Episodios

  • Where Confidence Comes From and Why it Matters in Sales

    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

    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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    43 m
  • 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 m
  • 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 m
  • 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 m
  • 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 m
  • 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 m
  • 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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