6 reasons why salespeople win or lose a sale

6 reasons why salespeople win or lose a sale

Why do salespeople win or lose a sale?

When salespeople win, they assume it’s because of their sales expertise or their solution’s high-level performance. But when they lose, it’s easy to say it was marketing’s fault, or the customer just wasn’t buying, or they couldn’t gather a considerable discount.

The truth is, the majority of salespeople don’t take the time to analyze why they lost or won a deal in the first place. They really don’t know one way or another.

Here’s a list of reasons that can make all the difference between winning or losing a sale.

1. Focusing on the product rather than the problem

Today, many salespeople feel they take a problem-focused approach. However, their actions say otherwise. They keep falling back on the idea that they need to influence customers or sway them to do something.

It comes as no surprise that customers frequently feel the need to push back under such circumstances. It’s essentially a battle of wills, one that is being fought on a simmering ground of distrust and doubt.

In lieu of examining the customer’s problems, these salespeople spend the majority of their time trying to shove their product on customers.

Addressing the problem

Your customer probably won’t care about your product until you highlight the problem it solves. A sales strategy based on the obstacles you help your clients overcome instead of the products you offer moves the focus back to where it should be — your customers!


The more effort you put into understanding the prospect or their problems, the more they tend to persuade themselves to buy, moving you closer to product-market fit.

So, always try to highlight features of your product that impact your prospects’ pain points. Instead of simply naming product features, link each one to a clear benefit. Also, make sure to describe how the solution you provide is different from other players in the market (but be careful not to exaggerate).

2. Not targeting the decision-makers

Recent statistics show that a mind-boggling 68% of salespeople struggle to reach decision-makers.

Sales leaders often wonder why their sales cycles are so lengthy, their margins are slipping away and the number of deals closed is going down. Unless salespeople bring value directly to the decision-makers’ tables, this will become the rule, not the exception.

When you're selling something, you first need to identify and then focus on the key decision-makers. After all, there’s no point convincing someone to purchase from you if they aren’t capable of buying your product or service.

Addressing the problem

Normally, there’s not one all-powerful decision-maker at the pinnacle of the totem pole – in reality, many elements need to come together to keep the pole intact.

To be truly successful in sales, there are often many stakeholders who need persuading. These include:

  • C-Level Managers
  • Business Users
  • Mobilizers

Selling to the right decision-makers increases your odds of winning a deal. This means maximum results with fewer dead ends and less wasted effort.

3. Lack of alignment of sales and marketing teams

Ah, the most cliché competition in business: marketing vs. sales. Each team has its own idea of how to communicate with customers, and both refuse to believe they share many similar traits.

This lack of agreement between marketing and sales weakens businesses all over the world.


Addressing the problem

The conventional, self-sufficient functioning of marketing and sales teams simply can’t survive anymore. The gap between marketing and sales should be bridged to supply the buyer with relevant, high-quality content in discussions.

With regular communication between marketing and sales, both teams can talk about the issues they’re facing and find answers together. For example, this communication can give the sales team better access to valuable content. Meanwhile, marketing can get customer data insights that help them focus on building the right leads.

Schedule weekly meetings to allow the two teams to answer each other’s queries, provide updates and feedback, and share relevant information that will help both teams improve their performance.

4. Not understanding the psychology behind closing sales

One of the major differences between a mediocre salesperson and a professional one is the ability to discern what’s going on in a prospect’s mind.


Understanding the mindset of the customers and using sales psychology hacks in your proposal is the secret to winning at sales.

Addressing the problem

Using past customer data, uncover the point in your customer interaction when the prospect is more likely to convert and use it to your advantage.  A delay here could give the prospect a chance to change their mind.

On the other hand, if the prospect notices that you’re overeager to close the deal, this could be lethal. In this case, the salesperson is placing primary focus on increasing the close rate rather than winning over the customer.

If at any point during the deal you think that you might have miscalculated the moment, go back to your sales presentation and highlight new reasonings that you’ve saved for just such an emergency. You will need a stash of good arguments if you want to be included in the category of professional salespeople.

5. Taking no at its face

“No!” Hearing that can be difficult for a salesperson.

Disappointment holds back many potentially good salespeople from attaining greater success.

Just because a prospect turns you down, doesn’t mean that the sale is lost forever. It’s imperative to dig deeper into the reason for the rejection, then follow up accordingly.

Addressing the problem

Before doing anything else, ask yourself: “Am I sure my pitch was turned down?”

At times, a response along the lines of “We don’t the budget to do that at the moment” really means just that. In this case, you can try asking when budgets will be reviewed.

Similarly, if the prospect says, “We already have a solution for this,” try asking them which one, and figure out if their contracts are going to be up soon. If not, simply stay on their radar by connecting with them over social media or at business events.

Then, set a reminder to revisit the conversation in the future.  Some customers re-emerge down the road and make a purchase weeks (or even years) later.

When you have your data neatly stacked into a CRM, you’ll have full visibility into your sales pipeline and access to your prospects’ history at a glance. This helps you streamline conversations and close more deals. That’s why a CRM is an essential tool for successful follow-ups.

6. Taking an excessively aggressive approach

"What can I do to get you to decide right now?"

"If you don't make the purchase now, you’ll miss the offer."

"If you don't want to do business with us, just tell us so we won't be wasting our time either."

The aggressive approach (i.e. the "hard sell") is more likely to alienate customers than draw them to you.  Even if the customer makes a commitment, they may resent being pressured. Often, this kind of customer will find ways to delay a deal or get out completely.

Addressing the problem

An aggressive salesperson tries to take control of the conversation and focuses on showing how much they know about their product. The problem is this: your customer isn’t really interested in what you know. They’re more interested in how that knowledge can help them.


A solutions-based salesperson has an in-depth understanding of their product, but they don’t feel the constant need to dig into these details. They help the customer by asking about their difficulties and presenting solutions within the offer.

During this process, they get the customer to talk and use the information they acquire to close deals.

Know the reasons why you win or lose

When salespeople are questioned about their selling style, they frequently come up with answers like “strategic,” “consultative,” “challenging,” and even “lucky.” Regardless, it’s nearly out of the question to classify a selling style in one word, since each one is usually very dynamic.

Your style is largely influenced by the product you sell, the buyer, how far away you are from your quota, and how much time you have left to reach it.

Your individual sales style can help you win deals, but don’t rely on that exclusively. Instead, look at the data. Compare yourself to the points above. Do you focus on the product or the problem it solves? Are you overly aggressive? Do you tend to take “No” at face value?

By watching out for these factors, you’ll be able to see why you lose some deals. Plus, you’ll be able to use these insights to improve your skills and win more deals in the future.

Everybody can learn to become a better negotiator if they focus on building the right skills and attitudes. Download our free book, The Founder's Guide to Sales Negotiation.