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Sales Gravy: Jeb Blount
Sales Gravy: Jeb Blount
Author: Jeb Blount
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© 2025 Jeb Blount, All Rights Reserved
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From the author of Fanatical Prospecting and the company that re-invented sales training, the Sales Gravy Podcast helps you win bigger, sell better, elevate your game, and make more money fast.
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You’re Coachable, But Are You Truly Humble?
You’ve been coachable your entire career. You take feedback, adjust your approach, read books, listen to podcasts, and implement what works. Yet being coachable doesn’t automatically make you humble—and that gap may be costing you more than you realize.
Nicolas Restrepo, Senior Vice President of Sales at World Emblem, shared on a recent Sales Gravy Podcast episode: “What advice would I give myself ten years ago? Be humble. There’s a difference between being coachable and being humble.”
Most sales leaders assume coachability covers everything. If you’re open to learning, you’re set—right? Not quite. The best sales leadership is built not only on willingness to learn, but on recognizing that your success was never yours alone.
What Being Coachable Actually Means
A coachable leader stays receptive. Feedback isn’t a threat. Adjustments aren’t a burden. You ask questions, try new techniques, and pivot when something stops working.
Coachable leaders attend training sessions and apply what they learn. They don’t cling to “the way we’ve always done it” when the market shifts. Adaptability is their baseline.
But it’s only half the picture.
What Being Humble Actually Means
Humility isn’t self-deprecation. It’s acknowledging the full story behind every win.
Humble leaders recognize the customer service rep who handled tough calls, the operations team that pulled off a miracle to meet a deadline, and the mentor who guided them through a high-stakes negotiation.
Humility shows up when leaders look at a win and say “we did that” instead of “I did that.” It changes the way you speak, how you coach, and how your team shows up around you.
Why Sales Leaders Confuse the Two
It’s easy to blur the lines. Coachability requires some humility. You have to acknowledge you don’t know everything. But it’s possible to be coachable and still operate from ego.
Some leaders take feedback on their discovery process while taking full credit for the deal. They embrace a new objection-handling framework but never acknowledge the people who supported the outcome. They accept coaching but keep score of how often they were right.
Coachability grows your skills. Humility grows your people.
The Risks of Only Having One
Coachability without humility burns teams out. You may improve individually, but hoarding credit discourages collaboration. When that happens, reps start withholding help because they know their contribution won’t be recognized. They stop sharing insights. They stop going the extra mile. Coachable-but-not-humble leaders also tend to ask for help too late. They’ll accept advice when it arrives but rarely seek it out until they’re underwater.
Humility without coachability leads to stagnation. You may share credit generously and build strong relationships, but if you refuse to learn hard truths about your blind spots, your team stalls with you. Some leaders disguise resistance to growth as modesty, deflecting responsibility rather than owning the need for improvement.
You need both.
Where These Traits Show Up in Real Leadership
Consider how coachability and humility show up in everyday situations:
After a big win:
Coachable leaders debrief to find the repeatable actions.
Humble leaders publicly recognize who made the win possible.
When something fails:
Coachable leaders ask what they could have done differently.
Humble leaders avoid placing blame on the team.
During onboarding:
Coachable leaders stay open to feedback from new hires about broken processes.
Humble leaders acknowledge when a new rep brings a skill they don’t have.
In pipeline reviews:
Coachable leaders adjust their forecast based on data.
Humble leaders give credit to the rep who spotted a risk early.
Why This Matters for Long-Term Sales Leadership
Sales leadership is a long game. You’re not just managing this quarter’s number. You’re shaping the culture that determines whether top performers stay or bolt.
Coachability keeps you sharp. Humility keeps your team aligned.
When both traits are active, people share ideas more freely because they know you’ll listen. They fight for deals because their effort is seen. They stay through hard quarters because they trust you’re not in it for personal glory.
How to Develop Both Traits
To strengthen coachability:
Ask your team for feedback on your leadership and apply it.
Work with a peer or mentor who will challenge you.
Notice when you resist feedback and explore why.
Read one sales leadership book per quarter and implement one idea.
To strengthen humility:
When talking about a win, name three people who contributed.
Ask for help early instead of waiting until you’re stuck.
Start meetings by recognizing someone else’s win.
Pay attention to how often you use “I” versus “we.”
Questions to challenge yourself:
When I talk about a win, who gets credit?
Do reps bring me ideas, or wait to be told what to do?
Am I more focused on being right or being effective?
When was the last time I publicly recognized someone?
The Bottom Line
Being coachable gets you in the room. Being humble keeps you there.
You can study every methodology, attend every training session, and absorb every leadership book. But if the goal is proving how great you are instead of elevating how great your team can become, you’re building on sand.
The sales leaders who last, who build high-performing cultures and develop reps who grow into leaders, all understand one truth: success was never a solo act.
Stay coachable so you keep growing. Stay humble so your team grows with you.
Your people will feel the difference. So will your results.
Being coachable and humble is just the start. Learn how to inspire your team, earn trust, and create a culture that drives results. Grab your free chapter of People Follow You and discover the leadership strategies top sales leaders use every day.
Here's a question that'll stop you in your tracks: Would you let someone walk up to you, take your wallet, empty out all your cash and credit cards, and leave your family with nothing?
Of course not. That's insane.
But if you're in sales and you let rejection stop you from making calls, booking appointments, and closing deals, that's exactly what you're doing. You're handing over your commission check to fear.
That was the powerful insight from Wendy Ramirez, a leading Mexican sales expert and author of Lo que nadie habla de las ventas: Estrategias para no ser llamarada de petate or What Nobody Talks About in Sales: Strategies to Avoid Being a Flash in the Pan, on a recent episode of Ask Jeb the Sales Gravy Podcast. When you give rejection the power to stop you, you're literally taking money away from your family. Let that sink in.
The Science of Why Rejection Hurts
Let's get one thing straight right now: I'm not going to sit here and glorify rejection. Nobody wants to be rejected. Unless you're a pure sociopath who feels nothing (and there aren't many of those in sales), rejection is going to hurt you.
It doesn't matter if you're highly outcome-driven like me or highly empathetic. Rejection hurts everyone in different degrees, but it hurts. Period.
Here's what's actually happening inside your body when you get rejected: Your brain treats rejection like a physical threat. Fight or flight kicks in. It's a neurophysical response that dumps adrenaline into your bloodstream, makes your heart race, and creates this overwhelming urge to either run away or fight back.
That uncomfortable feeling? That's not weakness. That's just science.
The Problem: Sales Is a Rejection-Dense Profession
Here's the brutal reality about selling: If you don't face rejection, you're going to fail.
Sales is what I call a rejection-dense profession. When you hit rejection in sales, you don't have the option of going backwards. You can go over it, through it, around it, or dig under it. But your job is literally to go out into the world, find rejection, and bring it home.
That's the job description. That's what we signed up for.
Think about it like this: A few years back, I got invited to jump out of an airplane with the Golden Knights, the U.S. Army's elite parachute team. I'm not a skydiver (just like I'm not a Spanish speaker), but what an honor to jump with probably the best parachute team worldwide.
I asked the guy I was tandem jumping with how many times he'd jumped. Ten thousand times, he said. So I asked him, "Do you ever get afraid?"
His answer changed everything for me: "Of course I get afraid. I'm jumping out of an airplane. Your body is going to get afraid. I've just done it so many times that I know exactly what the process is. I'm able to get myself to jump even though my brain says this is the wrong thing to do."
That's exactly what you have to do in sales.
Building Obstacle Immunity
In my book Objections, I talk about something called obstacle immunity. It's the process human beings go through of facing something that feels really big and uncomfortable, but doing it enough times that we lower the size of that obstacle.
The fear of being rejected never fully goes away. But you can lower that fear.
Here's how you do it:
Develop the Ledge Technique
The ledge technique allows you to interrupt or break the pattern you feel in fight or flight when you get rejected. It helps you regain your poise and confidence so you know what to say next. It's about taking control of the conversation when someone gives you an objection.
Understand the Difference Between Objections and Rejection
An objection isn't the same as a rejection, even though they feel essentially the same in your body. When someone objects, they're giving you information. When someone rejects you, they're saying no. Learn to tell the difference.
Focus on Emotional Discipline
In emotionally tense situations, you've got to be emotionally disciplined. You've got to gain control, gain poise, and handle those objections in a way that allows you to achieve your desired outcome.
The Mindset Makes All the Difference
Sales is a skill position. There are particular skills, techniques, and tools you need to deploy to be good at the craft. But the thing that makes all the difference is what's in your head.
This is no different than athletics. Elite athletes all operate at similar skill and talent levels. They'll tell you that winning or losing happens between the ears.
I'm a big golfer. The difference between me having a really good game or a really bad game is one hundred percent what's in my head. My body knows what to do. I know how to swing the club. The mental game is everything.
If you don't fix your mindset, you're not going to get the results you're expecting. People think they're stuck and can't move forward. But it's just about moving your mindset. Get more information. Learn something new. Apply what you learn. That's how you increase your mindset and get better results.
Stop Giving Away Your Power
When Wendy said, "When you give to the clients, when you give to the people that rejected you, the power to stop you, that's what exactly you do," it hit me like a freight train.
You wouldn't let someone take your wallet. You wouldn't let someone steal from your family. So why would you let rejection steal your future?
The next time you feel that uncomfortable feeling in your chest after getting rejected, remember this: That feeling is just your body doing what it's supposed to do. It's not telling you to quit. It's telling you that you're doing something hard, something that matters, something that will pay off.
Face your fear. Make the next call. The difference between average salespeople and elite performers isn't talent. It's the willingness to go through rejection instead of around it.
That's how you win.
Ready to take your sales game to the next level? Check out The LinkedIn Edge to learn how to leverage the world's most powerful B2B social selling platform to fill your pipeline, build relationships, and close more deals.
Your prospects know when you're waiting for your turn to talk. They can feel when you're performing instead of partnering. And the moment they sense you're treating them like a transaction, you've already lost the sale, or at least the loyalty that comes after it.
The difference between good salespeople and unforgettable ones isn't about closing techniques or fancy proposals. It's about becoming the trusted sales advisor your buyers can't imagine doing business without. It's about evolving from vendor to linchpin—the person who holds everything together.
What Does It Mean to Be a Linchpin?
A linchpin is the small pin that holds a wheel on its axle. Remove it, and everything falls apart.
In sales, being a linchpin means you're more than someone who takes orders or delivers quotes. You're the trusted sales advisor buyers turn to for guidance, validation, and expertise. They don't just buy from you; they believe in you. They want your opinion. They rely on your consistency. And when things get messy, they know you'll help them make sense of it all.
But most salespeople never reach linchpin status. They stay stuck in the vendor zone: quoting, pitching, following up, moving on. It's safe. It hits metrics. But safety doesn't create loyalty.
Why Most Sellers Stay Vendors
The vendor zone is comfortable. You know what to do. You have a process. You check boxes.
But here's the problem: your prospect can feel when you're focused on yourself instead of them. They know when you're running through a script or waiting to launch into your pitch. And that feeling—that sense of being just another number—kills trust before it ever has a chance to grow.
Being a trusted sales advisor requires something different. It requires you to slow down, tune in, and genuinely care about the person across from you. That's where the magic happens.
Build Emotional Connection Through Reading the Room
The best salespeople don't take behavior at face value. They interpret it.
When a buyer seems distracted or cold, linchpin sellers pause and ask themselves: What's really happening here? Is this person overwhelmed? Skeptical because of a bad past experience? Or just thinking deeply because they need time to process?
Here's how to sharpen your ability to read buyer emotions:
Match and mirror. Notice their pace, tone, and energy, then subtly align with it. People feel safer with people who move at a similar rhythm.
Say what you're thinking. Use your inside voice as your outside voice. Try: "It sounds like this project has a lot of pressure behind it" or "You seem hesitant—can I ask what's causing that?" Naming emotions and behaviors politely opens doors.
Embrace the silence. Silence doesn't mean rejection. It means your buyer is thinking, absorbing, processing. This is where most salespeople blow it. They open their mouths too soon because they can't handle the quiet. Five extra minutes of patience is often what stands between winning and losing a deal.
Reading people is empathy in motion. But it takes work. And most salespeople don't take the time.
Lead With Curiosity
Curiosity is the trait that rarely gets enough attention in sales training. But when you're genuinely curious about what makes your buyers tick—what drives their decisions, what matters most to them, what keeps them up at night—you move past small talk and into real conversations.
When you show up to serve instead of showing up to sell, curiosity becomes natural. You ask questions to understand what your customers actually need. You build solutions together. And that's the moment you become essential to solving their problems.
Here's how to leverage curiosity as a trusted sales advisor:
Ask one more question. When your buyer answers, don't jump into your pitch. Say, "Tell me more about that" or "What else is behind that concern?" That extra question is where the truth often lives.
Replace judgment with wonder. When a prospect makes an odd request, don't think "That's ridiculous." Think "I wonder what's driving that?" That mindset shift changes your energy completely—and they can feel it.
Prep curiosity prompts before each meeting. Write down three open-ended questions that start with "how" or "what." Questions like "How will this impact your team's workload?" or "What happens if nothing changes?" uncover real motivation.
The phrase "I'm so curious about..." has become a game-changer in discovery calls. It opens doors to deeper conversations. Most buyers will jump right in, and the conversation flows naturally. Your job is to listen, take notes, and get even more curious as they open up.
Evolve Into an Indispensable Consultant
Most salespeople understand the concept of being consultative: asking questions, offering insights, guiding decisions. But the best take it further. They become so valuable that their clients' success feels harder to imagine without them.
When you become indispensable, things don't function properly without you. People need you, not just want you. You bring unique value that can't easily be replaced, because nobody is you.
Here's how to go beyond helpful and become essential:
Diagnose before you recommend. Don't rush to fix. Take time to fully understand the client's situation. Ask deeper questions. Look for patterns. Confirm what really matters before offering solutions. You'll gain trust faster through understanding than urgency.
Teach through insight. Help your clients see their business from a new angle. Bring context, data, or perspective they haven't considered. When they walk away from a meeting thinking differently because of you, you're no longer just a vendor—you're a resource.
Lead with consistency and integrity. Show up when it's easy, but also show up when it's not. Be steady, dependable, and transparent, especially when outcomes are uncertain. Indispensable consultants don't disappear when things get complicated. They stay close, communicate clearly, and make it easier for clients to move forward with confidence.
When you understand deeply, teach clearly, and lead consistently, you become more than a salesperson. You become part of your clients' strategy. You become the trusted sales advisor they call first.
People Buy You First
Being a linchpin isn't about what you sell. It's about how you show up for the buyer.
When markets shift or leadership changes, your product might change—but your presence shouldn't. People will always buy you first.
Show up curious. Listen for meaning, not just for answers. Teach what you know. Stay steady when others panic.
This approach moves you from being one of many to being the one they call first. That's how you go from vendor to linchpin.
Ready to master the techniques that turn you into the trusted sales advisor your buyers can't live without? Download the FREE Sales Gravy Book of Play by Gina Trimarco and get the tools, tactics, and techniques to become a more effective and agile communicator in spontaneous sales conversations.
The automated "Great job, team!" email blasted to 47 people at 4:37 PM on a Friday isn’t authentic appreciation. Neither is the generic gift basket ordered by someone in HR who’s never met your top performer, or the corporate recognition program where nobody actually feels valued.
These things look like recognition, but your people know the truth: leadership is outsourcing one of the most human tasks—seeing the people who show up every day and make things happen. And your teams feel the disconnect.
As Jeb Blount Jr. recently said on the Sales Gravy Podcast: "Don't make your appreciation to customers, to your team, to yourself a completely outsourced behavior. It will be cheap, and everyone will know it."
Authentic appreciation can’t be delegated to your human resources team or automated through your CRM. And that's exactly why it works.
Where Sales Leaders Go Wrong with Recognition
Most sales leaders fall into one of two camps.
Camp one believes they don't have time for appreciation because they're focused on results. The numbers are what matter. Recognition is soft skills territory—nice to have, but not essential.
Camp two wants to show appreciation but defaults to the path of least resistance. They sign the company card. Approve the budget for the year-end gift. Forward the congratulatory email from the VP. Box checked.
Both camps are missing what actually moves people. Recognition that matters requires you to see the work that often goes unseen. It demands that you pause long enough to notice not just the outcome, but the effort behind it. That's not something you can outsource.
Why Small Moments Compound Into Big Results
There’s a concept in professional development about making 1% improvements every single day. Over 365 days, those tiny adjustments compound into exponential growth.
Authentic appreciation works the same way.
You don’t need a massive recognition program. You don’t need elaborate gestures or expensive rewards. You need consistency in the small moments that tell your team: I see you, and what you are doing matters.
Consider the sales rep who stays late to prep for tomorrow’s presentation. The account manager who defuses a client issue before it reaches your desk. The teammate who mentors the new hire without being asked. These moments happen every day, and most leaders miss them entirely because they’re scanning for the big wins.
But your team isn’t just looking for recognition when they close the monster deal. They’re looking for it on Tuesday afternoon when they’re grinding through their 50th prospecting call. They’re looking for it when they’ve had a brutal week and still show up ready to perform.
Small acts of authentic appreciation in these moments build trust faster than any annual award ceremony ever will.
3 Elements of Authentic Appreciation
Authentic appreciation has three non-negotiable elements.
Specific means recognizing exactly what someone did and why it mattered. Not "great work on that account," but "the way you handled that objection about pricing showed real creativity—you reframed value instead of dropping price, and that's exactly the approach we need more of."
Timely means you don’t wait for the quarterly review or the annual celebration. You recognize the effort when it happens, while it’s still fresh and meaningful.
Personal means you deliver it in a way that resonates with that individual. Some people want public recognition. Others prefer a quiet conversation. Some treasure a handwritten note. Others just want to hear it directly from you in the moment.
Here’s what this looks like in real leadership: One sales leader makes it a practice to handwrite notes to team members. Not emails. Not Slack messages. Actual pen-on-paper notes. Some are two sentences. Some are three paragraphs. But everyone is specific to something that person did and why it mattered to the team.
Is it efficient? No. Does it scale? Not really. But those notes end up on office walls, in desk drawers, and tucked into planners. Years later, people still have them. That’s the difference between authentic and outsourced.
Integrate Authentic Appreciation Into How You Already Work
Most sales leaders know they should show more appreciation. They feel guilty about it. They add it to their to-do list. And then the day gets away from them.
The problem is treating appreciation as an extra task instead of integrating it into what you’re already doing.
You’re already having one-on-ones. Reviewing deals. Walking the floor or jumping on calls. The question isn’t whether you have time—it’s whether you’re paying attention in those moments.
When reviewing pipeline, don’t just look at the numbers. Notice the effort. "I see you’ve been hitting activity goals consistently for six weeks straight. That discipline is setting you up for a strong Q1."
When someone sends an update email, reply with more than “thanks.” Take 30 seconds to acknowledge what they did: "This breakdown made my job easier. I didn’t have to dig for answers. That kind of communication makes our team more efficient."
These aren’t grand gestures. They’re small moments of paying attention and responding like a human being who notices when people do good work.
Building a Culture Where Authentic Appreciation Flows Both Ways
The best team cultures don’t just flow from leader to team member; they flow in every direction.
When you model authentic appreciation, your team starts doing it for each other. They notice the work that happens behind the scenes. They start going the extra mile. The culture shifts from everyone waiting for the leader’s approval to everyone building each other up.
One practice that works: create space in team meetings for peer recognition. Not forced or formal—just an open moment where anyone can call out something they appreciated from a teammate that week. Keep it optional. Keep it genuine. You’ll be surprised how quickly it becomes part of your team’s rhythm.
Additionally, most high performers are terrible at acknowledging their own progress. They hit a goal and immediately move to the next one without pausing to appreciate what they just accomplished.
In coaching sessions, start by asking: “What’s a win from this week?” Make them say it out loud. Make them acknowledge their own growth. That internal recognition builds resilience and momentum that external praise alone can’t create.
What Happens When You Get This Right
When you stop outsourcing appreciation and start building it into your leadership, everything shifts.
Retention improves. People stay where they feel seen and valued. They leave when they feel invisible.
Team energy changes. Appreciated people bring more to the table. They take ownership. They go the extra mile because they want to.
Difficult conversations get easier. When someone knows you genuinely care about their success, they’re more open to feedback and coaching.
Culture becomes magnetic. Top performers want to work on teams where their contributions matter. They can feel the difference between authentic and transactional leadership from a mile away.
Take Action This Week
Stop waiting for the perfect appreciation program or the right company initiative. Start with what you can control right now.
This week:
Write one handwritten note to someone on your team. Be specific about what they did and why it mattered.
In your next one-on-one, ask “What’s a win from this week?” and let them acknowledge their own progress.
Catch someone doing something right—however small—and tell them in the moment.
End your next team meeting with clear recognition for one person. Not generic praise, tell them exactly what you noticed and why it mattered.
This month:
Create a recognition moment in every team meeting. Make it specific, not generic.
Ask yourself: What recognition do I wish I were receiving? Then give that to someone else.
When reviewing pipeline or performance, comment on the effort, not just the outcome.
Stop Outsourcing What Should Be Human
The work you do as a sales leader matters. The people on your team matter. And the small moments where you choose to show up and recognize their effort—those matter most of all.
Your team isn’t waiting for the next corporate initiative or the annual awards ceremony. They’re waiting for you to notice. They’re waiting for you to care enough to say something about the work they’re doing right now.
Stop outsourcing what should be human. Lead with authentic appreciation today, and watch your team thrive.
Want to turn recognition into motivation that sticks? Our Sales Gravy University course, 4 Keys to Keeping Your Sales Team Motivated When Everything Hits the Fan, gives you the proven framework to transform appreciation into performance. Learn how to build a sales culture where people feel seen, valued, and driven — even in hard times.
Here's a question that'll expose one of the most common productivity killers in sales: How much research should you do before making a cold call?
That's the challenge Michael Bricker from West Monroe, Louisiana brought to a recent Ask Jeb episode. Five months into his role at Cantara Networks, a fiber-backed internet provider, Michael was supposed to spend three minutes researching each prospect. Instead, he found himself spending 15 to 30 minutes per call, terrified he'd miss the one critical insight that would unlock the door.
Sound familiar? If you're nodding right now, you're not alone. This "research paralysis" is one of the most insidious productivity traps in modern sales, and it's killing your pipeline velocity.
The Big Lie Your Brain Tells You
Let's get one thing straight: Research is not prospecting. Research is research.
Every minute you spend digging through a prospect's LinkedIn profile, reading their latest press release, or analyzing their org chart is a minute you're not actually doing any prospecting activity. You're not talking to anyone. You're not having conversations. You're not moving deals forward.
But here's where it gets dangerous. When you add in the basic human fear that comes with making cold calls, research becomes an emotional crutch. Your brain lies to you and whispers, "If I just know all this information, it'll be so much better."
So you spend 15 minutes researching, make the call, and it goes to voicemail. You make 12 calls a day. Everyone goes to voicemail. All that research, and you didn't get anywhere.
How Much Do You Actually Need to Know?
Michael had a breakthrough realization that changed everything: "I'm not looking to make a sale on that initial cold call. I'm looking to make a connection."
That's the insight that separates efficient prospectors from research addicts.
On your first cold call, you're not selling them anything. You're trying to set an appointment so you can ask questions and figure out whether it makes sense to keep talking. That's it.
So how much do you really need to know to set that appointment? The answer is not a lot.
Think about it this way: The more you get to know your customers, your business, and your industry, the more business acumen you gain. Over time, you'll talk to ten businesses just like the one you're about to call. You'll recognize patterns. You'll see that companies in a certain sector or geographic area all face the same three challenges.
You don't need 15 minutes of research to recognize those patterns. You just need to build a message around them.
When Research Actually Matters
Now, before you throw all research out the window, let me be clear about when it does matter.
If you're sending a prospecting email, do some research. You're putting something in writing, so you better have some insight that's not AI-generated garbage.
If you make a call, get a hard no from the CEO, and want to try again with a different message, do the research before you call back. You've hit a wall. Now you need ammunition.
If you've had a first meeting and you're going into discovery, absolutely do deep research. You're walking in armed because you know they'll be there waiting. All that effort will pay off.
But for that first cold call? Stop overthinking it.
The Batching Solution
If you feel like you absolutely need to do research (and I get it, some people do), here's the fix: Schedule time before your call block for research.
Do all your three-minute lookups in one batch. Write your notes next to each name. Then go make the calls.
Why does this work? Because you're going to hit voicemail a lot anyway. But at least you'll have the research done and maintain your call momentum.
Let's say you run a call block on 25 cold leads. You talk to five people. Those five give you information like "I'm not the right person" or "We don't have that problem." Now you know something. Now go back and do deeper research on those five so you can come back with a better message.
That's efficiency. That's strategy. That's how you maximize your prospecting time.
The Power of Targeted Messaging
Here's what really unlocks productivity: Creating targeted messages for roles or industries instead of personalizing every single call.
If you're calling 25 CIOs in the healthcare sector, you and I could sit down and quickly identify what they're dealing with. What issues are they facing? What do they want from their business? How could you help them?
We could build one or two messages that'll connect with most people on that list without researching every single prospect.
Then you make 25 calls in an hour instead of researching five people and making five cold calls in three hours.
Which approach do you think sets more appointments?
Every Meeting Has One Job
Michael asked about moving deals forward after discovery, and here's the framework that keeps everything simple:
The entire purpose of a prospecting cold call is to get the first meeting.
The entire purpose of the first meeting is to get the next meeting.
Everything else is academic.
Each step in your sales process exists to advance to the next step with a committed micro-commitment. When deals stall, it's almost always because you didn't nail down that next step or you didn't test stakeholder engagement.
If a prospect says "I'll get you that information next week" and next week comes and goes, what are they telling you? They're not that into this. It's not a priority.
Keep deals moving by driving momentum through committed next steps.
The Bottom Line
Stop letting research become a productivity trap. The goal isn't to know everything before you make a call. The goal is to have enough conversations to fill your pipeline while making each one count.
Be confident in your ability to get someone on the phone and convert them into an appointment. If you hit a wall and get valuable information, then go back and research for your next attempt.
But if you're researching every prospect before every cold call, you're lying to yourself about productivity. You're avoiding the hard work of actually prospecting.
Batch your research. Build targeted messages. Focus on conversations that convert. That's how you build a pipeline that actually moves.
Want to transform your approach to prospecting and turn LinkedIn into your ultimate lead generation machine? Check out The LinkedIn Edge and learn how to leverage the world's most powerful B2B platform to fill your pipeline with qualified opportunities.
This is a very special Monday because it's Thanksgiving week here in the United States.
This is the week we pause to express gratitude for the people in our lives, for what we've been given, and for what we've accomplished.
But gratitude isn't just a feel-good emotion reserved for the holidays. It's also a performance- and life-enhancing routine that can give you sales superpowers.
Gratitude Builds a Strong Mindset
Sales is a mental game. Your mindset, attitude, and beliefs have more impact on your sales outcomes and ultimate success than any technique, script, or strategy ever will.
This isn't soft psychology. This is neuroscience. Gratitude activates the parts of your brain associated with reward and emotional regulation. It releases dopamine and serotonin, neurotransmitters that make you feel good, leading to increased happiness and decreased anxiety and stress. Your confidence rises, your mind clears, you gain emotional control, and you make wiser decisions.
Gratitude fundamentally rewires how your brain processes the world around you. When you practice gratitude consistently, your brain shifts from focusing on what could go wrong and starts seeing what could go right.
Gratitude and insidious self-pity cannot coexist. Instead of dwelling on the deal you lost, the prospect that rejected you, or the leads you don’t have, you appreciate the lessons you’ve learned and the opportunities still in front of you.
But it goes deeper than just feeling better.
Gratitude Builds Resilience
In sales, you face rejection constantly. Bad weeks, tough months, prospects who ghost you after months of work, and deals that fall apart at the last minute, even though you did everything right.
In this brutal profession, the salespeople who survive and thrive are the ones who bounce back faster from these inevitable setbacks.
One of the key traits of highly successful people is an enduring belief that everything happens for a reason. When you can find something to appreciate even in difficult situations, you maintain your emotional stability. You don't spiral into negativity. You don't let one bad call ruin your entire day. Instead, you process the setback, learn from it, and move forward.
Abundance vs Scarcity Thinking
When you focus on what you do have—your skills, your relationships, your opportunities, your resources—you shift from scarcity thinking to abundance thinking.
Scarcity thinking is the mother of negativity. It says: "I don't have enough leads. I don't have enough time. I don't have enough support. I'm going to miss my number."
Abundance thinking is a mindset of opportunity and potential. It says: "Look at the skills I've developed. Look at the customers who trust me. Look at the opportunities in my pipeline. Look at what's possible."
When you operate from gratitude and abundance, you become more creative, more energetic, more persistent. You stop fixating on limitations and start exploring possibilities.
You show up differently. You bring positive energy. And people feel it. They want to work with people who are confident, positive, and focused on what's possible rather than what's impossible.
Cultivating an Attitude of Gratitude
But here’s the thing. You don't wait to feel grateful. You choose to practice gratitude. The feelings follow.
Every morning, you are empowered to make a conscious choice about where to focus your attention. You can focus on what's missing, what's wrong, who’s against you, and what's hard. Or you can focus on what's present, what's working, what's possible. Both perspectives contain truth. But only one moves you forward toward the success and happiness you are seeking.
Here are some practical ways to build gratitude into your daily routine:
Keep a gratitude journal. Every morning or evening, write down three things you're grateful for. My friend Eric, who suffered from a severe brain injury, does this, and the impact it has had on his recovery is nothing short of a miracle.
Thank someone every day. Send a text, an email, or better yet, make a phone call. Thank a customer. Thank a colleague. Thank a team member. Express genuine appreciation for something specific they've done.
People naturally gravitate toward those who express genuine appreciation. When you thank a customer for their business, when you acknowledge a colleague's help, when you recognize someone's support, you strengthen those relationships. It makes you someone people want to work with, buy from, and help succeed.
Mentally acknowledge the good. During your day, when something positive happens, pause for just a moment and mentally acknowledge it or say a prayer of thanks. Don't let it pass by unnoticed.
Reframe challenges. When something goes wrong, ask yourself: "What can I learn from this? What opportunity might this create? What's the hidden gift in this situation?" This isn't about pretending problems don't exist. It's about looking for the lessons and possibilities within them.
Start your week with gratitude. Every Monday, give thanks for the week ahead and the opportunity you’ve been given to make a difference in your life, for your family, company, and customers.
The beautiful thing about gratitude is that it is like a muscle; it gets stronger with exercise.
My Gratitude to You
Before wrapping up, I want to take this opportunity to pause and express my gratitude to you.
I'm grateful to you for listening to the Sales Gravy podcast. My team and I pour our hearts into producing this show, and your support means everything to us. Your comments, your reviews, your messages telling us how the podcast has helped you, fuels us.
I'm thankful for the fans of my books. Writing is one of my greatest joys in life, and you make that possible. Every time someone tells me that "Fanatical Prospecting," or "Sales EQ," or "The LinkedIn Edge" changed their career, it reminds me why I do this work.
I'm grateful for the companies around the world that trust Sales Gravy to train their teams. You let us into your organizations, trust us with your people, and give us the opportunity to make a real difference. That's a privilege we never take for granted.
I'm grateful for the sales professionals who invest in themselves through Sales Gravy University. Your commitment to getting better inspires us to keep creating better content.
And most of all, I'm grateful for the amazing people who choose to work at Sales Gravy. We are blessed with an incredible team that wakes up every morning focused on serving you and making a difference. They're the reason we can do what we do.
Thank you for allowing us to be part of your professional journey.
Reflecting on Gratitude
So as we head into Thanksgiving week, I’ll leave you with this simple reflection:
Be thankful that you don't already have everything you desire. If you did, there would be nothing left to reach for, no reason to dream, no horizon pulling you forward.
Be thankful that you don't know everything. It means life still has mysteries to reveal and lessons waiting to shape you.
Be thankful for the difficult times. It's in these seasons that you grow stronger, wiser, and more resilient.
Be thankful for your limitations. They remind you that there is still room to stretch, improve, and become more than you are today.
Be thankful for challenges and obstacles. They forge your strength, your courage, and your character. These are the things that truly endure.
Be thankful for your mistakes, because each one is a teacher guiding you toward better choices and deeper understanding.
Be thankful for what you've been given. Every gift is proof that someone cares, someone believes in you, someone has invested in your journey.
Be thankful for the people who push you, support you, frustrate you, and inspire you. Each one plays a role in shaping the person you are becoming.
Be thankful for beginnings, endings, and every transition in between. They are the chapters and seasons of a life story still being written.
Be thankful for Monday, because Monday brings new possibilities.
And at the end of the day, when you are tired and weary, when you’ve stopped and made one more call, be thankful because it means you've made a difference.
An attitude of gratitude changes how you approach your day—and your prospects. My new book, The LinkedIn Edge, shows you how to leverage that mindset to build genuine connections, engage with your network, and create opportunities that actually convert.
Most new account executives stare at their territory list and feel the weight of it immediately. Fifty accounts. A hundred accounts. Sometimes more. Each one needs research, a plan, and outreach that doesn't sound like every other cold email clogging their prospect's inbox.
Jake McOsker, an account executive at Forrester Research, found himself facing exactly this problem when he moved from BDR to AE. He cracked it by changing how he used AI for account planning.
"Rather than taking 10 to 15 minutes to get an account plan out or understand who the notable stakeholders and the decision makers that I need to go with," he explained, "it's a 2 to 3 minute process to go through each one of these accounts."
The traditional approach to AI account planning doesn't solve the territory problem. You ask ChatGPT or Claude for company information, and you get Wikipedia summaries. Founded in 1987. Headquartered in Dallas. 15,000 employees. The chief sales officer you're calling doesn't care about any of that, and showing up with generic facts makes you look lazy, not prepared.
When you're new to the role, you don't have years of pattern recognition to fall back on. You don't know what good account planning looks like yet. You just know you need to get meetings with people who have better things to do than talk to a rep they've never heard of.
The solution isn't using AI as a search engine. It's using it as a sales assistant with a specific job to do.
The Problem With How Most Reps Use AI for Account Planning
Here's what usually happens. A rep needs to prepare for a call with a VP of Marketing at a healthcare company. They open their AI tool of choice and type: "Tell me about [Company Name]."
The AI spits back:
Company history
Product offerings
Recent press releases
Maybe some executive names
The rep skims it, copies a few bullet points into their CRM, and calls it account planning. Then they get on the call and realize they have no idea what this VP is actually trying to accomplish this quarter. They ask surface-level questions. The prospect checks out. The meeting goes nowhere.
This happens because most reps are using AI like a faster Google. They're asking for information instead of asking for intelligence.
AI account planning only works when you give the AI a role and a specific outcome to deliver. Not "tell me about this company." Instead, "You're an account executive trying to book a meeting with this company's CMO in the next two weeks. Based on their recent announcements and what their executives are posting on LinkedIn, what initiatives are they likely prioritizing right now?"
How to Set Up AI Agents for Account Planning
The difference between a basic AI chat and an AI agent is memory and context. When you create an agent, you're teaching it what kind of output you need every single time. You're not starting from scratch with every account.
Here's the framework that works:
Step 1: Give Your AI Agent a Clear Role
Don't just ask questions. Set up the scenario with urgency and context. For example:
"You are an account executive at [Your Company]. You've been tasked with bringing in [Target Company] as a new customer within the next 90 days. Your first call is with their [specific role, like Chief Sales Officer]. Based on the materials I'm providing, what are the top three business initiatives this person is likely focused on right now?"
This does two things. First, it forces the AI to think from your perspective instead of just summarizing data. Second, it prioritizes current, actionable information over historical background.
Step 2: Feed It the Right Source Material
Wikipedia summaries don't help you. But these sources do:
Recent press releases about new initiatives or leadership changes
LinkedIn posts from executives at the company (especially the person you're calling)
Company blog posts about their strategic direction
Industry news articles mentioning the company
Their "About Us" or "Newsroom" page for current priorities
Analyst reports or industry trend pieces relevant to their sector
If you're selling to publicly traded companies, earnings call transcripts and annual reports (10-Ks) are gold mines. But most new AEs aren't calling on Fortune 500 companies. The good news is that smaller companies often share more on LinkedIn and their blogs because they're trying to build their brand.
Upload PDFs or paste content directly into your AI tool. Then let it analyze the content through the lens of the role you gave it. The output will focus on strategic priorities, not corporate history.
Step 3: Ask Follow-Up Questions Based on Persona
If you're calling into marketing, tech, security, or customer experience, the priorities are different. Your AI agent should help you understand how company-wide initiatives affect the specific person you're talking to.
After the initial analysis, ask: "How would these initiatives specifically impact the VP of Marketing's goals this quarter?"
Now you have talking points that matter to the person on the other end of the call.
Step 4: Validate With Human Intelligence
AI gets you 80% of the way there in three minutes instead of fifteen. But you still need to cross-check. Look at LinkedIn. Check recent news. If you have access to account managers or customer success reps who work with similar companies, ask them if the trends you're seeing match reality.
AI account planning is a tool, not a replacement for critical thinking. If the output feels off, it probably is. Trust your gut and adjust.
How to Turn Research Into Value Messages
The goal of account planning isn't to memorize facts about a company. It's to walk into a conversation with an informed hypothesis about what they're trying to accomplish.
When you do this right, your opening changes. Instead of starting cold with "Tell me about your role," you can say:
"I saw your CEO recently posted about accelerating your digital customer experience, and I'm assuming that's putting some pressure on your team to modernize how you're approaching customer engagement. But I could be completely wrong. What's actually taking up most of your time right now?"
Here’s how you’ve impacted your prospect: First, it proves you did real research. Second, it gives the prospect something specific to react to instead of making them explain their entire world from scratch. Third, and this is critical, it still leaves room for discovery.
You're not skipping the "What are your biggest challenges?" question. You're earning the right to ask them by showing you've already thought about their business. When prospects talk about their challenges in their own language, you learn how they frame problems, what matters to them, and where your solution might actually fit.
Even if your hypothesis is wrong, you've separated yourself from the 90% of reps who show up with nothing. And when you're right, you skip past the surface-level conversation and get straight into the dialogue that matters. That's how you earn credibility as a new account executive, even when you don't have ten years of experience to lean on.
Building a Repeatable AI Account Planning Workflow
This only scales if you systematize it. You can't rely on remembering the perfect prompt every time or recreating your process from scratch for every account.
Create separate agents for different use cases. One for account planning. One for prospecting outreach. One for call preparation. Train each agent for the output you need so you aren’t constantly course-correcting.
Save your account plans in a central location. The information changes, so plan to refresh your research quarterly. What mattered in Q2 might not matter in Q4, and your account planning needs to reflect that.
The key is building a system that you can repeat across your entire territory without burning out. Two to three minutes per account. Not fifteen. Not thirty. That's how you research 50 accounts in a week instead of just five.
What This Actually Looks Like in Practice
Let's say you're targeting a mid-market software company. You start by checking their LinkedIn. The CEO posted last week about expanding into healthcare verticals. You pull up their blog and find three recent posts about compliance challenges in healthcare tech.
You upload screenshots or copy the text into your AI agent and give it the prompt:
"You're an AE trying to close this software company in 90 days. The first meeting is with their Chief Revenue Officer. What are the top three priorities they're likely focused on, and how do those connect to the company's broader goals?"
The AI analyzes the content and tells you:
They're investing heavily in healthcare vertical expansion, but facing longer sales cycles due to compliance requirements
They're dealing with the need to build credibility fast in a regulated industry
Their CEO has committed to proving ROI in healthcare within two quarters
Now you have a hypothesis. The CRO is probably under pressure to close healthcare deals faster while managing a team that doesn't have deep healthcare expertise. That's your angle.
You cross-check this with LinkedIn and see that the CRO has been engaging with posts about sales enablement in complex verticals. You look at recent news and find they just hired a VP of Healthcare Sales. Everything lines up.
Your outreach message writes itself. You're not pitching. You're acknowledging what they're working on and offering a perspective on how companies in similar situations have approached the same problem.
What to Do After the Meeting
Your AI workflow doesn't end when the call does. This is where most reps leave value on the table.
After your meeting, take the transcript from your call recording tool (Fathom, Gong, Chorus, whatever you use) and upload it to your AI agent. Then ask specific questions:
Here's a question that hits closer to home than most sales reps want to admit: What do you do when you've been away from prospecting for a while and suddenly the call reluctance feels brand new again?
That's the situation Dwayne Malmberg from Sugar Land, Texas found himself in. He'd been crushing it in inside sales and appointment setting since the 90s. He was good at it. Really good. But after taking just over two years away from the phones, a new opportunity came along and suddenly he was facing something he didn't expect.
The call reluctance. The trepidation. The mental resistance to picking up that phone and dialing invisible strangers.
If you've ever taken time away from prospecting and felt that same knot in your stomach when it's time to get back on the phones, you're not alone. And more importantly, there's a systematic way to rebuild that muscle and get back to crushing it.
The Raw Truth About Cold Calling Fear
Let's get brutally honest: Cold calling creates emotional angst. Period.
I've made tens of thousands of cold calls. I make them with my clients during training sessions. I'll make them tomorrow morning. And I still feel that trepidation on the first couple of calls of the day.
It's just human. It's natural. It never completely goes away.
Think about it like jumping out of an airplane. A few years ago, I got the chance to jump with the United States Army Golden Knights. I was terrified. My heart was pounding. A sergeant even asked if I was okay because apparently I looked frightened.
When we got strapped in, I turned to the Golden Knight I was jumping with and asked, "Do you ever get scared?" His answer was revealing: "Yeah, of course I do. My heart's beating a little bit because it's an airplane and I don't know what's going to happen. But I've done it so many times and I've got a routine."
That's the key. The routine. The process. The mental preparation that gets you past the fear and into action.
The Big Pull: Why You Need Something Worth Fighting For
Here's the problem with facing fear: If you don't have something pulling you forward that's bigger than the discomfort you're feeling right now, you'll procrastinate forever.
The discipline to run a prospecting block and do your prospecting is the discipline to sacrifice what you want now for what you want most.
So before you even think about picking up the phone, sit down and write out what you want. Why are you doing this? What's the goal? Is it a paycheck? A promotion? Financial freedom? Providing for your family?
That's your big pull. That's what you focus on when you start your day, not whatever might happen on the call. Because when you're thinking about something as scary as facing rejection, if you don't have a big pull driving you, you'll end up avoiding the work that matters most.
For Dwayne, part of his why was clear: He's a caregiver for his disabled wife and needs the flexibility to work from home while still providing for his family. That's a powerful pull. That's something worth pushing through fear for.
Building the Muscle: You Can't Bench Press 250 on Day One
Let's say you were a bodybuilder in your 30s. You were strong, lifting heavy, crushing it in the gym. Then life happened. Kids came along. Your career took off. You quit working out.
Now you decide it's time to get back in shape. What happens if you walk into the gym and try to bench press 250 pounds on day one?
You're going to hurt yourself. Maybe badly.
The same principle applies to prospecting after time away. You already know how to do it. You've got the muscle memory. Everything inside you is saying, "I got this." But you can't expect to jump back in at the same intensity level you had before.
You have to rebuild the muscle gradually. Start with the equivalent of those 20-pound dumbbells and work your way back up.
The High-Intensity Sprint Strategy
When I found myself in a similar situation years ago, uncomfortable and fearful about making calls, I developed a strategy that I now call high-intensity prospecting sprints.
Here's how it works: Break your prospecting into very small, short blocks. Sometimes just five minutes. Make five calls in five minutes. Or ten minutes. Or fifteen minutes.
The key is this: Make it so small and manageable that your brain can't talk you out of it. If I tell you to make cold calls all day long, that feels overwhelming. But if I ask you to knock out just five calls, you can do that.
Then here's the critical part: Follow each sprint with something inspiring. Read a chapter from Fanatical Prospecting. Listen to a segment of your favorite sales podcast. Watch a training video. Put good stuff in your ears and in front of your eyes that builds your courage and strengthens your heart.
Then do another sprint. More inspiration. Another sprint. Repeat.
What happens is two things: First, by actually doing it instead of thinking about it, you get better at doing it. You get what I call sales endorphins. You feel good about yourself because you realize, "Hey, I can do this. Everything's okay."
Second, by backing up each sprint with inspirational content, you're feeding your mindset. You're building back that mental muscle alongside the practical muscle.
The Time Management Factor for Busy Sales Professionals
If you're like Dwayne and have a lot of responsibilities outside of sales, time management becomes critical. You can't afford to waste time or dilute your prospecting efforts.
The solution is ruthless prioritization and time blocking.
Start your day with your most important, highest priority sales activity. Get your prospecting done first thing in the morning when your willpower is strongest and your emotional energy is highest.
Here's why this matters: When you've got a lot going on and you're also doing the hardest job in sales (making outbound calls), by the time you get later into your day, you're worn out. Your willpower is depleted. It's going to be exponentially harder to find the motivation to interrupt strangers.
But first thing in the morning? You're fresh. You're ready. You can knock out that prospecting block and then ride that momentum through the rest of your day.
Block your calendar in core chunks for everything you need to do. If you have an appointment at 3 PM that'll take three hours, fine. But that first hour of your day? That's sacred prospecting time. Nothing else touches it.
The Mindset Foundation: Feed Your Mind Daily
The first section of Fanatical Prospecting focuses on mindset because that's where everything begins. If your mindset isn't right, technique doesn't matter. Scripts don't matter. Nothing matters because you won't execute.
Feed your mind daily with content that builds you up. Listen to a sales podcast three days a week. Read sales books. Watch training videos. Surround yourself with messages that reinforce the behaviors you want to develop.
When you're in a situation where you feel fear or emotional angst, putting good stuff in your ears and eyes has a tendency to make your heart stronger and build your courage.
This isn't fluffy motivation. This is practical psychology. You're literally rewiring your brain to associate prospecting with positive emotions instead of fear and anxiety.
The Bottom Line
Getting back in the prospecting game after time away isn't about summoning superhuman courage or pretending the fear doesn't exist. It's about acknowledging the fear, building a routine to work through it, and gradually rebuilding the muscle you once had.
You already know how to do this. You've done it before. You just need to give yourself permission to start small, build consistently, and focus on progress over perfection.
Start with your why. Build your prospecting sprints. Front-load your day. Feed your mind with the right content. And remember: The first call is always the hardest because you're lifting that 10,000-pound weight. But once you make it, the momentum starts building.
You've got this. Now go pick up the phone and prove it to yourself.
Want to learn how to leverage LinkedIn to fill your pipeline and never run out of opportunities? Check out Jeb Blount's latest book with Brynne Tillman, The LinkedIn Edge, and discover how to turn social selling into your secret weapon.
A few years ago, I was on a desperate search for a dining table. My favorite from my old place was a gorgeous, single-piece antique that mathematically wouldn’t fit in my new home. I loved that table, and losing it felt like losing a member of the family. So I started the hunt for a replacement, a piece worthy of its memory.
I found a potential candidate at a high-end furniture store: a stunning cherry table.
I ran my hand along its smooth, cool surface, picturing it loaded with platters of food, surrounded by the people I love. But then I saw the price tag. It was prohibitively expensive. My wallet slammed shut. I knew it was perfect, but I just couldn’t bring myself to pay for it. I walked out, resigning myself to a life of settling.
In the end, I found a mass-produced, joined-piece from a department store. And for the next six months, I was miserable. My kitchen table was just … a table. It was functional, but it had no soul. I griped about it constantly, and every time I looked at it, I was reminded of what I'd given up.
Discovering Sweat Equity
Finally, out of options and patience, I took the advice of an antique store owner.
"Go see a woodworker," she said.
I drove to the address, a dingy, dark garage on the southside of town that smelled of sawdust and varnish. Here, in this dusty, disorganized space, I found the most beautiful tables of every shape and size imaginable.
A gruff man with calloused hands appeared. I told him about my predicament and my budget. He gave me a direct response: “I can’t build you a table for that price.”
Just as I was giving him an obligatory thanks and turning to leave, he hit me with an unexpected question: “Are you interested in learning how to make one? It might cost you less than what I’ve already made.”
He wasn’t selling me a table. He was selling me an experience. A partnership.
Becoming a Co-Creator
And so, we began. He showed me the design software. We walked through different scenarios, from Christmas dinner to my kids doing their homework. We chose the wood, figured out the curves for the legs, and decided on the thickness for the top. Every line was to my specifications. I was a co-creator, not a consumer.
When he finally showed me the quote for materials and his lessons, it was 30% more than the expensive showroom table. And yet, the decision was simple. I looked at the plans, the time we’d invested in the design, the conversations we had shared, and I said, "Let's build this."
I picked out the perfect piece of maple. He taught me how to cut it, sand it, and shape it. How to use a router to create decorative edges. How to apply gloss for a perfect shine. And when we were done, I paid that higher price gladly—despite all its imperfections (I am not a professional carpenter.).
This was my table, built with my sweat, crafted with my hands. I’d earned it.
One leg was a half-inch too short.
The decorative edges I’d spent hours on didn’t quite match. And the lacquer? Let’s just say it had a certain, unique texture. This table was, objectively, flawed. And yet, I loved it more than any piece of furniture I had ever owned.
When I brought it home, I was so proud. I invited people over just so I could show it off. Every time I looked at it, I found myself thinking how perfect it was, even with its flaws. That slightly askew table wasn’t just furniture; it was a blinding flash of the obvious and a lesson in the concept called The IKEA Effect.
Applying the Principle in Sales
Not long after my dive into woodworking, I found myself in a similar situation with a prospect.
We were selling a sales training program, and the decision-maker leveled with me in our proposal meeting: "I love what you're proposing, but your competitors are beating your price. We're on a budget."
I was about to chalk the deal up to closed-lost when the memory of that woodworker's shop flashed through my mind.
“How about this,” I said, "I know our price is higher, but I think we—you and I—can design something perfect for your team. What if we work together to craft a custom solution, one that covers all your needs and fits into your company culture?"
He was skeptical, but he agreed. So we began our own version of a woodworking project.
Instead of sawdust and maple, we worked with spreadsheets and shared documents. We spent hours in meetings, outlining their team's specific pain points, the obstacles they faced with pipeline hygiene, and the skills they were lacking. We designed a plan with the right workshops, the right coaching, and the right support for their specific problems.
When I finally presented the final proposal, it included a fee that was 20% higher than the competition. But it wasn't a surprise. We had built it together, every step of the way. He saw not just a list of services, but a reflection of his own team's needs. He had invested time, effort, and insight, and had a sense of ownership.
How Co-Creation Wins the Deal
With our co-created plan in hand, the client happily paid our higher fee. We’d edged out the competition not because of our price, but because we had triggered The IKEA Effect. This behavioral economic principle states that people place a disproportionately higher value on things they have helped to create.
Every frustrating moment, every small victory when we are building something creates what behavioral economists call "effort justification." Your brain can't accept that all that work you put in was for something ordinary, so it reframes the result as extraordinary. It's the same reason my handmade table, with its slight wobble and imperfect edges, felt more valuable to me than the flawless, expensive showroom piece.
And it's exactly why that prospect was willing to pay a premium for our sales training. By involving him in crafting the solution—by making him a co-creator rather than just a buyer—we triggered the same psychological principle. He didn't just purchase a program; he helped design it.
The Lesson: Ownership Matters
When people build something—whether it's furniture, solutions, or relationships—they don't just create the thing itself. They create ownership.
Here’s how you can apply this to your own sales process:
Discovery is the new co-creation. Your discovery calls shouldn't be a simple Q&A. It should be a collaborative workshop. Use tools like a shared whiteboard or a live-edited document to build the solution with your prospect in real time. Frame it as, "Let's figure this out together."
Your proposal is a project plan, not the final word. Think of your proposal as the culmination of shared work, not a final document you deliver. Refer to it as "our plan" or "the solution we designed." This language reinforces the joint effort.
Make it their idea. The more effort your prospect invests in the process—even just by providing a little bit of input—the more they'll value the outcome. Ask open-ended questions that require them to provide genuine insight. Say things like, "Help me understand...," or "What would the ideal outcome look like for you?" When they tell you, it's their vision, and you're helping them bring it to life.
The Big Takeaway
The IKEA Effect is far more than a psychological quirk; it's a strategic weapon for every salesperson who wants to stop losing on price. The truth is, your customers aren’t buying a product or a service—they're buying the feeling of a win.
When you empower your prospects to become co-creators in the sales process, you don't just solve their problem; you make them the hero of their own story.
You don’t need to be the low-price leader to get the business. You just need to have the courage to ask them to build a solution with you.
Hear more insights based on real-life business successes and flops on Jeb Blount Jr.’s podcast 30 Minutes or Less: How Flawed Sales Incentive Programs Cost Domino’s $78 Million, part of The Sales Gravy Podcast.
To a sales leader, it’s a familiar story.
Month one: Your new SDR is on fire. Energy through the roof. They’re excited about cold calling.
Month two: Still strong. Meetings are getting booked. Dashboard looks good.
Month three: Cracks appear. Rejections pile up. But they hang in.
Month four: Burnout.
The dials drop. The energy’s gone. That superstar you hired 90 days ago is updating their LinkedIn profile—and you know exactly what that means. Now you’re back in hiring mode, your team’s pipeline is slipping, and your recruiting budget just took another hit.
But it’s not that the SDR role is broken—the system is. Sales teams are great at starting fast and terrible at sustaining it. People get thrown in with a script and a quota, celebrate quick wins, then act surprised when burnout becomes inevitable.
Tim Hester, VP of Sales Development at Alliance HCM, leads one of the fastest-promoting SDR teams in the industry. His team survives month four and keeps thriving. Some SDRs promote out in 60 days. Others stay because they’re growing, not just grinding.
It’s a tactical framework that stops inefficiency.
The Problem: You’re Forcing SDRs to Run Without a Finish Line
When Tim inherited his SDR team, he saw the pattern immediately. One SDR position. No progression. No momentum. Just grind.
Talented people hit quota, kept hitting quota, and then started asking themselves: Why am I still doing the exact same job six months later? “Just wait your turn” doesn’t cut it anymore. Maybe it never did.
The wake-up call came when Tim realized something critical: The things that kill SDR motivation aren’t trainable.
Work ethic. Mindset. How someone approaches their day and prospecting blocks. That’s character. You can’t coach it in a workshop. Tim tried way too many times before figuring that out.
You can teach someone objection handling. You can show them how to use the CRM. But if there’s no light at the end of the tunnel, no amount of training fixes that. That’s on leadership, not the rep.
The Solution: Build a Roadmap That Rewards Performance, Not Tenure
Tim flipped the script on how SDR performance gets measured and rewarded. He created tiered SDR levels based purely on performance thresholds. Not tenure. Not politics. Not “when a spot opens up.”
The roadmap has clear levels: from new SDR to quota-hitting SDR to exceeding SDR who now trains the team. Each level comes with a comp bump and more responsibility. Most importantly, it proves effort matters.
This framework ensures that when your reps look at the dashboard, they see a clear, actionable path for progression. It’s the sales leader’s job to ensure that dashboard clarity is tied directly to the next level.
The impact is immediate. Reps see exactly what they need to level up. There’s no waiting for someone to quit so that a spot opens. Those who want to move fast can; those who need more time have a clear path, too.
This framework changed recruiting entirely. Tim could tell candidates on day one: People move up at their own rate; you control your trajectory at this company.
Suddenly, the SDR role wasn’t a holding pattern. It was a launchpad.
The Dashboard: Four Metrics That Actually Matter
Metrics are your scoreboard. If your reps don’t trust the score, they stop playing hard.
When Tim took over, the dashboard was a mess. Crowded with metrics nobody understood or trusted. Reps tuned it out because they didn’t know what half the numbers meant or how they connected to their success.
Tim stripped it down to four metrics:
Dials – Shows effort and how they’re working the database. Everyone can pick up the phone.
Connections – Only counts conversations with decision-makers. Not gatekeepers. Not assistants. This shows outreach quality.
Meetings Scheduled – The conversion from connection to meeting. This is where you see who’s actually selling.
Meetings Ran – If they don’t show up, what’s the point?
For Tim, the most important is the latter three because of their impact. He’s measuring what drives meetings and revenue. Simple. Clear. Actionable. No vanity metrics.
The Training: Start with Mechanics.
Most companies try to turn SDRs into product experts on day one. Tim does the opposite.
He breaks training into three buckets:
Mechanics – CRM management, using the dialer, and objection handling. These are fundamental basics that must be mastered before there can be further movement.
Knowledge – Developing an ICP and persona basics. Narrow and focused. Build your knowledge on the people who matter.
Art – The intangible skills that develop over time as reps sit in on meetings and watch demos.
Setting that expectation allows reps to move fast. It might not be the straightest line, but they’re executing, gaining confidence, and booking meetings in week two instead of week eight.
SDRs aren’t closing six-figure deals. They’re scheduling introductory meetings and bringing in the account executive who has the expertise to close. Expecting perfect performance on day one slows ramps and kills confidence. Employ mechanics first and let the art follow.
The Mindset: Small Changes, Big Impact
Before Tim was a leader, he spent too much time searching for the silver bullet. He’d toss the whole playbook after one bad call, desperately seeking the one "secret" that would make prospecting easy.
His breakthrough was realizing his job as a leader wasn't to teach the art of the perfect call, but to build the system that rewarded consistent effort.
Now, he drills this into his team: consistency. It's a direct result of the structure he built. Reps commit to consistency because they know the roadmap proves that their small daily progress will compound into a promotion.
The commitment to consistency starts during onboarding. By clearly presenting the tiered performance levels and the four key metrics on day one, leadership sets the expectation that results are driven by process, not luck. When the path is clear, reps stop searching for a shortcut.
Consistency beats flash every time. Average SDRs become consistent producers. Consistent producers become top performers. The system is the guarantee that their consistency will pay off.
Month Four Doesn’t Have to Be the End
The SDR graveyard isn’t full of lazy people; it's full of frustrated talent who were put on a treadmill when they needed a ladder. By month four, a high-performer has mastered the basics and is staring at the ceiling. Same script. Same job. Same quota. They burn out from futility, not from effort.
Tim Hester's approach stops this cycle. He proves that the only way out is up.
Clear metrics keep the focus sharp.
Tiered levels create propulsion.
A performance-driven roadmap ensures reps know they control their destiny.
The question every sales leader must ask is: "What message does our system send on day one?"
Empower your reps with a plan they can believe in, and your top talent will be busy working toward their next title, not updating their resume.
Your roadmap gives your SDRs the path, but they still need the tactics to fill their calendar and earn that promotion. Download Sales Gravy's 25 Ways to Ask for the Appointment on a Cold Call guide.
Here’s a truth most car dealerships don’t want to admit: people don’t hate buying cars. They hate buying cars from salespeople who make the customer experience painful.
That’s the challenge Brendan Carlington from Mount Pleasant, Michigan brought to me on a recent episode of Ask Jeb. Brendan jumped back into auto sales this year after spending time in other industries and he noticed something big. Traditional sales positions are disappearing. Customers can research everything online, get quotes instantly, and even start negotiations with a click. What’s missing is training that teaches sales pros how to create an experience people actually enjoy.
The vehicle isn’t the differentiator. The experience is.
Why the Experience Matters More Than the Product
I told Brendan something I have felt for a long time. Customers already know what they want before they walk into the dealership. They have seen every trim, every feature, every price point. What they do not know is whether they will enjoy the buying process.
That is where you, the salesperson, become the product. Your job is not just to sell the car. Your job is to guide your customer through the process, reduce friction, build trust, and make them feel confident that they are making the right decision.
When I buy a car, I already know what I want. If the experience is miserable, I put it off. If I know it will be smooth, engaging, and human, I buy immediately. Modern buyers are craving a guide, not a grinder.
The Power of Frameworks
Brendan had a simple but powerful philosophy. He said there are three conditions to win: sell a car, give the customer a great experience, and make as much money as possible without compromising those things. That mindset is exactly what great sales frameworks are built on. A framework gives you rails to run on while keeping you flexible in the conversation. It is not a script. It is a repeatable system that lets you adapt to the customer while staying disciplined.
When you take complex sales processes and make them simple and repeatable, you create reliability and confidence. That principle is at the heart of fanatical prospecting and objection handling. Learning to simplify complex ideas into actionable steps separates average salespeople from top performers.
How to Become the Trusted Guide
If you are in car sales or any sales role where buyers can research online, here is the playbook:
Unpack your customer’s fears. They walk in with emotional baggage from past experiences. Acknowledge it.
Ask better questions. The more they talk, the better they feel. When the customer does most of the talking, they have a good experience.
Create a VIP moment. Buying a car is a milestone, not a transaction.
Build a repeatable system. Know your greeting, discovery questions, and closing flow cold and practice it until it is second nature.
Using systems that focus on outcomes, such as first-time appointments, conversion rates, and pipeline velocity, makes the difference between a salesperson who spins their wheels and one who consistently drives results. Practicing this every day builds the kind of discipline that leads to consistent performance and customer loyalty.
Making It Fun Again
Brendan shared something I loved. Before car sales, he worked in the Vegas nightlife industry and he asked, “Why can’t buying a car be fun?” That is the kind of thinking that transforms an industry. Fun does not mean loud music or strobe lights. It means energy, curiosity, and enthusiasm. When people enjoy buying from you, they tell everyone they know.
If your dealership or team has lost that spark, it is time to rebuild your sales culture. Focus on making the customer experience unforgettable. Strong sales leadership and coaching techniques help teams focus on guiding the buyer through the process instead of just pushing products. Developing those skills consistently pays huge dividends in customer retention and referrals.
The Big Lesson
At the end of our conversation, I told Brendan something simple. The car industry does not need more closers. It needs more guides. When every spec and price is a Google search away, the only true differentiator left is how the customer feels.
You cannot automate human connection. You cannot AI your way into trust. You can build systems that make people feel seen, heard, and valued. Simplify the process. Ask more questions. Be a guide. Make it an experience worth repeating. That approach works whether you sell cars, software, or consulting services.
If you are serious about building influence and opportunity in the modern sales landscape, my newest book with Brynne Tillman, The LinkedIn Edge, is your playbook for creating meaningful professional connections.
We are moving into the most dangerous time of year for sales professionals . . . the holidays.
From now until the first week of January, you're going to face a perfect storm of distractions, excuses, and temptations that can absolutely destroy your year-end number and your first-quarter production next year. Sadly, most salespeople don't even see it coming. It’s not until the end of December that they realize they’re in trouble, but by then, it’s too late.
The Trouble With the Holidays
The trouble typically starts Thanksgiving week in the United States and continues as we move into the first week of December. That's when distractions start flooding in. You've got company parties, family obligations, and shopping to do. All of which knocks you off your routine, causing your daily prospecting and follow-up activities to drop.
And let’s be honest, you’ve been grinding hard for the entire year, and you’re ready to let your guard down and coast a bit before the end of the year.
By the second and third week of December, many of the opportunities in your pipeline that you were counting on closing start to ghost you or tell you that they're pushing decisions off to next year. And by now you’re so mentally checked out that you're barely doing any prospecting at all.
Once we move into the Christmas and New Year's weeks, your office is a ghost town, the phones are silent, your pipeline is stalled, and you’ve missed your forecast. You convince yourself there's no point in even trying.
And just like that, you've lost an entire month of selling.
My book The LinkedIn Edge gives you the master blueprint for turning LinkedIn into an optimized, revenue-generating sales engine—whether you're deploying Sales Navigator or not.
Learn to work LinkedIn like a professional with step-by-step, immediately actionable tactics that supercharge your presence on the world's largest networking platform. Get it today wherever books are sold.
Holiday Sales Math
But here's the brutal truth: You didn't just lose a month. You lost three months. Because all of those prospects that pushed off decisions until the new year are not coming back, and that empty pipeline you're staring at, as you move into January, is going to haunt you through March and potentially, through the entire year.
Your average sales cycle is probably 60-90 days. That means deals you put into the pipeline over the next two to three weeks are crucial for a good January. Likewise, the ones you add in December are the key to delivering a solid February and March.
But if you allow the Holidays to take you off your game, you might not recover until April or May. Your entire first quarter is shot.
This is the killer, and how so many promising sales careers end prematurely. I've witnessed far too many salespeople get fired in March for pipeline problems that started in November when they let their discipline slip during the holidays.
Do Not Allow Active Deals Stall and Die
The deals currently in your pipeline are more vulnerable right now than at any other time of year. Your prospects have the perfect excuse to push decisions.
When deals sit idle for a month, bad things happen. Stakeholders change. Budgets get reallocated. Priorities shift. Your champion gets distracted by seventeen other initiatives. Your competitors slip in while you're eating fruitcake and drinking eggnog.
I've watched salespeople lose six-figure deals that they thought were "locked up" in November, simply because they took their foot off the gas during the holidays.
I’ve said this before, and I’ll say it again. Pipeline opportunities that push into the new year are not coming back. Do not count on them. Do not allow yourself to be delusional about them. If you don’t get forecasted opportunities closed by the end of the year, consider them dead!
For this reason, you must be vigilant with follow-up, assertive with your communication, and do whatever it takes to get those deals closed.
The Holiday Discipline Advantage
When it comes to prospecting, the activity that keeps your pipeline healthy, the real reason you struggle during the holidays is that you give yourself permission to slack off. You tell yourself little lies to justify taking it easy. "Nobody's making decisions right now anyway." "Everyone's on vacation." "I'll ramp back up in January."
Yes, some prospects are on vacation. But not all of them. Yes, some decisions get pushed. But not all of them. Yes, it's harder to get people on the phone. But not impossible.
The salespeople who crush it during the holidays understand something that everyone else forgets: Outselling the holidays is all about discipline. It is discipline that transforms holiday impulsiveness into intention and a higher income.
This is where mental toughness pays off and shows up in your bank account. During the holidays, more than ever, you need a concrete plan and the discipline to execute it.
5 Keys to Outselling the Holidays
Here's what you need to do right now, and I mean this week:
Step One: Conduct a Pipeline Audit
Go through every deal in your pipeline. Assess the risk of each one stalling during the holidays. Then decide what needs to be done before year-end to get them closed.
For your most important opportunities, create a specific action plan. Don't assume anything will "just keep moving forward" on its own. These deals will not close themselves. Nothing moves forward without your effort.
Step Two: Block Your Calendar
Pull up your calendar for the rest of this year. Block time for daily prospecting, deal advancement, and follow-ups.
Yes, I know you have holiday parties and family obligations. Put those in, too. The key is planning everything in advance so you don't drop the ball.
You may have to get creative. Maybe you prospect for an hour before the rest of your family wakes up or make follow-up calls during your lunch break. Maybe you work a few hours on the weekend.
The point is, if it's not on your calendar, it won't happen. And if your calendar is blank for the next month, your pipeline will be blank in January.
Step Three: Set Non-Negotiable Activity Targets
This is critical. Decide right now what your daily minimums are going to be during the holiday season. Set the targets. Write them down. Commit to them. Then—and this is the important part—review your progress against these targets every single morning and every single afternoon to hold yourself accountable. Nobody else is going to do this for you. You have to be your own accountability partner.
Step Four: Front-Load December
We know that the last two weeks of the year are going to be a circus, so double down and bank as much activity as possible at the end of November and into the early part of December. That way, by the time Santa comes down the chimney, you've already done the work to keep your pipeline healthy.
Step Five: Plan Your January
Don't wait until January 2nd to start thinking about your first quarter. Plan it now. What's your goal for Q1 revenue? How much pipeline do you need to hit that goal? What actions do you need to take now to start strong in January? Top performers don't "get back into it" in January. They hit January running because they planned for it in November.
This isn't about working 80-hour weeks. It's about being strategic with your time so you can be productive AND enjoy time with your family. By maintaining discipline during the holidays, you actually feel less stressed and enjoy them more.
Take Action Now
Now here’s your assignment: Block two hours on your calendar this week. Use that time to conduct your pipeline audit, build your holiday schedule, and set your activity targets.
Don't wait. Don't tell yourself you'll get to it next week. Do it now.
The salespeople who take this seriously will end the year strong and start off next year even stronger. The salespeople who ignore this advice will spend the first quarter digging themselves out of a hole.
The only question that remains is which one of these salespeople are you going to be?
And remember, when it's time to go home, especially during the holidays when you're tempted to call it early, always stop and make one more call. That discipline is often the difference that will help you outsell the holidays.
Every salesperson knows that feeling, the one right before the big meeting when confidence wavers and doubt creeps in.
Alex Weber knows it, too. He’s one of the few people to go from hosting American Ninja Warrior to competing on the show. When I asked him what separates winners from everyone else on an episode of The Sales Gravy Podcast, he said:
“Winners believe they're going to win. You’re not going to win every deal. But even as I say that, I’m never going to let myself actually believe that.”
This is a masterclass in sales mindset—the mental toughness every top salesperson needs. The difference between a competitor who freezes and one who performs is simple: The winner chooses belief over hesitation, every single time.
Stop Managing Doubt, Start Dictating Belief
The average salesperson walks into a deal trying to manage their doubt. They worry about the competition, they worry about the price, and they worry about rejection. That hesitation bleeds through every presentation, email, and follow-up.
The average rep tells themselves, "I hope I get this deal."
Winners decide before the phone rings that they are the best solution, they deserve the business, and they are going to win. That mindset is the foundation of high-performance selling.
The moment you let the "what if I lose?" question become dominant, you pull back. You ask soft closing questions. You accept the first objection. Top salespeople know that a soft sales mindset guarantees a hard loss. You must carry the confidence of a winner, even when the odds are stacked against you.
Failure is Feedback: Burn the Ship and Move On
In high-stakes competitive environments, you can’t dwell on failure. If a Ninja Warrior misses a jump, they can't afford to spend five minutes replaying the error in their head; they are already in the water.
In sales, the deep end is rejection. Too many salespeople treat a "no" like a personal failure instead of professional feedback. They let one bad call destroy their attitude for the entire week. This is why their sales mindset is fragile.
Winners understand that every loss is simply data to be analyzed. What did the client object to? Where did you lose control? What did the competitor do better? Process it immediately, then move on.
When you fail, you need to "burn the ship." You acknowledge the loss, extract the lesson, and sever the emotional attachment. The inability to recover fast is the #1 killer of a sales mindset. You are guaranteeing an underperforming pipeline if you can't reset your mental state between calls. Commit to the next interaction, not the last one.
Build Your Muscle Memory for Pressure
You can't expect to be calm and collected during a high-pressure, high-dollar negotiation if you haven't trained for it. Elite competitors don't rely on game-day adrenaline. They rely on muscle memory built through intentional practice under pressure. Practice is how you develop the sales mindset that never wavers.
Identify the parts of the sales cycle that make you uncomfortable. If handling tough objections is your weakness, practice them relentlessly until your response is automatic. If you freeze up when cold calling top-tier decision-makers, role-play the opening three minutes of that call until you can deliver it with confidence. Your pipeline grows on competence, not hope.
Stop Waiting for Motivation: Execute on Discipline
The worst lie in sales is the idea that you have to feel motivated to prospect. Motivation is an emotion. It comes and goes. Discipline is a decision.
The champion's sales mindset relies on routine and process. You don't need to feel excited to make that fifth cold call or send that critical follow-up. You just need to execute your process.
If you let your feelings dictate your schedule, you will only prospect when the conditions are perfect. That is an amateur move.
Winners know the work is non-negotiable. Discipline is showing up every day, executing the critical, revenue-generating tasks, whether you feel like it or not. Action generates confidence, not the other way around.
Mindset Self-Check
Before your next call, take a quick inventory. Are you waiting to feel motivated before you move? Trying to perfect your pitch before you prospect? Avoiding rejection instead of embracing feedback? Hoping your natural talent alone will carry you?
These are the quiet traps that keep a sales rep average. Winners don’t eliminate fear or doubt—they acknowledge those feelings and act in spite of them. Awareness is the first step to changing your mindset.
The Champion's Blueprint: Practical Sales Mindset Application
Belief is useless without action. Here is how you convert these principles into real-world results:
Sign the Pre-Game Contract: Before every high-stakes call, mentally commit to executing your process perfectly. Measure success on execution, not outcome.
Implement the 10-Minute Failure Review: Immediately after a significant loss, spend five minutes documenting the facts and five minutes identifying one tactical weakness. Then burn the ship and reset before the next call.
Drill the Difficult: Identify your five hardest objections. Role-play them ten times in a row until responses are instant and fluid. This builds pressure-proof sales muscle.
Anchor to Ownership: Eliminate excuses. If you lose, it’s your responsibility to figure out why and fix it. Ownership anchors performance in proactive power.
The 60-Second Reset: Before each appointment, take a brief break. Stand up, walk away from your desk, and reset your mental state to give the next customer 100% focus.
The Bottom Line: Dive In
The choice is clear. Fear can dictate your actions, or you can adopt the sales mindset of a champion.
Show up tomorrow and do the work whether you feel like it or not. Make the calls that scare you. Go after the deals that feel out of reach. Stack evidence that you're getting better.
It all comes back to belief. The winners who dive into the deep end don’t wait for confidence to appear—they tell themselves they’re going to win, then act like it until it’s true.
The deep end isn’t where you sink. It’s where you prove you belong.
If you’re ready to build the mindset, discipline, and belief that top performers rely on, we can help. Whether you’re a salesperson leveling up, a leader developing your team, or a business owner driving growth, we’ll build a coaching path around you. Check out our coaching programs!
Here's a question that'll mess with your head: What do you do when you're making seven figures in sales, crushing every goal, and suddenly … you just don't feel the same motivation anymore?
That's the question Matthew Feit from Toms River, New Jersey, posed on an Ask Jeb episode. Matthew's living the dream that most salespeople chase their entire careers. He's at the top of his game financially. He's proven everything he set out to prove. And now he's stuck in this weird limbo where the fire that got him there has gone cold.
If you're shaking your head right now, thinking this is a champagne problem, you're missing the point. This is one of the most dangerous positions a high achiever can find themselves in, and it's costing top performers their edge every single day.
The Jim Story: When Achievement Becomes Your Enemy
Let me tell you about Jim. Years ago, when I was living in Florida, I had this sales rep who was an absolute monster. Top of the ranking report. Presidents Club. Rolex on his wrist for winning. Then one day, his director of sales wanted to put him on a performance improvement plan. In sales, a PIP means you are a dead man walking.
I drove up to Jacksonville thinking there had to be some mistake. When I sat down with Jim, I realized the problem wasn't his ability. The guy was still incredibly talented. The problem was he'd won everything there was to win, and he just didn't have the next goal driving him anymore.
Here's what I learned: The things we do in sales are hard. They're repetitive. We deal with difficult people. It takes massive discipline, which is simply sacrificing what you want now for what you want most. But when you don't know what you want most anymore, that discipline evaporates.
Jim's answer surprised me. He wanted a Harley-Davidson, but his wife wouldn't let him buy it. So I worked out a way to structure his commissions so he could get his Harley while still bringing home the money his wife expected. Suddenly, his sales went through the roof again. He had something driving him.
The Cognitive Dissonance of High Achievement
Here's what's happening with guys like Matthew and what happened with Jim: They've got this level of cognitive dissonance. Part of them is a stone-cold high achiever who needs to be achieving. The other part is saying, "I don't feel it anymore. I don't have that juice."
When you're younger or earlier in your career, you're sketching out goals constantly. I remember having a goal book where I wrote down everything I wanted. One of my goals was a house on the inter-coastal waterway in South Florida. I achieved that goal. Then one day I'm sitting there going, "Well, what do I do now?"
It's easy to get comfortable when you don't know where to go next. But comfortable is the enemy of excellence in high-performance sales cultures.
What Do You Really Want?
I hit the same wall this year. Twenty years building this business, book number 17 coming out, and I'm asking myself the same question Matthew asked: "What now?"
I finally figured it out. My wants aren't things anymore. Maybe in my 20s and 30s it was about what I was going to own, but today it's different. It's about what I want to accomplish and who I want to work with.
I realized I want to work with people and companies I know I can help. That are a challenge for me. Where I can watch them grow and enjoy seeing them succeed. Who really want to work with me and see me as part of their organization, not as a vendor.
As a result, I've been rearranging my world so I can be very picky about what I'm going to do, who I'm going to work with, and who I'm going to speak to. I want to do things that give me joy and fulfill my purpose, which is to help people sell more. That's why I believe God put me here.
The Twenty Year Vision
When I was a little older than Matthew, I looked at my life and asked: "What are the next 20 years going to be like?"
I had won every award you could win in sales. I was operating at the top level of a Fortune 200 company. I had the accolades, the money, all of it. So I asked myself that simple question.
What happened over those 20 years completely changed my life. Everything shifted. I wrote my first book when I was 38. It wasn't great. But it was my story, and it was the beginning. I made a goal to write five books in five years. Twenty years later, The LinkedIn Edge is book is number 17.
Here's the thing: When I was 38, I didn't know exactly where I'd be at 58. I just knew I was going to make a massive impact over the next 20 years as I pursued my purpose. It was simply about helping people.
Stop Thinking, Start Doing
Matthew mentioned wanting to write a book about his journey and helping other people. That's a perfect path for someone at his level.
Here's my advice: Sit down and look ahead. If you were looking at yourself 20 years from now, what would you want that person to look like? It's not so much about what you want to achieve. It's about who you want to be.
Don't wait for the perfect vision. I didn't have some crystal clear picture of where I'd be today. I just knew I needed to change and make an impact. The journey gets you there, but you have to start moving.
For Matthew and for anyone else who's climbed every mountain in their current world: You have everything it takes to do whatever you want. You know that already. But if you get more time to just sit in your vacation home, you're going to go out of your mind in no time because you'll know you're not living up to your potential.
The question isn't whether you should keep pushing. The question is: What are you pushing toward? Answer that, and the fire comes back. Ignore it, and you'll keep wondering why success doesn't feel like it used to.
The best part? Once you reconnect with your purpose and set new goals that actually matter, you'll discover that all those skills that got you to seven figures become even sharper. You're not starting over. You're leveling up.
Jeb Blount is the author of 17 books including the groundbreaking classics Fanatical Prospecting, Sales EQ, Objections, and Inked. In The LinkedIn Edge, co-authored with Brynne Tillman, Jeb teaches sales professionals how to leverage LinkedIn to build their personal brand and fill their pipeline with qualified prospects.
This time of year is critical. As sales leaders map out their budgets for the new year, the conversation always centers on a core conflict: How to cut expenses and, simultaneously, motivate teams to hit larger quotas.
What's the first line item to feel the squeeze? Training and development.
It is often incorrectly labeled a 'want' and not a 'need.' We hear leaders say, "It can wait until next quarter," or, "Once we stabilize revenue, we'll invest in the team."
This short-sighted thinking doesn’t save money. Instead, it's costing organizations a significant, quantifiable amount of revenue and talent. When professional development is treated like a luxury, we undermine the foundational ability of our teams to perform consistently at a high level.
Training is the Foundational Requirement for Peak Performance
Sales leaders should consider peak performance in any high-stakes environment. In the military, or in elite professional sports, ongoing training is not a choice—it is a non-negotiable, daily priority.
So why is it that, in Sales, we view continuous development as optional or too expensive? The simple truth is that lack of training is the most expensive mistake you can make.
Think about the rate of technological change. Most of us have upgraded our cell phones in the last three to five years because the old ones simply couldn't keep up.
The same principle applies to your sales team’s skill set. If your representatives are still relying on techniques learned 5, 10, or 15 years ago, then they are operating at a competitive disadvantage. They will be outmaneuvered and outperformed by competitors who are strategically investing in modern sales frameworks every time.
Henry Ford’s famous quote still holds true: "The only thing worse than training employees and losing them is to not train them and keep them." If you believe training is expensive, you must take a moment to calculate the monumental loss of reps consistently missing their quotas.
The True Cost of Inconsistency and Turnover
Look at the numbers. Assume three of your representatives are consistently missing quota by just 20%. That deficit is lost revenue—but it also represents wasted leads, missed opportunities, and the corrosive ripple effect of deals that never even make it into your pipeline. The amount of potential revenue lost due to underperformance is often far greater than the entire annual budget you would allocate to comprehensive sales training.
Action Plan for Sales Leaders & Managers
To reverse this loss, you must treat coaching as a continuous operational requirement, not a perk.
Calculate the 'Cost of Inaction' to Justify Budget: Reframe thinking of training as an expense and start focusing on the cost of the status quo. Calculate the annualized revenue loss from your bottom 20% of underperforming reps (e.g., missed quota * average deal size). Use that concrete number to justify and secure a budget for development, proving that not training is your biggest liability.
Implement a Continuous Coaching Framework: Don't rely on annual training events. Transform your managers into daily coaches by mandating 30 minutes of structured, one-on-one coaching per week focused on skill development. This reinforcement is what locks in new behaviors and prevents the initial energy gained in training from fading.
The Hidden Expense of Disengagement
Talent turnover is another critical cost of lack of training that is often overlooked. A representative who feels unsupported, or who consistently misses quota because they don’t have the necessary tools and coaching, is highly likely to seek opportunities elsewhere.
The cost of recruiting, onboarding, and ramping a replacement—which includes the loss of established customer relationships and the disruption to team morale—significantly outweighs the expense of proactive investment.
How to Take a Struggling Rep From Liability to Asset
A struggling representative is not necessarily a failure. More often than not, they are simply a motivated individual who has not been properly coached, developed, or given a clear framework for success. They begin their job eager to prove themselves, but without guidance, that initial energy quickly dissipates.
Investing in development can be the deciding factor that transforms a dedicated, yet struggling, team member into a consistent top performer. When you strategically invest, you convert what could have been a liability into a high-value asset for your organization. You also ensure that the talent seeking growth and success will find it with you, not with your competition.
Action Plan for Sales Leaders & Managers
Implement a Mandatory Tiered Coaching Cadence. Shift from generic pipeline reviews to mandating a structured, tiered coaching system: Tier 1 (The Weekly Huddle) for metric accountability; Tier 2 (The 1-on-1 Call) for strategic deal review; and Tier 3 (The Dedicated Call Critique Session) where the rep listens to and dissects a recent call recording (a win or a loss).
Run a Quarterly 'Skill Obsolescence' Audit. Your team's skills are your greatest asset, but they have a shelf life. Conduct a quarterly audit to identify the top three techniques that are obsolete but still being used by your underperformers (e.g., leaving long, rambling voicemails or sending generic proposals). Then, mandate a one-week "kill period" where your entire team replaces that obsolete technique with a modern, proven one.
The Strategic Advantage of a Cohesive Culture
When you commit to consistent training, you don't just sharpen skills—you create alignment, clarity, and confidence across your organization. Every team member speaks the same sales language, follows a unified playbook, and builds the same winning habits.
Training sharpens individual skills, but it also creates a culture where representatives feel supported, valued, and fundamentally equipped to win. The world’s best-performing organizations, from elite sports teams to world-class businesses, all share one critical characteristic: They never stop training.
As you plan for the year ahead, move past the outdated notion that development is an optional line item. See it as the essential fuel for your sales engine.
If you are serious about hitting bigger quotas, accelerating deal velocity, and retaining your high performers, sales training has to be a strategic priority. The organizations that win are not the ones that cut corners on development; they are the ones that double down on it.
Don’t budget for failure. Invest in the skill set that guarantees your next quarter's revenue.
Don't let your pipeline run on empty. Take control of your team's performance today. Enroll your team in the next Fanatical Prospecting Bootcamp Live or visit Sales Gravy University to find more high-impact training options and learn more from Master Trainer Jessica Stokes.
Every sales professional has a horror story that still makes them break out in a cold sweat years later. The deal that imploded spectacularly. The customer interaction that went sideways in ways you couldn't predict. The moment you sat in your car afterward in complete silence, questioning every decision that led you to this career.
These moments feel intensely personal and isolating. But the truth is, every rep who’s lasted in this profession has been there. On an episode of The Sales Gravy Podcast, Ashley Blount and I collected nightmare sales stories from our years in the automotive and telecommunications industries, plus stories from the sales community. We found 16 tales that prove no one faces this alone. Here are some of the most terrifying.
Smelly Dave: The Angel of Death
This sales horror story comes from the automotive industry, posted on Reddit by someone who still sounds traumatized. Dave started at the dealership after Sears closed. We found out he’d been the “Angel of Death” at several franchises—Sears, Future Shop, RadioShack. Every place he touched eventually shut down.
Dave was in his early 40s, wore the same shirt with the same coffee stain on it every single day, and smelled terribly. Customers would flee after test drives, refusing to come back into the building with him. On one occasion, a customer was dry heaving. Management tried to delicately bring up the hygiene issue, but Dave wouldn’t listen.
One day, the manager was told to drop off a sold vehicle to a customer, and Dave drove the chase car. As they returned together, the smell in that enclosed space was so unbearable that the manager walked into the boss's office afterward and apologized for whatever he had done to deserve that punishment. The boss laughed, called Dave in, and fired him on the spot.
The Bluetooth Incident That Still Haunts Ashley
Ashley had been selling cars for a few months when a sweet older couple came into the dealership. The husband was retiring, probably late 60s, and they were one of those rare couples who were actually pleasant to work with. He picked out a lime green Ford Fiesta for his retirement car.
They completed the test drive, finished all the paperwork, and Ashley sent the vehicle back to get ready for delivery. When delivering a new vehicle, you always get in with the customer to help them connect their phone to Bluetooth and walk them through all the features. Since it was a couple, the husband was in the driver's seat, his wife was in the front passenger seat, and Ashley was sitting in the middle of the back seat.
They got his phone connected to the Bluetooth, matched the code, and turned up the volume on the car. He went to open his phone. The most explicit, obscene audio you can imagine came blasting out of the speakers.
Dead silence in that vehicle for what felt like forever. Ashley wished them well, exited the car, and walked back inside, mortified. When asked how it went, she told them the story and muttered, “I don’t really want to follow up. I’m not sure that’s appropriate.”
The Telecom Contractors Who Started a Gunfight
I had door-knocked a large hair salon and built a relationship with the salon owner, who also owned the building. He helped me get in the door with all four of his tenants. Because he was switching, they all switched. I closed three to four months of quota on this one deal because of what he did for me.
Installation day arrives. At 6 a.m., my phone rings. I try to sound as awake as possible with my gravelly morning voice, and the owner immediately screams, "Jeb, what the f**k?"
He explains that our contractors came out the night before, got in a huge argument, waved guns at each other—he swears one of them shot at the other. Then they came back in the morning and dug a trench that cut every single internet line to the building. Every single one. No internet on the salon’s busiest day, and all the other stores were out, too.
I arrived at 6:45 a.m. to a foxhole-sized trench and abandoned equipment everywhere. My heart sank. I escalated straight to the senior VP—two levels below the CEO. It wasn’t elegant, but the problem got fixed. I still use that hair salon to this day/
The $1.4 Million HIPAA Violation
One sales rep had a pediatrics practice ready to purchase his product for $1.4 million. They had already negotiated terms. The last step was to follow up with references, and then they were going for the signature.
Someone on the sales operations team had the brilliant idea to put them in an early adopter program without a test server. They crashed the client's entire live system, and one of the consequences was sending bills to the wrong addresses, which violated HIPAA law. This cost the pediatrics practice not just money but also reputation with its patients.
The deal was completely killed, and the practice announced that it was leaving for a competing system. The rep also lost $600,000 in annual recurring revenue. The sales rep did everything right and watched it all disappear because of a decision someone else made.
The VP Who Sabotaged Everything
Ashley worked on a high-volume account for multiple years. Hitting the mark on everything. The CEO and entire organization loved the work. Then renewal time came, and one of the VPs started making everything difficult.
Meetings became confusing. Clear agreements would somehow transform into something else. Ashley would leave meetings questioning whether she was interpreting things correctly. Her team felt it, too. Was this actually happening, or were they all going crazy?
Eventually, this VP went out with someone from Ashley's company and admitted the whole thing. She was intentionally making everything difficult because she wanted to work with a friend at another firm. Nothing against the work. Nothing against Ashley. Just personal preference dressed up as professional obstacles.
Ashley still won the account. The VP found another job. But the psychological warfare of working on an account where someone is actively sabotaging you—not because of performance but because of hidden agendas—takes a serious toll.
The First Door Knock That Went Horribly Wrong
Sales horror stories aren't always about lost deals; sometimes they're about getting chased out of a building. Ashley was doing her first day of field sales training with a senior rep. They found new construction, talked to someone on-site, and were directed to the owner's main office.
The gatekeeper walked them straight back to the owner's office. He seemed pleasant enough at first. They introduced themselves and mentioned the new building. The minute they started talking about their services, he flipped like a switch.
He started screaming at them to get out, demanding to know why they were soliciting, how they made it all the way back to his office, and who let them in. He chased them out of the building in front of all his employees, yelling the entire time. His office was in the literal back of a shotgun-style building, so it was a long walk of shame past everyone.
They got in the car and sat in silence. Finally, the senior rep looked at Ashley and said, "They're not all like that. I promise." A brutal first lesson in field sales.
When Sales Goes Wrong: What The Best Reps Do
These sales horror stories all share something important: Sales will always put you in situations you can’t predict or control. You can do everything right—prospect well, qualify hard, deliver value—and still watch a deal unravel for reasons that make no sense.
What matters is how you respond. The best reps don’t disappear or point fingers. They show up fast, escalate when needed, and take ownership even when the problem isn’t their fault. They fight for their customers and for the relationship.
If a story like this brings up your own nightmare deal, take it as a good sign. It means you care about your work and take your commitments seriously. That’s what defines a true professional.
The pain doesn’t last. The customer who had the Bluetooth issue still bought the car. The salon owner stayed as a client. Ashley won that renewal. What once felt like failure becomes proof that you stayed in the fight, and that’s what the best reps do.
You're Not Alone
The worst part of a nightmare scenario is feeling isolated. But every rep has a story that still makes them cringe.
What matters is what you do next. Process it, learn from it, and bounce back stronger. Knowing every other sales professional has their own version of disaster can be the fuel that keeps you going.
Listen to the full episode of The Sales Gravy Podcast for all 16 sales horror stories and a reminder: Your worst day in sales doesn’t define your career. How you respond does.
If you’ve lived through your own sales nightmare, don’t let it haunt your next call. Start winning more on cold calls with our free guide, 25 Ways to Ask for the Appointment on Cold Calls, and turn your next “no” into a comeback story.
Here's a problem that'll tie you in knots: You've got a killer software solution that saves companies massive amounts of money on employee benefits. You know exactly who needs it: Fortune 1000 companies with self-insured health plans. But you can't get a single meeting with the people who matter.
That's the situation Peter Kleinman from Provo, Utah, finds himself in. As the sales and marketing guy for his dad's startup, he's tasked with landing enterprise clients while juggling full-time classes at BYU. He has LinkedIn, Sales Navigator, and a burning desire to make it work.
He also has virtually no chance of success using his current approach.
If you're nodding your head right now, keep reading. Because Peter's problem is your problem if you're trying to sell into enterprise accounts without the business acumen, social proof, or strategy to break through.
The 100-Foot Wall Problem
Here's the biggest issue: Fortune 1000 CHROs and C-suite executives have built a wall around themselves that's about 100 feet high. Their entire job is keeping people like you from wasting their time.
And if you're young, inexperienced, or new to enterprise sales? That wall might as well be 1,000 feet high.
Peter is doing everything the sales books tell you to do. He's going straight to the top. He's messaging decision makers on LinkedIn. He's targeting the right titles.
He's also getting absolutely nowhere.
Here's why: It has nothing to do with age and everything to do with business acumen. You can't speak the language of enterprise buyers if you've never lived in their world. You don't understand their buying process, their risk aversion, or the organizational politics that determine whether your deal lives or dies.
Most critically, you're trying to sell something they don't even know they need. And you have zero social proof to back up your claims.
That's not a recipe for success. That's a recipe for frustration, burnout, and a pipeline full of nothing.
The Bottom-Up, Top-Down Strategy
If you can't get to the top, start at the bottom.
I'm not talking about giving up on enterprise accounts. I'm talking about running a multi-threading strategy that builds your business acumen while creating pathways into those massive organizations.
Here's how it works:
Find the amplifiers. These are the people in the trenches who actually deal with the problem your solution solves every single day. They're not directors or VPs. They're managers, analysts, and coordinators who feel the pain but lack the authority to fix it.
These people are 100 times easier to talk to than C-suite executives. They'll take your call. They'll teach you. They'll tell you exactly what's broken in their organization and how decisions actually get made.
Compress your experience. When you talk to these amplifiers, you're not selling. You're learning. You're asking questions like, "Help me understand how you make these decisions," and "What problems are you running into?"
Every conversation compresses years of experience into hours. You learn the language. You understand the pain points. You gather insights that become ammunition for conversations with decision-makers.
Surface the insights upward. Now when you finally get in front of that CHRO or VP of Benefits, you're not some kid with a PowerPoint. You're someone who understands their organization better than they do. You can tell them stories about what their own people are experiencing and how you can close the gap.
That's how you get meetings. That's how you build credibility. That's how you win deals when you have no business acumen and no social proof.
The Insurance Broker Shortcut
Here's another path Peter needs to explore: Insurance brokers.
If you can't talk to the self-insured companies directly, talk to the people who advise them. Insurance brokers work with these organizations every day. They understand the buying process. They know the pain points. They're infinitely more accessible than Fortune 1000 executives.
Better yet, they can become your distribution channel. If your software helps them serve their clients better, they'll sell it for you.
This is classic fanatical prospecting. When your ideal customer is hard to reach, find the people who already have relationships with them. Build those relationships first. Let them open doors you can't open on your own.
Stop Playing in LinkedIn's Sandbox
Peter spends a lot of time on LinkedIn. Posting to the company page. Messaging prospects. Running outreach campaigns.
Here's the truth: C-suite executives aren't hanging out on LinkedIn waiting for your cold outreach. They're not there. And the few who are there ignore 99% of the messages they receive.
LinkedIn is great for research and building your personal brand. But if that's your entire go-to-market strategy, you're dead in the water.
You need real tools. A proper CRM like HubSpot to manage your pipeline and run marketing campaigns. A platform like ZoomInfo to identify the right people and get their actual contact information. An integrated stack that lets you execute across email, phone, and social simultaneously.
Most importantly, you need to pick up the phone. Real conversations with real people will always beat automated LinkedIn messages. Always.
The Real Investment Required
Peter's dad hates sales. He wants to build a great product and have customers magically appear. The company is running its entire sales operation on an Excel spreadsheet.
That's not going to cut it.
If you want to win enterprise deals, you need to invest in the tools, training, and processes that make it possible. You're looking at $50,000 per year minimum for the tech stack alone. Plus conferences, trade shows, and face-to-face relationship building.
That sounds expensive until you land your first six-figure deal. Then it looks like the smartest investment you ever made.
Your Action Plan
If you're in Peter's shoes, here's what you do right now:
Stop going straight to the top. Identify the amplifiers at the bottom of your target organizations and start having conversations with them. Learn the language. Gather insights. Build your business acumen fast.
Find adjacent markets. If decision-makers are too hard to reach, find the brokers, consultants, or advisors who already have relationships with them.
Invest in real tools. Get off the Excel spreadsheet. Build a proper sales tech stack with a CRM, contact database, and marketing automation. Use AI to accelerate everything.
Get face-to-face. Attend conferences. Work trade shows. Build relationships in person where trust forms faster than it ever will over LinkedIn.
Enterprise sales doesn't require working harder. It requires working smarter with the right strategy, the right tools, and the relentless discipline to execute even when the path forward isn't clear.
That's how you break through the wall. That's how you win deals you have no business winning. And that's how you turn yourself from a struggling startup intern into an enterprise sales machine.
Ready to master LinkedIn and build a prospecting system that actually works? Grab a copy of The LinkedIn Edge for the complete handbook on leveraging LinkedIn, AI, and modern sales tools to win more deals.
The year was 1938. Families across America gathered, listening during the golden age of radio. On the eve of Halloween, a broadcast interrupted their evening: A live report claimed Martian cylinders had landed in Grovers Mill, New Jersey. Within minutes, panic erupted as citizens fled their homes, convinced Earth was under alien attack.
The entire event was fake. It was a perfectly executed radio drama by 23-year-old Orson Welles.
Here's the sales lesson tucked into The War of the Worlds sci-fi scare: Welles wasn’t just reading a script. He was executing a masterful lesson in emotional engagement. He had listeners hooked, buying into his story emotionally before their brains had time to register, "Wait, this can't be real."
That emotional buy-in is a core tenet of sales: People buy on emotion and then justify it with logic and facts.
If rational adults can flee their homes over a fictional Martian invasion, imagine the force of emotion you can unleash when you find your prospect's emotional trigger. Sharpen your emotional intelligence, and you deploy a powerful sales tool.
Emotion Gets the Attention, Data Seals the Deal
Welles sold tension, uncertainty, and gravity, not a product. His voice was calm yet urgent, delivered with the authority of a trusted news anchor. The audience felt an adrenaline surge—heartbeats rising, eyes widening—before they had time to check the facts.
This is the non-negotiable first step in sales. Your passionate storytelling creates the emotional charge. Your tone carries more weight than any spreadsheet full of ROI data. Emotion gets your buyer leaning in and invested in the outcome. The data you provide simply helps them sleep well at night after they’ve already made their decision.
If your message isn't landing, stop reviewing your product deck and start analyzing your delivery. Are you speaking with urgency, and are you connecting to their emotional state? Without that emotional resonance, even the best solution just adds to the noise.
Authority Isn't Arrogance, It's Command
Welles dressed his fictional story in familiar trappings like live news bulletins, eyewitness reports, and crackling radio static. Each detail made the unbelievable feel legitimate. He commanded belief by establishing immediate, undeniable authority.
Bring that same presence to your sales interactions. Authority isn’t arrogance; it’s commanding belief. Sound like someone who’s been there, knows the terrain, and has the solution. Communicate with unwavering authority, and you build trust before price discussions begin.
This is how you sell the experience. Prospects must believe in you and your company; belief in your product comes next. They buy the experience of working with you before seeing the product. If you sound uncertain, you’ll never build a foundation of trust.
Stay Steady to Control the Chaos
Welles predicted a strong reaction to his broadcast and stayed calm, controlled the narrative, and guided the audience through the panic he was creating.
In sales, moments of crisis or uncertainty test your professionalism. When a prospect goes cold, objections arise, or a competitor attacks, do not panic. Do not mirror their anxiety—it only feeds chaos and cedes control of the deal.
Control the process, control yourself, control the outcome. When deals wobble and emotions spike in your buyer, that is your moment to shine. Breathe, slow down, ask questions, and lead steadily. Be the calm voice that reassures, guides, and inspires confidence. Mastering internal composure is the essence of emotional intelligence in sales.
Your Action Plan: Develop Your Sales EQ
Mastering composure under pressure is a skill, not a gift. It requires commitment to developing emotional intelligence so you can use logic while others react in fear.
Start a 'Rejection Journal' Drill. Stop letting rejection or setbacks paralyze you. Create a Failure Log to immediately document your feelings (frustration, anger, anxiety) and behaviors (rushing calls, getting defensive). This practice builds self-awareness and helps you identify emotional triggers before they hijack your sales process.
Practice the 'Mute Button' Listening Exercise. On your next call, mentally mute your urge to speak. Analyze the prospect’s delivery: tone, pace, hesitation. This drill sharpens social awareness and forces you to catch subtle emotional cues—the things they won’t email. This is how you truly understand their situation.
Implement the 'Two-Second Pause' Rule. When a high-stakes moment occurs—a sharp objection, competitor mention, or deal crisis—pause for two seconds before speaking. This creates a cognitive buffer, shifting you from reactive to controlled.
Your Story Is Your Greatest Weapon
The Orson Welles broadcast is nearly a century old, yet it still teaches us today that a gripping story delivered well can move mountains. The way you connect, build trust, and influence emotion hasn’t changed since radios ruled the living room.
You aren't a broker of features and benefits. You are a storyteller, and the calm in your prospect’s noisy, chaotic world. You are the guide who connects the dots between their terrifying "Martian invasion" of a problem and your ultimate solution.
Embrace this role, and you move past objections and skepticism. You stop triggering defensive panic and start inspiring action.
Your ability to command a room starts with your ability to command your own emotional intelligence. When the sales airwaves get noisy, keep your voice steady, your mind sharp, and your heart connected.
Master your emotions, and you will close deals your competition can’t.
The real battlefield in sales is psychological, and if you can't master your own emotions, you will never master your prospects. Jeb Blount’s book Sales EQ gives you the psychological edge to win the business your competition can't even touch.
AI in sales isn't coming soon. It's already here, and it's quietly separating the salespeople who will thrive from those who won't.
On the Sales Gravy Podcast, sales expert and author Victor Antonio shares this quote: "You won't lose your job to AI. You'll lose your job to people who are using AI."
While everyone debates whether artificial intelligence will replace salespeople, the real shift is already happening. What you need to know is which parts of your job will still matter when a machine can do everything else.
The Trust Formula Still Requires Humans
Most people think AI in sales is about automation. It's not. It's about augmentation.
Yes, AI can write your emails. It can analyze your pipeline. It can schedule your meetings and generate your proposals. But it can’t build trust with a buyer who's about to make a six-figure decision they're terrified of getting wrong.
Trust in selling comes down to three things:
Understanding the buyer’s point of view
Demonstrating real expertise
Keeping the buyer’s best interest front and center
When a buyer is staring at a purchase order that could make or break their business, they don't want a chatbot. They want a human being who says, "I've got you. This is the right move."
Simple Sales No Longer Require a Sales Rep
Transactional jobs are disappearing.
AI sales agents can already handle simple sales from start to finish. A customer calls about a broken window seal. The AI analyzes the image, checks inventory, schedules a technician, verifies the warranty, and puts the appointment on the calendar. No human required.
This isn't science fiction. These systems exist today.
AI handles simple tasks easily, but complex sales still require humans. Everything on the straightforward end—cold outreach, basic prospecting, routine follow-ups—is getting automated fast.
But complex B2B sales are different. When deals involve multiple stakeholders, custom solutions, and high-stakes decisions, buyers still need salespeople. Humans don't trust machines with decisions that keep them up at night.
Your job security lives in complexity. If you're selling simple products with simple processes, you need to start adding value now.
What You Should Be Doing Right Now
Most salespeople are waiting while AI transforms the industry. Don’t make that mistake.
Here’s how to start experimenting with AI today:
Use ChatGPT, Google's Notebook LM, or your AI of choice to digest long articles and research reports in minutes instead of hours.
Feed it information about your products and competitors to create your own custom knowledge base.
Role-play objection handling by assigning it different buyer personas and practicing your responses.
Ask it to critique your proposals before you send them to catch weak points you might miss.
These tools aren't perfect. They'll feel clunky at first. But you're not trying to master AI today. You're building comfort with technology that will be 100 times more powerful in just a few years.
The salespeople who are experimenting now will be the ones who know how to use AI when it really matters. The ones waiting for their leaders to force them to adopt AI will scramble to catch up.
The Skills That Survive AI
So what actually matters when AI handles the busywork?
The biggest obstacle in complex sales isn't convincing buyers that your solution works. It's helping them trust their own judgment enough to decide.
Buyers freeze not because of your pitch, but because of fear: What if I’m wrong?
AI can show data, ROI models, and comparison charts—but building buyer confidence still requires human judgment.
That's the skill that matters: Building buyer confidence.
You need to get exceptional at reading hesitation—when a buyer goes quiet or starts asking the same questions in different ways. They’re not confused about your product. They’re uncertain about themselves.
Your job is to help them trust their judgment. That means understanding internal politics, knowing who has veto power, and recognizing when more information helps, or when it just creates more doubt.
The other critical skill? Using AI tools effectively. Knowing what AI can handle lets you offload routine work and focus on moments that require your human judgment.
The salespeople who win will be the ones who master both. Human skills for the moments that matter. AI skills for everything else.
The Bottom Line
AI isn’t your replacement. It's your upgrade.
The sales skills you need most are the ones that have always mattered: understanding people, building trust, solving complex problems, and giving buyers confidence in risky decisions.
What's changing is everything else. The admin work, research, and proposals are getting automated whether you like it or not.
Irreplaceable reps are the ones who use AI to eliminate grunt work so they can spend more time doing what only humans can do. The ones who lose are the ones still doing everything manually while insisting they don't need help from a machine.
Pick one AI tool this week and start using it. Get uncomfortable. Make mistakes. Learn.
The future of sales is happening right now. And the only question that matters is whether you are ready.
Want to master AI in sales? Get The AI Edge for the complete blueprint on leveraging artificial intelligence to dominate your competition and accelerate your sales results.
Here's a question that'll keep you up at night: How do you take a company from $300K in annual revenue to $1.5 million in 18 months, then scale to $3-$5 million within five years?
That's the challenge facing Greg Hirschi from Colorado. He's the new executive leader of an 18-year-old company selling ethics assessment services to professional licensing boards. They've expanded from an entrepreneurial model to a small team with one salesperson and one customer service representative. The goal is aggressive growth, and Greg needs to know where to focus his limited resources to get the biggest bang for his buck.
If you're nodding your head right now because you're in a similar situation, pay attention. Because the mistakes you make at $300K will haunt you at $3 million.
The Resource Reality Check
Let's be brutally honest about what a $300K revenue company means: You have no money. You have a razor-thin budget. You have one salesperson and one leader trying to do everything.
At this stage, you have exactly one priority: REVENUE.
You don't have the luxury of fixing operations, perfecting your tech stack, or building elaborate systems. You need to sell. Period.
Here's where most small companies screw this up. They think selling means taking anything with a pulse. If it can fog a mirror, they'll do business with it. That's a death spiral disguised as growth.
The Operator's Dilemma
Greg comes from an operations background. He's analytical, process-driven, and systematic. Those traits are incredible assets for building a business, especially when the goal is to scale fast. But they can also be a liability when managing salespeople.
Here's what happens: Operators think in systems and logic. Salespeople think in relationships and emotion. Operators want everything organized and predictable. Salespeople throw deals on the table that are messy and unpredictable.
If you're an operator trying to lead sales, you need to understand this fundamental tension. Your salesperson is out there getting hammered with objections every single day, building narratives in their head about why people won't buy. You're thinking, "Just brush it off and do it again. What's wrong with you?" They're thinking, "You have no idea what it's like out here."
This is why reading New Sales Simplified by Mike Weinberg is non-negotiable if you're an operator managing sales. You need to learn how salespeople think, how they operate, and how to lead them effectively without losing your mind.
Start With Your ICP or Die Trying
The single most important thing Greg needs to do right now to scale is get laser-focused on his Ideal Customer Profile.
Not kind of focused. Not "we have a general idea." I mean obsessively, precisely, ridiculously dialed in on exactly who they should be targeting.
Why does this matters so much at $300K? Greg's salesperson has a $600K pipeline and will close 50% of it. Sounds great, right? But if half those customers churn because they're the wrong fit, requiring constant re-education and hand-holding, Greg's salesperson will get stuck in account management mode. They'll stop prospecting for new business because they're too busy re-selling existing accounts.
That's how you stay stuck at $300K forever.
Your ICP drives everything. It determines your messaging, your marketing, your presentation materials, and which stakeholders you need to reach inside target organizations. It helps you build relevant social proof stories. It allows you to coach your salesperson on handling specific objections instead of generic brush-offs.
Most importantly, it gives you guardrails. You can ask your salesperson in pipeline reviews: "Tell me the strategic reason why we should chase this account. How does it fit our ICP? Why is this worth our limited resources when our singular goal right now is growth?"
When you're running a $300K company with one salesperson and one leader, you cannot afford to chase every deal. You need to focus on the right deals that will close and stick around.
The Resell Problem
Greg's company doesn't have contracts. They discovered that larger organizations with stable staff become sticky customers once they see the value. Smaller organizations with high turnover require constant re-education and reselling.
This is not how you scale.
If you don't segment your market correctly and build processes around retention, you'll hit a wall fast. Your salesperson will close deals, then get pulled back into account management, abandoning the pipeline. Salespeople will always choose talking to people they already know over talking to strangers.
You don't have this problem yet at $300K. But you will as you begin to scale. Start thinking strategically now about your retention process and which customer segments are worth the ongoing investment.
The Foundation That Changes Everything
Getting your ICP right isn't just about qualifying accounts. It's about building a foundation that allows you to scale without constantly backtracking to fix problems you created by going after the wrong customers.
Every time you chase the wrong deal, you're creating downstream problems. You're wasting limited resources. You're building frustration in your team. You're teaching your salesperson bad habits about what constitutes a qualified opportunity.
The leap from $300K to $600K in annual revenue is hard. The leap to $1.2 million is harder. The leap to $3.5 million is brutal. But if you get the foundation right now while you have backing and support, those leaps become exponentially easier.
Your Playbook for Growth
Start with objection handling fundamentals that are specific to your ICP. When you know exactly who you're targeting, you can anticipate their concerns and craft precise responses that resonate.
Build your messaging around the multi-threaded stakeholders in your target organizations. Who needs to be involved in the buying decision? What does each person care about?
Create a systematic, process-based approach to pipeline management. As an operator, this is your superpower. You can bring discipline and structure to a highly emotional profession.
The Bottom Line
At $300K, you're essentially starting from scratch. You have aggressive growth targets, limited resources, and one shot to get this right.
Stop being reactive. Start being strategic. Get obsessed with your ICP. Build processes around the right customers. Coach your salesperson with precision instead of frustration.
That's how you scale from $300K to millions. That's how you avoid the mistakes that kill small companies. And that's how you build a business that doesn't just grow, but grows sustainably.
The good news? You have the backing to do this right. Don't waste it chasing the wrong customers just because you need revenue today. Build the foundation that generates revenue for years to come.
Lead your salesperson, focus on the right deals, and scale from $300K to millions—start Jeb Blount's Sales Leadership Essentials course on Sales Gravy University today.

























this was great interview on how to start a podcast lots of great tips