Episodes

  • Why Great Salespeople Are Great Listeners (Ask Jeb)

    Why Great Salespeople Are Great Listeners (Ask Jeb)
    Jan 13 2026
    Here's a question I get asked all the time: What's the single biggest misconception holding salespeople back? That question came from a room full of college students at BYU-Idaho, ages 19 to 24, all exploring sales careers. And my answer is the same whether you're just starting out or you've been in the game for decades. The biggest lie about selling is this: Good salespeople have the gift of gab. You know the stereotype. The smooth talker. The fast-talking closer. The person who can talk their way into or out of anything. We've all seen it in movies, TV shows, and plays like Death of a Salesman. It's been around for a century, and it's completely wrong. The Truth Top Performers Know Here's what the best salespeople actually do: They listen. The greatest salespeople aren't the best talkers. They're the best listeners. They're individuals who know how to ask the right questions and know how to ask questions in a way that create these aha moments for prospects and customers. They understand something fundamental that average performers miss: Closing happens in the discovery process, not at some magical point where you lay the hammer down and ask for a sale. Think about that for a second. The deal isn't won when you deliver your polished presentation. It's not won when you overcome the final objection. It's won in those early conversations when you're asking questions, uncovering pain, and building relationships. Why the Stereotype Persists The negative stereotype of salespeople has been pervasive in society for generations. Part of it's because no one really likes to be sold. And there are salespeople who are bad. They talk at people instead of actually taking the time to listen. But here's the reality: Lots of professions have negative stereotypes. Lawyers. Politicians. Salespeople aren't the worst of them. And here's the good side of that negative stereotype: Nobody wants to be in sales. So if you're in sales, you're making a whole lot more money than anybody else. That's a good thing. The people who look at the profession of selling and say "I could never do that" or "I could never interrupt people or take that type of rejection" are the same people who will never experience the income, freedom, and impact that comes with being great at sales. The Power of Questions When you shift your mindset from talking to listening, everything changes. Instead of thinking about what you're going to say next, you're focused on what your prospect is telling you. You're asking questions like: What's driving this decision right now? What happens if you don't solve this problem? Who else is involved in this decision? What does success look like for you? These aren't manipulative tricks. They're genuine attempts to understand your prospect's world, their challenges, and their goals. And when you do that well, you create trust. You build relationships. You position yourself as a partner, not a vendor. The discovery questions you ask matter more than any pitch you could ever deliver. Handling objections starts with asking the right questions early in the process. Who's Really in Control Here's the truth: The person in control of the conversation is rarely the talker. In fact, it's almost always the listener. If you want to move deals, stop performing and start discovering. Build your calls around three things: smart opening questions, deep follow-ups, and crisp advances to the next step. You'll gain insights, not just air time. And insights are what close deals. Success in sales isn't about being the loudest voice in the room. It's about being the most curious, the most engaged, and the most intentional about moving the sale forward. What You Need to Unlearn Right Now If you've been operating under the assumption that you need to be a great talker to succeed in sales, unlearn that immediately. Replace it with this truth: You need to be a great asker and an even better listener. Your job isn't to convince people. Your job is to help people convince themselves by asking questions that lead them to their own conclusions. When prospects discover the solution themselves through your questioning, they own it. They believe it. And they buy. That's the relationship you build through asking questions. That matters the most. The Bottom Line Stop trying to out-talk your prospects. Stop preparing 47-slide presentations. Stop thinking that your job is to educate and inform. Your job is to discover. To listen. To understand. To ask the questions that help your prospects see clearly what they need to do next. The best salespeople aren't the smooth talkers. They're the smart listeners who know that the power of the sale is in the questions they ask, not the words they say. If you master this one fundamental truth, you'll close more deals than all the gift-of-gab salespeople combined. And you'll build a career based on relationships, trust, and value instead of pressure, manipulation, and empty talk. That's how you win in sales. That's ...
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    5 mins
  • Your Calendar Is Lying About Why You’re Not Prospecting (Money Monday)

    Your Calendar Is Lying About Why You’re Not Prospecting (Money Monday)
    Jan 12 2026
    You declined another prospecting block today, didn't you? That internal meeting popped up. Someone needed "just five minutes." Your CRM screamed for attention. Before you knew it, another day passed without a single cold call, without one new connection request, without moving the needle on your pipeline. But hey, at least your calendar looked impressively full. Here's what nobody wants to admit: your jam-packed calendar isn't proof that you're too busy to prospect. It's proof you've made prospecting optional. And optional activities don't close deals or pay commissions. The Meeting Excuse Is Killing Your Pipeline Sales professionals love to point at their calendars as evidence of why they can't prospect. Look at all these internal meetings. See how packed my schedule is. How could I possibly find time for outbound activity? The real question is: when did you last decline an internal meeting to protect your prospecting time? Most salespeople never have. They treat every meeting invitation as a welcome escape from the discomfort of cold outreach. It's the perfect alibi when your manager asks about pipeline activity. But your calendar tells the truth about your priorities. If time blocking for prospecting isn't on it, prospecting isn't actually a priority. And if prospecting isn't a priority, why exactly are you in sales? You Don't Need Hours—You Need 15 Minutes The biggest lie salespeople tell themselves is that prospecting requires massive blocks of uninterrupted time. Two hours minimum. Otherwise, why bother starting? This is the same mental trap that keeps people from reading, exercising, or learning new skills. They convince themselves that 15 minutes isn't enough to matter, so they do nothing instead. Consider this: reading for 15 minutes daily gets you through 20-25 books per year. Walking for 15 minutes adds nearly a mile to your day. Fifteen minutes of focused prospecting can generate six to ten cold calls, dozens of personalized connection requests, or several high-impact video messages to ghosting prospects. The power isn't in the duration, but in consistent, focused execution of time blocking for sales activities. The 15-Minute Power Block Rules These 3 rules are requirements if you want your time blocking strategy to actually work. Rule 1: Single-task only. Your 15-minute prospecting block is for prospecting. Not prospecting while monitoring email. Not prospecting between Slack messages. Just prospecting. If you spend three minutes calling and twelve minutes scrolling Instagram, you didn't prospect for 15 minutes. Rule 2: Everything else can wait. Yes, that includes your boss. You will not lose a customer or your job because you ignored email for 15 minutes. Responding at the end of your block is still professional. Think about it—if you were sitting face-to-face with your top client, would you stop mid-conversation to check email? Treat your power blocks with the same respect. Rule 3: Protect the block like your commission depends on it. Because it does. Top performers don't ask permission to prospect. They schedule it, block it, and defend it against every interruption. The coworker who needs "just a minute" can wait sixteen minutes. What Actually Happens in 15 Minutes Specificity kills procrastination. You're more likely to execute when you know exactly what you're doing during your time blocking windows. Eight to fifteen cold calls fit comfortably in 15 minutes. That's enough to connect with two or three decision-makers if you're efficient. Send ten to fifteen LinkedIn connection requests to stakeholders outside your network. Write and mail three handwritten notes to accounts you closed this month. Record personalized video messages for three prospects who've gone dark. None of these activities requires elaborate preparation or perfect conditions. They require you to show up for 15 minutes and do the work. That's it. Schedule Your Priorities or Someone Else Will Stephen Covey said the key isn't prioritizing your schedule, but scheduling your priorities. Most salespeople do the opposite—they let their calendars fill with whatever lands there first, then wonder why revenue-generating work never happens. Your calendar should reflect your income goals. If hitting quota requires consistent prospecting, your calendar should show consistent prospecting blocks. If building relationships with key accounts matters, those touchpoints should be scheduled. When you schedule your sales priorities first, everything else fits around them. When you don't, everything else crowds them out entirely. Look at your calendar right now. How many prospecting blocks do you see this week? If the answer is zero, you've just identified why your pipeline feels thin. How to Apply Time Blocking Starting Now Open your calendar and block three 15-minute windows for prospecting tomorrow. Morning, midday, and late afternoon. Label them "Prospecting Power Block" and set them as busy. Before each block, decide on one ...
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    9 mins
  • Why Sales Professionals Fail at New Year’s Fitness Goals (And How to Actually Succeed)

    Why Sales Professionals Fail at New Year’s Fitness Goals (And How to Actually Succeed)
    Jan 8 2026
    Are your fitness goals realistic for the life of a busy sales professional? "I find that a lot of sales leaders I work with are operating at about 110% capacity. So when we're talking about tackling health and fitness, we have to really understand what is going to be the few habits that are really easy to do and have the biggest bang for buck." That's Josh Hulsebosch, a fitness coach who specializes in working with sales professionals, speaking on the Sales Gravy podcast. His observation cuts straight to the real reason most January fitness resolutions fail: they're trying to add more to an already overflowing plate. The typical sales professional is already drowning in competing priorities while operating at maximum capacity. When New Year’s hits, the instinct is to overhaul everything at once. New diet. New workout plan. New morning routine. That approach might work for people with open calendars and low pressure. For salespeople pushing through Q1 kickoffs, territory planning, and quota pressure, it is a fast track to burnout. The All-or-Nothing Trap Meet Steve. He's an individual contributor who decided January 1st would mark his transformation. No more coffee. Five-mile runs every morning. Intermittent fasting. Four hours of cold calling daily because he just finished reading Fanatical Prospecting. Ten days in, Steve slept through his alarm, missed his workout, and ordered a triple-shot latte on the way to work. That emotional crash bled into his work. His prospecting activity dropped. His confidence dipped. His motivation evaporated under the weight of his own perfectionism. Steve's mistake wasn't lack of commitment. He turned ambitious goals into self-sabotage by refusing to acknowledge a simple truth: sustainable change requires starting where you are, not where you wish you were. Most sales professionals approach fitness goals like they approach pipeline building—more activity equals better results. But health doesn't work like prospecting. You can't brute force your way into better sleep or lower stress. The body requires a different strategy. The 110% Capacity Problem Sales is a cognitively demanding profession. You're the quarterback of the business. Every day requires strategic thinking, relationship management, objection handling, and staying mentally sharp through rejection. When you're already operating at 110% capacity, adding extreme fitness commitments creates another obligation you can't meet, another source of stress, another thing to feel guilty about when you inevitably miss a workout or eat fast food between calls. The sales professionals who successfully improve their health identify which habits will support their performance, then build them into their existing routine. They do not chase trends. They focus on fundamentals. The Four Pillars of Health for Sales Professionals Fitness and health goals for sales professionals need to be realistic for people working at maximum capacity. You can't afford to waste energy on complicated protocols or fitness fads. You need the fundamentals: exercise, nutrition, sleep, and stress management. When these four pillars are strong, everything else becomes easier. Pillar One: Exercise The fitness industry wants you to believe you need intense workouts, complicated programs, and hours at the gym. For sales professionals, the single most effective exercise habit is walking 8,000 steps daily. This number is achievable for most people regardless of fitness level. It builds momentum without requiring a complete schedule overhaul. When you consistently hit 8,000 steps, you prove to yourself that you can follow through on a commitment without sacrificing your work performance. Movement improves cognitive function, reduces stress hormones, and helps with sleep quality—all critical for sales performance. Make it automatic. Take calls while walking. Park farther away from the office. Walk to get coffee instead of ordering delivery. Use a standing desk and pace during internal meetings. Build movement into what you are already doing rather than treating it as another task. Once 8,000 steps become effortless, you can layer in strength training or other activities. But walking is the foundation. It's the one exercise habit that compounds without breaking you. Pillar Two: Nutrition Sales professionals tend to fall into two nutrition traps. The first is eating like garbage because they're too busy to care. The second is attempting some extreme diet overhaul that lasts nine days before they're back to their old patterns. The solution isn't meal plans or macro tracking or cutting entire food groups. It's having a system that works when you're slammed. Start here: don't skip meals. When you're running between meetings and surviving on coffee, your blood sugar crashes. That kills your cognitive performance and drives you toward quick fixes that leave you feeling worse an hour later. Keep protein-rich foods accessible. Greek yogurt, hard-boiled eggs, ...
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    34 mins
  • Build Your Personal Brand Without Conflicting With Your Company (Ask Jeb)

    Build Your Personal Brand Without Conflicting With Your Company (Ask Jeb)
    Jan 6 2026
    Here's a question that keeps salespeople up at night: How do you build a powerful personal brand without stepping on your company's toes? That's the question Taylor Deadrick asked me during a recent live event. Taylor works for Insperity (a fantastic company that handles all our HR and payroll at Sales Gravy, by the way), and she wanted to know how to establish her own brand while staying aligned with her employer. If you've ever felt this tension, you're not alone. The fear of conflicting with your company's brand holds too many salespeople back from building the authority they need to win more deals. Let me show you how to build a personal brand that actually amplifies your company's message instead of competing with it. The Only Real Conflict You Need to Worry About Here's the brutal truth: The only way you'll conflict with your company's brand is if you assert that your own opinion is that of your employer, or what you're posting, saying, or writing conflicts with their core values, their marketing message, or the way they go to market. That's it. That's the line. If you start trying to speak for your company or post things that contradict their values, you've got a problem. But if everything you do supports those core values, you're going to be just fine. Think about it this way: Your company hired you because you aligned with their mission. Now your job is to amplify that mission through your own authentic voice and expertise. The mistake most salespeople make is thinking their personal brand needs to be separate from or independent of their company. Wrong. Your personal brand should be the human face of your company's value proposition. Your Personal Brand Is Bigger Than Your Logo Your personal brand isn't just what you post on LinkedIn. It's not your profile picture or your witty headline. Your personal brand is the confidence you show when you hop on a microphone and ask a tough question. It's your smile and the way you treat people. It's whether you're kind, whether you invest in yourself, whether you show up with expertise that actually helps people solve problems. Your personal brand is the human being who walks into businesses every day and shows up for those businesses. That's the most important part of your brand, and that's the part that builds trust and causes people to buy you. Everything else (your LinkedIn posts, your content, your online presence) is just an extension of that core identity. Authority: The Secret Weapon of Personal Branding When I think about building a personal brand, I think about one word: authority. Authority is your expertise. It's what you know that helps other people win. And here's the beautiful thing: When you build authority in your space, you're not competing with your company's brand. You're reinforcing it. Let's use Taylor's situation as an example. She works with small and medium-sized businesses, helping them grow by taking HR and payroll off their plate so they can focus on what matters. That's exactly why we came to Insperity in the first place. If Taylor builds her authority around understanding the problems small business owners face, if she becomes known for helping companies break through growth barriers, if she consistently shares insights about the challenges her buyers deal with every single day, that authority doesn't conflict with Insperity. It amplifies everything they stand for. When you focus on your expertise and how you help people, your personal brand becomes a magnet. You create leads. When prospects research you before a meeting, they see someone they actually want to talk to. You're building trust before you ever shake hands. The Five S Framework for Building Authority In my book The LinkedIn Edge, I walk through what I call the Five S's for building your personal brand, especially on LinkedIn. This framework keeps you aligned with your company while establishing your unique authority. The key is sending the right message to the marketplace about the expertise you bring, your authority in solving specific problems, and how you can help people win. When you focus there, everything else falls into place. Your content should showcase the patterns you're seeing with your buyers, the problems you solve consistently, and simple frameworks they can use right away. That's what creates familiarity. That's what warms up the room before you ever make a call. Think of LinkedIn as your familiarity engine. When you show up consistently with practical insights, every outreach gets easier and every conversation becomes more productive. Know Your Company's Social Media Policy Inside and Out Before you post a single piece of content, take a hard look at your company's social media policy. Understand what they allow you to say and what they don't. Know those boundaries cold. This isn't about limiting yourself. It's about operating with confidence. When you know exactly where the guardrails are, you can create boldly within them. Most companies have ...
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    7 mins
  • How to Set Sales Goals That Actually Stick: From Vision to System (Money Monday)

    How to Set Sales Goals That Actually Stick: From Vision to System (Money Monday)
    Jan 5 2026
    This Money Monday Sales Gravy podcast episode is special because it kicks off our 20th season! It’s hard to believe that we’ve been producing the Sales Gravy continuously for 20 years. Over the last 20 years, thanks to you—our incredible audience—we’ve consistently ranked as the #1 most listened to sales podcast in markets all over the world. I remember my first podcast episode all those years ago, produced with a microphone I bought at Guitar Center and recorded under a blanket for sound suppression. Today, we produce our podcast in professional studios at Sales Gravy and have a full production team on staff to ensure we are giving you the highest quality sound possible. What hasn’t changed is my unwavering focus on making the complex simple by cutting through the noise, eliminating the fluff, and giving you the basics and fundamentals that actually work in the real world. We’ve got a ton of new episodes and bonus content coming your way, so be sure to subscribe on your favorite podcast app and listen every week. Sales Professionals Must Have Goals to be Successful Your personal goals are the aspirations that drive you, inspire you, and push you through the tough days. These goals are essential to helping you maintain sales discipline throughout your sales year. When developing personal goals, I break them down into three buckets: To-Have Goals These are the things you want to acquire or buy. Whether it’s a house, a new car, or building up your savings, to-have goals are about acquiring something that enhances your life. To-Be Goals These are about evolving into the person you want to become. Maybe you want to be a sales manager, or if you’re a manager, you want to be a director or VP of sales. You might want to go back to school for a degree or an MBA. Or you want to be a better spouse, a better leader, or a better peer. Maybe you want to be a President’s club winner or be recognized as an expert in your industry—whatever it is, to-be goals help you level up as a person and a professional. To-Do Goals These are experience goals. Think about experiences that create lifelong memories—maybe you want to travel somewhere special or take on a meaningful project or hobby you’ve always dreamed about. Four Reasons Why Goals Matter in Sales Number one, goals massively increase the likelihood that you’ll actually achieve the things you want. Speaking your goal out loud, writing it down, and being intentional about it has a powerful psychological effect. Number two, goals make life meaningful. It’s unbelievably fulfilling to look back and see what you accomplished—how far you’ve come over the course of a year, five years, or a decade. Number three, we work in a tough, competitive profession, and it’s just plain satisfying to put your commission checks, bonuses, and hard-won earnings toward something that improves your life or the lives of the people you love. But the biggest reason to set goals—especially in sales—is that the sales profession is hard work and it can be brutal. It’s loaded with rejection. At every turn, we face potential “nos,” whether it’s prospecting calls, asking for next steps, pushing to level up to a decision-maker, or closing the deal. We even face internal rejection when we try to sell a complex deal internally to our own company or get approval for special pricing. Rejection is everywhere, and the fear of rejection—or avoiding it—is the number one reason salespeople fail to perform. Add to that the grind: making call after call, stuffing data into the CRM, pushing through proposals, handling endless follow-ups, and selling becomes tedious, hard, rejection-dense work. For this reason, it requires discipline to stay on track and keep grinding day after day and month after month over the course of the sales year. But here’s the rub: discipline can wane, especially if we’re not hyper-focused on a bigger prize. Goals Give You the Discipline to Do the Hard Things I want you to pay attention to this next part because understanding the real definition of discipline is critical. Discipline is sacrificing what you want now for what you want most. Human nature wants easy. We’d rather that customers call us than have to chase them. We’d rather deals close themselves than invest hours into multi-step follow-ups. We don’t want to face that “no.” But success in sales is paid for in advance, with facing rejection and hard work. Therefore, if you don’t have a clear, compelling reason—something you want most—it’s easy to cave in and take the easy route instead of doing what really needs to be done. This is the reason why having a strong set of personal goals is crucial for sales professionals. You need that powerful “why” to keep grinding when the going gets tough. When the pipeline’s not as full as you’d like or you’re hitting roadblocks, you need something more important than convenience to drag you back into...
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    10 mins
  • The 4-Step Fix for Sales Goals That Always Fall Short

    The 4-Step Fix for Sales Goals That Always Fall Short
    Jan 2 2026
    Do you plan to hit your sales goals, or just hope you will? You set goals in January. By March, they are forgotten. It's because most salespeople confuse wanting something with planning for it. “I want to close more deals this year.” That is not a goal. That is a wish. “I want to be better at prospecting.” Still not a goal. Just a vague intention that leads nowhere. Real sales goals require a system. Not motivation. Not inspiration. A repeatable process that turns big numbers into daily actions you can actually execute. This four-step sales goal planning system turns annual quotas into weekly, executable actions that salespeople can control and measure. Why Most Sales Goals Fail Before February Most salespeople treat goal-setting like a New Year’s resolution. They write something down, feel good about it for a week, then watch it disappear under the weight of quota pressure and full calendars. Three things kill sales goals before they have a chance: Lack of specificity. Your brain cannot attach to something vague. There is no finish line, no way to measure progress, and no emotional connection to the outcome. No breakdown. Big numbers paralyze you. Looking at an annual quota feels impossible. Your brain shuts down. You don’t know where to start, so you don’t start at all. Zero accountability. Goals that live only in your head are easy to abandon. There is no consequence for missing them because nobody, including you, is really tracking them. Research consistently shows that people who write down specific, challenging goals and track them perform significantly better than those who rely on vague intentions or hope. The difference between hitting your number and missing it is having a systematic approach to sales goal planning and the discipline to execute it. Step 1: Identify Your Major Milestones Big goals overwhelm you. When you stare at “close $1.5 million this year,” your brain checks out. It feels too big, too far away, and too abstract. The first step in effective sales goal planning is breaking that number into key checkpoints. These milestones tell you whether you are on track or falling behind. For a $1.5 million annual goal: Q1: $375K Q2: $375K Q3: $375K Q4: $375K Now you are not chasing $1.5 million. You are chasing $375K this quarter. Still significant, but manageable. Take it further. What does $375K mean for your pipeline? If your average deal size is $50K, you need eight closed deals per quarter. If your close rate is 25 percent, you need 32 qualified opportunities in your pipeline each quarter to close those eight deals. Suddenly, that intimidating annual number becomes a concrete monthly target of roughly 11 qualified opportunities. You cannot control whether a deal closes, but you can control how many qualified opportunities you put in your pipeline. That is the number you chase. Step 2: List Your Specific Tasks Milestones tell you where you need to be. Tasks tell you how to get there. These numbers will vary based on your market, deal size, and conversion rates. The point is forcing your goal all the way down to weekly actions you can control. This step requires brutal honesty about the activities that actually generate results in your sales process. If you need 11 qualified opportunities per month and your prospecting-to-opportunity conversion rate is 10 percent, you need 110 prospecting conversations monthly. What does that look like in weekly tasks? 30 outbound calls 15 LinkedIn connection requests with personalized messages 10 follow-up emails to lukewarm prospects 3 referral conversations Assign realistic timeframes to each task. Making 30 calls doesn’t require four hours. It requires 45 minutes of focused effort. Block the time, make the calls, move on. The more specific you get, the less room there is for excuses. You either completed the tasks or you did not. You are either on pace or you are behind. If you cannot list the specific weekly tasks required to hit your goal, you do not have a sales goal. You have a hope. Step 3: Consider Obstacles and Resources Every goal has obstacles waiting to derail it. Ignoring them does not make them disappear. Identify what will try to stop you, then plan around it. The biggest time killers in sales are rarely mysterious. Meetings that don’t move deals forward. Prospects who will never buy but keep you engaged. Administrative tasks that someone else should handle. Reorganizing your CRM instead of filling it with opportunities. Here is how to expose them. Track your time for one week. Write down every activity in 30-minute blocks. No editing. No judgment. Just honest data. At the end of the week, categorize everything: Income-producing activities like prospecting, discovery, and closing Income-supporting activities like proposals, follow-up, and research Waste, which is everything else Most salespeople discover they spend less than 30 percent of their time on income-producing activities. If that is you, you just found...
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    37 mins
  • How to Negotiate Sales Compensation Without Burning Bridges (Ask Jeb)

    How to Negotiate Sales Compensation Without Burning Bridges (Ask Jeb)
    Dec 30 2025
    Here's a question that keeps salespeople up at night: How do you ask for more compensation when you're getting competitive external job offers without sounding like you're issuing an ultimatum? That's the question posed by Brady from Arkansas. Brady's been getting legitimate job offers from recruiters, and he's wondering how to leverage these opportunities into better compensation at his current company without burning bridges or coming across as disloyal. If you've ever found yourself in this position, you know it's a delicate dance. You want to be paid what you're worth, but you also don't want to destroy the relationships and goodwill you've built. So how do you navigate this conversation? The Right Way to Have the Conversation If you're getting external job offers from legitimate companies with strong brands, the key is in how you frame the conversation with your boss. Here's the approach: "I really like working here, and I want to stay at this company. I love it. But I've got another company out there that's a good company. They're a great brand, they're well known, and they're making this job offer to me at a significantly higher level of compensation. It's hard for me to say no to that. I feel like I need to bring this to you before I make a decision because I like working here." Notice what you're NOT saying. You're not walking in with an ultimatum saying, "If you don't give me this, I'm leaving." Instead, you're saying, "I want to stay here. I like it here. I'm just in a situation where they're offering me enough that it's turning my head and I'm looking their way." This approach keeps the door open for a productive conversation about what might be possible without threatening your current employer or damaging your relationship. When Loyalty Actually Matters Now, before you go schedule that meeting with your boss, you need to ask yourself a hard question: Do you owe this company some loyalty? If you were down on your luck, lost a job, and they came along and gave you something that saved you, you probably owe them some loyalty for that. Not forever, but there's a little bit of honor in not just jumping to the next place immediately. You also need to think about your resume. If you've just got there and a year later you're jumping to another place, that's on your resume. And believe it or not, even in today's world, that still means something. I won't hire people who jump from job to job every year. I don't care how good they are because they're probably going to jump again. So think long term: Am I demonstrating to a future employer that I'm worth investing more money in? The answer is yes when you gave them three years of your life, performed at a really high level, and now you're going to leverage that to go level up elsewhere. Speaking Your Boss's Language Here's what most salespeople get wrong when asking for more money: They forget to speak the language their boss understands. If you walk into your sales leader's office and say, "I want to make more money," you know what they're going to tell you? "Go sell more." And they're right. If you've got a great compensation plan with no limit on how much commission you can make, the answer is simple: crank out more sales. So before you ask for more base salary, ask yourself: Do I have a limit on how much commission I can make? If the answer is no, then your first conversation should be about getting bigger opportunities. Try this approach: "I can sell. I'm hitting numbers, but I'm not making the money I want. What can you do to give me bigger accounts, bigger opportunities, bigger customers? Give me better leads. What can you do to get me in a situation where I can earn more?" This is speaking the boss's language. You're showing that you want to produce more, not just get paid more for the same work. If you get shut down in that situation, then you have another conversation. The Commission vs. Base Salary Play If you're a baller and you've proven you can sell, here's a move most salespeople never consider when negotiating compensation: Ask for a higher commission percentage instead of a higher base salary. I honestly don't care about base. I think a base matters when you're getting started, and it's nice to have, but I would much rather have a higher commission percentage than a higher base. Here's how you position it: "In the open market, I can take a similar job and make $400,000. I want to make the same thing here. Now there's two ways we could do this. One is that you can increase my base salary. Two is you give me a higher commission rate, and I think the commission rate should be this. I think I'm worth that." What you're basically saying is that your cost of sales is going to be variable. They only pay you if you sell it, so their carrying costs stay the same. In my company, the people who don't take a base salary make more than double in commission what people who do take a base salary bring home. There's a massive difference because the ...
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    15 mins
  • The $1 Billion Sales Psychology Mistake: Why Selling Logic Kills Deals (Money Monday)

    The $1 Billion Sales Psychology Mistake: Why Selling Logic Kills Deals (Money Monday)
    Dec 29 2025
    Is your sales strategy built around how buyers should behave—or how they actually behave? Imagine walking into a store and seeing a shirt for $50. Fine. Unremarkable. You might buy it, you might not. Now imagine seeing that same shirt with a tag that reads: $100 NOW $50. Suddenly, you're interested. You found a deal. You beat the system. You're a hero. Same price. Same shirt. Completely different emotional response. That psychological gap between logic and emotion cost JCPenney roughly $1 billion and offers one of the most important lessons in sales psychology you'll ever learn: people don't buy with logic—they buy with emotion and justify with logic later. The Fair and Square Disaster In 2012, JCPenney hired Ron Johnson as CEO. Johnson was a retail rock star, the architect behind Apple Store's legendary success. He walked into JCPenney and saw chaos: endless coupons, manufactured "original prices," and constant sales cycles. His solution? Kill it all. Johnson launched "Fair and Square"—a radically transparent pricing model. No games. No coupons. No inflated prices marked down. Just one everyday low price on everything. That $100 shirt marked down to $50? Now it was simply $50. Honest. Logical. Clean. The market's response was brutal. Within one year, sales dropped 25%. The company lost nearly $1 billion. Stock price went into freefall. Johnson was fired. What Johnson Got Wrong About Sales Psychology Johnson made a catastrophic assumption: he believed customers were rational economic actors who would reward transparency and honesty. He was dead wrong. For decades, JCPenney's customers had been playing a game. They clipped coupons, timed sales, scrutinized flyers, and planned shopping trips around promotions. The weekly coupon wasn't just a discount—it was a ritual. Their insider advantage, their badge of savvy shopping honor. Johnson stripped away their emotional satisfaction and replaced it with sterile efficiency. Without the "$100 now $50" comparison, the flat $50 price lost all psychological weight. No thrill. No victory. No story to share. Same price. Different feeling. The Sales Psychology Principle You're Ignoring Loss aversion is twice as powerful as gain motivation. Your prospects don't just want to gain something—they want to feel like they won, like they're in control, like they made a smart decision that will impress their boss. When you strip away their buying process, when you force them into your "more efficient" workflow without their input, they don't see the gain. They experience loss. You've taken away their control, their ritual, their power, their role as the hero. In sales, that feeling is deadly. Your Customers Have Rituals Too Think about your best accounts. What do they actually value? It's probably not your features or your ROI calculator. It's the rep they've worked with for years. It's the quarterly business review they rely on. It's the reporting cadence that makes them look good internally. It's the buying process that lets them feel competent and in control. That's their ritual. When you try to "streamline" their process, when you push them toward a different point of contact, when you change the reporting structure they trust—you're doing exactly what Ron Johnson did. You're selling logic when they're buying a feeling. Stop Leading With Features and Benefits Most salespeople lose deals before they even start because they lead with logical arguments: "Our platform reduces processing time by 40%." "We integrate with 200+ systems." "Our customer support response time is under 2 hours." All logical. All true. All useless if your buyer doesn't feel something first. Your prospect doesn't wake up excited about efficiency gains. They wake up stressed about looking good in front of their VP, avoiding mistakes, and maintaining control of their budget. Research is clear: emotional decisions get made first, then logic comes in to justify them. Your job isn't to build a logical case. Your job is to help your buyer feel like a hero, then give them the logical ammunition to defend that emotional decision internally. How to Apply This Starting Today Identify Their Rituals Watch how your customers actually operate. Do they need three stakeholders in every meeting? Do they always loop in procurement at a specific stage? Do they have a preferred communication cadence? Don't fight it. Work with it. Their process is their psychological anchor for stability. Frame the Win They Can Own Frame your solution so the customer feels in control and gets the credit. Instead of: "Our platform will solve your problem." Try: “This approach could help you demonstrate a 30% cost reduction in Q2—giving your team clear wins to share with leadership.” Make them the hero of their own story. Highlight Emotional Outcomes, Not Just Logical Ones Don't just talk about what your product does. Talk about how it makes them feel. "You'll have complete visibility so you're never caught off guard in ...
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