#703 - A Tribute to Scott "The Professor" Plum - 6/13/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
Release Date: 06/16/2026
#716 – Why Prospects Ghost You: Interest Isn't Commitment - 9/11/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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, and the warning signs around trust, value, qualification, decision process, and next steps that salespeople may be overlooking. Sales Prospect Ghosting Solutions Bill and Brian discussed the common sales challenge of prospects "ghosting" after showing initial interest. They identified several key...
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#715 - The Identity Problem: Why Talented People Underperform in Sales - 9/4/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 Discussion Bill and Stefani discussed examining and learning from sales failures to identify mental blocks, with Bill emphasizing the importance of reviewing their processes. Bill shared his experience teaching public speaking, noting that fear often stems from past negative experiences, and...
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#714 - The Decision Collision - 8/28/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 your needs or the needs of your customer? On today’s episode, we will consider the following question: When the pressure to produce and the responsibility to serve the customer collide, what guides your decision? Decision Collision in Sales Jimmy discussed the concept of decision collision in...
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#713 - Guest: Erik Therwanger - The Ponder Principle - 8/21/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 Prospects to Ponder Erik and Bill discussed the importance of causing prospects to "ponder" rather than just hear or listen during sales presentations. Erik explained that when sales professionals make people think deeply about their message, it leads to better decision-making,...
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#712 - The Power of the Plan - 8/14/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 preparing to fail.” Benjamin Franklin Bill Hellkamp LinkedIn: Bill Hellkamp Website: Bill Hellkamp email: Erik Haugen LinkedIn: Erik Haugen Contact: PROP Coaching and Consulting website:
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#711 - Why Every Great Sales Meeting Starts with an Agenda - 8/7/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 next. The agenda isn't just about organizing a meeting, it's about earning the right to lead it. Golden Nugget: “Success is nothing more than a few simple disciplines, practiced every day.” ~ Jim Rohn. In this episode: Brian Maas LinkedIn: Brian Maas Contact: Bill...
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#710 - The Follow-Up is the Sale - 7/31/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 of effective follow-up in sales, emphasizing that it's not about being pushy but about serving the client by staying relevant, adding value, and deepening trust. She shared a structured follow-up methodology using her "convert method" where each touchpoint should achieve one of three...
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#709 - Establish a Connection Right Away and the Right Way - 7/24/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 and allow their stories to guide you to a valuable solution. Active Listening in Sales Techniques Jimmy discussed the importance of active listening in sales, emphasizing the need to listen to understand rather than to respond. He explained how asking clarifying questions and showing genuine...
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#708 - Guest: Steve Keating – Turning a Great Commission into Long Term Wealth - 7/17/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 measure your success by how much you make; but the top sales professionals measure their success by how much of that money they are able to keep. In this episode Bill Hellkamp welcomes sales leadership coach, Steve Keating to discuss sound fiscal principles that salespeople should employ if...
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#707 - Are you making it easy for your customer to buy? - 7/10/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 ones really connect with the prospect. In sales cultures that are so focused on selling we are being counterintuitive to why people buy! Telling is selling and people don’t like being sold but they love to buy! SO let’s make it easy… Customer-Centric Sales Strategy Erik discussed the...
info_outlineOn 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 some of the fun and interesting conversations and diatribes that give the best profile of what he believed and stood for.