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3 Big Sales Challenges

Posted by Jeni Wehrmeyer on Thu, Mar 17, 2022

Top producers have mastered many skills. However, we know that all salespeople, including top salespeople, still struggle with 3 primary sales challenges.


Selling is not for everyone but for those “elite” salespeople, it is a most rewarding career. These top producers have mastered many skills including positioning their value to prospects and clients, as well as following a stage-based sales process. Additionally, we know that all salespeople, including the cream of the crop, struggle with 3 primary sales challenges

Sales Challenge #1: Differentiating– how to be Unique

Everyone in selling has been taught the elevator speech, the 15-second commercial, the value proposition, the positioning statement, etc.  You know it's supposed to describe what you do: 

  • "I help companies like yours manage their insurance risk." 
  • "I sell customized clothing to busy executives."
  • "I own a CPA and tax consulting practice specializing in the needs of companies that generate between 5 and 10 million dollars in revenue".

Sound familiar? That's the problem. There is nothing unique about the approach from any one of these statements. That is why being unique is one of the biggest sales challenges.

You have to give the prospect a compelling reason to keep listening. What you say should cause the person with whom you are talking to respond either verbally or mentally in one of three ways;

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

When creating your “unique sales approach” (USA) or elevator pitch, answer the following questions;

  • What people or companies have chosen to do business with you/your company?
  • Why did someone buy the product/service that you offer?
  • What problem was it that they wanted to solve? 
  • What benefit were they looking for that they weren't getting?

Here are a few examples:

  • 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!)

Sales Challenge #2: Selling consultatively

Consultative selling is a vague term which is why it’s one of the biggest sales challenges. The OMG sales evaluation, the top sales assessment tool for 11 years, has identified these 9 specific attributes for consultative selling:

  1. Asks “great” questions. These are questions that help uncover a problem or opportunity. They should not cause you to go into presentation mode.
  2. Asks “enough” questions. Do you dig down beneath the surface to understand the impact of the problem on their personal or business situation? Do you stop when you think you have enough to put together a proposal or continue to drill down?
  3. Develops strong relationships. This goes beyond the chit-chat to a place where real trust develops. It is a process, not an event.
  4. Presents at the appropriate times. Sometimes it doesn’t make sense to present and, other times, we get ahead of the prospect.
  5. Uncovers issues. Skilled salespeople uncover real problems that exist or might come about if the situation is neglected.  It is understanding your prospect's business challenges beyond the “product” you might offer.
  6. Understands how prospects will buy. Remember, it’s their process; however, your questions can help drive self-discovery and urgency.
  7. Takes nothing for granted. Elite salespeople understand that at any time, things can go south – they always have a bit of skepticism. It is a process to build a relationship-based solution.
  8. Asks tough questions. Anyone can ask the layups; prepare to ask questions even when it is uncomfortable.  That is really the best way to establish yourself as a trusted adviser but it takes courage.
  9. Listens and asks questions with ease. Listening does not mean waiting for your turn to talk.  Listen to understand what the prospect is really trying to tell you and then ask your question to clarify what you heard.  Don’t assume you know.

Sales Challenge #3: Knowing when it’s over

What do all salespeople struggle with the most? They have a difficult time recognizing that their pursuit of a prospect is over (even when the prospect hasn’t told them in those exact words). Most don’t want to entertain the possibility and that is why it is one of the biggest challenges in sales. But, why? I mean, it’s not like it has not happened to them before.

One of the most frequently asked questions we receive is; “how do I/we increase sales” or “how do I become more successful in sales?” And the best answer I have is that you get better when you recognize two fundamental truths:

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

Stop dreaming and start asking questions. Ask questions that allow you to confirm that your prospect has a problem they have to fix and that now is the time to fix it. Operate with a bias for disqualification so you are not so surprised when the conclusion is it’s time to move on. No is ok provided you hear it at the right time in your sales process.

Learn More About the  21 Core Competencies!

Topics: sales challenges, biggest challenges in sales


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    Anthony Cole Training Group has been working with financial firms for close to 30 years helping them become more effective in their markets and closing their sales opportunity gap.  ACTG has mastered the art of using science-based data and finely honed coaching strategies to help build effective sales teams.  Don’t miss our weekly sales management blog insights from our team of expert contributors.


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