Dec 2025 - Do I Really Need a Mentor
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
Release Date: 12/11/2025
#721 - Would You Hire You? Sales Interview Mistakes to Avoid - 10/16/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 prepare for your next interview with the same discipline you would bring to an important sales call. Sales Interview Preparation Strategies Brian shared five key things salespeople should focus on before interviews to demonstrate their skills effectively. He emphasized the importance of knowing and...
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#720 - I Fell Into Sales...Now What? - 10/9/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 discussed the importance of having a structured sales process rather than relying on untrained "accidental salespeople" who wing it without a clear methodology. Stefani emphasized that a sales structure doesn't make you less human but actually frees you up to be more present and confident in...
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#719 - The Posture of Partnership - 10/2/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 doesn’t close, the relationship opens. Assistant Buyer Success Strategies Jimmy discussed his approach to becoming an assistant buyer, inspired by Frank Boettcher's book "How I Raised Myself from Failure to Success in Selling." He explained that the assistant buyer posture involves coming alongside...
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#718 - Stop the Sales and Marketing Disconnect - 9/25/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 never uses. So how do we get sales and marketing working together in a way that actually helps both teams win? Sales-Marketing Team Alignment Challenges Bill, Beau and John discussed the challenges in the relationship between sales and marketing teams, highlighting how poor communication and silos...
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#717 - Overcoming the Stall - 9/18/2026
Winning at Selling | Sales Leadership, Training and Development by Bill Hellkamp
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 makes it easy for them to buy TODAY. Handling Sales Objections Positively Erik discussed how a pause or objection from a prospect during a sales process should be viewed as a positive sign indicating the customer has moved into the reasoning stage of the buying cycle. He emphasized that...
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#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:
info_outlineMany 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, and accelerates the progress you can’t create alone. If you’re questioning whether now is the time, join Bill and me as we contemplate Do I Really Need A Mentor? and other evidence on Episode 698 of the Winning at Selling Podcast
Handout: Do I Really Need a Mentor - 10 Questions to Ask Yourself
Ep 626 - The Gift of Mentorship
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Next Book - Aligning Strategy and Sales by Frank Cespedes
https://www.amazon.com/Aligning-Strategy-Sales-Behaviors-Effective/dp/1422196054/ref=sr_1_1
Bill Hellkamp – See my LinkedIn profile and send me an invite
Visit my website: http://www.reachdev.com/
Scott “Professor Plum” Plum – See my LinkedIn profile and send me an invite
Visit my website: https://www.mnsales.com