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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

Stop Whining and Start Winning Deals in Regulation

Posted by Tony Cole on Tue, Jan 25, 2022

One of the biggest challenges in sales is outplaying your competition, especially if that competition currently has the business.

When you are playing against the incumbent relationship make sure you ask the following question: “Who wins a tie?”


If you are a football fan, you will clearly know what I’m talking about when I mention the Overtime Rule in the NFL. What the NFL’s Overtime Rule boils down to is:

  • If the game ends in a tie after regulation time, then an overtime period will be played.
  • The official flips a coin, and whoever wins the toss decides if they want to be on offense or defense.
  • If the team that has the first possession in overtime scores a touchdown the game is over, the scoring team wins.

This is what happened in the Chiefs vs Bills Divisional Playoff game Sunday, and the Bills lost. This is also what happened in the Chiefs vs Patriots AFC Championship game three years ago, and the Chiefs lost.

What does this have to do with selling and losing to the competition? Everything.

It almost never fails. Of the over 2 million salespeople tested by the Objective Management Group Sales Force Evaluation, 90% of the top 7% of all salespeople take responsibility for their outcomes. They don’t play the blame game. When you ask them why they didn’t get a sale, close an opportunity, or hit their quota, their answer will start with “I”.

Based on the research we’ve done over the last 25 years using the OMG tool, we know that at least 66% of the non-elite salespeople (93% of all salespeople evaluated) blame either the competition, the economy, or their company for lack of results or failure to close an opportunity.

It sounds something like this when a deal doesn’t close: “What happened?” “The incumbent came in and matched our price and kept the deal.”

Translation – I lost the toss of the coin, the other team got the last look, and they got the deal across the goal line and won.

What happens when we are in competition and it’s our own client that is shopping the market: “What happened? They looked at a competitor, told me what they were offering, we sharpened our pencil a little, and got the deal.”

Translation – I won the coin toss, saw what the competitor was doing, altered our original proposal, and won the deal.

When we win the toss, we don’t complain about a prospect shopping and picking us. When we don’t win the toss and don’t win the deal, we complain that the prospect wasn’t honest with us, used us to get a better deal, or the competition simply won on price.

You can’t have it both ways. I assure you that if the Buffalo Bills had won the toss and won the game no one in Buffalo would be complaining about the Overtime Rule.

The best way to deal with the overtime coin toss is to avoid getting there. When you are in competition against the incumbent make sure you ask 100% of the time the following question: “Who wins a tie?”

The answer will help you determine if you should risk a loss by going into overtime against an incumbent relationship that has already won the toss.

Need Help?  Check Out Our  Sales Growth Coaching Program!

Topics: Qualifying skills, sales challenges, biggest challenges in sales

The Pull of Resistive Inertia: One of the Biggest Sales Challenges

Posted by Mark Trinkle on Thu, Jan 13, 2022

One of the biggest sales challenges to overcome is a prospect who becomes indifferent when they decide that doing nothing is the easiest thing to do.

How do you challenge the decision and not the prospect to help them overcome their choice to maintain the status quo?


There is no question that the most disappointing outcome for a salesperson to receive after their presentation is the outcome where the prospect does nothing. Not only did you not get the business…neither did any of the other firms that pitched the deal. The prospect simply stayed with the incumbent provider. They did nothing.

Before we go any further, let me give you two acronyms:

PI = Prospect Indifference
CSQ = Cost of Status Quo

I would argue that those two things are perhaps even more powerful than the other firms that provide you with ongoing competition. Just like Reese Cups, potato chips, and certain adult beverages, the gravitational pull of doing nothing can be hard for prospects to resist. Prospects become indifferent when they decide that doing nothing is the easiest thing to do. But here is the reality – while it may be the easiest thing to do, it is not often the right thing to do. Here is a general life principle: the hard thing to do and the right thing to do are often the same things.

You have two options when your prospect does nothing (they simply stick with the incumbent):

  1. Eat another Reese Cup and do nothing yourself (walk away)
  2. Challenge the decision (challenge the decision, not the prospect)

How do you do that? You do that by asking the prospect if they have calculated the cost of maintaining the status quo (CSQ). Ask them what their tolerance is to continue to deal with the problems you uncovered during your discovery process. Ask them what those problems will likely cost them going forward.

I will close with two questions: when do you want to know about the likelihood of your prospect maintaining the status quo? And when do you want to know that the pull of resistive inertia will just be too powerful and will likely prevent the prospect from making a move? Don’t forget the set of questions you should be asking towards the end of your first call: does your prospect have a problem that they have to fix, and who gets to fix it?

Or you can do nothing. Just take a bag of candy to snack on during your ride back to the office.

Need Help?  Check Out Our  Sales Growth Coaching Program!

Topics: sales challenges, biggest challenges in sales, challenges of a sales representative


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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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