5 Quick Tips To Help You Win Over Your Difficult Customers

by Jeff Shore 

There’s an old saying about sales. “Sales is the perfect business…if people weren’t involved.” Boy, isn’t that the truth?

As I work with sales professionals across the country I hear horror stories of nasty and contentious customers that even the best of the best would want to avoid.

But before we focus on them, can we begin with a handful of honesty? We have all—every one of us at some point in our past—worn the moniker of “challenging customer.” Whether it was ultimately warranted or not, we have walked in those shoes.

That is a very important point; don’t miss it. From our own perspective our behavior is neither belligerent or inappropriate. We always feel justified to act in the manner we choose.

Put it this way: There is no such thing as irrational behavior. Every outburst, every comment, every sneer—all are rational actions in that moment. That is true for each of us, and it is true for our customers.

Because of this truth it would stand to reason that the most appropriate action on our part would be neither judgment nor derision, but rather a desire to truly understand.

Difficult customers are a huge opportunity to close more sales.

Think about it. Most people have zero desire to work with someone who is “difficult.”

The greatest crime is to confuse behavior with character. To define the individual as being mean versus acting mean. There is a ginormous difference. When we find ourselves in stressful situations we simultaneously find an adjustment to our behavior.

I would contend that the strategy of top sales professionals should be to embrace challenging customers. The process of understanding and serving challenging customers is the key to unlocking the door to big-time sales success.

While other salespeople are blowing off challenging prospects, top professionals are landing deals right and left.

Here are five tips to help you gain the mindset you need to expand your pool of potential purchasers and be on your way to establishing a distinct advantage over your competitors.

#1. Expect The Challenge 

Whatever “the difficult” presents as — entitled, mean, confused, greedy, unreliable, emotional or indecisive — expecting it is the first step toward winning these folks over. When you anticipate the possibility that your customers may be challenging, it won’t surprise you when they are!

In martial arts, they teach the best way to win a fight is to not get in one in the first place. By having a neutral response versus a defensive reaction, you are more likely to disarm the difficult customer.

#2. Exercise Your Curiosity Muscle 

I know this goes against your instinct to run from difficult customers, but here’s the truth: These people are still people! They’re looking for a solution, they have a problem that needs to be solved. And the more curious you are about them, the more likely they are to engage in a positive way. When we encounter a difficult customer, it is up to us to challenge our own perception with three questions:

1. “Am I seeking to understand?”

2. “Am I being fair?”

3. “Am I assessing this person’s motives correctly?”

#3. Choose Positivity 

Mark my words; five minutes into the conversation someone will have changed. Either their negative energy turns positive or your energy turns sour.

This is a game that you cannot afford to lose. The only way to win is with a firm commitment to your own positive approach. This is a choice, and that choice must be renewed day by day, hour by hour, customer by customer.

#4. Practice Empathy, Not Judgement 

If you are judging someone, there is no way you can have empathy. As Brené Brown says, “Empathy drives connection.” That being the case, judgment would drive disconnection. So, what is empathy? In a nutshell, it is feeling with people.

Try to identify what your customer is feeling and think of a time when you felt the same way. This will help you understand your customer on a deeper level.

#5. Go Above And Beyond 

To be certain, challenging customers will require more energy than most, but they also represent a market share that too many in our profession simply dismiss.

Since every other salesperson is running for the hills and avoiding difficult customers, you will do well to go above and beyond expectation. In fact, the more difficult they are, the more you should extend your efforts to serve.We’ve all had difficult customers. They are inevitable in the world of sales. They come in various forms and styles, but come they will.

And how we deal with them will directly determine our level of sales success.

That’s why I wrote Dealing With Challenging Customers: 7 Reality-Based Techniques for Tackling Tough Customers. In this short book I identify seven types of difficult buyers and share insights into how you can guide each of them through a positive purchasing process.

You’ll discover that the problem is not typically related to the buyer’s character as much as it is about their purchasing style.

Once you gain that mindset, you will expand your pool of potential purchasers and be on your way to establishing a distinct advantage over your competitors.


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About the Author: Jeff Shore

Jeff Shore

Jeff Shore is the Founder and President of Shore Consulting, Inc. a company specializing in field-tested and proven consumer psychology-based sales training programs.

Jeff is a top-selling author, host of the popular sales podcast, The Buyer’s Mind, and an award-winning keynote speaker. He holds the prestigious Certified Speaking Professional designation from the National Speakers Association and is a member of the NSA’s exclusive Million Dollar Speaker’s Group.

With over 30 years of real-world, frontline experience, Jeff’s advanced sales strategies spring from extensive research into the psychology of buying and selling. He teaches salespeople how to climb inside the mind of their customers to sell the way their buyers want to buy. Using these modern, game-changing techniques, Jeff Shore’s clients generated over $30 billion in sales last year.