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3 Big Challenges Facing Salespeople and How to Fix Them

By Jeni Wehrmeyer, COO & CMO of Anthony Cole Training Group

For top salespeople, Sales can be a rewarding and lucrative career. But (and it’s a big “but”) selling is not for everyone. The top performers have mastered many skills-- they do all the important things “right.” Even the best of the best, though, struggle with what I see as the 3 biggest challenges in a sales career. Let’s go through them and some possible solutions. 

Sales Challenge #1: Going Down with Your Elevator Pitch

Here’s the issue in a nutshell. Every salesperson has been taught to make an elevator pitch. So what can you really say in 15 seconds that fundamentally sounds different from your competitors? More importantly, what can you say in 15 seconds that allows prospects to mentally connect your company’s USP (Unique Selling Proposition) with their problem?

Let’s illustrate my point with a few examples:

  • HR: "I help companies like yours manage their talent onboarding." 
  • FinTech: "I sell customized software to specialty retailers for better cash flow management."
  • Accounting: "I’m a CPA specializing in the tax needs of smaller companies like yours."

And that's the issue. What you offer becomes so reduced to become a commodity…. and no one listens anymore.

Pushing the Up Button-- Try a Differentiated Elevator Pitch

When you make your pitch, you need to give the prospect a compelling reason to keep listening. Your words should provoke the message receiver to respond in one of three ways:

  1. "That's me!"
  2. "How do you do that?"
  3. "Tell me more."

These responses can be mentally as well as verbally. The idea is to get at the core as to why clients have chosen you/your company/your products/your services in the past. What problem was it that they wanted to solve? What’s the pain point you addressed? What benefit were they looking for that you were able to give them? 

Take that insight and create your "unique sales approach."


  • Insurance: "I provide people buckets of money in the right amount, at the right cost, and at the right time." (How do you do that?)
  • Banking:  "My clients are companies that discovered that working with a bank should be more than just a place to get money or leave money." (Tell me more.)
  • Accounting:  "I'm in the business of helping small businesses that are sick and tired of sending the government more money and keeping less." (That's me!)

Speaking directly to their ultimate pain point allows your unique sales approach to land effectively and personally with your prospect.

Sales Challenge #2: Consultative Selling

Consultative selling is an approach that’s hyper-focused on the customer. More than “the customer is always right,” it’s all about them to the Nth degree. The technique helps you as a sales professional better understand your customers’ challenges so you can more effectively position your solution in a compelling way.

There are 9 specific attributes for consultative selling defined within the Objective Management Group (OMG) sales evaluation, the leading sales assessment tool in the industry for over a decade:

1.   Develop strong relationships…. Deeper questioning helps this aspect. Going beyond small talk is how real trust develops. Don’t expect it to happen overnight; it is a process.

2.   Ask “Great” Questions….  These are questions that help uncover a problem or opportunity. They should not launch you into “presentation mode.”

3.   Ask “Enough” questions….  Do you probe enough to understand what’s going on beneath the surface? How is the problem impacting their personal or business situation? Do you stop when you think you have enough to put together a proposal?

4.   Listen and ask questions with ease…. Listening does not mean waiting for the pause for your turn to talk. Listening to understand is what you do when trying to understand what the prospect is really trying to tell you.  Don’t assume you know. When they pause, you then ask clarifying questions.

5.   Ask tough questions…. The best way to establish yourself as a trusted adviser is to ask the uncomfortable questions. (But it takes courage). Anyone can ask the easy ones.

6.   Uncover issues…. Understanding the prospect’s business challenges is what you actually offer. (It goes well beyond the “product” you’re trying to sell). Skilled salespeople uncover or foresee real problems and advise accordingly. 

7.   Understand how prospects will buy…. Remember, it’s their buying process (not your sales process). However, your questions are key in helping prospects drive urgency and self-discovery.

8.   Present at appropriate times…. Timing is everything. Sometimes we get ahead of the prospect, and other times it just doesn’t make sense to present at all. Learn to modulate your conversations so you and they can be in sync.

9.   Take nothing for granted….  Even when you do everything right, things can still go wrong, and very quickly. Elite salespeople always have a bit of skepticism.  It is a process to build a relationship.

Sales Challenge #3: Knowing When to Call it Quits

The question I get most often is “How can I be more successful in sales?”  To answer this question, I am going to, instead, answer a correlated question...“What do nearly all salespeople struggle with the most?

The answer: calling off the chase. Knowing when to say it’s over.

Many salespeople have an extraordinarily difficult time recognizing when it’s time to call it quits. The pursuit of the deal and the ensuing adrenaline rush of closing the deal are simply tough enticements to walk away from.

Maybe the prospect has told them to “get lost” in those exact words (or not). Regardless, some sales professionals take on an “I have not yet begun to fight!” attitude and go all in (again). They just don’t want to accept—nor even entertain the possibility-- that the prospect is just not into them/their offer.

Why?... maybe it’s bad timing?

The best answer I have is that, as a sales professional, you get better when you recognize two fundamental truths:

  1. You will lose more often than you win.
  2. When you are going to lose, you want to lose early.

To allow these truths to sink in, let's consider what your “pull-through rate” looks like:

Number of new clients / Number of initial sales conversations = Pull-through rate

If you have 100 initial sales conversations (or go on 100 prospect calls) in a year, and you win 15 new clients, then your pull-through rate is 15% (15/100= 15%). With a 15% pull-through rate, don’t you think you should go into your calls with a different mindset?After all, statistically, there is a far greater chance of you not landing the business than there is you will. Perhaps you should go into your calls with a bias for disqualification

Remember, not every prospect is one that you should have.

So, stop dreaming about turning every prospect into your perfect prospect. Start asking questions instead. Ask questions that confirm for you that your prospect has a problem they need to fix with you and now is the time to fix it. Operate with a bias for disqualification so you are not surprised when you conclude that it’s time for you to move on. It’s ok to hear “No, thanks,” from a prospect provided you hear it early on in your sales relationship.

Want to make your salespeople into top performers?

Anthony Cole can help your team overcome its biggest challenges.

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Last updated: 18 Oct 2022
Jeni Wehrmeyer
Guest Author, COO/CMO of Anthony Cole Training Group

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