Sales managers, here's how to handle a rebellious rep

You’re managing a successful sales team, but one of your reps frequently rebels against you. They don’t play by the rules, and they resist many of your directions.

You tell them to focus on three product features per demo, but the rep often shares ten. To make matters worse, they brag about it to the rest of the team: “I showed the prospect way more than I was supposed to and he loved it!”

Little infractions like this can cause problems over time, especially when a rep also fails to meet sales expectations.

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In these situations, there are two questions you need to ask:

  • Why is this person disobeying me?
  • How is this person disobeying me?

If they ignore your directions just because they can, or they complain without taking any action, that's a big problem. When this happens, you need to have a straightforward conversation with them. Let the rep know that you appreciate their strong-willed attitude, but they need to act like part of the team or find a company more aligned with their personality.

If that doesn’t work, give them one last warning. If they can’t follow directions so the team can accomplish its goals, it’s time to let them go. Give them two or three days to show immediate improvement. Anything more than that is a waste of time.

But if they’re disobeying you for the right reasons—if they care about an idea and take immediate action to generate results—you might not even have a problem. Seriously. This happens all the time at Close.

In fact, we probably wouldn’t exist today if people didn’t disobey me for the right reasons. I could list a hundred examples, but I’ll focus on a few big ones:

We wouldn’t have launched in January 2013

When we started Elastic Sales, we built a powerful internal tool to help our team close deals faster. We knew that one day we’d try to release our software so that other companies could transform their sales teams, too. A few Elastic employees thought Close might be the future of our company.

But here’s the problem: I really didn’t want to launch a separate business. Not then. I was confident that we’d built something special, but I resisted the idea of launching Close right away. We had too many other things to do.

Thankfully, Phil—our Head of Product—pushed me to launch Close. He was convinced that releasing our software was the company’s best move and he said so every day. I finally gave in because he was so persistent, and because his passion for the product created a real sense of urgency.

I don’t know if we’d exist today if we hadn’t launched as early as we did. It was a game changer, all because one person refused to listen to me.

We’d have no logo

The only reason we have a logo is because two people ignored me.

Kevin and Jason kept saying, “We need a logo. We can’t launch without a logo.” But I didn’t care about a logo. I wanted to write out the name of the company and worry about branding later.

But did they listen to me? Of course not. They posted on 99designs, collected a bunch of logos, picked three that they liked, and sent out an email thread that said:

“Hey guys, here are three logos. We really like Option A. What does the rest of the team think?”

Here’s the best part: we didn’t spend a lot of time on this. They made a quick decision and we all liked Option A. End of discussion.

Close would not have email integration or search functionality

As we prepared to launch, Anthony—one of our cofounders—fought for two key features: email integration and search functionality. He kept saying, “Why is search so horrible in CRM platforms? Shouldn’t it be one of the most powerful features?”

In my mind, these were nice-to-haves. I really wanted to focus on call functionality.

Thankfully, the team didn’t listen to me. Product built both features and, not surprisingly, they became two crucial elements of our software.

We wouldn’t have a blog

It’s hard to believe, but I didn’t want the one thing that’s become our most critical marketing tool. Just like the logo, email integration, and search, I said we’d deal with it later. We had more immediate priorities.

But Nick—our Head of Growth—didn’t listen to me. As we neared our launch date, he said, “By the way, we have a blog and I’ve already written three posts.”

He’d already done the work and it looked great, so what could I say? I had no choice but move forward, and it’s a good thing I did. The blog became our #1 customer acquisition channel.

In every one of these scenarios, people were right to disobey me

And they did so for the right reasons. They understood the Why and the How. They believed their ideas were good for the company, and they generated results quicker than I could argue with them.

I don’t care if someone disobeys me, as long as they’re making Close better. We all learn valuable lessons from people who take calculated risks. Every once in awhile, you need to double down and champion risk-takers.

An October 2019 piece in The Economist titled In praise of dissenters pointed out the value of encouraging cognitive diversity in your company. You want people with different perspectives and intellectual backgrounds.

Now these guys don’t disobey me every day. They choose the moments when they’re most passionate about an idea and when they’re confident we’ll succeed. That’s the problem with the earlier scenario. The sales rep disobeys for the wrong reasons. There wasn’t a good Why and How.

If you have a healthy company culture, people occasionally break the rules

It’s proof that your team is confident and passionate about what they do.

Amy Edmondson of Harvard Business School coined the term "psychological safety" in work teams already in 1990. It's about the ability to speak up within an organization, without fear of sanction, and the concept has since been explored in many sales management articles.

When they disobey for the right reasons—when they take immediate action and produce results—you have a team capable of outperforming your wildest expectations. That’s the only kind of team I want to be on.

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