Your Best Salesperson Will Probably Bomb as a Sales Manager

Every company does this. Their best rep is crushing quota month after month, so they hand him the manager title. Seems logical, right? He's great at selling, so he should be able to teach everyone else.

Nope. We've learned this the hard way at Bartlett Roofing. More often than not, that promotion blows up. The things that make someone a killer closer are completely different from the things that make someone a great leader. One person lives for the chase. The other gets fired up watching a team hit a number together. Two totally different animals.

Now look, it's not impossible. We've had top reps here at Bartlett who turned into phenomenal sales leaders. But they're the exception. Your typical top performer doesn't have the patience to sit down with someone for 45 minutes and develop them. He wants to go close the deal himself. And that's great when you're setting the pace on the board. But it falls apart fast when your job is to motivate other people and hold them accountable.

So we're changing how we think about this. This is the start of a series where I'm laying out the actual playbook we're running at Bartlett right now. Not theory. Not something I picked up at a conference. This is how we're actually operating day to day.

The Two Things You Have to Nail in Sales Leadership

There's a razor's edge you have to walk as a sales leader. Relationship on one side. Accountability on the other. You need both. And most people are terrible at it.

If you try to hold someone accountable without building a relationship first, you're just a jerk boss. We've all had that boss. The guy who pushes and pushes but never took five minutes to actually know you. Think about the worst boss you ever had. I guarantee the relationship wasn't there. I've asked this question probably a hundred times over the years and the answer is always the same. That terrible boss? They never built the relationship.

Now flip it around. Nobody says, 'Yeah, he really knew me. He understood my goals. He was helping me get where I wanted to go. But he was a total jerk.' Those things don't go together. When the relationship is real, being direct doesn't blow people up. It builds them up. You eliminate the jerk boss problem by doing the relationship work first.

Salespeople love shortcuts. They want to say the easiest thing to close the deal. But in leadership, there aren't any shortcuts. You have to put in the relationship work. And then you have to do the accountability work. Every single day.

Build Relationships Two Levels Deep

Here's something I always teach our people at Bartlett. You should have relationships two levels deep. Know the people who report directly to you on a personal level. And know the people one level below them too.

Why? Because sometimes a person just doesn't click with their direct leader. It happens. If they've got nowhere to go and nobody to talk to honestly, you lose them. They're gone. But if you've built that relationship two levels deep, they've got someone they trust. Someone who can shoot straight with them. And you keep your people instead of watching them walk.

This isn't about going around your managers or blowing up the chain of command. It's about making sure nobody falls through the cracks because one relationship isn't working. That's how you protect your team.

Most People Think They're Working Hard. They're Not.

I'm going to be blunt because this is the part nobody wants to hear. Most people think they're high performers. They're not. Most people think they're working hard. They're not. And most people tolerate average when they shouldn't.

Here's where it gets real. What you expect from your team isn't what you say you expect. It's what you tolerate. Read that again. You can tell your team you expect greatness all day long. But if you let mediocre results slide, mediocre is your actual standard. That's what they hear. Not your speeches. Your tolerance.

That's dishonest leadership. And it's where you lose people. If you say one thing and accept another, your team sees right through it. You have to understand what real performance looks like, get genuine buy-in from people, and then hold the line. Because you can't really hold someone accountable unless they've given you permission to do that. And that permission comes from the relationship and from honest expectations that you actually enforce.

What Good Sales Leadership Development Actually Looks Like

This episode is the foundation. But there's a lot more coming. We're going to cover how to have hard conversations without destroying trust. How to coach performance. How to run meetings that actually move the needle instead of wasting everyone's morning.

We're going to talk about how to identify, promote, and develop leaders the right way. And we're going to get into how to handle underperformance and termination when you have to, and how to do it with integrity.

All of this is stuff we're actively putting into practice at Bartlett Roofing right now. I'm not teaching from a stage here. I'm showing you what we're building inside a $50 million company, in real time. We're using these exact trainings with our own sales team and our own sales managers. If it's good enough for us to bet our business on, it's worth your time.

Whether you're leading a team of 50 or you're a salesperson trying to figure out what it actually takes to perform at the top, this series is for you. Stick around and let's see if it helps.