Épisodes

  • 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 min
  • 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 min
  • 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. They timed sales. They 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 ...
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    9 min
  • 4 Ways Top Performers Stay Motivated and Close More Deals (Even When Sales Gets Hard)
    Dec 26 2025
    How Do Top Performers Stay Motivated When Sales Gets Hard? You know the feeling when you close a big deal. The rush. The quiet satisfaction of updating your pipeline. Maybe a quick high-five with your manager. And then, almost immediately, it fades. You’re back to cold calls that go unanswered, emails that disappear into inboxes, and prospects who promised they were interested suddenly going silent. In sales, rejection isn’t a side effect of the job. It is the job. That reality is exactly why most people don’t last in sales. And it’s why the people who do last tend to get paid very well. Over the past quarter, we talked with some of the most consistent sales leaders in the business. Here are four moments from the Sales Gravy Podcast that reveal how top performers stay motivated and close more deals, even when the work feels heavy. Find Your Carrot and Make It Specific Will Frattini, VP of Sales at ZoomInfo, keeps a small Christmas ornament on his desk. His daughter gave it to him when she was five. That ornament is his carrot. During a recent podcast conversation, Will explained that when sales gets hard, that ornament reminds him exactly why he keeps pushing. Not in an abstract or inspirational-poster way, but in a deeply personal one. It represents his family, his responsibility, and the future he’s building for them. That distinction matters. Many salespeople say they’re motivated by family, freedom, or financial security. Those values are real, but on their own, they’re often too broad to sustain sales motivation during a brutal stretch of rejection. When you’re fifty dials deep with no connects and another demo just canceled, vague motivation doesn’t hold up. Will doesn’t just think “my family.” He sees a moment, a memory, and a tangible reminder of what’s at stake. That specificity gives his motivation weight. Top performers anchor their sales motivation to something concrete and emotionally charged. A down payment they want to make by a certain date. A trip they want to take without checking their bank account. A milestone that matters beyond quota. The more specific the carrot, the more powerful it becomes when sales gets hard. How to define yours: Write down one specific outcome you want to achieve in the next six months. Not “hit quota,” but the real-world result that quota enables. A number. A purchase. An experience. Put it somewhere you’ll see it every day. Work With Customers Who Actually Value You One of the fastest ways to drain sales motivation is closing deals with customers who make you miserable. On an episode of Ask Jeb, Jeb broke down how companies grow faster by focusing on the right customers, not just more customers. When you’re behind on quota late in the year, it’s tempting to take anything that looks like revenue. Any company that shows interest. Any prospect willing to meet. You convince yourself that a deal is a deal. Then January arrives. That customer floods your team with support tickets, questions every invoice, demands exceptions, and slowly erodes the satisfaction of the win you celebrated just weeks earlier. Consistent performers learn to protect their energy. They get ruthless about fit. Not just company size or industry, but values. They ask questions like, “What do you value most in a partner?” and they listen carefully to the answer. Some buyers want constant responsiveness. Others value expert perspective and challenge. Some want efficiency and minimal interaction. None of those preferences are wrong. But only one aligns with how you actually sell. When sales gets hard, motivation comes easier when you’re pursuing customers who respect your approach instead of fighting it. How to clarify your ideal customer: Look at your three favorite customers. The ones your entire team enjoys working with. What do they share beyond surface-level traits? How did they behave during the buying process? Those patterns matter more than any firmographic filter. Slow Down Before You Create Your Own Problems When pressure builds, speed starts to feel productive. You rush contracts. You promise timelines without checking internally. You say yes to custom requirements because slowing down feels risky. On an episode of the Sales Gravy Podcast, Jeb Blount, Jr. shared one of the most painful stories we heard this year. A $1.4 million deal with a pediatrics practice unraveled after someone rushed the process and placed the client into an early adopter program without a test environment. The result was catastrophic. The client’s live system crashed, HIPAA was violated, and the company lost not only the deal but $600,000 in annual recurring revenue. Top performers understand something most reps learn the hard way: smooth is fast. They build guardrails around high-risk moments. Before sending a contract, they align internally. Before committing to timelines, they check with the people who actually do the work. Slowing down at the right moments ...
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    37 min
  • How to Hit Your Number When Production Can’t Keep Up (Ask Jeb)
    Dec 23 2025
    Here's a problem that'll make your head spin: What do you do when you can sell way more than your company can produce? That's the question posed by Dylan Noah from Toronto. Dylan sells craft cider to bars and restaurants across his territory. He's the only salesperson for a small producer, working with limited tools (no proper CRM), and here's the kicker: he could sell a million dollars' worth of product, but production isn't enough to meet that demand. If you're shaking your head thinking this is a champagne problem, you're half right. But for Dylan trying to hit his income goals through commissions, it's a real constraint that's costing him money every single day. The CRM Obsession Is a Distraction Let's tackle the first issue head on. Dylan is worried he doesn't have the right CRM tools to manage his accounts and hit his numbers. Here's the brutal truth: at one point in time, salespeople sold a lot of cider, beer, wine, liquor, and all kinds of other stuff without any CRM at all. They used index cards in a box. They had lists on paper. And they crushed it. You're a small business with one salesperson working with 3,000 to 7,000 potential accounts in your territory. The last thing you should worry about right now is a $40,000 CRM system. Could you use automation for email sequences and promotions? Absolutely. Should you eventually invest in something like HubSpot or Pipedrive? Yes. But right now, what you need is a simple system to identify your best accounts and focus your time there. You're not going to hit $1 million across 3,000 accounts. You're going to hit it across 500 accounts that are the biggest restaurants and bars, where they like you, their customers like cider, and where you can create events and experiences that spike sales. Use a spreadsheet. Use index cards. Use whatever basic tool you've got right now. Create a 30-60-90 day system where you know who you're calling on in the next 30 days, the next 60 days, and the next 90 days. Build a list of your top 250 accounts that buy the most from you. That's where you live. Stop obsessing over tools you don't have and start maximizing the opportunity in front of you. Scarcity Is Your Secret Weapon This brings us to the real issue: production capacity. Dylan can sell it, but his company can't make enough of it. The bourbon distillers in America are dealing with this exact problem right now. They ramped up production years ago based on projected demand, and now they're sitting on excess inventory that's aging out. It's a delicate balance, and if you make too much, it goes bad and you lose everything. Here's what most salespeople don't understand about scarcity: it's actually a competitive advantage if you manage it right. When you have limited product, you're always going to be in an ebb and flow situation. Sometimes you'll have an abundance of one product type. Sometimes you'll have high demand products in short supply. The key is building a system that lets you move fast when opportunity strikes. This is where building buying profiles for every single customer becomes essential. You need to know which accounts buy which types of products, what their purchase patterns look like, and what their potential is (high, medium, or low). Think about it like your account coverage pyramid. When you have product available, you start at the top with your highest value accounts and work your way down. You're not treating all 150 accounts the same. You're prioritizing based on potential. When you have an abundance of one product type, you go directly to the customers who buy that product and say, "Hey, I've got product right now. Do you want to buy?" You can run specials. You can offer incentives (within legal limits). You move it fast. When your high demand products come in, you call your best accounts first and say, "I've got ten cases of this. I'm calling you first. How many do you want?" Then you go down your list. Most of the time, you'll sell out before you even leave your office. But if you've got 150 accounts and you're treating them all the same, it gets overwhelming fast. Segment them. Prioritize them. Work them strategically. Making Your Number When You Can't Control Supply The income issue is where this gets really interesting. Dylan wants to double his sales and earn more commissions, but he can't because the company keeps running out of product. Here's my take: if you're supposed to sell $1.5 million but your company only produces $750,000 worth of product that you could sell, they should pay you for the $1.5 million. Production was the reason you couldn't make your number, not your sales ability. Now, I know there are people in operations reading this who are going to say I'm full of it. But from a sales standpoint, if you've sold out of everything available, you've done your job. The constraint isn't you, it's production capacity. That's a hard conversation to have with ownership, I get it. But here's how you make that case: sell out of the...
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    17 min
  • How to Move from Regret to Reflection: A Year-End Sales Debrief (Money Monday)
    Dec 22 2025
    While regret anchors you to past failures, reflection acts as a catalyst for future sales growth. This article and Sales Gravy Money Monday Podcast episode explores how to break the "if-only" loop and provides a step-by-step year-end debrief to help you extract lessons from your wins and losses, ensuring you start the new year with clarity and a proven system for success. Explore: How to get out of your regret loop The power of reflection How reflection creates awareness A system for achieving your sales goals 7 Steps to year-end sales reflection Ways to Look Back at Your Sales Year For me, the last two weeks of the year have always been the chance to pause, take a break from the grind of selling, and really think about what happened over the past year—the good, the bad, and the ugly. If you are anything like me and do the same, there are two ways to look back on your last twelve months. You can do so with regret or reflection. These two opposing lenses are vastly different in the way they affect your view of where you’ve been and where you are going. The Trouble With Regret Let’s start by unpacking regret. Some of you are already feeling regret about goals you missed, deals you lost, opportunities that slipped through your fingers, or the people in your life you may have let down. Regret is that feeling you get when you look back on something you did (or didn’t do) and wish you could change it. In many ways, regret is similar to worry, except it’s focused on the past instead of the future. Worry is about what might happen; regret is about what already happened. That’s a big distinction. Although you can turn worry into action and change the future, you cannot rewrite the past. No amount of regret changes history. All it does is create a feedback loop in your mind where you keep reliving your mistakes, misses, and failures over and over again. Why Sales Professionals Get Stuck in a Regret Loop I’ve observed so many people get stuck in this endless loop of regret. They keep lamenting, "If only I had . . ." "made that call.” “handled that prospect differently.” “taken that chance.” “been there or done that.” Those “if onlys” can paralyze you. They sap your energy, crush your confidence, and keep you from moving forward. On one hand, regret can push you to change—you don’t want to feel that kind of pain again, so you work hard to avoid repeating the same mistakes. On the other hand, regret can become a debilitating emotion that drags you into an exhausting and useless mental loop of “would’ve, could’ve, should’ve.” But no matter how many times you complete that loop, it doesn’t change the outcome. It becomes an emotional anchor that weighs you down as you start the new year. The Power of Reflection Reflection, on the other hand, is entirely different—and far more productive. When you reflect, you detach from your emotions with objectivity to look at your entire body of work from the past year. You’re asking the questions, “What went well? What didn’t go so well? What did I learn?” You consider the wins that made you proud and the moments you’d rather forget. You figure out why you won so you can repeat those winning behaviors. You extract value from the lessons of failure. Reflection isn’t about punishing yourself for what went wrong. It’s about gaining clarity on why it went wrong—and what you can do about it next time. How Reflection Creates Awareness Reflection also helps you find gratitude in unexpected places. Maybe there’s a hidden lesson in overcoming an obstacle, or perhaps you gained a new perspective because a challenging person came into your life. It’s important to realize that each decision you made over the past year shaped your present circumstances. But you are not defined by these circumstances, only by how you respond to them. Reflection creates awareness. Where there is awareness, there is the potential for change. Awareness is like the sun; anything it touches has a tendency to transform. The bottom line is that reflection is about learning, growing, and transforming. Regret is stagnation. Why Reflection Matters at Year-End The reason I’m talking about the impact of reflection as we close out this year is because, for most of us, the slate really does feel clean come January 1st. In the sales world, we get a brand-new quota and brand-new targets. There’s an air of possibility as we think: “This year is going to be different. “This year, I’m going to crush my numbers.” “Hit my income targets.” “Make it to President’s club.” “Get a promotion.” “Finally, close that dream account I’ve been chasing.” But if you don’t take a moment to reflect on what worked and what didn’t, you’re likely to find yourself repeating the same missteps. Reflection is like an internal debrief—a chance to say, “Here’s what happened, here’s why, and here’s how I’m going to fix it.” Why ...
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    12 min
  • How to Get More from a Sales Mentor—and Be One Who Matters
    Dec 18 2025
    Why Do So Many Mentorship Relationships Fail Before They Ever Work? “You can't be more committed to somebody’s success than they are.” That insight comes from Colleen Stanley, author of Be the Mentor Who Mattered, during a recent conversation on the Sales Gravy Podcast. It's a simple statement that cuts through all the noise about mentorship and gets to the heart of why most mentoring relationships fail to deliver results. Sales professionals constantly talk about wanting mentors. They want access to someone who's been there, done that, and can show them the shortcuts. But when they get that access, they squander it. They show up unprepared. They argue with advice. They never implement what they learn. On the flip side, experienced sales leaders say they want to give back and mentor the next generation. But they get burned out after investing time in people who don't follow through. So they stop offering help altogether. The problem isn't a lack of willing mentors or eager mentees. The problem is that nobody understands their role in making mentorship work. What Mentees Get Wrong About Mentorship Most people treat mentorship like a magic pill, assuming that simply being near someone successful will transfer that success to them. It doesn’t work that way. Getting real value from a mentor requires more than just showing up. You need to actively do the work that makes their guidance worthwhile. Start by focusing on these key actions: Ask Directly The biggest barrier to mentorship isn’t that successful people won’t help you. It’s that you never ask. You assume they’re too busy, too important, or too far removed from your situation to care. You’re wrong on all three counts. Successful people got where they are because someone helped them along the way. Most of them want to pay that forward. But they’re not mind readers. If you want help, ask for it directly. Respect Their Time When you do ask, come prepared. Don’t ask for “15 minutes to pick your brain.” That’s code for “I haven’t thought about what I actually need, so I’m going to waste your time figuring it out.” Instead, be specific. “I’m struggling with qualifying early in the sales process. Could you share how you approach qualification conversations?” Specific questions get specific answers. Vague requests get vague responses—or none at all. Do What They Tell You to Do This is where most mentoring relationships die. You ask for advice. You get great guidance. Then you come back with a list of reasons why it won’t work for your situation. Stop that. If you’re going to ask someone for their expertise, try their approach before explaining why your situation is different. You’re there because they know more than you do. Acting like you know better defeats the entire purpose. Your mentor’s reward isn’t money or recognition. It’s watching you take their advice and succeed because of it. When you implement what they teach and come back with results, they’ll invest even more in your development. When you make excuses, they’ll move on. Take Tough Feedback Without Getting Defensive Not every mentor has read the latest book on constructive feedback. Some of them are direct or blunt. Take it anyway. When someone cares enough about your success to tell you the truth—even when it’s uncomfortable—that’s a gift. Don’t reject it because it wasn’t wrapped perfectly. The best mentors don’t sugarcoat feedback because they respect you enough to be honest. They see potential in you that you can’t see yet, and they’re not going to let you waste it by staying comfortable. What Mentors Get Wrong About Mentorship If you’re in a position to mentor others, you already know the frustration of investing in someone who doesn’t follow through. It’s exhausting. Eventually, you start to wonder if it’s worth your time at all. Before you close yourself off completely, it’s important to understand the common patterns that cause mentoring relationships to stall. Waiting for the Perfect Mentee There is no perfect mentee. Everyone who asks for your help is going to be rough around the edges. They’ll make mistakes. They might waste some of your time. That’s the cost of mentoring. The real question isn’t whether someone is polished. It’s whether they’re committed. Are they showing up prepared? Are they implementing what you teach? Are they making progress, even if it’s slow? If the answer is yes, keep investing. If it’s no, redirect your energy elsewhere. Just don’t let one bad experience make you cynical about everyone. Trying to Control Their Path Your job as a mentor isn’t to create a clone of yourself. It’s to help someone develop their own approach using the principles that made you successful. They might take your advice and apply it differently. They might adapt it to their personality, their market, or their selling style. That’s not wrong. That’s the point. Stay unattached ...
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    47 min
  • Why Rejection Hurts and What To Do About It (Ask Jeb)
    Dec 16 2025
    Here's a truth that'll make you uncomfortable: Getting rejected isn't the real problem. The real problem is that you're not doing the work upfront to lower the probability of rejection in the first place. That's the insight that hit when Wendy Ramirez, a leading Mexican sales expert and author of Lo que nadie habla de las ventas: Estrategias para no ser llamarada de petate or What Nobody Talks About in Sales: Strategies to Avoid Being a Flash in the Pan, joined this week's episode about handling rejection on Ask Jeb on The Sales Gravy Podcast. After forty years in sales, I've been rejected yesterday, I'll get rejected tomorrow, and I've been rejected so many times that I almost don't even feel it anymore. But that doesn't mean you can just "let it roll off your back" like some sales trainers tell you. If you're struggling with rejection, you're not alone. And more importantly, you're not broken. There's a biological reason it hurts so badly, and there are concrete techniques you can use to handle it. The Biology of Rejection: Why Your Brain Is Working Against You Here's what most sales trainers won't tell you: Rejection is supposed to hurt. It's baked into your DNA. Forty thousand years ago, human beings lived in small groups around campfires. If you got kicked out of the group and walked away from that campfire into the dark, you were in danger. You were part of the food chain. There were things out there hunting you, rival tribes fighting over scarce resources, and being alone meant you probably weren't going to pass on your genes. So human beings who avoided rejection were more likely to survive. This fear of rejection became an evolutionary advantage, and it's still with us today. That's why selling is so hard. It's why most people don't want to go into sales. Walk into the accounting department and ask if anyone wants to make cold calls with you. They're going to look at you like you've got four heads because nobody wants to be in a profession where you have to do something that unnatural. This avoidance of rejection serves us really well in most of our life. You need to get along with your family, your coworkers, other people in the world. Knowing where the line is that would get you rejected is super important to being able to work as a team. But in sales? It's killing your performance. The Truth About Objections: You're Creating Them When people reject you or give you an objection, what they're expressing is their fear. They're expressing their fear of moving forward, their fear of change, their fear about whether or not you'll do what you say you're going to do. And here's the brutal part: Most of the time, you created that fear. The easiest way to deal with an objection is to do good discovery and do a good job in the selling process. When salespeople make the mistake of not doing any discovery, they don't have any ammunition. So the rejection sounds like this: "Your price is too high." That's the only way a person really knows how to explain it. If they don't like you, they'll say, "We need to go think about this." Think about it this way. If you do a great job of building the relationship, asking questions, listening, getting all of their pain and aspirations on the table, and then telling their story back to them in the context of how you can help them solve their problems, then you've earned the right to ask them. When you ask and they give you an objection, you know what to do because you already have that information. You're just bringing back and putting on the table the things that they already told you. The worst rejections I've gotten? They're usually when I lost a deal because I didn't do discovery. And then I found out after the fact that I missed something I shouldn't have missed. It's not so much the rejection that hurts. It's the shame and the gut punch that I didn't do my job as a salesperson, and therefore I created the environment that made that objection so big that I couldn't get past it because I had no information to work with. The Ledge Technique: Your Magic Quarter Second Let's get practical. You're on a prospecting call, you're engaging another person, and they hit you with an objection which feels like rejection. What do you do? Use a technique called the ledge. Neuroscientists would call it the magic quarter second that allows your executive brain (your prefrontal cortex) to get in control of your emotional brain (your limbic system) and that little structure inside your brain called the amygdala that triggers the fight or flight response. The ledge is just something you've memorized that you say automatically whenever you get that particular objection. The thing about prospecting objections is that we know every potential one. They're not surprising. People are going to say, "I don't have any time," "I'm not interested," "I'm already working with someone," "Your prices are too high," "This is not a good time for me," "I'm not the right person." So if someone ...
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    21 min