Using AI Agents for Strategy

“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.