Building a Sales Culture That Scales Without Breaking with Dayna Williams

Why do even high-performing sales teams plateau or collapse under growth? In this episode, Jeb Blount sits down with Dayna Williams, author of The Diligence Fix, to explore how disciplined leadership, aligned teams, and a resilient sales culture keep revenue organizations from breaking under pressure. Learn the ten dimensions of organizational diligence and practical strategies to build a high-performing, scalable sales culture that drives results.📚 Explore Dayna Williams' courses on Sales Gravy University.👉 Read the blog on "Why Your Best Salespeople Make Terrible Sales Leaders"📝 Download our free Leader's Guide to Sales Training▶️ Watch the full episode on YouTube🔗 Follow us on LinkedIn!

Here’s a question that should stop you in your tracks: What do you do when you’re booking meetings but prospects keep ghosting you? That was the challenge posed by Brittany, a sales rep watching her show rates crater quarter after quarter, on this week’s episode of Ask Jeb on The Sales Gravy Podcast featuring Will Frattini. Brittany was putting in the work, getting prospects to say yes on the phone, and then sitting alone on Zoom watching the clock tick. If you’ve been there, you know how demoralizing that is. The first thing you need to understand is the math. The best show rate you can hope for on first-time appointments is about fifty percent. If you’re above that, keep riding it. But fifty percent is the benchmark. That means for every ten meetings you book, expect five no-shows. The fix isn’t magic. The fix is volume and process. Stop Pushing People Into Meetings They Don’t Want Before you even think about your confirmation sequence, go back and listen to your prospecting calls. Ask yourself honestly: did that prospect agree to meet because they were genuinely interested, or because you wore them down and they said yes to get off the phone? If you’re so good at closing for the meeting that you’re talking people into it rather than compelling them, you’ve already lost. That’s not a show rate problem. That’s a buyer’s remorse problem. The prospect hangs up, questions their decision, and when Thursday rolls around they’ve convinced themselves they never really needed to meet in the first place. Strengthening your prospecting approach so that prospects are genuinely curious when they agree is the only real fix for that. The Confirmation Process That Actually Works Assuming you have a real reason to meet, the work doesn’t stop when they say yes. Here’s what actually stops prospects from ghosting. Before you get off the phone, confirm the meeting out loud. Say it. “I’m looking forward to seeing you Thursday at two.” Get that verbal confirmation back. Then ask for their email address on the spot and send the calendar invite immediately. Do not wait. And when you title that invite, don’t put “Meeting with Will.” Put your name, your company, their name, their company, and what you’re meeting about. A prospect who sees a generic calendar placeholder will delete it without a second thought. A specific, descriptive invite looks like real business and that’s exactly the psychological signal you need to send. The ten-and-two rule is worth using when you’re booking the meeting. Give two time options, not an open-ended “what works for you.” Something like: “I have Tuesday between ten and ten-thirty or Thursday around two. Does Thursday at two work?” Give a choice, take one away, let them pick. It creates agency and it creates commitment. Stay Visible, Stay Relevant Between the booking and the meeting, do not disappear. Send a short personalized video or email mid-week that reinforces why the meeting is worth their time. “I looked into your organization and I’m looking forward to learning more.” That’s it. No pitch. No agenda. Just warmth and presence. What you’re doing is building what I call the guilt asset. You’ve shown up. You’ve done the work. For most people, not showing up now would feel rude. You’ve made it harder for them to ghost you. For high-stakes meetings, large accounts, or anything where you’re bringing additional executives, confirm directly. Call or email. The calculus changes when the cost of a no-show is high. But for a standard first-time appointment with a single stakeholder, skip the confirmation call because it hands them an easy exit. Instead, if you have their office number, call the night before after hours and leave a voicemail. Let them know you’re looking forward to it and you’ll see them tomorrow. Now they have to do the work to cancel, and most people simply won’t. Keeping your pipeline full of qualified first-time appointments is the foundation. But turning booked meetings into actual conversations is where the money lives. When They Still Don’t Show You did everything right. They still ghosted. Now what? Here’s the message: “Hey, I hope everything’s okay. I was on the meeting for about seven minutes. I’ve got time reserved Thursday and Friday morning between nine and ten. Just let me know if you’re okay, and if you don’t want to meet, I have really thick skin.” Keep it human. Keep it short. Then, if they’re a real account worth pursuing, reach out to reschedule by suggesting the same time on the same day of the following week. They agreed to that slot once, which means it was likely open. Don’t make them think about a new time. Just reset the existing appointment. Here’s the principle behind all of this: when you do the work, you own the moral high ground. And when you own the moral high ground, your prospect feels like they owe you. That means a higher probability they reset the meeting, and a much higher probability they actually show up next time. Treat them like a transaction and they’ll treat you the same way. This is the system, the discipline, and the follow-through necessary to win. Not just activity for activity’s sake, but deliberate execution at every step of the process. The Bottom Line Stop blaming prospects ghosting you on bad luck. Most of the time it comes down to one of three things: you pushed someone into a meeting they weren’t sold on, you didn’t build enough relevance and visibility between the booking and the meeting, or you let the confirmation process fall apart. Fix those three things and your show rates will improve. Not to one hundred percent, because that’s not real life. But to a level where your pipeline starts working for you instead of against you. Jeb and Will go even deeper on getting past the people standing between you and the deal. Watch their Reach Decision Makers Faster: Beating AI & Human Gatekeepers webinar and put these tactics to work today.

Have you ever had a moment where the answer you were looking for was right in front of you? I’m talking about a giant neon sign moment where you realize that a strategy is working, and the proof is undeniable. Today, I want to share a quick story about an unexpected moment of validation that I recently had, and the valuable lesson that every top sales producer needs to keep front of mind. The Annual Sales Summit That Changed Everything I have a client that I’ve worked with for several years now. Each month, I deliver virtual training workshops focused on different areas of sales. Some months our topic will be on prospecting best practices, and other months we may focus on things like sales negotiation skills or how to advance deals in the pipeline. These workshops are optional for the sales team to attend at this particular company. So recently, I was invited to attend their annual sales summit. It was the first time that I’d be putting faces to names and shaking hands with the people who showed up to my sessions, month after month. It was a pretty big event. There were hundreds of members of the sales team from around the US. After grabbing my badge at the registration desk, I walked towards the main event space, and the sound of hundreds of conversations filled the room. It was that feeling of energy and the buzz of excitement when you’re surrounded by people who are having fun together. As I walked through the mingling crowds, I saw it. There was a giant board, I’m guessing about five feet tall, and at the top it read “Top Producers of the Year.” Now, if you’re in sales, you know what these boards represent. It’s the ultimate recognition and a testament to your consistency, grit, and incredibly hard work. I found myself looking through the photos and the names. These were my clients’ top producers, the ones who really earned their spot. And as I looked at each photo, a pattern started to emerge. I noticed a face that I recognized and then another. And then another. I couldn’t help but start to smile as I kept scrolling through this list of the fifteen names on the wall. All but one of them were people who were showing up to the monthly workshops month after month. I was shocked. Not just proud, but genuinely humbled. Now, I’d like to believe that our training played a part in their success. But the truth is, they earned it. Their spot on that board, their results, their massive recognition—it was a direct reflection of the continuous investments that they had been making in themselves. They didn’t wait to be great. They were proactively working on stepping up their skills one month at a time. What You Need to Remember Now, if you take one thing from this article, let it be this: top producers don’t wait for success. They prepare for it. That board wasn’t just a list of the most talented sales reps. It was also a list of the most intentional. It was a direct consequence of four behaviors that they had displayed: Showed up to the monthly workshops even though they were optional. Asked hard questions in these workshops. Applied new techniques and tools and put them into action immediately. Treated sharpening their skills as a non-negotiable. Here’s the truth: the person who dedicates one hour a week to getting better will always beat the person who’s naturally gifted but a little lazy. Intention beats talent every single time. 6 Best Practices to Inject Intention Into Your Week So how do you inject that kind of intention into your own week? Here are six best practices to help you: Show Up Before You Need To These top sales reps on the board didn’t wait for their production to dip before they started investing in training. They were already winning, and they still kept showing up. Skill building is like compounding interest. Small, consistent investments create exponential returns. Treat Sales Training Like a Workout You don’t go to the gym once and expect to be in shape. You show up three times a week for a year. That’s how you need to approach your professional development. Consistency is greater than intensity. Every session you attend adds a new tool, a perspective, or an edge to sharpen your game. Decide That You Are Always a Learner The reps who excelled weren’t afraid to ask questions that other people might consider basic. They were seeking clarity, not just validation. Remember, ego is expensive. Curiosity is profitable. Never stop being the most curious person in the room. Don’t Confuse Activity for Growth Many sales reps are busy; they’re active. But how many are truly intentional about growth? Top producers set aside uninterrupted time for professional development even when their schedule is getting full. So block out time to get better, not just to do more. Implement One Thing Immediately After attending a workshop or even listening to a podcast episode, challenge yourself to pick one tactic to put into action within twenty-four hours. Knowledge is power. Implementation is what turns that knowledge into results. Surround Yourself with Other Top Performers It’s easy in sales to get frustrated when we lose a deal or when things are not going our way. By surrounding yourself with other top performers, you’re going to help lift yourself up in those moments when you need a little extra support and motivation. Why This Moment Mattered Seeing that board of top performers, that physical printed validation, it really struck me—the emotion of realizing that the reps who had quietly and consistently invested in themselves all year long, had literally risen to the top. It was a powerful moment and reminded me why not only I do the work that I do, but it also absolutely confirmed that top performers are the ones disciplined enough to invest in themselves. I encourage you to commit to just one of these six tips that I shared today. Write it down and put it into action within twenty-four hours. Momentum doesn’t come from waiting. It comes from action. — The top performers on that board didn’t wait—they invested in training that got results. Explore my courses on Sales Gravy University and get the same strategies they used to reach the top.

Morgan Keim, founder of Ocean Ridge Capital, raised over $400 million in venture capital before he turned 35. One of his companies alone pulled in over $300 million pre-revenue—convincing pension funds and VCs to invest hundreds of millions in a company that hadn’t made a single dollar yet. On a recent Sales Gravy podcast, he broke down exactly how he did it. The surprising truth? It had almost nothing to do with the pitch itself. “Your single biggest tools in your toolkit are going to be your eyes and ears,” Morgan said. “It’s about listening and seeing where your prospect is and what they really want. That might be different than the words they use.” Consider this: only 7% of communication comes from actual words. Another 38% comes from tone, and the remaining 55% shows up in body language and nonverbal cues. If you’re in high-ticket sales, you’re probably spending most of your time perfecting that 7%, while missing the other 93% of what your prospect is really telling you. What You’re Missing in Every Conversation Most salespeople obsess over crafting the perfect email. They rehearse their pitch until it’s flawless. They tweak their value proposition endlessly. All of that lives in the 7% of communication that comes from words. Meanwhile, prospects are giving away everything you need to know through their tone, body language, and the questions they ask—or avoid. Morgan learned this quickly when raising capital for a food tech startup. Different investors wanted completely different things, even when they all said they cared about “returns.” One investor cared deeply about sustainability and environmental impact. Another focused purely on velocity of capital and exit timelines. A third had unusual mandates that weren’t apparent until Morgan listened carefully in person. “It all comes down to having a real understanding of the emotion that person’s feeling, the desired state of where they want to be,” Morgan explained. “Living in that reality of who they are and what they want.” High-ticket sales often fall apart here. Salespeople treat follow-up like a broadcasting exercise: same message, same pitch, same value proposition to everyone because it’s “efficient.” Efficiency without effectiveness is wasted motion. The Language Barrier Costing You Deals There’s a language of entrepreneurial speak, a language of corporate speak, and a completely different language people use at home. You might communicate seamlessly with colleagues, but explaining your day to your spouse can feel like speaking a foreign language. The same disconnect happens between you and your prospects. Most sellers speak “sales language,” while their buyers speak business or personal language. Top salespeople code-switch naturally. They pick up on how prospects talk, the patterns they use, and the words that matter to them—and mirror that style back. In high-ticket sales, you’re asking someone to make a significant investment. They need to feel understood before they’ll trust you with that decision. Take an HR leader versus a marketing leader in the same organization: HR cares about employee retention, engagement, and compliance. Marketing focuses on campaign ROI, conversions, and brand lift. The same pitch to both? One will check out halfway through the first sentence. Understanding Their Desired State Make the prospect the hero of the story. Put your ego aside. Stop thinking about your quota. Focus entirely on their desired outcome. Morgan never leads with what Ocean Ridge Capital offers. He starts by understanding their situation: Are they trying to create passive cash flow? Looking for tax efficiency after selling a business? Building generational wealth for grandchildren? Each scenario requires completely different emotional framing. A person focused on legacy thinks about family and long-term impact, while a recent entrepreneur selling for eight figures cares about protecting capital and deploying it efficiently. Same product, completely different language. Send the same follow-up email to both, and you’re solving the wrong problem for one of them. How This Changes Your Follow-Up Strategy Once you realize that 93% of your communication lives outside words, your follow-up strategy has to change. Morgan uses multiple channels: Video messages let him read facial expressions and body language. Phone calls provide tone, pacing, and emphasis that email strips away. Handwritten notes show he’s willing to slow down in a world that automates everything. Educational content positions him as a resource, not just a seller. He runs A/B/C testing across messaging angles because he can’t assume he knows what a prospect wants. When someone doesn’t respond to initial outreach, he shifts to “passive value creation”—delivering insight, education, and context—while still prospecting actively through multiple channels. Every touchpoint adds value. Every channel gives a new way to read the prospect, learn their language, and adjust. What to Do on Your Very Next Call Here’s your homework. Not next week. Not when you have time. On your very next sales call: Spend five minutes reading the room before you pitch anything. Notice: When their energy shifts. Words they repeat. Moments they lean in or check out. Mirror it back. If they say, “We’re building something sustainable,” don’t respond with, “Our solution drives ROI.” Stay in their language. Stay in their world. Try a different channel. Been emailing for weeks with no response? Pick up the phone. Send a 60-second video. Mail a personalized note. The mechanics haven’t changed. You still need multiple touches. But if you ignore tone, body language, and emotional state, you’re having a completely different conversation than your prospect is. Why This Approach Wins High-ticket sales are about human connection more than polished words. Prospects respond to feeling understood, recognized, and respected. The words you say matter far less than how you convey empathy, awareness, and relevance. Morgan’s results speak for themselves: reading the unspoken signals and adapting builds trust, shortens sales cycles, and secures investments that others can’t reach. High-ticket sales aren’t only about what you say—they’re about what you see. Pay attention, and everything changes. – Take your follow-up strategy to the next level. Download the FREE ACED Buyer Style Playbook and learn how to read what your prospects really want.

Here’s a question that cuts to the heart of what makes sales hard: What do you do when your commodity is identical to every competitor’s, the buyer knows it, and the only lever they want to pull is price? That’s the challenge Ash from Chennai, India brought to me on a recent Ask Jeb episode. Ash works as a trader importing textile goods from Asian manufacturers and selling them into Spanish-speaking markets in South America and Spain. No proprietary product. No unique features. Pure commodity, all the way down. And yet Ash is holding customers. Getting repeat orders. Building relationships across borders and languages. He just needed a framework to understand why it was working and how to make it work even harder. The Trap Every Commodity Salesperson Falls Into When everything looks the same, most salespeople default to one of two bad moves: race to the bottom on price, or get paralyzed trying to explain a value they can’t articulate. Here is the brutal truth. Your buyer already knows the product is a commodity. They know they could go direct to the factory and cut you out entirely. They are not confused about that. What they are evaluating is whether the risk and hassle of cutting you out is worth the savings. Your job is to make sure the answer is always no. That requires you to stop thinking about what your product does and start thinking about what YOU do. Three Reasons Customers Keep Buying From Ash When I asked Ash why his good customers keep coming back, he gave me three answers that every salesperson in a commodity business needs to write down. You make it easy. Ash speaks Spanish. His customers speak Spanish. If they go direct to a Chinese or Vietnamese factory, they face language barriers, cultural friction, and communication breakdowns. Ash eliminates all of that. Business people will pay for less hassle. Time is money, and you are saving them both. You are someone they like and trust. Ash follows up. He wishes customers a happy New Year. He remembers what matters to them. That is not fluff. That is relationship equity that compounds over time. When customers feel like they can trust you, when a familiar voice picks up the phone, they do not want to start over with a stranger. You reduce financial risk. In Ash’s business, buyers put down a 20% deposit, sometimes a hundred thousand dollars or more, and pay the balance when the container arrives. The nightmare scenario is that container showing up full of the wrong product. Ash’s company has been operating for over 20 years. They do what they say they are going to do. That longevity is not just a stat. It is a security blanket. The Power of the Micro Story Knowing your value is half the battle. Being able to articulate it when a buyer pushes back on price is the other half. Here is what I told Ash: You need stories. Not case studies. Not bullet points. Short, vivid, real stories that make the risk of cutting you out feel tangible. Something like this: “I get it. You could go directly to the factory and save ten percent. Some of my customers tried that before working with me. One of them got a container full of product that was not what they ordered. It cost them more than they saved, and they had no one local, no one they trusted, to help them fix it. That is why they work with me now.” That story is doing three things at once. It validates the buyer’s instinct to compare prices. It quantifies the real cost of the cheaper alternative. And it positions you as the solution to a problem they have not had yet but definitely do not want. If you are newer to sales and do not have your own stories yet, go talk to your senior teammates. Read industry articles. Find examples of what goes wrong when buyers skip the middleman. Then make those stories part of your standard value conversation. Not Every Buyer Is Your Buyer This is the part that stings a little, but it is important. Some buyers are going to push back on your margins until the conversation goes nowhere. They will tell you the price they need, and if you cannot hit it, they will walk. That is okay. What they are telling you is that they do not value what you bring to the table. They want the cheapest option, and that is a legitimate business decision. They are just not your customer. Your job is not to convert every skeptic. Your job is to keep your pipeline full and find the buyers who genuinely value ease, safety, and responsiveness. Those are the ones who become long-term accounts. Those are the ones who, two or three years in, cannot imagine buying from anyone else. Ash is already doing this well. He has visited customers in Mexico, Colombia, and Spain. He has done office meetings and factory tours. When a customer says yes to a visit, they are telling you something: you matter to us. That is what I call an engagement test, and Ash is passing it. Your Value, Packaged Simply In commodity sales, your pitch does not need to be complicated. It needs to be consistent. Here is how I would frame it every time a buyer pushes back: I make this easy for you. I am responsive. And your money is safe with me. Then back each of those up with a story. That is the whole game. Not features. Not specs. You. When you are tired and ready to wrap up the day, remember this: the prospecting you do today pays you for the next three months. Pick up the phone and make one more call. The buyers who value what you do are out there. Go find them. Want to take this to the next level in person? Join Sales Gravy at one of our live events, where we work with sales professionals and leaders to build the skills, mindset, and habits that drive elite performance. See all upcoming events at salesgravy.com/live.

You’ve heard people say, “Sales is a grind.” And they’re right. Sales requires relentless effort. You’ve got to make the calls, run the process, deal with internal roadblocks, handle piles of rejection, and show up every day with a smile on your face, ready to do it all over again. But the dirty little secret is that plenty of salespeople push through the grind day after day and still don’t seem to get ahead. They put in the effort and work hard, but get nowhere. All grind, but little progress. Here’s the truth they don’t always tell you: You can grind yourself into the ground and still fail if you don’t have the right mindset and belief system underpinning that effort. To keep it real, I’m the person who shouts from the rooftops that you’ve got to “grind to shine.” I say that in my book Fanatical Prospecting. It’s printed on coffee mugs. I love that mantra because it’s about doing the things other people are unwilling to do. But raw grind isn’t always enough. Sometimes, we need to pair grinding it out with tenacity. Tenacity is a Sustainable Sales Trait In sales, tenacity is a more sustainable trait than raw grind or pure persistence because tenacity combines persistent determination with process certainty and strategy. Grind is about doing the daily, repetitive, rejection-dense work required for success, but it can quickly lead to frustration and burnout when it isn’t paired with enduring faith that the hard work is going to pay off.  Tenacity, on the other hand, is grinding combined with the absolute certainty that what you expect to happen is eventually going to happen. That’s the difference between the rep who grinds hard for a quarter, feels that they are getting nowhere, and burns out because they’re not seeing results, and the sales professional who consistently runs the sales playbook, without immediate evidence that it’s working, because they have faith that the process will eventually produce their desired outcomes. Uncertainty Causes You to Constantly Change Your Approach One big problem with grinding without certainty is that when results don’t show up on your impatient timeline, you start changing everything. You make 100 calls this week using one approach. Next week, you try a different script. The week after that, you switch your targeting. Then you read an article about social selling and abandon cold calling altogether. You’re working hard, but you’re also second-guessing every move. You change your messaging before you’ve run it long enough to know if it works. You abandon techniques after a handful of attempts. You skip or change steps in your company’s sales process after a couple of deals don’t go your way.  When you put in massive effort, but spread that effort across ten different approaches instead of trusting the proven process and playbook long enough to let it produce results, you end up in an exhausting, demoralizing quagmire of chaos and eventually give up.  The True Meaning of Process Certainty When I say “certainty,” I’m not talking about positive thinking or affirmations or manifestation or any of that rah-rah motivational stuff. Certainty in sales means knowing—not hoping, but knowing—that if you do the right things the right way for long enough, the outcomes are inevitable. That you get the Sales Gravy.  That’s what allows tenacious salespeople to keep grinding when others quit. They’re not grinding on blind faith. They’re grinding on proven evidence that the process works.  For example, in Fanatical Prospecting, I explain the 30 Day Rule, which states that the prospecting you do in any given 30 days tends to pay off over the next 90 days.  The 30-day rule is always in play. It is proven. It is truth. But you’ll never see it work if your prospecting is sporadic rather than consistently executed every single day.  The Three Types of Certainty that Power the Tenacity Engine If you want to develop real tenacity—the kind that sustains you through tough markets, rough quarters, and slumps—you need to build certainty in three core areas. 1. Certainty in Your Value You need conviction that what you’re selling genuinely improves your customers’ businesses in a meaningful way. When you have that certainty, something shifts. You stop feeling like you’re bothering people or being pushy and start feeling like you are helping them. That you belong there.  And buyers can feel this difference. They sense and respond to your confidence, enthusiasm, and passion for helping them. Which gives you even more certainty. 2. Certainty in Your Process You need confidence that your sales process and playbook actually work.  Most sellers have been provided a proven, repeatable approach to building pipeline, qualifying opportunities, running discovery, handling objections, building consensus, negotiating, and closing business.  If you don’t have a process, read or listen to my books Fanatical Prospecting, The LinkedIn Edge, Sales EQ, Objections, Virtual Selling, and Inked. Collectively, these books give you a powerful playbook for success.  But regardless of whether you get your playbook from your company or me, believing that it will work for you is a choice and mindset that only you can step into.  If you are constantly second-guessing the process every time things don’t work out the way you want them to, you are doomed to frustration and failure. You’ll be a slave to flavor-of-the-day thinking and winging it from call to call and situation to situation. But when you trust the process, you’ll be steady, consistent, and confident. And you’ll relax because you know that you won’t win every time, no one does, but over time, because your process is proven, win probability is in your favor.  3. Certainty in Probability This is the big one. You need certainty that the math works in your favor over time. The simple truth is that sales is a numbers game played with human emotions. Not every call will book a meeting. Not every meeting will turn into an opportunity. Not every opportunity will close. But if you control the inputs—activity level, message quality, process execution—the outputs become predictable and win probability bends in your favor.  Ultra-high performers understand this at a bone-deep level. They know their numbers and conversion rates. This gives them certainty that the statistics are working in their favor.  On the other hand, the reps who are winging it are sky high when something goes well and in the dumps when things don’t—without knowing what they did in either situation to affect the outcome. And it is on this emotional roller coaster where they eventually burn out and quit.  Top performers never board this emotional roller coaster because they’re anchored to math, not mood. How to Transform Sales Grind into Certainty-Fueled Tenacity Maybe you’re thinking, “Jeb, this all sounds great, but how do I build this certainty that you speak of?” Fair question. Here are four ways:  Track Process Metrics, Not Just Outcomes If you only measure outcomes—meetings set, deals closed, revenue generated—you’re going to struggle with certainty during the lag time between the grind and results. So instead, track the inputs like calls, conversation ratios, meetings, next step advances, or proposals delivered. When you measure the right activities, you can see progress and celebrate small wins even when results aren’t there yet. This builds certainty that the process is working, which sustains your effort through the gap. Practice Until You Don’t Have to Think Competence begets certainty. Competence comes from practice and repetition. Role-play your cold calls. Rehearse your discovery questions. Murder-board your presentations. Practice, practice, practice your sales story, messaging, and handling objections. Record yourself doing it and watch it back. When you’ve practiced something until it is pure muscle memory, you don’t get nervous when it matters. You don’t freeze up or get embarrassed when you fumble. You execute with relaxed confidence. Emotionally Detach from Individual Deals The fastest way to lose certainty is to attach your identity to one opportunity. Tenacious sellers want to win every deal, but they don’t need to win every deal to feel okay about themselves. They treat each opportunity like one at-bat in a long season. Emotional detachment isn’t indifference. It’s a form of professionalism. It’s caring about the outcome without being controlled by it. Install a Mental Script for Rejection When you get rejected, it hurts, and your brain immediately tries to explain why. When you are in pain, it is super easy to default to stories that weaken your mindset and belief system. You say things to yourself like, “I’m not good at this or this isn’t working.” Tenacious sellers consciously replace that story with self-talk that maintains certainty. “Not now isn’t never.” “This is part of the math.” My inputs are correct, I executed my process, but this just wasn’t the right time for this buyer.” This is how top salespeople think because they know that the greatest threat to tenacity isn’t the rejection, it’s the meaning you assign to the rejection. Grinding Without Certainty is Just Another Form of Suffering Sales will always be a grind. The calls don’t make themselves. The pipeline doesn’t fill itself. The deals don’t close themselves. But grinding without certainty is just another form of suffering. It’s unsustainable. Eventually, you get frustrated, burn out, and give up. Certainty doesn’t eliminate the hard work, but it does make the hard work sustainable. So if you’re grinding right now and not seeing the results you want, don’t just grind harder. Build certainty. Get clear on the value you deliver. Trust your process. Know your numbers. Track the inputs. Practice your craft.  Because tenacity isn’t about being tougher than everyone else. It’s about being certain enough to keep going when everyone else quits. And remember, when you are tired, worn down, and feel like you can’t take another objection, when all you want to do is quit and go home, always stop and make one more call. Because that one more call is the ultimate demonstration of your trust in the process. Get your tickets today to OutBound – the world’s biggest, baddest sales and leadership training conference. Go to OutBoundConference.com

I spent an afternoon at Ramsey Solutions in Tennessee with Jason Williams, Vice President of Sales for the EntreLeadership Division. What stood out wasn’t the size of the operation or the fancy building. It was walking into a room where sales reps genuinely wanted to talk to their leader. Most sales floors feel like number factories. Reps avoid their managers. One-on-ones get rescheduled. And everyone wonders why performance stays flat despite “investing in our people.” Sales leaders say coaching matters. They talk about developing talent. Then they spend their days staring at dashboards and asking why the team isn’t getting better. Real sales coaching looks nothing like what most organizations call coaching. And after watching Jason work, I’m reminded why so few leaders actually get this right. What Sales Coaching Actually Looks Like Jason told me about one of his reps who started missing quota. Here’s what usually happens: Manager pulls up the CRM, points at red pipeline metrics, asks what happened. The conversation goes nowhere. Rep gets defensive, makes excuses, promises to work harder. Nothing changes. Jason took a different approach. He asked about his rep’s life. Turned out he was stressed about buying his first house. That weight was bleeding into his work, affecting his confidence on calls, making him hesitant to push for commitments. So Jason got into the field with him. He listened to calls. He rode along on appointments. He watched where deals were actually stalling. Then they debriefed what he observed. “Here’s what happens when pricing comes up.” “Let’s tighten how you handle that objection.” Zero mention of quota or pipeline metrics. The rep turned it around because someone cared enough to understand what was broken and help him fix it. That’s what coaching looks like. Managers react to outcomes they can’t change. Coaches focus on behaviors that create future outcomes. Why Most Leaders Don’t Coach The biggest barrier isn’t that leaders don’t want to coach. Most genuinely do. The problem is they don’t know what they’re looking for because they never see their reps in action. Think about last week. How many discovery calls did you listen to? How many demos did you observe? How many customer meetings did you attend just to watch your rep work? If the answer is zero, you’re coaching from spreadsheets instead of reality. You’re looking at lag indicators (closed deals, pipeline value, activity counts) and trying to diagnose skill gaps without ever seeing the skills in action. Jason blocks time every week to observe his reps. He’s not there to supervise them or take over calls. Just to watch. Then the coaching becomes specific. He can say, “when that prospect brought up budget concerns, you deflected instead of asking questions,” instead of just “you need to handle objections better.” You can’t coach what you don’t see.  The second barrier is culture. In typical organizations, admitting weakness feels dangerous. You’re supposed to be confident, crushing it, always having answers. So problems stay hidden until they show up in the numbers. By then, it’s too late to coach. You’re in damage control. Creating an Environment Where Problems Surface Early Jason builds what he calls a “safe space” for his team. When a rep is struggling, he starts the conversation with curiosity instead of judgment. He asks open questions about what they’re experiencing, where they’re getting stuck, what feels hard right now. When reps admit struggles, he treats it as useful information, not a character flaw. A rep says, “I’m nervous on C-suite calls,” and Jason’s response is “okay, let’s work on that,” not “you shouldn’t be nervous.” Then he follows through. If someone admits they’re stuck, he actually helps them. He role-plays the situation. He rides along on the next similar call. He provides tools and frameworks. The rep sees that honesty led to help, not punishment. Over time, reps learn that surfacing problems early gets them solved. Hiding problems just makes things worse. So they start talking about what’s actually happening instead of pretending everything is fine while their numbers slide. The first time someone admits a weakness and you respond with frustration, you train the entire team to stay quiet. Managers say they want transparency. Few consistently reward it. How to Actually Build a Coaching Culture If you want to coach instead of manage, you have to make developing people the primary job.  Jason is clear that his main responsibility is making his reps better. Everything else supports that goal. Pipeline reviews and forecasting matter, but they exist to serve sales coaching, not the other way around. Protecting coaching time is non-negotiable. One hour per rep per week, minimum. When conflicts come up, the internal meeting gets moved, not the coaching session. Getting better at coaching matters too. Most of us got promoted because we were individual contributors. Nobody taught us how to develop other people. So we replicate whatever leadership we experienced, which is usually mediocre. Your reps practice selling every day. You should practice coaching. Role-play difficult conversations with your peers. Practice giving feedback. Work on observation skills. Treat coaching like the professional skill it is. And you have to measure what matters. If you only track team revenue, you’ll optimize for short-term numbers at the expense of development. Start measuring coaching conversations. Track whether your reps are improving on specific skills. Monitor how long it takes new hires to ramp. When I walked through Ramsey Solutions that day, I could feel the difference. Reps weren’t avoiding their leader. Retention was better. Performance was compounding over time instead of bouncing around based on whoever happened to be hot that quarter. What Happens Next Look at your calendar from last week. How much time did you spend observing your reps versus reviewing their numbers? How many true coaching conversations did you have versus pipeline reviews? If that ratio doesn’t reflect what you say your priorities are, you’ve found the gap. Your reps don’t need another dashboard. They need a leader who sees the work, understands where it’s breaking down, and knows how to help them improve. Sales coaching isn’t reacting to results. It’s shaping the behaviors that create them. The question is whether you’re willing to make that your real job. — Ready to build a stronger sales team? Download our FREE Small Business Guide to Sales Training and get the framework for developing high-performing reps.

Here is a question that should keep every sales leader up at night: What do you do when your team has gotten so comfortable managing their existing accounts that they have stopped prospecting for new ones? That is the challenge Jeff Velez brought to a recent episode of Ask Jeb. Jeff works in the real estate services industry, where referrals from agents, brokers, and affiliates drive most of the business. Retention matters. Relationships matter. But because there is always natural attrition, his team has drifted into full farmer mode. If you are shaking your head right now, you are not alone. This is one of the most common and most dangerous patterns I see in sales organizations today. The Farmer Mentality Is Killing Your Pipeline Your book of business is shrinking a little bit every single day. Accounts churn. Contacts leave. Referral partners move on. If your team is not consistently bringing in new logos, you are not standing still. You are moving backward. The reason salespeople drift into pure farming mode is just pure human nature. The bigger a rep’s book gets, the more comfortable they become. They are making money. Things are fine. Why grind through cold calls and new outreach when warm conversations with happy clients feel so much easier? And here is the other thing: calling invisible strangers is hard. The people in your existing accounts are happy to hear from you. The people you are prospecting to are not. That gap in friction is exactly why reps gravitate toward the path of least resistance every single time. The solution is not to yell at your salespeople. This is a leadership problem, not a salesperson problem. If you want your team to prospect, you have to build a system and a culture that makes prospecting non-negotiable. That starts with you. Leaders Are Repeaters If you want your team to prospect, you have to talk about it constantly. Every team meeting. Every one-on-one. Every morning huddle. Leaders are repeaters. You set the tone by what you say, what you measure, what you celebrate, and how you show up. That means when someone brings in a new logo, you ring the bell louder for that than you do for an account renewal. Renewals matter. High margin, great for the business. But if you want prospecting behavior, you have to reward and celebrate prospecting outcomes. Make sure you are not accidentally incentivizing people to farm existing account growth rather than hunt new business. That is a trap I have walked into with more organizations than I can count. You also need to take the guesswork out of who your team should be calling. Sales leaders who expect their reps to build their own prospecting lists and figure out their own targeting are setting their people up to fail. Build the list. Point them in the right direction. Get them in position to win. Then run prospecting blocks together. And I mean together. Do not send your team to the phones and retreat to your office. Lead from the front. Split the Job When You Can One of the hardest things about managing a referral-driven or relationship-heavy business is that you need people who can both hunt and farm. And the honest truth is that most people are not equally gifted at both. Hunters tend to get new business but sometimes burn relationships. Farmers build and maintain accounts beautifully but stop hunting the moment their book is comfortable. If your business can afford it, split the role. Have dedicated hunters focused on new logo creation. Have dedicated farmers or account managers focused on retention and expansion. Most small and mid-size organizations cannot do this fully, which means your leaders have to work twice as hard to build systems that force both behaviors. When you cannot split the job, you have to build structure into the day. Block time every morning specifically for new logo prospecting. It does not have to be a huge window. An hour. Two hours. But it has to be protected, consistent, and non-negotiable. And the leaders have to be visibly engaged in it, not hiding behind their screens while their people make calls. That single behavior sends more of a message than any speech ever will. This Is a Long Game Here is what I told Jeff, and what I will tell you: do not expect this to change overnight. Cultural shifts in sales organizations are slow and painful. You will have reps who resist. You will have leaders who get uncomfortable holding people accountable because they do not want the friction. Push through it anyway. Stake it in the ground. If you stay consistent in your messaging, your structure, and your expectations, you will start to see movement in twelve to eighteen months. New business will start coming in. Your team will start to feel the momentum. And that momentum builds on itself. I am dealing with this in my own organization right now. We got comfortable with our existing customers and pulled back on new outreach. The book feels fine until the day it does not, and by then you have already lost ground you cannot easily recover. A shrinking book is not sustainable. Full stop. Your Action Plan If you are a sales leader: Reset the expectation now. Make it clear that prospecting for new logos is part of the job description, not optional. Put it in writing. Talk about it constantly. Fix your compensation structure. If you are paying higher on renewals than on new business, fix that. You are paying for the behavior you are getting. Run prospecting blocks with your team. Not near your team. With your team. Lead from the front. Give them the list. Stop expecting reps to research, target, and build their own outreach pipeline. That is a leadership function. Celebrate new logos loudly. Ring the bell. Make it a bigger deal than anything else you celebrate. If you are a sales rep: Do not wait for your leader to force you. The reps who prospect consistently, even when their book is comfortable, are the ones who build the most durable careers. Treat your book like a leaky bucket. Something is always draining out. Your job is to fill it back up, every single day. Pick up the phone. Calling strangers is uncomfortable. Do it anyway. That discomfort is exactly what separates average reps from elite ones. The message is simple. A book of business that is not growing is a book of business that is dying. This is who we are. This is what we do. We prospect, every day, without exception. Want to take this to the next level in person? Join Sales Gravy at one of our live events, where we work with sales professionals and leaders to build the skills, mindset, and habits that drive elite performance. See all upcoming events at salesgravy.com/live.

I’m going to ask you a question that might sting a little. As a sales professional, are you just friction with a friendly face? Think about it. A whole lot of salespeople are good people. They’re polite, fun to be around, and are good conversationalists. They are good at building relationships and getting along with people. They’re the type of people that buyers say they like. The problem is, those buyers who say that they like them often don’t buy from them. They stall. Ghost. Go dark and say things like, “Let’s circle back next quarter.” But they don’t pull the trigger on purchases. When push comes to shove, they justify not buying with words like, “We really liked you and thought you had a great presentation, but in the end decided to go in a different direction.” The truth is that they went in that direction not because of the relationship (they truly liked you). Not because your product isn’t competitive or that your solution wasn’t a fit (they were). And not because they thought your intentions were bad (you wanted the best for them). They decided not to do business with you because dealing with you over the course of the buying process was too much work. And by the way, buyers don’t experience your good intentions. They experience your process. So today, I’m going to give you a wake-up call and a fix. Because in the age of AI, people expect seamless, frictionless buying experiences. And they compare you—consciously or not—to the easiest experience they’ve had anywhere. Not just to your competitors. How Salespeople Become Friction for Buyers Let me paint you a picture. A buyer sits through a discovery call. You’re friendly. You build rapport. You ask good questions, and they ask hard questions. You end the call with, “Thank you for your time today. I’ll get with my team and send over answers to your questions.” They say okay, and you end the call. A week goes by, and they don’t hear from you because you moved on to the next thing on your list and forgot to follow up with your team and them. Finally, after a week and a half, they remind you that you haven’t provided any answers to their questions. Embarrassed, you jump on it and send over the answers. But it’s not your best work because you were under the gun and moving too fast. Three days later, you email: “Hey! Just checking in. Wanted to see if I answered your questions.” The buyer is busy. They’ve got a million things going on, and they’re irritated because you didn’t give them the complete answers they were looking for. And now your email is another item piled onto their overflowing plate. They don’t respond. So you send another email: “Bumping this to the top of your inbox.” (Trust me, overwhelmed people just love it when you bump stuff to the top of their inbox.) You create even more irritation. Then you call and leave a voicemail: “Just following up on the answers I sent you.” You’re thinking: I’m being persistent. I’m doing my job. They’re thinking: You made me follow up on you to get the answers I needed, then you failed to give me what I want, and now this is suddenly urgent. From their perspective, no matter how nice you’ve been, you are friction. Your delay slowed down their decision-making process, the conversation was left open-ended, and now all they have are loose ends, and you’re driving them nuts. The Hard Truth About Relationships in the Age of AI Here’s the brutal truth: Relationships are vitally important. Trust matters. But relationships only carry you so far if buying from you isn’t easy or pleasurable. You can be likable and still be a drag. You can be “a great person” and still be the person the buyer avoids—because every step with you along the decision-making process comes with friction. And the thing about friction is that it shows up in small ways that feel normal to you but are exhausting to your buyer. Here are just a few examples: Meetings that end with no decision map or next steps Follow-up messages that add no new value Slow answers to simple questions Stakeholders have to push you The buyer is repeating the same story over and over because you are not listening and taking notes Your failure to follow through when you say you will Proposals that are generic marketing documents rather than valuable insight, value bridges, and recommendations AI Just Set the NEW B2B Sales Bar This problem is getting worse right now because of AI. And I don’t mean this in some hypey, “AI is changing everything” way. I mean, AI is retraining buyers. Buyers are being conditioned to expect frictionless experiences: instant answers, clear options, smart recommendations, and smooth paths from questions to answers to decisions. So when they hit your sales process, and it feels like walking through mud, they notice. They may not say it out loud, but their behavior says it for them. They stall faster. They ghost faster. They lose patience faster. This is a big part of what I talk about in my bestselling book, The AI Edge. Your edge isn’t that you use AI to crank out more activity. Your edge is that you understand the expectation shift and use AI to help you reach that new bar. In the age of AI, the new bar is FASTER with less FRICTION. For this reason, you need to combine your gift for connecting with people and developing relationships with leveraging AI to: make progress faster, follow up faster answer questions and provide clarity faster give insight faster understand your buyers’ organizations and problems faster deliver proposals and recommendations faster help your buyers feel trust and certainty faster. All with less friction for your buyers. How to Conduct a Sales Friction Audit To gain insight into how buyers may view you, take a hard look in the mirror and run a Sales Friction Audit. This takes five minutes, and it will tell you exactly what’s killing your deals. Score yourself 1 to 5 on these seven areas: Clarity: After every interaction, does the buyer know exactly what happens next? Speed: Do you respond at the speed of the buyer’s curiosity or the speed of your internal process? Effort: Are you reducing the buyer’s workload or adding to it? Progress: Do your meetings create decisions and movement, or just conversation? Packaging: Do you make it easy for the buyer to share your insights, information, and recommendations internally to their team? Certainty: Do you reduce uncertainty and risk, or do you create more? Reliability: Do you do what you say, when you say, without reminders? Now, after you add this all up, if you don’t like the number, don’t get defensive. Change your mindset. Because the fix is simple: Stop trying to be liked and start making it easier to work with you. Because if you are just friction with a friendly face, in today’s marketplace, you are going to get crushed by competitors who are friendly, competent, fast, and frictionless. But I want to be crystal clear: Frictionless doesn’t mean spineless. It doesn’t mean you turn into a people-pleasing slave to your buyer’s every whim. It certainly doesn’t mean handing out discounts like candy to make buyers happy. It means you run a sales process with structure, discipline, and competence, and that you understand that the buying experience and how you sell matter more than what you sell. Two Easy-to-Implement Ideas for Eliminating Friction in Your Sales Process Here are two easy actions you can implement immediately to reduce friction in your sales process. End Every Meeting with a Map and Next-Step Commitment The map is clear on who does what, by when, and what done looks like. Too many sales calls end with vague commitments. “I’ll send you some information.” “Let’s reconnect next week.” “Think about it and let me know.” That’s not a map or a next step. Those loose ends are friction. A map sounds like this: “Here’s what happens next. I’m going to send you a detailed proposal by Wednesday at noon. You’re going to review it with your team on Friday. We’ll reconvene on Monday at 2 PM to give it a thumbs up or thumbs down. Will this work for you?” A map is clear, specific, and has no ambiguity. You are leading the process and driving it forward to a conclusion. Turn Proposals into Recommendations Don’t dump choices on the buyer and say, “Let me know what you think.” Give options AND your recommended path. “Based on what you’ve told me, here are three options. Option A is the safe play. It has the lowest risk but only a moderate impact. Option B is my recommendation because it solves your core problem and gives you room to scale. Option C is the aggressive play. It’s also a higher investment with the highest potential return and the highest risk. Here’s why I’m recommending Option B . . .” In a world filled with uncertainty, your confident, assertive, expert advice reduces friction and helps your buyer make faster decisions. How AI Can Give You the Edge for Removing Friction Now here’s where AI comes in. If we’re honest, most sellers use AI to write emails. That’s fine, but it’s not the edge. The edge is using AI to remove friction for the buyer and to shorten the distance from interest to decision. Generate decision-ready call recaps: outcomes, risks, open items, next steps, deadlines Speed up the process of understanding your buyer’s organization and beef up your industry-specific business acumen Create a one-page business case that the buyer can forward internally, along with stakeholder-specific FAQs Record your meetings so that you never forget anything the stakeholders tell you and use those recordings to speed up the process of crafting personalized proposals and expert recommendations. Wake Up B2B Salespeople. The World Has Changed. The bottom line is that the relationships you build are crucial but not enough, because people do business with people they like, trust, and who remove friction from the buying process. They reward sellers who engineer a buying experience that feels seamless. But if you are just friction with a friendly face and buying from you feels like a slog, buyers will do what people always do when something feels too onerous. They’ll avoid it, delay it, or take the path of least resistance and buy from your competitor. The world has changed. Buyers have been retrained by frictionless experiences everywhere else in their lives. And they’re bringing those expectations to you. So be the seller who’s both likable and easy, who builds relationships and eliminates friction, who uses AI not to spam harder but to sell better. That’s the AI Edge. And remember, when you are tired, worn down, and feel like you can’t take another objection, when all you want to do is quit and go home, always stop and make one more call. https://www.amazon.com/AI-Edge-Strategies-Unleashing-Competition/dp/1394244479

Brad Beeler, author of Tell Me Everything and retired Secret Service agent who has conducted more criminal polygraphs than anyone in the agency’s history, was clearing a house on a search warrant when he came across two dogs: a pitbull and a Chihuahua. His focus locked on the pitbull. The stereotype. The threat. Meanwhile, the Chihuahua circled behind him and jumped up, latching onto him right between the legs while his partner stood there laughing. We assign horns and halos fast. Brad learned that lesson with dogs. You learn it every time a prospect shuts down before you finish your introduction. Horns mean danger. Hurtful. Someone here to take from me. Halo means safe. Helpful. On my side. Over 25 years of getting people to confess to federal crimes, Brad discovered something powerful: the same instincts that get hardened criminals to talk work in conference rooms. The techniques that break through with people who have every reason to lie also work on prospects who have every reason to brush you off. Because in both environments, trust determines everything. Why Building Trust With Prospects Is Harder Than You Think Your brain’s been running this horns-and-halos program for 300,000 years. When something rustled in the bushes, you made a split-second decision: climb a tree or fight. That quick judgment kept you alive. The moment you walk into a prospect meeting, their brain assigns you horns automatically. You are the salesperson. The interruption. The person asking for their budget. In their mind, you represent risk before you ever speak. It happens on cold calls. You say, “Hi, this is…” and they are already calculating how to end the conversation. On discovery calls. In demos. At conferences when you introduce yourself. Every single time. You are fighting ancient wiring every time you engage a buyer. So what can you control? The first 90 seconds. How to Build Trust in the First 90 Seconds We remember first impressions and last impressions. In most meetings, it begins and ends with a handshake. Brad puts antiperspirant on his right hand. He warms his hands before entering a room. He holds eye contact for one second. Faces the person straight on. Slows his pace. Lowers his tone. It sounds mechanical. But every one of these micro-decisions either confirms horns or begins to build a halo. Wet handshake? You’re nervous, unprepared, not confident in what you’re selling. Avoiding eye contact? You’re hiding something or you don’t believe in your own pitch. Talking too fast? You’re trying to get something past them before they catch on. When you control these variables, people’s guard comes down faster. You’re giving their brain evidence that maybe, just maybe, you’re not the threat they assumed you were. The Trust-Building Technique Most Salespeople Get Wrong Brad would sit across from murder suspects and open with one line: “I need you to help me understand.” Humans are hardwired to explain. When you position yourself as the learner, something shifts. They become the expert. Their guard drops. They start talking. Most salespeople walk in ready to educate. Your deck. Your case studies. Your demo. You’re there to prove you know their problems better than they do. Sometimes that works. But think about what it communicates: “I already know what’s wrong with your business. I just need you to agree with me and sign here.” Instead, try: “Walk me through what happens when your team processes a new order.” “Help me understand how you’re handling onboarding right now.” “What’s your biggest bottleneck?” Invert the dynamic. You’re not there to impress them. You’re there to learn from them. Once buyers start explaining their world, they reveal what matters. The workaround their team built. The spreadsheet that breaks every month. The process leadership thinks is automated but is completely manual. That’s the information that moves your deal forward. How to Build Rapport Before the Real Conversation Starts Before interrogating two suspects, Brad bought them food. Popeyes for one. McDonald’s for the other. Twenty-two dollars total. The next day, the woman’s on a jail call: “Yeah, they got me with the McDonald’s. That’s why I confessed.” It was not about the food. It was about comfort. Lowering the guard. Creating what Brad calls a confessional environment where people feel safe telling the truth. You’re probably not buying prospects lunch before your first call. But the principle still applies. Show up five minutes early so they don’t feel rushed. Ask about their weekend before diving into business. Acknowledge that you know their time is valuable. Turn your camera off if they seem uncomfortable on video. Send the agenda beforehand so there are no surprises. These are small friction eliminators. They signal: I’m not here to ambush you. I’m not trying to catch you off guard. We’re having a conversation, not a pitch. The prospect who feels safe tells you what’s really going on. The prospect who feels ambushed gives you the corporate line and ends the call early. What Happens When You Actually Build Trust With Buyers When buyers move you from horns to halo, everything changes. They stop filtering their answers. They tell you what keeps them up at night. They admit where the process breaks. They share internal pressure you would never see in a polished demo. I’ve watched this play out hundreds of times. The rep who asks better questions closes more deals than the rep with the better demo. The rep who makes prospects comfortable gets to real problems faster than the rep with the perfect pitch. Brad spent 25 years getting people to confess to federal crimes. He still warms up his hands before handshakes. Still slows his speech. Still positions himself as someone who needs to learn. Why? Because building trust isn’t about personality or natural charisma. It’s about technique. These methods work because they’re based on how humans actually operate, not how we wish they operated. And when buyers tell you the truth, you can actually help them. — Download our free Sales EQ Book Club Guide to master the emotional intelligence skills that help you read prospects and close more deals.