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Relationship Selling is the Key to Your Sales Challenges

Posted by Tony Cole on Thu, Jun 02, 2022

Most organizations and advisors have been working long term to be more customer-focused. The challenge is for advisors to be productive and assertive without coming across to customers as sales-driven.

One of the key sales challenges is to stay focused on adding value and leading with relationship selling.


In today’s volatile markets, one of the key sales challenges is to stay focused on adding value and leading with relationship selling. This is not new news to those of us who work in sales. In fact, most organizations and advisors have been working long term to be more customer-focused. The challenge is for advisors to be productive and assertive without coming across to customers as sales-driven.

Assertive (not aggressive) salespeople win more business than others. These people care so much about doing the right thing for their clients that they are willing to risk the relationship and the sale to ensure the prospect or customer makes good decisions. Does this describe you? This is the essence of relationship selling.

What does assertiveness have to do with relationship selling?  In a word, EVERYTHING. If done properly, the early conversations and meetings will help to qualify or eliminate a suspect. This will save time for those prospects who are really not prospects as well as streamline your efforts and pipeline, giving you more time and energy to focus on finding more and better prospects for whom you can solve problems. One of the biggest sales challenges for many salespeople is spending time on unqualified prospects who will never buy.

In initial “assertive” conversations, you must be gathering information that leads to a full understanding of what pain or problems your prospect has to solve, what they have done to address those, and what their current provider has done to help. It is only through the intelligence that is gained and utilized in these conversations that will lead to long-term mutually beneficial relationships.

In this discovery process, the skill of asking the right questions, the right way, at the right time is critical.  In our selling system, for a prospect to qualify, they must:

  1. Have compelling reasons to buy, make a change, or do something different
  2. Have the capability and willingness to invest the necessary time, money, and effort
  3. Be willing and able to make the decision to fix the problem, AND be able and willing to make the money decision

There are lots of questions that need to be asked to find out if the prospect qualifies in these three areas.  Some of these questions require a salesperson to be assertive.  Questions such as:

  • “How will you go about telling your current broker/banker/relationship that you are no longer going to do business with them?”
  • “If you don’t have the money, how will you solve the problem?”
  • “The budget you have won’t be enough to get you the outcome you want. What part of the solution do you want to eliminate?”
  • “What will you tell your partner when they say they don’t want to make the change?”

Imagine if you were gutsy enough to have these types of conversations. What would happen?  You might fear that you would lose more business. But suppose that wasn’t the case.  Suppose by being more assertive, you are actually helping the prospect by discovering what is in the way of them reaching their objectives.  Suppose this leads to the elimination of think-it-overs and actually helped people to make decisions.  Imagine that you stopped making presentations to people who could only say “no” and never had the authority or intention of saying “yes”.  What would happen?

You would sell more and build stronger relationships.

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Topics: relationship selling, sales challenges

Houston, We Have a Problem (How to Avoid Selling on Price)

Posted by Mark Trinkle on Thu, Apr 14, 2022

In all moments of selling, there are many things that can go wrong. And when something goes wrong, it is in fact time to say “Houston, we have a problem.”  But who is the “we” that caused the problem?


How to Avoid Selling on Price

I have always loved President Theodore Roosevelt’s quote on problems: “If you could kick the person in the pants who is most responsible for most of your trouble you would not sit for a month.”  Just like in tennis or golf, many of our problems are self-induced.  They are “unforced errors.”

Our sales coaches, we are always dealing with sales challenges that span the entirety of the typical sales process.  From the opening moments of finding a lead to uncovering an opportunity to presenting and getting a decision, there are many things that can go wrong.  And when something goes wrong, it is in fact time to say “Houston, we have a problem.”  But who is the “we” that caused the problem?

Speaking of Houston, I was there this week delivering a keynote address at the 2022 Mid America Lenders Conference.  My training was on selling in a rate-sensitive environment which is a hot topic given that 2022 will be a year with multiple rate increases.  In my keynote, I asked the attendees if they were working on the right end or the wrong end of the problem.  When a prospect asks you at the end of the sales process for a concession (rate or terms), that tends to be a real trouble spot for salespeople.

Every company we work with believes in the power of having a value-based selling approach.  None of them want to be the low-cost provider in their respective industry.  And while we are called upon to help with last-minute or late-cycle negotiations, that is working on the wrong end of the problem.  The right end of the problem is at the beginning of the sales process where it is essential to introduce value into the equation.  After all, the primary reason why salespeople struggle to defend value at the end of the sales process is that they fail to introduce that value at the beginning of the sales process.  

From the sales assessment tool that we use by Objective Management Group, here are the skills of a value-based seller:

  • Focused on value over price
  • Comfortable discussing money
  • High threshold for money
  • Willing to walk if the prospect does not see value
  • Always positions value
  • Sales process supports value
  • Learns why prospects will buy
  • Doesn’t need approval
  • Asks enough & great questions
  • Avoids making assumptions
  • Quickly develops rapport
  • Not compelled to quote

Start helping yourself by positioning your value early.  Make it impossible for your prospect to miss it.  Find out if your prospect values it and protect your bottom line.

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Topics: sales challenges, value-based selling

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.

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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.

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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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    About our Blog

    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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