Episodios

  • First Month Sales Results Gut Check (Money Monday)
    Feb 2 2026
    On this first Monday of the second month of the year, it’s time for a gut check. First we need to check where we are against our new year goals. Next we need to take stock of our first month sales performance and make adjustments. We’re just a little more than 30 days away from our new year intentions, resolutions, and goals. A month ago, we set out into the new year with hope and ambition that this year would be our best ever and that we’d make positive lasting changes in our lives. It’s Easy to Slip Off the Track You’ll remember that discipline is sacrificing what you want now for what you want most. But as time goes by and sticking with new habits gets more challenging, it’s easy to forget what motivated us to make the changes in the first place. It’s easy to let down our guard and go back to our comfort zone. The farther away we get from our intentions, the more likely it is that we allow our discipline to slip and get off track. It’s just human nature. Small Slips in Discipline Can Add Up Quickly Let’s say you kicked off the new year determined to have your best sales year ever, and you knew that meant filling your pipeline daily by getting Fanatical about Prospecting. But upon reflection, you realize that days have passed since you picked up the phone, knocked on a door, or talked with customers. You’ve been making excuses to avoid the very activities that move you closer to your goals. I’ll admit that it happened to me just this past week. This month has been non-stop travel — 12 flights, 10 cities, 8 keynotes, 5 full days delivering training to sales teams. Toward the end of the week I got tired, made excuses, and let my exercise and nutrition routine slide. This was something I promised myself I wouldn’t do when the year started. I know that if I don’t stop right now and recommit to my goals, then there is a good chance that I’ll continue down this negative path — because it’s easy. Revisit Your Goals and Resolutions This is exactly why NOW is a good time for a gut check and a look in the mirror. Pause and carve out time today, to revisit your goals, resolutions, and intentions. Sit down and think about what you decided to achieve back in early January. Visualize what it was that motivated you. Picture what you want most and where you want to be at the end of this year. Go back and re-listen to the Money Monday episodes on building a personal business plan, reflection vs. regret, and why personal goals are essential for sales discipline. Then recommit to your goals. Remember the feelings you had when you set them, and make an intentional decision to get back on track. Evaluate Your First Month’s Performance Against Your Sales Goals Next, step back and evaluate your first month’s sales performance. As you do, you’ll likely find one of three scenarios: You Crushed It – You had a killer month and blew your goals out of the water.You Were Average – You hit quota or did “okay,” but you know you’re capable of much higher performance.You Bombed – You missed your number and ended the month worse than you hoped. Great Sales Month If You Crushed it, and you’re on the top of the ranking report fantastic, congratulations! But be very careful not to let off the gas. It’s likely you worked very hard last month to achieve these results. There will be the temptation to take a breather. Trust me, if you do, this complacency will come back to bite you. Now is the time to recommit to doing the activity that fueled your success last month so you don’t end up with a lackluster February and a disastrous March. In other words, you’ve set the foundation for a huge year, take advantage of what you have accomplished and keep the pedal to the metal! Average Sales Month If you had an average or just OK month — maybe you hit quota, maybe you came close, but you know you’ve got more in the tank — then it’s time for some honest self-reflection. Ask yourself: What held you back from greatness?What could you have done differently that would have resulted in higher sales productivity? Maybe you needed to prospect harder. Perhaps you could have pushed a little more to get some of your pipeline opportunities to close. It could have been that your pipeline wasn’t big enough from the start, and you ended up scrambling to make your numbers; but, otherwise you did everything right. It’s okay, you haven’t hurt yourself. You are still in a good position to have a great year. But you’ll need to identify your performance gaps and plan to overcome them in February. This is a good time to sit down with your coach or mentor, breakdown your performance, and get guidance on where you can make tweaks and get better. If you don’t have a coach and you want to talk with someone go to https://salesgravy.com/coach to get help. Bad Sales Month If you bombed, if your month was downright awful, then you’re going to need to move fast to make adjustments. ...
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    10 m
  • Why Founder-Led Sales Teams Struggle to Scale
    Jan 29 2026
    “Buyers want a machine, a sales machine, not a mystery. If the sales machine only works because of the founder, it’s not that valuable. It’s actually quite risky.” Chris Spratling, founder of Chalkhill Blue Limited and author of The Exit Roadmap, shared this on a recent episode of the Sales Gravy podcast. He works with business owners preparing to sell their companies, helping them get operations, finances, and sales engines ready for new ownership. That insight cuts straight to the reason so many founder-led businesses hit a ceiling they can’t break through. If you are a founder who still carries most of the revenue, or you have a founder-led sales team that depends on you to close critical deals, this is bigger than exit planning. It determines whether your business can grow beyond your personal capacity. The Golden Handcuffs Problem You built the business. You know the product better than anyone. You can sell it without thinking. That is exactly where the risk starts. When major clients only trust you, when your sales process lives in your head, when new reps struggle to replicate what comes naturally to you, you aren’t running a sales operation. You are running a one-person engine with a support team around it. Spratling calls this the “golden handcuffs.” It looks like success from the outside, but underneath, it creates dependency. Every time you step in to save a deal, you reinforce the idea that the business only works when you are involved. Most founders focus on how this affects valuation at exit. Fewer recognize the more immediate cost. That dependency limits how fast the company can grow right now. Where Founder-Led Sales Breaks Down The transition from founder-led sales to a functioning team is where momentum often stalls. You hire your first salesperson. They do well. Then a second. Then a third. Suddenly, deals slow down, messaging gets inconsistent, and you find yourself pulled back into conversations you thought you had delegated. They don’t sell the way you do. They miss cues you catch instinctively. They hesitate where you would push forward. So you jump in, coach through objections, and close deals yourself. What feels like instinct is actually a method you developed through hundreds of conversations. The problem isn’t that your team lacks talent, but that your approach has never been translated into something they can use without you standing next to them. As long as that stays true, scale will remain out of reach. Turning Intuition Into a Usable Process The hardest shift for founder-led teams is codifying what the founder does without thinking. You know which deals are worth pursuing. You know when to apply pressure and when to step back. You know how to redirect a conversation when resistance shows up. That knowledge is pattern recognition built over time, and it can be used to create a process. Start by defining how deals actually move through your pipeline. Not a generic framework pulled from a template, but the real stages your customers pass through, with clear criteria for each transition. What has to be true before a lead is qualified? What information must be present before a proposal goes out? Then look at discovery. What questions do you ask every time? What do you listen for before positioning your solution? Which objections show up consistently, and how do you respond when they do? The goal is to document the structure beneath the conversations so that someone else can navigate the same terrain with confidence. Why Your CRM Is Not Pulling Its Weight Most founder-led teams have a CRM, but they only use it to track contacts and deal size. However, a functioning, high-performing sales system treats the CRM as a learning tool. That means capturing more than surface-level data. It means recording what buyers actually say, why deals move forward, where they stall, and who influences the decision. When that information is tracked consistently, patterns become visible. You see which prospects convert fastest, which objections actually kill deals, and where momentum typically breaks down. That insight does more than improve forecasting. It gives you a concrete way to train new reps based on real deals you have closed, not abstract theory. Three Steps to Build a Sales Engine That Does Not Depend on You The objective isn’t to remove yourself from sales completely. It’s to make your involvement a choice rather than a requirement. Step 1: Define Clear Qualification Criteria Your team needs to know which leads are worth pursuing and which ones are a waste of time. If you’re constantly redirecting their focus, you haven’t defined “good fit” clearly enough. Get specific—industry, company size, buying triggers, decision-making structure. Step 2: Create Documented Playbooks How do you handle discovery? What’s your approach to proposals? How do you navigate the closing process? Your team needs a framework they can adapt. Think decision trees, not ...
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    22 m
  • Jeb Blount’s 3 Non-Negotiables for Modern Sales Success (Ask Jeb)
    Jan 27 2026
    Here’s a question that’ll change how you think about this profession forever: What’s the one moment that reveals you’re built for sales success? For most people, that moment never comes. They stumble into sales, struggle with the stereotypes, and either quit or spend their entire career fighting against what they think selling is supposed to be. But for those of us who get it, there’s a moment of clarity so powerful it changes everything. Mine happened in high school when I was chasing a girl and ended up on the yearbook staff. Thirty days later, I handed over $3,800 in checks while everyone else struggled to hit their $300 quota. The Sales Crack Moment When Mr. Hall at Hall’s Hardware Store wrote me that first check for a yearbook ad after I had done little more than ask outright for the money, something clicked. This wasn’t complicated. Walk in, shake hands, present value, and people give you money. While my classmates were paralyzed by the same stereotypes you hear today (“I’m not a salesperson”), I was out there having conversations. That’s all prospecting really is. Talking to people. The gasp in that room when I revealed my numbers? That was better than the money. That was the competitive fire igniting. That was me realizing I could outwork, outsell, and out-earn anyone if I just committed to the process. The Discipline Problem Most Sellers Miss Here’s what nobody tells you about sales success: It’s not about talent. It’s not about charisma. It’s about ruthless execution of proven processes. By the time I was 21 or 22, I was making $300,000 in the early nineties. That’s equivalent to making close to a million today. Not because I was special, but because I understood something fundamental that most people never figure out: The more people you talk with, the more you sell. And here’s the beautiful part. There are lots of people to go talk with. The pipeline never runs dry if you’re willing to fill it. The Three Non-Negotiables for Modern Sellers The future of selling is blending. Not choosing between video and phone and in-person. Blending all of them based on one critical question: What communication channel gives me the highest probability of capturing my desired outcome at the lowest cost of time, energy, and money? When I started selling, we had two channels. Maybe three if you count snail mail. Phone and in-person. That’s it. Today? You’ve got a dozen ways to connect. WhatsApp lets you text, call, and video chat almost instantly. The options are endless. But here’s where Gen Z sellers (and honestly, every generation) screw this up: They get single-siloed. “I’m only good at email.” “I only do video calls.” “I hate the phone.” That mindset is killing your income potential. You need to be good at everything. Master every channel. Because the channel doesn’t matter. The outcome does. Synchronous Beats Asynchronous Every Single Time Here’s the second non-negotiable to sales success: Stop hiding behind asynchronous communication. We do deals in a synchronous world. Real-time conversations. Phone calls. Video meetings. Face-to-face interactions. If you think you can close business through email threads and text messages, you’re delusional. Why? Because robots can write better emails than you can. AI can craft more persuasive text messages. But sales is the ultimate human career in the age of AI precisely because of the human connection required in synchronous conversations. Lead with phone calls. Get face-to-face when the deal size justifies it. Use video when it makes sense. But always, always prioritize real-time conversations over digital hide-and-seek. Ask Questions and Actually Listen The third non-negotiable is mastering the art of asking great questions and listening to the answers. People make five decisions before they buy from you: Do I like you? Do you listen to me? Do you make me feel important? Do you get me and my problems? Do I trust and believe you? Notice what’s not on that list? Your product features. Your company’s awards. Your clever sales pitch. They’re evaluating you. Your ability to connect. Your capacity to understand. Your commitment to making them feel important. And the only way to get five affirmative answers to those questions is through synchronous conversations where you ask intelligent questions and actually listen to what they’re telling you. The Make It Rain Principle When Mr. Rouse made me editor of the yearbook after I brought in $3,800, I learned something that shaped my entire career: When you can make it rain, you can get anything you want. That principle holds true whether you’re selling yearbook ads in high school or enterprise software to Fortune 500 companies. Revenue solves problems. Performance opens doors. Results create opportunities. Most people in sales stumble into it. They take the job because it was available. They stick with it because the money’s decent. But they never ...
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    13 m
  • What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday)
    Jan 26 2026
    I’m not sure if you noticed this, but there is a massive gap between what salespeople and leaders know and what they actually do. I’ve written 18 books and trained hundreds of thousands of salespeople. I can’t tell you how many times someone comes up to me and says, “Jeb, I read Fanatical Prospecting. Great book. But that stuff doesn’t work for me.” Or they’ll say, “I tried that objection handling technique you taught, but it didn’t work, so I went back to what I was doing before.” Here’s what they don’t understand: The problem isn’t the technique. The problem is that they gave up too soon. The brutal truth is that most people fail to implement what they learn. The Skate Park Lesson A couple of weeks ago, I was traveling for business, working with one of my clients’ sales teams. One afternoon, I decided I needed some exercise, so I went for a walk. Along the way, I came across a skate park where kids were riding their skateboards and doing tricks. There was a bench nearby, so I sat down to watch for a while. Close to me was a group of young guys, probably 13 or 14 years old. They were huddled around a phone watching a YouTube video of someone doing a particular trick on their skateboard. They watched it, talked about it, and then one of them threw his skateboard down and attempted the trick. He immediately fell off and failed. The next kid tried, and he failed. Then the next one and the next one. All of them failed to do the trick. So what did they do? They went back and watched the YouTube video again. Then they threw down their boards and crashed and burned, but this time, slightly less dramatically than the first time. They repeated this process over and over. Watch the video. Try the trick. Fail. Watch again. Try again. Fail a little less badly. Until finally, one of them nailed it. When he landed the trick, they all erupted. Clapping, fist pumping, and cheering. And once one kid got it, the rest of them started getting it too. They practiced until they had the trick nailed down, then went back to YouTube to find another trick to learn. At that point, I got up and headed back to my hotel. But as I was walking, I couldn’t stop thinking about what I’d just witnessed. Too Often, We Give Up too Soon How often do we do the exact opposite in business and sales? We read a book, watch a video, listen to a podcast. We hear about a technique or concept that sounds really good. And we think, “Yeah, I’m going to try that.” So we give it one shot. Maybe two if we’re feeling ambitious. And when it doesn’t work perfectly the first time, we say, “Well, this doesn’t work for me,” and we give up and never try it again. Or worse, we read the book, feel really good about the concept, then put the book down and never even attempt it at all because we’ve already convinced ourselves it wouldn’t work for us before we even tried. But here’s the thing: Those kids at the skate park didn’t look at that trick and say, “This looks hard, it probably won’t work for me.” They looked at it and said, “We’re going to figure this out.” They understood something that most adults have forgotten: Just because you read about something or see someone else do it, doesn’t mean you’re going to master it on the first try. The Homemade Yogurt Failure Paradigm As I was walking back from the skate park, this lesson reminded me of something that had happened to me over the holidays. I’d seen something in my news feed about making homemade yogurt. It looked interesting, so I bought some milk, studied the recipe, and made an attempt. And I failed. My concoction didn’t turn into yogurt at all. My immediate reaction was, “Well, this isn’t going to work; it must be a bad recipe.” I gave up after one failed attempt. But after watching those kids at the skatepark, I realized the giving-up-too-soon trap I’d fallen into. So when I got home from my trip, I went back, reread the recipe, walked back through my steps to figure out what went wrong, and tried again. This time it worked, and I actually made yogurt. The recipe wasn’t the problem. My execution was the problem. And I only figured that out by trying again. The Human Overconfidence Fallacy Here’s the lesson: We are all susceptible to this human fallacy of believing that we can read something, watch something, or hear something once and then immediately do it perfectly. When it doesn’t work the first time (or even the second time), we conclude that the technique is flawed, or it won’t work for us, or our situation is unique and different. But the truth is, we gave up too soon, before we gave the technique a fair shot. That’s just being human. We’re wired for overconfidence, instant gratification, and immediate results. When we don’t get them, we move on. Why This Matters in Sales Let me bring this back to sales, because this pattern will absolutely kill your results. You read a book on ...
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    13 m
  • Coaching Sales Reps Who Think They Know Everything
    Jan 22 2026
    “That chip on my shoulder made me less empathetic, more rushed, too eager to solve things too fast, and less thoughtful. That chip built me, but then it started to tear me down.” I said that recently in a conversation with Harriet Mellor of Your Sales Co, and it captures something every sales leader needs to understand. I grew up in the sales training business. My dad literally wrote THE book on prospecting—several of them, actually. I worked at Paycom, Comcast, and various startups where I consistently crushed my numbers. But what I learned is that knowing the right techniques and getting your team to actually implement them are two completely different challenges. Sales training resistance is rarely about bad content. More often, it is about ego and pride standing in the way of growth. I had to recognize that in myself before I could address it in the people I lead. Why Your Top Performers Resist Training the Most When I was a rep, I was terrible at taking coaching. Not because I didn’t understand the concepts. I understood them better than most. But when someone tried to coach me, I tuned out. The problem was I’d already figured out a system that worked. I was hitting my numbers. Why would I mess with it? Think about learning golf. You chunk the ground twenty times, then suddenly you make contact. The ball doesn’t go straight or very far, but it goes. Someone tries to teach you proper form, your first thought is, “I already figured out how to hit the ball.” That’s where many top performers live. They’ve reached an equilibrium. Not peak performance, but functional competence. Training feels disruptive because it threatens what is currently working. They’re not resisting because they’re stubborn. They’re resisting because they have something to lose. What if they try something new and their numbers drop? They’d rather stay at 85% effectiveness than risk dropping to 60%, even if it means eventually reaching 120%. Two Ways Ego Hurts Performance Creates Rush Instead of Curiosity At Paycom, I carried a massive chip on my shoulder. I carried the same name as my dad. People knew who he was. I felt pressure to prove I belonged. So I rushed. I skipped discovery. I pushed toward proposals. I talked more than I listened. Every call felt like a test I needed to pass. You can hear this on your team’s calls. Reps who are trying to prove something move too fast. They stop asking questions. They perform instead of selling. That behavior is driven by ego, and it costs deals. Telling them to slow down will not fix it. You need to understand what they feel compelled to prove and why they associate speed with competence. Blocks From Actually Learning When I was carrying a quota, I thought I was a lifelong learner. I read every sales book. I listened to podcasts. I sat through hours of training sessions. But when it came to changing what I did on Monday morning, I defaulted right back to what I knew. I’d hear a new objection handling technique and think, “Yeah, I basically already do that.” I didn’t. But ego wouldn’t let me see the gap. Your salespeople are doing the same thing right now. They’re taking in your coaching but filtering it through their existing beliefs. They’re protecting the system that’s currently working. And they’re developing blind spots they can’t see. Watch for the reps who stop recording their calls because they “know what they sound like.” The ones who skip role play because it’s “not realistic.” The ones who tune out your coaching because you “don’t understand their territory.” Reps who do this aren’t trying to be difficult, but instead trying to protect their self-image instead of improving their performance. Why Your Team Listens to Outside Trainers But Not You One of the most frustrating parts of leadership is to preach a methodology for six months and nothing changes. Then an outside consultant shows up and says the exact same thing. Suddenly, everyone’s taking notes and engaged. I experienced this firsthand with my dad. He would offer advice, and I tuned out. Days later, I would hear the same message from someone else and think it was brilliant. It wasn’t about the message. It was about who was delivering it. When you try to coach your team, there’s history. There’s baggage. Maybe you’ve given conflicting directions before. Maybe they see you as “management” instead of someone who gets it. Maybe they just don’t like admitting to their boss that they need help. Outside trainers don’t carry that weight. They show up with a clean slate and credibility that’s granted just by being an outsider. The real question isn’t how to make your team listen to you. It is how to create an environment where learning feels safe, regardless of who delivers it. How to Break Through Sales Training Resistance Frame Training as Addition, Not Correction I stopped resisting coaching when my leaders stopped making me feel like ...
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    52 m
  • How to Save Neglected Accounts Before They Disappear (Ask Jeb)
    Jan 20 2026
    Here’s a question that’ll make your head spin: You just inherited 50 neglected accounts, and your customers feel taken for granted. How do you reposition yourself as a high-value partner instead of just another transactional vendor who’s about to disappoint them? That’s the question posed by Scott Northway, and it’s one of the most common challenges I see in sales today. A new account manager takes over, inherits a book of business that’s been ignored, and now has to figure out how to rebuild relationships with customers who’ve been collecting dust. If you’re nodding your head right now, you’re not alone. Poor account management is quietly bleeding companies dry, and most leaders have no idea how much revenue they’re leaving on the table. The Brutal Truth About Why Customers Leave When we survey customers through our consulting projects with clients who are hemorrhaging accounts, here’s what we find: About 70 percent of the time, customers don’t leave because of price. They don’t leave because of product quality or service issues. They leave because they feel taken for granted. Let me give you a real example. I pay six figures annually for a software program that’s critical to my business. Every time my contract comes up for renewal, it’s like a circus. They fly people in. They wine and dine me. They promise the moon about how they’re going to support us and be our partner. Then once the contract is signed? Crickets. My account manager disappears for three years. If I don’t call them, they don’t call me. And here’s the thing: I actually like my account manager. I genuinely want to work with them. There are products I could buy, optimizations we could make, but I have to do all the work to make it happen. This is insane. And it’s costing companies millions. What Won’t Work: The Rookie Mistakes So you’ve inherited these neglected accounts. Here’s what you absolutely cannot do: Show up on their doorstep apropos of nothing and try to sell them something. If I’m an existing customer doing business with your company, and you show up trying to pitch me without acknowledging the elephant in the room, we’re probably done. It’s rude. It’s bad behavior. And it tells me you’re just like every other transactional vendor who doesn’t actually care about my business. The second mistake is spreading yourself too thin across all 50 accounts without any strategy. You’ll burn out, deliver mediocre service to everyone, and end up losing accounts you could have saved. The Human-to-Human Approach That Actually Works Here’s what does work: Be honest. Be human. Name the problem. Pick up the phone and say something like this: “Hey, I’m your new account manager. I recognize that no one’s contacted you in a while, and I’m sorry about that. I apologize. I’d like to do a fresh start. Would you give me the opportunity to get to know you better and learn about what’s important to you?” That’s it. Simple. Direct. Human. Now here’s the hard part: When you have that conversation, some customers are going to unload on you. If they really have felt taken for granted, they’re going to say some nasty things. They might complain about the last account manager. They might air grievances about problems that have been festering for months. And the most important thing you can do in that moment is shut up and listen. Don’t try to defend the past. Don’t talk over them. Don’t promise you’re going to be so much better than the last person. Just let them get it all off their chest. Let them talk it out, because people like people who listen to them. Then, if there’s something specific you can help them with, don’t make promises you can’t keep. Commit to one thing. Take care of that commitment. Honor it. Build trust slowly. That’s how you become a high-value partner through fanatical prospecting discipline applied to account management. The Smart Way to Triage 50 Accounts You can’t effectively manage 50 accounts with equal attention, so you need to segment fast. Use a simple A, B, C ranking by revenue and risk: A Accounts: Your largest customers or those at highest risk of churn. These get weekly or bi-weekly touchpoints. B Accounts: Solid mid-tier customers with growth potential. These get monthly check-ins. C Accounts: Smaller accounts that are stable. These get quarterly touchpoints. But here’s the secret weapon most account managers miss: Use AI and your CRM data to find the low-hanging fruit. Look for patterns like former buyers who’ve moved to new companies in your territory, customers who mentioned specific challenges in past conversations, or accounts showing signs of expansion readiness. One of the smartest things you can do is ask your AI tools: “Did anyone on this account ever mention their favorite sports team? Do they like to cook? What matters to them personally?” Those human details are gold for building real relationships in ...
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    15 m
  • Where Confidence Comes From and Why it Matters in Sales
    Jan 19 2026
    Have you ever gone into a closing meeting, a sales presentation, or even a prospecting call with total confidence? That mindset and feeling that everything's going to go your way, that nothing can go wrong, that you're absolutely going to win? I've been there. I know you have too. It's one of the greatest feelings ever. But let's juxtapose that against going into a meeting feeling insecure, where your focus is on everything that could go wrong versus everything that could go right. And then, as soon as something does go wrong, everything starts to spiral downward. There is absolutely nothing that can make or break a deal like confidence. In this Sales Gravy podcast episode, we're going to explore exactly where confidence comes from, why it matters so much in sales, and most importantly, what you can do to build the unshakeable confidence that closes deals. The Insecurity Death Spiral Recently, I learned a profound lesson about confidence. I was invited to play golf with a group of business people in Florida. Beautiful day, sunshine, great course. It should have been perfect. Except I'm not a very good golfer. And these guys? They were good. Really good. The kind of golfers who carry single-digit handicaps and talk about their swing plane like it's a science project. So I'm standing on the first tee, watching them stripe their drives straight down the middle, and I can feel it happening. That little voice in my head starts whispering: "You don't belong here. You're going to embarrass yourself. Everyone's going to see how bad you are." I started strong enough. Made it through the first couple of holes without humiliating myself. But then I hit a bad shot. Then another. And instead of shaking it off like I normally would, I started fixating on those bad shots. That's when the downward spiral began. Every swing became an exercise in anxiety. I was so focused on not messing up that I couldn't help but mess up. My mechanics fell apart. My rhythm disappeared. By the end of the round, I had played one of the worst games of golf in my life. Not because I suddenly forgot how to swing a club, but because I let insecurity take over. Now, I managed to keep a smile on my face. We were playing golf in the Florida sunshine, after all. But inside, I was frustrated because I knew what had happened. I let my insecurity about being the weakest player in the group sabotage my entire game. And here's what hit me on the plane home: That's exactly what I see happen in sales all the time. One moment of uncertainty, one unexpected challenge, and suddenly a salesperson who is perfectly capable starts spiraling. Their confidence evaporates. And with it goes their ability to perform. Why Confidence Matters in Sales In sales, there is nothing that sells like confidence. Nothing. Buyers lean into confidence. They're attracted to it. They trust it. And because of emotional contagion—your ability to transfer your emotions to another person—you basically take your confidence and hand it to the buyer, who then gains more confidence in you. Think about it. When you walk into a meeting radiating confidence, the buyer thinks, "This person knows what they're doing. They believe in what they're selling. I can trust them." But when you walk in feeling insecure, the buyer picks up on that too. They start thinking, "Why is this person nervous? What aren't they telling me? Maybe this isn't the right solution." In sales, because we can't always control the playing field and because we don't always feel like we should be where we are—especially when we're dealing with the C-suite or high-level decision makers, when we're in super competitive situations, or when we don't really know what we're talking about—one thing that goes wrong can create a cascade of other problems, creating a downward insecurity spiral that is real and deadly. The Ultimate Source of Confidence So the question is: Where does confidence come from? Where do you get it? Well, confidence by its very nature comes from the inside. It's a mindset. It's something that you believe, just like insecurity is a mindset that comes from the inside. Confidence is mostly created by certainty. When you feel certain that you can control the outcome, you feel more confident. When you're in situations that feel familiar or you're talking about a product, your service, or some part of your offering that you totally understand, you feel more confident. When you've executed the sales process perfectly and built deep relationships with your customers, you feel more confident they're going to buy from you. When you've practiced your presentation multiple times and know it rote, you feel more confident. By the way, the same thing works in reverse. Uncertainty begets insecurity. When you walk into a situation and you feel uncertain—and this happens to a lot of brand-new salespeople who don't know what to say or feel like they don't really understand the product offering, their industry, or ...
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    14 m
  • Turn Boring Sales Pitches Into Conversations That Close
    Jan 15 2026
    You are on slide 34 when the CFO’s phone buzzes. She glances down. The VP to her left is nodding, but you can tell he checked out ten minutes ago. You know this pitch cold. You have rehearsed it. You built the deck. You covered every feature, every capability, every objection. And still, you are dying up there. You spent weeks on this presentation. None of it matters because everyone in that room has already sat through the same pitch from three other vendors this month. “Pitching sucks,” says Danny Fontaine, author of Pitch, on an episode of the Sales Gravy Podcast. “It sucks for the people doing it because we get so stressed out, and we spend weeks doing mountains of work. Meanwhile, there is a whole audience who has just as bad of a time as us because they have to sit through an hour of 100 PowerPoint slides and they’re bored.” He is right. The audience suffers just as much. They sit through identical presentations, back to back, trying to remember which vendor said what. Both sides leave exhausted. No one wins. There is a better way. Effective sales pitch techniques don’t rely on slides. They create engagement, tell stories, and turn monologues into conversations that actually move deals forward. Why Traditional Pitches Fail The standard pitch follows the same predictable pattern. Company overview. Capabilities. Case studies. Pricing. Questions at the end. Every competitor uses the same structure. That means you are asking your prospect to choose between nearly identical presentations. When everything looks the same, decision makers default to price or familiarity. Your carefully crafted message gets lost in the noise. You are treating the pitch like a presentation when it should be a conversation. You are trying to inform when you should be persuading. Experience Beats Information In 1979, a small advertising agency called Allen Brady and Marsh (ABM) competed against industry giant Saatchi & Saatchi for the British Rail account. ABM’s founder, Peter Marsh, knew he couldn’t win by playing it safe. When the British Rail executives arrived for the pitch, no one answered the door. They rang the buzzer three times before it finally opened, with no one behind it. The receptionist ignored them while filing her nails. The waiting area was filthy. After a while of being dismissed, the chairman stood up to leave. That is when Marsh burst through the doors and said, “Gentlemen, you have just experienced what your customers go through every single day. Shall we see what we can do to put it right?” ABM won the account. And it worked because the executives didn’t just understand the problem. They felt it. Most sales pitches fail because they ask buyers to care before they are emotionally engaged. Information alone doesn’t create urgency—experience does. Start With Them, Not You Pitches always start the same: ‘Thanks for your time. Here’s our agenda. Let me tell you about our company.’ Your prospect stops listening after the first sentence. If you want engagement, start with a question. Ask what matters to them. Ask what would make the time valuable. Ask what problem they are trying to solve. Before you show a single slide, say something like, “Before we start, what would make this conversation worth your time today?” Or, “What is the biggest challenge you are facing with this right now?” Those questions do three things immediately. They show respect. They give you intelligence. And they turn the pitch into a conversation from the first minute. This works even better over Zoom, where attention is fragile and distractions are everywhere. When you ask early questions, you pull people in instead of competing with their inbox. Stories Create Memory The most powerful stories aren’t pulled from case studies. They come from real life. Every meaningful achievement involves obstacles. Those obstacles contain lessons. Those lessons connect directly to the challenges your prospects are facing. A story without relevance is just noise. A story with a clear lesson becomes a lever. A consultant once shared a story about buying a secondhand Lego set. She started building it, only to discover key pieces were missing. After hours of searching for replacements, she had to start over. When pitching a complex implementation, she said, “That taught me something. At the beginning of any project, we have to make sure all the pieces are in the bag.” That story worked because it made preparation tangible. It made risk visible. It connected emotionally and logically. If the story does not clearly support the point you are making, don’t tell it. Ask Before You Lose Them Most salespeople cling to their script even when they can see the room drifting away. They are afraid of losing control, so they keep talking. That is how you lose the deal. Don’t wait until the Q&A to ask questions. Sprinkle them throughout your pitch to keep your audience engaged and the conversation alive. Ask if you’...
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