episodes
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#721 - Would You Hire You? Sales Interview Mistakes to Avoid - 10/16/2026
Salespeople spend their careers convincing prospects to buy, but many struggle when it comes time to sell themselves in an interview. Drawing from years of interviewing sales candidates, we'll look at the red flags sales leaders notice, the mistakes even experienced salespeople make, and how to...
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#720 - I Fell Into Sales...Now What? - 10/9/2026
Did you choose sales or did sales choose you? Stefani ran a LinkedIn poll. Nearly half of 496 people said they fell in. If that's you, this episode is going to hit differently. Because falling in is fine. Staying lost? That's a choice.". Structured Sales Process Implementation Stefani and Bill...
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#719 - The Posture of Partnership - 10/2/2026
People don't like to be sold; they like to buy. Lasting relationships come from being a valued partner to your clients. Unfortunately, not all sales professionals see it this way. Many of them are transactional and just looking to close the next deal. But if you are a valued partner the deal...
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#718 - Stop the Sales and Marketing Disconnect - 9/25/2026
Sales wants marketing to create demand, open doors, and make conversations easier. Marketing wants sales to take that momentum and turn it into revenue. But when the two teams operate in silos, sales ends up asking for things marketing never planned to create, while marketing creates things sales...
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#717 - Overcoming the Stall - 9/18/2026
You've made a great connection with your prospect, helped them identify their need and motivation, and guided them to a solution that makes sense for them only to run into hesitation. Today we get to unpack what your prospect's stall or objections are telling you and how to respond in a way that...
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#716 – Why Prospects Ghost You: Interest Isn't Commitment - 9/11/2026
A prospect tells you the meeting was great, asks for a proposal, and seems genuinely interested. Then, they suddenly disappear! Ghosting isn't always a follow-up problem. Often, something was missed earlier in the sales process. We'll look at the difference between interest and real commitment…
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#715 - The Identity Problem: Why Talented People Underperform in Sales - 9/4/2026
It's not skill. It's not knowledge. It's identity. When someone doesn't see themselves as a "salesperson," they unconsciously self-sabotage—underpricing, over-delivering before the sale, and avoiding the ask. Changing behavior without changing identity never sticks. Sales Failure Analysis...
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#714 - The Decision Collision - 8/28/2026
In sales, there can be a wide variety of pressure points. You may have a customer that claims they just want the lowest price. Your company may be demanding you sell more of one product over another. How do these factors influence the decisions you make in selling? Are you more concerned about…
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#713 - Guest: Erik Therwanger - The Ponder Principle - 8/21/2026
Although studies show that buying is an emotional decision, most salespeople tend to stay in the realm of logic. To move a prospect into emotional territory the seller needs to induce them to "think", to "ponder". And getting the prospect to ponder, can revolutionize your selling process. Causing...
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#712 - The Power of the Plan - 8/14/2026
Are you letting sales be done to you or are you planning and accounting for them so there are less surprises? With proper planning you can effectively have each quarter WON by the time it starts instead of waiting to see what happens at the end! Golden Nugget: "By failing to prepare you're...
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#711 - Why Every Great Sales Meeting Starts with an Agenda - 8/7/2026
One of the simplest things salespeople can do to improve their meetings is also one of the most overlooked: a well-planned agenda. In less than two minutes, you can establish credibility, show you're prepared, involve the prospect in shaping the conversation, and set expectations for what happens...
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#710 - The Follow-Up is the Sale - 7/31/2026
Most salespeople quit after one or two touches. But research says most decisions happen after five to twelve. This episode is about what to say on follow-up #3, #5, and #7. How do you add value instead of "just checking in". Sales Follow-up Strategies Discussion Stefani discussed the importance…
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#709 - Establish a Connection Right Away and the Right Way - 7/24/2026
As a salesperson it's easy to get excited about your product or service. So much so that you can find yourself explaining about the great benefits before you even know much about the prospect. In essence, we want to tell our story before we listen to their story. Instead, resist the urge to tell...
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#708 - Guest: Steve Keating – Turning a Great Commission into Long Term Wealth - 7/17/2026
The sales profession can be a very lucrative career. You can grow a client that buys regularly and provides a hefty commission. Or you might be a hunter who is especially suited to developing new clients which might pay even better. No matter which type of sales professional you are, you likely...
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#707 - Are you making it easy for your customer to buy? - 7/10/2026
Are you making it easy for your customer to buy? The job of Sales, in its simplest form, is to ask, say, and do things that make it easy for your prospect to say yes to your product/service/solution TODAY! Yet, it seems that some salespeople blather on about features long before they know which...
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#706 - Your Prospect Isn't the Final Decision Maker...Now What? - 7/3/2026
Have you ever finished what you thought was a great sales call only to hear, 'This looks good, but I need to run it by my boss?' Most salespeople breathe a sigh of relief because they think the deal is still alive. Sometimes it is. But what usually happens is you've just been removed from the…
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#705 - Stop Winging It. Start Winning! - 6/26/2026
Most salespeople who struggle with confidence think it's a personality problem. It's not. It's a structure problem. When you don't know what comes next, your brain fills the gap with anxiety, and that anxiety shows up as hesitation, over-explaining, or caving on price. Here's what I want every...
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#704 - How to Have a Great First Meeting - 6/22/2026
The first time we meet with a prospect is exciting and challenging. The whole opportunity waits for us to uncover it. But it is also fraught with dangers. Will we get along? Do we have a solution that meets their needs? Will I be able to understand the core issues the prospect needs to solve?…
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#703 - A Tribute to Scott "The Professor" Plum - 6/13/2026
On Tuesday January 13, 2026, Scott "The Professor" Plum, my good friend, business partner and the co-host of the Winning at Selling podcast died suddenly. After 5 years and over 300 weekly conversations a great advocate for the selling profession went silent. In this episode I attempted to find...
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#702 – Why Discipline Beats Distraction Every Time - Tim Murray
January has a way of forcing clarity. Some people lean into that through Dry January, which is about far more than alcohol. It's about recognizing the distractions we use to numb discomfort, delay discipline, and avoid our best work. In sales—and in life—success rarely breaks down because of a…
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#701 – The Value of Ranking Your Customers
Not all customers are created equal—and treating them as if they are is one of the most common and costly mistakes organizations make. Companies often pride themselves on "great service for everyone," yet fail to recognize that limited resources require intentional allocation. Consider how you...
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#700 - Ten Greatest Selling Questions -Dec 2025
Welcome to show number 700! For Bill and me this is show #300. Every week for the past 5 years, 8 months and 24 days Bill and I have worked to deliver the latest sales advice, strategy and tactics so you can win at selling. Asking the right questions is a key capability of the sales professional....
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Dec 2025 - Special Guest Eric Harkins
We all want to believe that we are great leaders – thoughtful, generous, capable. But are we really all that good? How do the people on our team feel on Monday morning? Are they excited and eager or are they dreading the thought of coming in to work? It's time to gauge your leadership…
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Dec 2025 - Do I Really Need a Mentor
Many professionals wonder if they really need a mentor, especially when they're already working hard and doing well. But effort without experienced guidance can slow growth, increase mistakes, and limit potential. A seasoned mentor sees the sharp edges you don't, challenges you in ways you won't,...
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Dec 2025 - Your Comfort Zone is Your Failure Zone
Most people think of "comfort" as a good thing. And in many situations, it is. Comfort can mean safety, familiarity, and the absence of immediate threats. But when it comes to growth, achievement, and personal transformation, comfort is often the silent saboteur. It's the invisible line that...
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Dec 2025 - Special Guest – Paul Boehnke
What if the biggest obstacle standing between you and your sales goals isn't your product, your price, or your prospects—but the voice inside your head? Negative self-talk silently sabotages even the most skilled salespeople, creating doubt, hesitation, and missed opportunities. In this episode…
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Nov 2025 - What's In the Well Comes Up In the Bucket
When life turns up the heat, we don't rise to the occasion—we fall back to our preparation. In moments of pressure, we draw from whatever we've been putting inside ourselves all along. Like a well, our inner world stores the beliefs, emotions, and habits that shape our reactions. And when stress...
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Nov 2025 - How to Close on the First Appointment - Part 2 of 2
Most salespeople are trained to build rapport, gather information, and follow up later. But what if your prospect is ready today? In service-based, in-home sales (home- improvement, senior care, children's services, etc.) the best close might happen on the first visit. Do you want to be strong in...
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Nov 2025 - Special Guest Dr. Chris Croner
Few business challenges are more painful than hiring a salesperson who interviews well but fails to deliver. A poor producer can cost your company six to seven figures annually in salary, training, lost customers, and missed opportunities. While most sales leaders say they want reps with "fire in...
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Nov 2025 - How to Close on the First Appointment - Part 1 of 2
Most salespeople are trained to build rapport, gather information, and follow up later. But what if your prospect is ready today? In service-based, in-home sales (home- improvement, senior care, children's services, etc.) the best close might happen on the first visit. Do you want to be strong in...
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Oct 2025 - Creative B2B Prospecting Ideas
One of the most crucial and creative aspects of selling is developing new customers. It is also what separates the farmers from the hunters. Unfortunately, in the current business climate it seems more difficult than ever to find and connect with your ideal client. But there are some strategies…
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Oct 2025 - Special Guest Bob Freytag
Most companies stumble when launching something new—not because the idea is bad, but because they treat the launch like a one-time event instead of a repeatable discipline. Whether it's a product, service, or strategic initiative, success depends on more than development—it hinges on execution.…
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Oct 2025 - Handling Rejection Like a Pro
Rejection sucks! At least that how I've always seen it. But others that I've worked with don't seem to get affected by it. As a matter of fact it seems to get a fire lit under them. So, what's the difference in our responses and how can we all get better at dealing with rejection Grab your smiley...
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Oct 2025 - Seven Tips to Goal Setting
We often celebrate outcomes — the closed deal, the big win, the promotion. But what if the way we got there says more about us than the result itself? Today, we'll explore why the means — the process, the behaviors, the discipline — matter just as much as, if not more than, the ends. So, put on...
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Sept 2025 - Special Guest Frank Cespedes
You've seen the picture of a bridge being constructed where the two side are supposed to meet and they don't! Well, that is what misalignment looks like. In most firms, the sales function is the largest lever for executing strategy—yet it's often misaligned with the choices leaders say they've...
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Sept 2025 - Leave Your Mother on The Bus
We all carry voices from our past into our present—from our parents, the pastor from Sunday, the last prospect who brushed us off, the customer who complained about delivery, even our boss reminding us about our quota. They echo in the back of our minds and distract us from the person sitting…
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Sept 2025 - Are You Coachable?
In our last episode we closed with a quote from Bob Nardelli, the former CEO of Home Depot: "I absolutely believe that people, unless coached, never reach their maximum capabilities." If true, we should be looking for coaching opportunities every day with the hope of finding someone who will work...
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Sept 2025 - Special Guest The Amazing Hondo
Sales isn't just about numbers—it's about sparking curiosity, creating connections, and leaving people amazed. Now, imagine a speaker who blends the precision of a teacher, the creativity of a magician, and the insight of a strategist. This isn't "just talk"—it's an experience that makes your…
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Sept 2025 - What Buyers Really Want
Sales isn't about tricks or scripts—it's about understanding people. When you sell with empathy, clarity, and respect, you don't just win deals—you build trust, loyalty, and long-term relationships. The question is, "How do you accomplish that?" Put on your EMPATHY hat as Scott and I discover…
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Aug 2025 - You Are Not Being Tested
Many salespeople think they're in a test every time they meet a prospect—measured on how much they know and how perfectly they can present. But selling isn't about passing a test. It's about uncovering what matters most to the prospect. In this episode, we'll look at how shifting from "proving...
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Aug 2025 - Special Guest - Stevie Ray on Improv that Works
How can a centuries-old art form help your organization engage employees, build teamwork, and create a culture of innovation? For decades, the techniques of improvisation, or "improv," have helped organizations do just that. Improv is more than just funny; it is fun and valuable training. If you...
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Aug 2025 - Belief and Execution
We don't execute on what we don't believe. Whether it's a sales process, a life change, or a new habit, our actions—or lack of them—are rooted in what we truly believe about ourselves and what's possible. In this episode, we'll explore how belief shapes behavior and how shifting what you believe…
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Aug 2025 - Features, Benefits and Motivation
In sales, there's a common pattern that many professionals follow with the best intentions. They ask questions. They probe. They dig into the mechanics of a prospect's situation—what systems are they using? How much are they spending? What's not working? Next they tie the pertinent features into...
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July 2025 - Special Guest - Mitch Larson - The Power of Purpose
Are you living with purpose—or just going through the motions? In today's episode, we explore how purpose shapes your work, relationships, and identity. Discover how alignment brings clarity and fulfillment, and learn practical steps to overcome fear, find direction, and start living the life...
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July 2025 - Should You Respond to an RFP?
Responding to a Request for Proposal (RFP) can be a powerful way to win new business—but only if it's the right opportunity. RFPs often demand considerable time, resources, and cross-functional coordination, so blindly responding to every one can lead to wasted effort, low win rates, and team...
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July 2025 - Should You Respond to an RFP?
Responding to a Request for Proposal (RFP) can be a powerful way to win new business—but only if it's the right opportunity. RFPs often demand considerable time, resources, and cross-functional coordination, so blindly responding to every one can lead to wasted effort, low win rates, and team...
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July 2025 - Start or Wait… What Should I Do?
Have you ever been torn between jumping into action or holding back to wait for the perfect moment? Today we explore the tension between taking immediate action and practicing delayed gratification. Can you really do both—and should you? You don't have to wait another moment as Bill, and I pause…
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July 2025 - Special Guest - Jason Talley
Scott and I have been pouring our knowledge and experience into this podcast for over 5 years with the hope that sales professionals would be able to use this information to sell more and win at selling. And that sales leaders would be able to augment their own training with the ideas presented…
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July 2025 - Special Guest - Jason Talley
Scott and I have been pouring our knowledge and experience into this podcast for over 5 years with the hope that sales professionals would be able to use this information to sell more and win at selling. And that sales leaders would be able to augment their own training with the ideas presented…
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June 2025 - Moving from Rep to Manager
As a salesperson - have you ever said behind your sales manager's back - I could do a much better job than they can. Be careful what you wish for. It may look more glamorous than it really is. There are some pros and cons to being a salesperson versus a sales manager than you think. Listen up as…
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ABOUT THIS SHOW
Welcome to the Winning at Selling Podcast. Your hosts Bill Hellkamp and Scott "Professor Plum."This podcast is dedicated to the overall success in the sales channel. From the CEO to the front line salespeople, every role must be aligned, trained and committed, every day to achieve the desired outcome. This is not done without a commitment to ongoing career development in learning market-relevant techniques, overcoming conceptual barriers, applying proactive and productive behaviors and projecting a positive attitude.Whether you are defending first place in the market or dedicated to fighting for first place, each episode will deliver proven advice you can apply that day to improve your sales results.
HOSTED BY
Bill Hellkamp
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Frequently Asked Questions
How many episodes does WINNING AT SELLING have?
WINNING AT SELLING currently has 102 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is WINNING AT SELLING about?
Welcome to the Winning at Selling Podcast. Your hosts Bill Hellkamp and Scott "Professor Plum."This podcast is dedicated to the overall success in the sales channel. From the CEO to the front line salespeople, every role must be aligned, trained and committed, every day to achieve the desired...
How often does WINNING AT SELLING release new episodes?
WINNING AT SELLING publishes regularly with 102 episodes available. Check the episode list for the typical release schedule.
Where can I listen to WINNING AT SELLING?
You can listen to WINNING AT SELLING on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts WINNING AT SELLING?
WINNING AT SELLING is created and hosted by Bill Hellkamp.
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