WINNING AT SELLING

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 cou...

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 most important part of the sales conversation." In this episode, Bill is joined by guest host, Brian Maas....

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 listener to hear: confidence is not something you either have or you don't. It's not a personality type....

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? This is such a valuable topic, because we all want to get started on the right foot in our first meeting w...

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 some of the fun and interesting conversations and diatribes that give the best profile of what he believ...

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 lack of talent. It breaks down because distractions keep winning. Today's conversation focuses on how dis...

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 might categorize your companies service philosophy as Scott and I discuss The Value of Ranking Your Custo...

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. So let us answer your questions with our questions as Bill and I reveal the Ten Greatest Selling Ques...

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 capabilities as Scott and I welcome author and leadership consultant, Eric Harkins to discuss his book Great Leade...

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, and accelerates the progress you can't create alone. If you're questioning whether now is the time, jo...

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 separates who you are from who you could become. So put your feet up as Scott and I sink into Your Comfort...

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, we explore how your inner dialogue directly impacts your sales performance and discover the Thoughts On...

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 hits, the "bucket" only brings up what's already in the well. So, get a grip on the rope as Scott and I...

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 influencing or persistent in follow-up to make a sale? Join Bill and me as we break down How to Clos...

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 the belly," few know how to identify it reliably. In this episode, we reveal the proven, scientific fo...

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 influencing or persistent in follow-up to make a sale? Join Bill and me as we break down How to Clos...

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 you can use. So, dust off that prospecting list as Scott and I put a stamp on Creative B2B Prospecting I...

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. In this episode, we'll explore why so many launches fall short, why launch success matters, and how a fe...

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 face buttons as Scott and I wrestle with Handling Rejection Like a Pro on Episode 689 of the Winning a...

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 your party hats as Bill and I explore Seven Tips to Goal Setting and other persnickety perceptions on Ep...

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 made. Fixing that gap is crucial for organizational success. So, get yourself straight as Scott and I wel...

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 right in front of us, now.   The problem is, those voices always seem to show up when we're trying to pros...

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 with on a long-term basis. But, if we don't listen and change we might find our coach has better thing...

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 sales message unforgettable, turning ideas into impact and audiences into believers.  Let's see if we can...

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 What Buyers Really Want and other ridiculous ramblings on Episode 683 of the Winning at Selling podcast....