The #1 Avoidable Mistake 99% of Sales Managers Make

It happens all the time. You catch yourself listening to the tail end of a sales call between one of your sales reps and a potential customer. Everything sounds right—the right words, tone, and energy.

You love what you're hearing, and you make up your mind right then and there—your sales guy must be crushing it.

But a week after the call, you have a rude awakening. The customer is nowhere to be found. At the end of your sales cycle, when you’re staring at dipping closing rates and missed quotas, the same rep you thought was flying high is actually nose-diving at 500 mph.

You’ll want to blame your sales rep when this happens- and it will. Don’t. It’s not his fault that you made a faulty leap of logic and prematurely decided that he was succeeding without any fundamental factual basis.

Our brains are hardwired to repeat this mistake over and over—but it’s a mistake that is entirely avoidable.

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Listen to Both Sides of the Conversation

Too many managers get stuck on their numbers and focus obsessively on their sales metrics and quotas. When evaluating sales calls, they treat the actual conversation part like a black box. That means that they only ever hear what their own sales reps are saying.

When we only hear part of the story, our brains fill out the rest. We make interpretations based on half of the data and incomplete pictures. What’s worse, these brief impressions guide how we think moving forward. It’s a common phenomenon that psychologists call confirmation bias.

Turning this around is easy, but it’s something that not nearly enough managers do: record the calls that your sales team makes.

That’s how you can actually decode what’s happening between prospects and your sales team, evaluate their performance, and coach them to improve.

It’s like flossing your teeth—everyone knows it’s good for you, but no one likes doing it. With your sales team, you must dig into the gums and work out the plaque.

Use a sales CRM like Close to log and record calls for each lead automatically.


Do it obsessively. The customer's answers, tone, and energy on the other line will often lead you straight to the problem. Having the full context allows you to narrow the gap between how you think your reps are performing and what the data actually shows.

Here are three examples of sales calls gone wrong and how you, as a manager, can coach your reps through them.

1. Failure to Ask the Right Questions

Sales rep:

"Our product is a productivity platform that allows you to streamline your whole team’s workflow. I’m just curious—what internal tools does your team use to collaborate?"

The “curious” prospect:

"Hmm. Well, we currently use Basecamp for this, but we’ve been having a lot of issues with it lately."

Sales rep:

"It’s a match made in heaven! Teams transitioning from Basecamp to our product have increased efficiency by 20 percent."

The “curious” prospect: …

It’s easy to think your reps are out there raking it in when you can only hear one side of the conversation. In the situation above, your rep checks off all the right marks—he’s asking questions before diving in with a value proposition. Listening to the whole conversation, however, almost physically hurts you.

Your rep is shooting value propositions in the dark, hoping one sticks. He's jumping prematurely to the close when he should still be trying to learn more about the customer and identify their fundamental pain.

It would be best if you coached your rep to ask deeper questions:

Sales rep:

"Tell me more! We have a lot of customers who previously used Basecamp. What specific issues does your team encounter with the app?"

Maybe the customer doesn’t like Basecamp because they find its design challenging to navigate, or perhaps they don’t like it because it’s too expensive for the size of their team. Whatever the reason, when your sales rep digs deeper, they will find the central pain and be able to offer a specific solution.

2. Failure to Create Urgency

The “window-shopper” prospect:

"I’m really interested in your product, but to be honest, we’re swamped right now, and it’s just not a priority. I’m going to take this back to the team, and get back to you later."

Sales rep:

"Amazing. It was great speaking to you, and I really look forward to working together in the future."

If you only heard the sales rep’s side of the conversation, it’d be easy to think everything was sailing smoothly. Listening to the recorded conversation, however, allows you to discover the real problem. Your sales rep has failed to even make your product a priority for the customer.

Hammer into the rep the fundamental importance of creating urgency in sales. Some prospects are always “interested” but have some excuse about why it isn’t the right time to buy. “This isn’t a priority for us right now” and “I’ll get back to you later” are never acceptable responses.

Hold mock calls with your rep where you practice relentlessly. Run him through several versions of the scenario, with different twists on why the prospect might not want to move forward.

You need to get the rep to add value for the customer at each stage of the sales process, saying something like:

Sales rep:

"I understand that you’re busy. But we talked before about how your sales team wastes X hours a week on data entry, and our product could reduce it to zero. Efficiency will never be a priority unless you make it one. Talk to your team, and let’s chat again next week."

Train your rep to always push prospects that extra step further and motivate them to change their businesses now. Building that urgency—and following up on it—is what closes the deal.

3. Failure to Say “No”

The “discount hunter” prospect:

"I know we said we could sign up and get started next month, but to make the deal happen, we need a 40 percent discount and 24/7 customer support by phone."

Sales rep:

"I’ll make it happen. I’m sending you the paperwork as we speak."

Listening to the sales rep talk, you think they just crushed that deal—when you couldn’t be further from the truth. A 40 percent discount given without any pushback is insane.

The recorded conversation shows that your rep has major difficulty responding to aggressive prospects who like to play hardball. Teach them how to instinctively sell value over price.

Run through a scenario where you play a high-maintenance prospect demanding special treatment so they can practice saying “no” and pushing back.

Sales rep:

"I’m sorry, but the price I quoted you isn’t subject to negotiation. We don’t have resources for phone support, but none of our customers have had any issues our team couldn’t fix through our in-app chat support."

Learning to give prospects firm answers and risk losing the deal is one of the most difficult things sales reps need to learn—but it’s also one of the most important. It teaches them how to maximize the power of friendly strength and stand by the value of the product they represent.

Momentum Comes From the Whole Team

As a sales manager, you’re defined by your drive. You always want to push forward—get your sales reps qualifying more prospects, making more calls, and closing more deals.

Momentum is everything, and when your startup is in that race to hit $10M in annual recurring revenue, taking a step back to listen to calls that your reps have already made may be the last thing you feel like doing.

It seems counterintuitive, but taking a step back and listening to past calls is one of the most important things you can do—especially when scaling your sales team. Sometimes, you have to take a couple of steps back to take a big leap forward.

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