Sales Gravy: Jeb Blount

“Buyers want a machine, a sales machine, not a mystery. If the sales machine only works because of the founder, it’s not that valuable. It’s actually quite risky.”

Chris Spratling, founder of Chalkhill Blue Limited and author of The Exit Roadmap, shared this on a recent episode of the Sales Gravy podcast. He works with business owners preparing to sell their companies, helping them get operations, finances, and sales engines ready for new ownership. That insight cuts straight to the reason so many founder-led businesses hit a ceiling they can’t break through. 

If you are a founder who still carries most of the revenue, or you have a founder-led sales team that depends on you to close critical deals, this is bigger than exit planning. It determines whether your business can grow beyond your personal capacity.

The Golden Handcuffs Problem

You built the business. You know the product better than anyone. You can sell it without thinking.

That is exactly where the risk starts.

When major clients only trust you, when your sales process lives in your head, when new reps struggle to replicate what comes naturally to you, you aren’t running a sales operation. You are running a one-person engine with a support team around it.

Spratling calls this the “golden handcuffs.” It looks like success from the outside, but underneath, it creates dependency. Every time you step in to save a deal, you reinforce the idea that the business only works when you are involved.

Most founders focus on how this affects valuation at exit. Fewer recognize the more immediate cost. That dependency limits how fast the company can grow right now.

Where Founder-Led Sales Breaks Down

The transition from founder-led sales to a functioning team is where momentum often stalls.

You hire your first salesperson. They do well. Then a second. Then a third. Suddenly, deals slow down, messaging gets inconsistent, and you find yourself pulled back into conversations you thought you had delegated.

They don’t sell the way you do. They miss cues you catch instinctively. They hesitate where you would push forward. So you jump in, coach through objections, and close deals yourself.

What feels like instinct is actually a method you developed through hundreds of conversations. The problem isn’t that your team lacks talent, but that your approach has never been translated into something they can use without you standing next to them.

As long as that stays true, scale will remain out of reach.

Turning Intuition Into a Usable Process

The hardest shift for founder-led teams is codifying what the founder does without thinking.

You know which deals are worth pursuing. You know when to apply pressure and when to step back. You know how to redirect a conversation when resistance shows up. That knowledge is pattern recognition built over time, and it can be used to create a process.

Start by defining how deals actually move through your pipeline. Not a generic framework pulled from a template, but the real stages your customers pass through, with clear criteria for each transition. What has to be true before a lead is qualified? What information must be present before a proposal goes out?

Then look at discovery. What questions do you ask every time? What do you listen for before positioning your solution? Which objections show up consistently, and how do you respond when they do?

The goal is to document the structure beneath the conversations so that someone else can navigate the same terrain with confidence.

Why Your CRM Is Not Pulling Its Weight

Most founder-led teams have a CRM, but they only use it to track contacts and deal size.

However, a functioning, high-performing sales system treats the CRM as a learning tool. That means capturing more than surface-level data. It means recording what buyers actually say, why deals move forward, where they stall, and who influences the decision.

When that information is tracked consistently, patterns become visible. You see which prospects convert fastest, which objections actually kill deals, and where momentum typically breaks down.

That insight does more than improve forecasting. It gives you a concrete way to train new reps based on real deals you have closed, not abstract theory.

Three Steps to Build a Sales Engine That Does Not Depend on You

The objective isn’t to remove yourself from sales completely. It’s to make your involvement a choice rather than a requirement.

Step 1: Define Clear Qualification Criteria

Your team needs to know which leads are worth pursuing and which ones are a waste of time. If you’re constantly redirecting their focus, you haven’t defined “good fit” clearly enough. Get specific—industry, company size, buying triggers, decision-making structure. 

Step 2: Create Documented Playbooks

How do you handle discovery? What’s your approach to proposals? How do you navigate the closing process? Your team needs a framework they can adapt. Think decision trees, not scripts. “If they say X, then ask Y. If they push back on Z, here’s how to reframe it.”

Step 3: Transfer Client Relationships

If every major client relationship is tied to you personally, your business is fragile. Start introducing your team into those relationships now. Bring them to calls. Have them lead the follow-up. Shift trust from you as an individual to your company as a whole.

What This Looks Like in Practice

Record your next three sales conversations, with the customer’s permission. Review them carefully. Note the questions you asked, when you asked them, and how you responded to resistance. Identify what made you confident that the opportunity was real.

Turn those insights into a simple framework your team can follow. Have them use it. Watch where it works and where it breaks. Refine based on what you see.

Done consistently, this process creates a system new hires can step into within months. It won’t make them identical to you, but it will make them effective without constant rescue.

The Real Test

You will know your found-led sales team has scaled when you can step away for two weeks without monitoring email, chat messages, or “quick calls” with prospects.

And when you come back, the pipeline has moved forward.

If that thought terrifies you, you don’t have a sales team. You have an expensive support staff for your one-person operation.

Building a sales operation that runs without you isn’t about making yourself irrelevant. It’s about making your business transferable and scalable, whether you’re planning an exit in three years or just trying to grow past your own capacity right now.

Because at some point, your ability to personally close deals stops being your greatest asset and starts being your biggest bottleneck.

The question is whether you’ll recognize that point before it costs you the next stage of growth.

If you want to start turning founder intuition into a repeatable sales system, download our free Small Business Guide to Sales Training. It walks through the frameworks that help teams scale without depending on a single closer.

Here’s a question that’ll change how you think about this profession forever: What’s the one moment that reveals you’re built for sales success?

For most people, that moment never comes. They stumble into sales, struggle with the stereotypes, and either quit or spend their entire career fighting against what they think selling is supposed to be.

But for those of us who get it, there’s a moment of clarity so powerful it changes everything. Mine happened in high school when I was chasing a girl and ended up on the yearbook staff. Thirty days later, I handed over $3,800 in checks while everyone else struggled to hit their $300 quota.

The Sales Crack Moment

When Mr. Hall at Hall’s Hardware Store wrote me that first check for a yearbook ad after I had done little more than ask outright for the money, something clicked. This wasn’t complicated. Walk in, shake hands, present value, and people give you money.

While my classmates were paralyzed by the same stereotypes you hear today (“I’m not a salesperson”), I was out there having conversations. That’s all prospecting really is. Talking to people.

The gasp in that room when I revealed my numbers? That was better than the money. That was the competitive fire igniting. That was me realizing I could outwork, outsell, and out-earn anyone if I just committed to the process.

The Discipline Problem Most Sellers Miss

Here’s what nobody tells you about sales success: It’s not about talent. It’s not about charisma. It’s about ruthless execution of proven processes.

By the time I was 21 or 22, I was making $300,000 in the early nineties. That’s equivalent to making close to a million today. Not because I was special, but because I understood something fundamental that most people never figure out: The more people you talk with, the more you sell.

And here’s the beautiful part. There are lots of people to go talk with. The pipeline never runs dry if you’re willing to fill it.

The Three Non-Negotiables for Modern Sellers

The future of selling is blending. Not choosing between video and phone and in-person. Blending all of them based on one critical question: What communication channel gives me the highest probability of capturing my desired outcome at the lowest cost of time, energy, and money?

When I started selling, we had two channels. Maybe three if you count snail mail. Phone and in-person. That’s it. Today? You’ve got a dozen ways to connect. WhatsApp lets you text, call, and video chat almost instantly. The options are endless.

But here’s where Gen Z sellers (and honestly, every generation) screw this up: They get single-siloed.

“I’m only good at email.”

“I only do video calls.”

“I hate the phone.”

That mindset is killing your income potential. You need to be good at everything. Master every channel. Because the channel doesn’t matter. The outcome does.

Synchronous Beats Asynchronous Every Single Time

Here’s the second non-negotiable to sales success: Stop hiding behind asynchronous communication.

We do deals in a synchronous world. Real-time conversations. Phone calls. Video meetings. Face-to-face interactions. If you think you can close business through email threads and text messages, you’re delusional.

Why? Because robots can write better emails than you can. AI can craft more persuasive text messages. But sales is the ultimate human career in the age of AI precisely because of the human connection required in synchronous conversations.

Lead with phone calls. Get face-to-face when the deal size justifies it. Use video when it makes sense. But always, always prioritize real-time conversations over digital hide-and-seek.

Ask Questions and Actually Listen

The third non-negotiable is mastering the art of asking great questions and listening to the answers.

People make five decisions before they buy from you: Do I like you? Do you listen to me? Do you make me feel important? Do you get me and my problems? Do I trust and believe you?

Notice what’s not on that list? Your product features. Your company’s awards. Your clever sales pitch.

They’re evaluating you. Your ability to connect. Your capacity to understand. Your commitment to making them feel important.

And the only way to get five affirmative answers to those questions is through synchronous conversations where you ask intelligent questions and actually listen to what they’re telling you.

The Make It Rain Principle

When Mr. Rouse made me editor of the yearbook after I brought in $3,800, I learned something that shaped my entire career: When you can make it rain, you can get anything you want.

That principle holds true whether you’re selling yearbook ads in high school or enterprise software to Fortune 500 companies. Revenue solves problems. Performance opens doors. Results create opportunities.

Most people in sales stumble into it. They take the job because it was available. They stick with it because the money’s decent. But they never commit to mastering the craft.

The question isn’t whether sales chooses you. The question is whether you choose sales. Whether you commit to being good at every communication channel. Whether you prioritize synchronous conversations over digital convenience. Whether you master the art of asking questions and listening.

Those fundamentals never change. The technology evolves. The channels multiply. But the core truth remains: Talk to more people, in real time, with genuine curiosity about their problems, and you’ll make more money than you ever thought possible.

That’s how you achieve sales success. That’s how you go from yearbook ads to seven figures. That’s how you make it rain.

Want to master the fundamentals of prospecting and build your own rocket ship career? Join us at Sales Gravy LIVE: Fanatical Prospecting Bootcamp in Atlanta, Georgia on March 10-11th. Two days of intensive training where you’ll learn the exact systems and processes that turn ordinary sellers into top performers.

I’m not sure if you noticed this, but there is a massive gap between what salespeople and leaders know and what they actually do.

I’ve written 18 books and trained hundreds of thousands of salespeople. I can’t tell you how many times someone comes up to me and says, “Jeb, I read Fanatical Prospecting. Great book. But that stuff doesn’t work for me.” Or they’ll say, “I tried that objection handling technique you taught, but it didn’t work, so I went back to what I was doing before.”

Here’s what they don’t understand: The problem isn’t the technique. The problem is that they gave up too soon. The brutal truth is that most people fail to implement what they learn. 

The Skate Park Lesson

A couple of weeks ago, I was traveling for business, working with one of my clients’ sales teams. One afternoon, I decided I needed some exercise, so I went for a walk. Along the way, I came across a skate park where kids were riding their skateboards and doing tricks.

There was a bench nearby, so I sat down to watch for a while.

Close to me was a group of young guys, probably 13 or 14 years old. They were huddled around a phone watching a YouTube video of someone doing a particular trick on their skateboard. They watched it, talked about it, and then one of them threw his skateboard down and attempted the trick.

He immediately fell off and failed.

The next kid tried, and he failed.

Then the next one and the next one. All of them failed to do the trick. 

So what did they do? They went back and watched the YouTube video again. Then they threw down their boards and crashed and burned, but this time, slightly less dramatically than the first time.

They repeated this process over and over. Watch the video. Try the trick. Fail. Watch again. Try again. Fail a little less badly. Until finally, one of them nailed it.

When he landed the trick, they all erupted. Clapping, fist pumping, and cheering. And once one kid got it, the rest of them started getting it too. They practiced until they had the trick nailed down, then went back to YouTube to find another trick to learn.

At that point, I got up and headed back to my hotel. But as I was walking, I couldn’t stop thinking about what I’d just witnessed.

Too Often, We Give Up too Soon

How often do we do the exact opposite in business and sales? We read a book, watch a video, listen to a podcast. We hear about a technique or concept that sounds really good. And we think, “Yeah, I’m going to try that.”

So we give it one shot. Maybe two if we’re feeling ambitious. And when it doesn’t work perfectly the first time, we say, “Well, this doesn’t work for me,” and we give up and never try it again.

Or worse, we read the book, feel really good about the concept, then put the book down and never even attempt it at all because we’ve already convinced ourselves it wouldn’t work for us before we even tried.

But here’s the thing: Those kids at the skate park didn’t look at that trick and say, “This looks hard, it probably won’t work for me.” They looked at it and said, “We’re going to figure this out.” They understood something that most adults have forgotten: Just because you read about something or see someone else do it, doesn’t mean you’re going to master it on the first try.

The Homemade Yogurt Failure Paradigm 

As I was walking back from the skate park, this lesson reminded me of something that had happened to me over the holidays.

I’d seen something in my news feed about making homemade yogurt. It looked interesting, so I bought some milk, studied the recipe, and made an attempt.

And I failed. My concoction didn’t turn into yogurt at all. My immediate reaction was, “Well, this isn’t going to work; it must be a bad recipe.” I gave up after one failed attempt.

But after watching those kids at the skatepark, I realized the giving-up-too-soon trap I’d fallen into. So when I got home from my trip, I went back, reread the recipe, walked back through my steps to figure out what went wrong, and tried again. This time it worked, and I actually made yogurt.

The recipe wasn’t the problem. My execution was the problem. And I only figured that out by trying again.

The Human Overconfidence Fallacy 

Here’s the lesson: We are all susceptible to this human fallacy of believing that we can read something, watch something, or hear something once and then immediately do it perfectly.

When it doesn’t work the first time (or even the second time), we conclude that the technique is flawed, or it won’t work for us, or our situation is unique and different.

But the truth is, we gave up too soon, before we gave the technique a fair shot. That’s just being human. We’re wired for overconfidence, instant gratification, and immediate results. When we don’t get them, we move on.

Why This Matters in Sales 

Let me bring this back to sales, because this pattern will absolutely kill your results.

You read a book on prospecting, learn a new cold calling technique, watch a sales training video on objection handling, or attend a conference or training and learn new ideas.

Then you try it. Maybe it feels awkward, or the prospect reacts differently than you expected. Maybe you stumble over the words, or you get shut down and rejected. So you conclude it doesn’t work, and you go back to what you were doing before, which, by the way, wasn’t working either. That’s why you were looking for something new in the first place.

Here’s what you’re missing: Sales is and always has been a numbers game. Statistics and the law of averages matter. Even the best techniques don’t work 100% of the time. You have to use them enough times to see the patterns and to understand what’s working and what needs adjustment.

The Iteration Process

Those kids at the skate park weren’t just repeating the same failed attempt over and over. They were iterating.

They’d try the trick, fail, and then make a small adjustment. They’d watch the video again, notice something they missed the first time, and then talk to each other about what went wrong and what to try differently.

That’s the process: Try, fail, learn, adjust, try again.

But most people skip the “learn and adjust” part. They just try, fail, and quit.

Let me give you a sales example. Say you’re trying a new prospecting email template. You send it to ten prospects and get no responses. The try-fail-quit people conclude the template doesn’t work. But a try-fail-learn-adjust-try again high performer would ask: 

Did I send it to the right prospects? 

Was my subject line compelling? 

Was the timing right? 

Did my call to action make sense? 

Should I test a different version?

They’d iterate and test different variables until they figured out what worked. That’s what separates top performers from everyone else. They don’t give up after one attempt. Instead, they iterate until they succeed.

The Success Leaves Clues Principle

Here’s something else those kids understood: If someone else is doing something successfully, that means it’s possible.

When they watched that YouTube video, they didn’t say, “Well, that guy is just naturally talented.” They said, “If he can do it, we can figure out how to do it too.”

This is the “success leaves clues” principle. If someone else is making something work, that’s proof it can work. Your job is to master their patterns and believe that you can make it work too.

When you read a book like Fanatical Prospecting, and you see examples of people who built massive pipelines using these techniques, that’s not fiction. Those are real people who learned how to execute these strategies.

When you watch a training video and see someone handle an objection smoothly, that’s not magic. It is someone who practiced that response dozens or hundreds of times until it became natural.

The clues and evidence are there. The only question is: Are you willing to put in the practice and endure the failures until you get there yourself?

The Practice Paradox

Here’s the paradox that trips people up: The techniques that work best often feel the most awkward at first. That’s because they’re different from what you’ve been doing, and anything different feels uncomfortable.

For example, when I teach salespeople to slow down and use silence in negotiations, they hate it. It feels unnatural. They want to fill the silence with words. But the ones who push through that discomfort and practice using silence close bigger deals at better margins.

When I teach salespeople to ask for referrals using a specific framework, they feel like they’re being pushy or scripted. But the ones who practice the framework until it becomes conversational generate more referrals than they ever thought possible.

The discomfort is temporary. The results are permanent. But you have to get through the discomfort in order to get to the results.

5 Keys to Mastering New Sales Skills

So, how do you actually implement what you learn? Here’s what I recommend:

First, commit to practicing any new technique at least twenty times before you decide if it works. Not once. Not twice. Twenty times minimum. That’s how long it takes to get past the awkwardness and start seeing results.

Second, track your results. Don’t rely on your feelings about whether something is working. Write down what happened each time you tried the technique. Look for patterns and notice what’s improving.

Third, iterate. If something isn’t working after multiple attempts, don’t just abandon it. Adjust it. What needs to change? What variable can you test differently?

Fourth, find someone who’s making it work and learn from them. If you’re struggling with a technique that others are using successfully, reach out to them. Ask questions. Watch how they do it.

Fifth, be patient with yourself. You’re not going to master anything instantly. Give yourself permission to be bad at something new while you’re trying to master it.

Your Homework this Week

Here’s what I want you to do this week: Pick one technique you learned recently – from a book, a podcast, a training – and commit to trying it at least twenty times this week. Track what happens each time. Notice what’s working and what’s not, make small adjustments, and keep at it.

Because here’s the truth: The techniques work. But you must put in the work before they will work for you.  

Those kids at the skate park didn’t give up after the first fall. They kept going until they nailed the trick. That’s what separates winners from everyone else. Not talent, luck, or some magical gift. Just the willingness to try, fail, learn, adjust, and try again until you get it right.

And remember, when it’s time to go home, make one more call. Because that one more call is one more rep, one more attempt to get better, and one more step toward mastering your craft.

 

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“That chip on my shoulder made me less empathetic, more rushed, too eager to solve things too fast, and less thoughtful. That chip built me, but then it started to tear me down.”

I said that recently in a conversation with Harriet Mellor of Your Sales Co, and it captures something every sales leader needs to understand. 

I grew up in the sales training business. My dad literally wrote THE book on prospecting—several of them, actually. I worked at Paycom, Comcast, and various startups where I consistently crushed my numbers.

But what I learned is that knowing the right techniques and getting your team to actually implement them are two completely different challenges. Sales training resistance is rarely about bad content. More often, it is about ego and pride standing in the way of growth. I had to recognize that in myself before I could address it in the people I lead.

Why Your Top Performers Resist Training the Most

When I was a rep, I was terrible at taking coaching. Not because I didn’t understand the concepts. I understood them better than most. But when someone tried to coach me, I tuned out.

The problem was I’d already figured out a system that worked. I was hitting my numbers. Why would I mess with it?

Think about learning golf. You chunk the ground twenty times, then suddenly you make contact. The ball doesn’t go straight or very far, but it goes. Someone tries to teach you proper form, your first thought is, “I already figured out how to hit the ball.”

That’s where many top performers live. They’ve reached an equilibrium. Not peak performance, but functional competence. Training feels disruptive because it threatens what is currently working.

They’re not resisting because they’re stubborn. They’re resisting because they have something to lose. What if they try something new and their numbers drop? They’d rather stay at 85% effectiveness than risk dropping to 60%, even if it means eventually reaching 120%.

Two Ways Ego Hurts Performance

Creates Rush Instead of Curiosity

At Paycom, I carried a massive chip on my shoulder. I carried the same name as my dad. People knew who he was. I felt pressure to prove I belonged.

So I rushed. I skipped discovery. I pushed toward proposals. I talked more than I listened. Every call felt like a test I needed to pass.

You can hear this on your team’s calls. Reps who are trying to prove something move too fast. They stop asking questions. They perform instead of selling.

That behavior is driven by ego, and it costs deals.

Telling them to slow down will not fix it. You need to understand what they feel compelled to prove and why they associate speed with competence.

Blocks From Actually Learning

When I was carrying a quota, I thought I was a lifelong learner. I read every sales book. I listened to podcasts. I sat through hours of training sessions.

But when it came to changing what I did on Monday morning, I defaulted right back to what I knew.

I’d hear a new objection handling technique and think, “Yeah, I basically already do that.” I didn’t. But ego wouldn’t let me see the gap.

Your salespeople are doing the same thing right now. They’re taking in your coaching but filtering it through their existing beliefs. They’re protecting the system that’s currently working. And they’re developing blind spots they can’t see.

Watch for the reps who stop recording their calls because they “know what they sound like.” The ones who skip role play because it’s “not realistic.” The ones who tune out your coaching because you “don’t understand their territory.”

Reps who do this aren’t trying to be difficult, but instead trying to protect their self-image instead of improving their performance.

Why Your Team Listens to Outside Trainers But Not You

One of the most frustrating parts of leadership is to preach a methodology for six months and nothing changes. Then an outside consultant shows up and says the exact same thing. Suddenly, everyone’s taking notes and engaged.

I experienced this firsthand with my dad. He would offer advice, and I tuned out. Days later, I would hear the same message from someone else and think it was brilliant.

It wasn’t about the message. It was about who was delivering it.

When you try to coach your team, there’s history. There’s baggage. Maybe you’ve given conflicting directions before. Maybe they see you as “management” instead of someone who gets it. Maybe they just don’t like admitting to their boss that they need help.

Outside trainers don’t carry that weight. They show up with a clean slate and credibility that’s granted just by being an outsider.

The real question isn’t how to make your team listen to you. It is how to create an environment where learning feels safe, regardless of who delivers it.

How to Break Through Sales Training Resistance

Frame Training as Addition, Not Correction

I stopped resisting coaching when my leaders stopped making me feel like I was doing things wrong.

Instead of pointing out flaws, the best managers invited experimentation. Instead of “you need to improve your discovery process,” the best managers said, “try asking this question in your next three calls and see what happens.” 

Position new techniques as tools to add to what’s already working, not corrections to what’s broken. Your team will actually try them.

Make It Safe to Fail

On the marketing team, I got my team members on sales calls. Yeah, marketers are making prospecting calls alongside me. It felt like a crazy concept until it started working. Importantly, I let them hear my wins and my mistakes so they knew I was in it with them the entire way.

I wanted them to see me stumble over a question. Get flustered. Say the wrong thing. Then watch me debrief it and do better on the next call.

When I started doing this, something shifted. My team stopped being afraid to try new things. If I could screw up a cold call and laugh about it, they could too.

The tide turned when they asked to jump in with me and started booking appointments. The win unlocked a new level of understanding. These marketers suddenly believed that they could, instead of simply being told that they could.

Your salespeople need to see you fail. Not in a performative way. In a real, vulnerable, “I’m still learning too” way.

That’s when they’ll give themselves permission to be imperfect. And that’s when actual learning happens.

Change One Small Thing at a Time

I didn’t transform my sales approach overnight. The managers who got through to me asked me to change one thing every few weeks. One question to add to discovery. One way to handle a specific objection.

After six months, I’d transformed my entire process. But I never had to risk everything at once.

Pick one behavior for your team. Make it specific. Make it small. Give them three weeks to practice it. Then add something else.

Stop trying to overhaul their entire approach in one training session.

Let Them Experience the Win

You can tell your team a technique works until you’re blue in the face. They won’t really believe you until they feel it themselves.

My marketing team didn’t enjoy making calls at first. They were uncomfortable. They were bad at it. But then they got their first yes. That moment when someone on the other end of the phone said, “Yeah, let’s set up a time to talk”—everything changed.

That lift in your chest when you close a deal? That high you get from hearing yes? You can’t explain that. Your people have to experience it.

Stop trying to convince your team that new approaches work. Create low-risk situations where they can discover it themselves. Role-play early, followed by real calls together. Small wins. Repeat.

When Ego Stops Being Their Engine

Every salesperson reaches a moment when the traits that fueled early success start creating friction. The confidence that helped them pick up the phone becomes arrogance that stops them from listening. The drive that made them a top performer becomes anxiety that makes them rush.

For me, that moment came when I realized that chip on my shoulder wasn’t serving me anymore. It had driven early success. Then it started tearing me down. I was less empathetic, more rushed, less thoughtful.

Most salespeople never recognize that moment. They keep pushing the same way they always have, wondering why it’s getting harder to hit their numbers.

Your role as a leader is to help them spot it. Not by calling it out directly—that triggers defensiveness—but by creating an environment where they feel safe enough to recognize it themselves.

The best salespeople develop the ability to notice when pride is shielding them from feedback. They know when to trust instinct and when to slow down and listen.

What to Do This Week

Look at who is hitting their numbers while quietly resisting coaching. Those are rarely problem reps. They are people protecting what feels safe.

Start with one person and one behavior. Keep the change small enough that it does not threaten their confidence. Model your own learning openly. When people see that improvement does not require perfection, they are more willing to try.

I spent years proving I was good enough instead of getting better. Many salespeople do the same thing. Ego does not disappear with success. It just gets quieter.

The leaders who drive sustained performance create environments where learning feels normal, progress is visible, and growth does not require losing face.

If you are leading a small sales team, coaching resistance gets magnified. Download our Free Small Business Guide to Sales Training, which gives you a clear framework for building coachable habits, consistent execution, and sustainable performance without overwhelming your team.

Here’s a question that’ll make your head spin: You just inherited 50 neglected accounts, and your customers feel taken for granted. How do you reposition yourself as a high-value partner instead of just another transactional vendor who’s about to disappoint them?

That’s the question posed by Scott Northway, and it’s one of the most common challenges I see in sales today. A new account manager takes over, inherits a book of business that’s been ignored, and now has to figure out how to rebuild relationships with customers who’ve been collecting dust.

If you’re nodding your head right now, you’re not alone. Poor account management is quietly bleeding companies dry, and most leaders have no idea how much revenue they’re leaving on the table.

The Brutal Truth About Why Customers Leave

When we survey customers through our consulting projects with clients who are hemorrhaging accounts, here’s what we find: About 70 percent of the time, customers don’t leave because of price. They don’t leave because of product quality or service issues.

They leave because they feel taken for granted.

Let me give you a real example. I pay six figures annually for a software program that’s critical to my business. Every time my contract comes up for renewal, it’s like a circus. They fly people in. They wine and dine me. They promise the moon about how they’re going to support us and be our partner.

Then once the contract is signed? Crickets.

My account manager disappears for three years. If I don’t call them, they don’t call me. And here’s the thing: I actually like my account manager. I genuinely want to work with them. There are products I could buy, optimizations we could make, but I have to do all the work to make it happen.

This is insane. And it’s costing companies millions.

What Won’t Work: The Rookie Mistakes

So you’ve inherited these neglected accounts. Here’s what you absolutely cannot do: Show up on their doorstep apropos of nothing and try to sell them something.

If I’m an existing customer doing business with your company, and you show up trying to pitch me without acknowledging the elephant in the room, we’re probably done. It’s rude. It’s bad behavior. And it tells me you’re just like every other transactional vendor who doesn’t actually care about my business.

The second mistake is spreading yourself too thin across all 50 accounts without any strategy. You’ll burn out, deliver mediocre service to everyone, and end up losing accounts you could have saved.

The Human-to-Human Approach That Actually Works

Here’s what does work: Be honest. Be human. Name the problem.

Pick up the phone and say something like this: “Hey, I’m your new account manager. I recognize that no one’s contacted you in a while, and I’m sorry about that. I apologize. I’d like to do a fresh start. Would you give me the opportunity to get to know you better and learn about what’s important to you?”

That’s it. Simple. Direct. Human.

Now here’s the hard part: When you have that conversation, some customers are going to unload on you. If they really have felt taken for granted, they’re going to say some nasty things. They might complain about the last account manager. They might air grievances about problems that have been festering for months.

And the most important thing you can do in that moment is shut up and listen.

Don’t try to defend the past. Don’t talk over them. Don’t promise you’re going to be so much better than the last person. Just let them get it all off their chest. Let them talk it out, because people like people who listen to them.

Then, if there’s something specific you can help them with, don’t make promises you can’t keep. Commit to one thing. Take care of that commitment. Honor it. Build trust slowly. That’s how you become a high-value partner through fanatical prospecting discipline applied to account management.

The Smart Way to Triage 50 Accounts

You can’t effectively manage 50 accounts with equal attention, so you need to segment fast. Use a simple A, B, C ranking by revenue and risk:

A Accounts: Your largest customers or those at highest risk of churn. These get weekly or bi-weekly touchpoints.

B Accounts: Solid mid-tier customers with growth potential. These get monthly check-ins.

C Accounts: Smaller accounts that are stable. These get quarterly touchpoints.

But here’s the secret weapon most account managers miss: Use AI and your CRM data to find the low-hanging fruit. Look for patterns like former buyers who’ve moved to new companies in your territory, customers who mentioned specific challenges in past conversations, or accounts showing signs of expansion readiness.

One of the smartest things you can do is ask your AI tools: “Did anyone on this account ever mention their favorite sports team? Do they like to cook? What matters to them personally?” Those human details are gold for building real relationships in sales.

The Retention Secret Nobody Talks About

Here’s what kills me about account management: Retention is actually easy. If you’re just nice to people, for the most part, they’re going to be nice to you.

It doesn’t take grand gestures. It takes consistency.

A random text message: “Hey, just thinking about you. How’s everything going?”

A quick video message once a quarter checking in.

Remembering to ask how their kids’ soccer season went.

Sending them an article relevant to their business with a note: “Saw this and thought of you.”

Human beings at the core just want to be understood and they want to feel important, like they matter. That’s it. That’s the whole game.

Your 30-60-90 Day Stabilization Plan

If you’re inheriting neglected accounts, here’s your action plan:

Days 1-30: Triage and stabilize. Reach out to every A account with your honest, human approach. Listen more than you talk. Identify immediate fires to put out.

Days 31-60: Earn the right to advise. Deliver on your initial commitments. Start providing value without asking for anything in return. Build familiarity and trust through effective sales communication.

Days 61-90: Focus on expansion. Now that you’ve proven yourself, you can start identifying opportunities to grow these accounts. But not before.

Don’t bite off more than you can chew. Build familiarity, then trust, then earn the opportunity to expand the business.

The Bottom Line

Stop treating your existing customers like an afterthought. They’re your easiest path to revenue growth, but only if you actually treat them like they matter.

Account management isn’t complicated. It’s about being human, being consistent, and actually caring about the people who are already paying you money.

So pick up the phone. Send that text. Schedule that coffee. Make the small investments in relationships that compound into massive retention and expansion wins.

That’s how you turn neglected accounts into your most profitable relationships. That’s how you build a book of business that actually grows. And that’s how you stop losing customers you already have.

Ready to master the prospecting and relationship-building skills that drive account growth? Join us at Sales Gravy Live: Fanatical Prospecting Bootcamp in Atlanta, GA on March 10-11th. Two days of intensive training that will transform how you approach every customer conversation.