Sales Gravy: Jeb Blount

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.

Have you ever gone into a closing meeting, a sales presentation, or even a prospecting call with total confidence? That mindset and feeling that everything’s going to go your way, that nothing can go wrong, that you’re absolutely going to win?

I’ve been there. I know you have too. It’s one of the greatest feelings ever.

But let’s juxtapose that against going into a meeting feeling insecure, where your focus is on everything that could go wrong versus everything that could go right. And then, as soon as something does go wrong, everything starts to spiral downward.

There is absolutely nothing that can make or break a deal like confidence.

In this Sales Gravy podcast episode, we’re going to explore exactly where confidence comes from, why it matters so much in sales, and most importantly, what you can do to build the unshakeable confidence that closes deals.

The Insecurity Death Spiral

Recently, I learned a profound lesson about confidence.

I was invited to play golf with a group of businesspeople in Florida. Beautiful day, sunshine, great course. It should have been perfect.

Except I’m not a very good golfer. And these guys? They were good. Really good. The kind of golfers who carry single-digit handicaps and talk about their swing plane like it’s a science project.

So I’m standing on the first tee, watching them stripe their drives straight down the middle, and I can feel it happening. That little voice in my head starts whispering: “You don’t belong here. You’re going to embarrass yourself. Everyone’s going to see how bad you are.”

I started strong enough. Made it through the first couple of holes without humiliating myself. But then I hit a bad shot. Then another. And instead of shaking it off like I normally would, I started fixating on those bad shots.

That’s when the downward spiral began.

Every swing became an exercise in anxiety. I was so focused on not messing up that I couldn’t help but mess up. My mechanics fell apart. My rhythm disappeared.

By the end of the round, I had played one of the worst games of golf in my life. Not because I suddenly forgot how to swing a club, but because I let insecurity take over.

Now, I managed to keep a smile on my face. We were playing golf in the Florida sunshine, after all. But inside, I was frustrated because I knew what had happened. I let my insecurity about being the weakest player in the group sabotage my entire game.

And here’s what hit me on the plane home: That’s exactly what I see happen in sales all the time. One moment of uncertainty, one unexpected challenge, and suddenly, a salesperson who is perfectly capable starts spiraling. Their confidence evaporates. And with it goes their ability to perform.

Why Confidence Matters in Sales

In sales, there is nothing that sells like confidence. Nothing.

Buyers lean into confidence. They’re attracted to it. They trust it. And because of emotional contagion—your ability to transfer your emotions to another person—you basically take your confidence and hand it to the buyer, who then gains more confidence in you.

Think about it. When you walk into a meeting radiating confidence, the buyer thinks, “This person knows what they’re doing. They believe in what they’re selling. I can trust them.”

But when you walk in feeling insecure, the buyer picks up on that too. They start thinking, “Why is this person nervous? What aren’t they telling me? Maybe this isn’t the right solution.”

In sales, because we can’t always control the playing field and because we don’t always feel like we should be where we are—especially when we’re dealing with the C-suite or high-level decision makers, when we’re in super competitive situations, or when we don’t really know what we’re talking about—one thing that goes wrong can create a cascade of other problems, creating a downward insecurity spiral that is real and deadly.

The Ultimate Source of Confidence

So the question is: Where does confidence come from? Where do you get it?

Well, confidence by its very nature comes from the inside. It’s a mindset. It’s something that you believe, just like insecurity is a mindset that comes from the inside.

Confidence is mostly created by certainty.

When you feel certain that you can control the outcome, you feel more confident.

When you’re in situations that feel familiar, or you’re talking about a product, your service, or some part of your offering that you totally understand, you feel more confident.

When you’ve executed the sales process perfectly and built deep relationships with your customers, you feel more confident that they’re going to buy from you.

When you’ve practiced your presentation multiple times and know it by rote, you feel more confident.

By the way, the same thing works in reverse. Uncertainty begets insecurity.

When you walk into a situation, and you feel uncertain—and this happens to a lot of brand-new salespeople who don’t know what to say or feel like they don’t really understand the product offering, their industry, or their customer’s business—it creates a level of insecurity.

So the answer, if we want to be more confident, is to create more certainty.

Certainty Creates Confidence

Let me give you an example from my horrible, awful, terrible round of golf.

In the middle of that terrible round, I got desperate for anything that would give me confidence. So I started playing entire holes with my 7-iron because that was the one club I felt I was certain I could hit.

Except for putting, I would hit the 7-iron off the tee, on the fairway, and chip with it around the green. 150 yards at a time with my 7-iron, I could make it go straight down the fairway and hit the green.

That certainty in that particular club helped me feel more confident, and my game actually improved when I stuck with what I knew worked.

Now, in sales like golf, there is nothing you can be 100% certain about, simply because there are too many variables. We’re dealing with human beings, nasty competitors, and a shifting landscape. Even in accounts that are in our pipeline, things are always changing.

So for us as sales professionals, there’s no absolute certainty. But there are ways you can boost certainty in order to gain more confidence.

Four Ways to Create Certainty and Boost Confidence

1. Invest in Yourself Through Education

If you get insecure when you’re talking about things in your industry or about your product that you don’t understand, then go educate yourself.

Take the time to learn. Take classes. Go to your LMS and take e-learning. Read everything about your product. Become an expert—not just in your product, but in your industry.

Also, learn about business. The more you can educate yourself about business, the more you gain business acumen, which makes you feel more confident in conversations with executives.

When you know your stuff cold, understand your product inside and out, and can speak intelligently about your industry and your customer’s business challenges, uncertainty evaporates, and with it, goes insecurity.

2. Plan Every Single Call

Winging it is wickedly stupid on sales calls because when you wing it, you create uncertainty.

So sit down and think about every single call.

What am I going to do?

What questions am I going to ask?

What’s my objective for being there?

What am I going to close for at the end (targeted next step)?

Build a plan, write it down, and review it in advance of your meeting. Planning creates certainty.

3. Murder Board Your Big Meetings

Along with planning comes the concept of murder boarding, red teaming, or scenario playing. Murder boarding creates certainty around handling the unexpected.

Especially in large presentations and closing calls, you need to start pulling the thread on everything that could possibly go wrong. Every objection you could get. Every pushback. Every hard question.

Think about the different stakeholders who are going to be around the table, and the types of questions they’re going to ask, and the potential things they may say. Then find somebody on your team or somebody in your household to role-play all those scenarios with.

I’ve found that nothing gives me more confidence in big sales meetings than murder boarding. Because when I get into those situations—especially with objections or negotiations that can be super intimidating—the more I role-play those things, the better I am at them and the easier they are to deal with. In fact, they’re far less difficult in real life than they were in the role-playing.

4. Keep a Full Pipeline

This is powerful: There’s nothing that makes you more confident than being able to sell like you don’t have to sell.

When you are fanatical about prospecting and build a full pipeline, it gives you lots of options. You know you can walk away from anything. You’re detached from the outcome.

When it doesn’t make a difference if you win or lose, you gain immense confidence, which is why a full pipeline is the ultimate confidence builder.

With Confidence, Mindset Matters

When it comes to confidence, mindset matters. If you are obsessed with how you might fail or what you might do wrong, there’s a tendency to get the thing you’re focused on. It’s called target obsession. Whatever we focus on, we tend to attract and move toward. So be careful what you’re focused on.

One of the things I do—and I know this is kind of weird, but it works—is before I walk into a sales meeting, I look into the mirror and tell myself, “I’m a great salesperson.”

I actually say the words out loud. It’s a little bit cheesy. But by saying those words, changing my body language, pushing my shoulders up, my chin out—the power pose, as some would say—that actually begins to change my mindset and makes me feel more confident.

Add to that eating well, getting plenty of sleep (sleep really does wonders for your confidence), exercising, and making sure, before you go into a big presentation, that you’re not going in on an empty stomach.

How to Overcome Insecurity in the Moment

I sell every single day, and I’ve been doing this for 30 years. I know what it’s like to walk into a meeting with a prospect or customer and feel insecure. It happens to me still. But here’s the thing: I’m very careful not to let people see me sweat because insecurity and sales make a poor mixture.

Because emotions are contagious and people have a tendency to respond in kind, I want to avoid transferring my insecurity to them, causing them to feel uncertain about me. So I’m very careful with my body language, eye contact, voice inflection, and how fast I speak.

One tactic I use when I feel insecure is to slow down, pause, and ask a question. This gives me a moment to regain my composure and manage my body language.

Build Confidence with Knowledge, Planning, Practice, and Pipeline

Confidence isn’t something you’re born with. It’s something you build through preparation, knowledge, practice, and a full pipeline.

The good news is that all of these things are within your control. You can choose to educate yourself, to plan, practice, and prospect.

Here’s what I want you to do this week:

First, identify your gaps. Where do you feel uncertain in your sales process? Is it product knowledge? Industry knowledge? Objection handling? Closing? Write it down.

Second, create a learning plan. For each gap you identified, create a specific plan to fill it. What books will you read? What training will you take? Who will you shadow or learn from?

Third, plan your next three calls. Don’t wing another call this week. Sit down and plan your next three sales conversations. Write out your objectives, your questions, and your close.

Fourth, murder board your biggest opportunity. If you’ve got a major presentation or closing call coming up, spend an hour this week role-playing every possible scenario with a colleague.

Fifth, evaluate your pipeline. Is it full enough that you can sell without desperation? If not, block time this week for serious prospecting.

This is how you build the kind of unshakeable confidence that buyers respond to, competitors fear, and that feels so good.

And remember, when it’s time to go home, and you’re tired and worn out, always stop and make one more call. Because that one more call gives you the confidence that you can walk in any door, anytime, stand toe to toe with any buyer, and have a winning sales conversation.

Over a million sales professionals and sales teams have become more confident prospectors with the Fanatical Prospecting system. Learn more here.

You are on slide 34 when the CFO’s phone buzzes. She glances down. The VP to her left is nodding, but you can tell he checked out ten minutes ago. You know this pitch cold. You have rehearsed it. You built the deck. You covered every feature, every capability, every objection. And still, you are dying up there.

You spent weeks on this presentation. None of it matters because everyone in that room has already sat through the same pitch from three other vendors this month.

“Pitching sucks,” says Danny Fontaine, author of Pitch, on an episode of the Sales Gravy Podcast. “It sucks for the people doing it because we get so stressed out, and we spend weeks doing mountains of work. Meanwhile, there is a whole audience who has just as bad of a time as us because they have to sit through an hour of 100 PowerPoint slides and they’re bored.”

He is right. The audience suffers just as much. They sit through identical presentations, back to back, trying to remember which vendor said what. Both sides leave exhausted. No one wins.

There is a better way. Effective sales pitch techniques don’t rely on slides. They create engagement, tell stories, and turn monologues into conversations that actually move deals forward.

Why Traditional Pitches Fail

The standard pitch follows the same predictable pattern. Company overview. Capabilities. Case studies. Pricing. Questions at the end. Every competitor uses the same structure. That means you are asking your prospect to choose between nearly identical presentations.

When everything looks the same, decision makers default to price or familiarity. Your carefully crafted message gets lost in the noise.

You are treating the pitch like a presentation when it should be a conversation. You are trying to inform when you should be persuading.

Experience Beats Information

In 1979, a small advertising agency called Allen Brady and Marsh (ABM) competed against industry giant Saatchi & Saatchi for the British Rail account. ABM’s founder, Peter Marsh, knew he couldn’t win by playing it safe.

When the British Rail executives arrived for the pitch, no one answered the door. They rang the buzzer three times before it finally opened, with no one behind it. The receptionist ignored them while filing her nails. The waiting area was filthy. After a while of being dismissed, the chairman stood up to leave.

That is when Marsh burst through the doors and said, “Gentlemen, you have just experienced what your customers go through every single day. Shall we see what we can do to put it right?”

ABM won the account. And it worked because the executives didn’t just understand the problem. They felt it.

Most sales pitches fail because they ask buyers to care before they are emotionally engaged. Information alone doesn’t create urgency—experience does.

Start With Them, Not You

Pitches always start the same: ‘Thanks for your time. Here’s our agenda. Let me tell you about our company.’

Your prospect stops listening after the first sentence.

If you want engagement, start with a question. Ask what matters to them. Ask what would make the time valuable. Ask what problem they are trying to solve.

Before you show a single slide, say something like, “Before we start, what would make this conversation worth your time today?” Or, “What is the biggest challenge you are facing with this right now?”

Those questions do three things immediately. They show respect. They give you intelligence. And they turn the pitch into a conversation from the first minute.

This works even better over Zoom, where attention is fragile and distractions are everywhere. When you ask early questions, you pull people in instead of competing with their inbox.

Stories Create Memory

The most powerful stories aren’t pulled from case studies. They come from real life. Every meaningful achievement involves obstacles. Those obstacles contain lessons. Those lessons connect directly to the challenges your prospects are facing.

A story without relevance is just noise. A story with a clear lesson becomes a lever.

A consultant once shared a story about buying a secondhand Lego set. She started building it, only to discover key pieces were missing. After hours of searching for replacements, she had to start over. When pitching a complex implementation, she said, “That taught me something. At the beginning of any project, we have to make sure all the pieces are in the bag.”

That story worked because it made preparation tangible. It made risk visible. It connected emotionally and logically.

If the story does not clearly support the point you are making, don’t tell it.

Ask Before You Lose Them

Most salespeople cling to their script even when they can see the room drifting away. They are afraid of losing control, so they keep talking.

That is how you lose the deal.

Don’t wait until the Q&A to ask questions. Sprinkle them throughout your pitch to keep your audience engaged and the conversation alive.

Ask if you’re hitting the mark, what they want to explore deeper, and what matters most to them.

When you ask questions, you aren’t giving up control. You are gaining it. The person asking the questions is always in control of the conversation.

Emotion First, Logic Second

Buyers like to believe they are rational. They are not. Emotion drives decisions. Logic justifies them.

If you want someone to care, you have to make them feel something. Frustration. Relief. Possibility. Urgency.

That is why the British Rail experience worked. Marsh didn’t argue that customer service was bad. He made them experience it. The feeling came first. The logic followed.

Once a buyer is emotionally engaged, they start looking for reasons to say yes. They look for data to support the decision they already want to make.

This is why information-first pitches fall flat. You are asking people to care before you have given them a reason to.

Create the emotional connection first. Then give them the facts.

When the Room Goes Cold

Even the best sales pitch techniques don’t work every time. Sometimes the wrong people show up, there is a fire you didn’t know about, or your message just doesn’t land.

When that happens, don’t push harder. Pivot. Call it out. Ask what would be more valuable. Acknowledge the moment instead of pretending it is not happening.

That level of honesty builds trust. It shows you are there to solve a problem, not deliver a performance.

Why This Matters

Your prospect didn’t show up to be entertained or to be bored.

When you give them an experience they didn’t expect, you separate yourself from every competitor running the same tired deck. You become memorable. You become relevant. You become human.

The pitch that feels risky is usually the one that wins. The personal story. The direct question. The willingness to have a real conversation.

Because the alternative is being forgotten the moment you leave the room, no matter how many slides you showed.

Want to take your pitch from forgettable to unforgettable? Download the FREE A.C.E.D. Buyer Style Playbook, which shows you exactly how to read your buyers, adapt your approach, and turn every conversation into a deal-closing opportunity.