Retail Sales Training Tip: How To Sell To Difficult Customers

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Updated December 6, 2023
If you've been in retail sales at all, you’ve had an experience selling to a difficult customer.

It's like this...

You’re going along in a sale, and somehow, somewhere, a light bulb goes off, and you realize you just aren’t clicking with your customer.

They’re being difficult.

Maybe while selling a luxury watch, you are emphasizing a feature and your customer finds a flaw in your thinking and challenges your conclusion.

Or...maybe while you’re trying to “close” the sale on a purple plaid outfit, your customer turns away and starts looking around the store, picking up and examining a red low-cut outfit or a paisley mini.

Or ...maybe while you’re trying to build rapport, the customer interrupts you with short, pointed questions about delivery and availability.

Or maybe you’re selling your customer on the features of a product, and they want to make small talk about your kids or theirs.

Those customers are just so darn difficult

Or are they?

Maybe it’s you.

Customers buy from sellers who know who they are.

I butted my head against a lot of customers before I figured out my sheer force-of-nature personality cost me as many big sales as I won. I had to learn how to sell better...

It wasn’t until I learned that most customers aren’t difficult by nature but that:

Customers buy from someone who doesn't expect them to be someone else.

One of the most powerful lessons in how to sell to difficult customers I ever learned was that all salespeople and customers are one of four distinct personality styles - either a Driver, an Analytical, an Expressive or an Amiable.

You can take my free personality quiz to find out right now which personality style you are here.

Once I understood my Driver personality style and how I expected to be treated as a customer, I could call on my other three less-dominant personalities to treat customers who were not like me in a way they would respond to.

Natural Selling Styles of the Four Personality Styles

When it comes to sales, this is how the four personalities naturally behave in dealing with customers:

The Driver: Wants to separate the wheat from the chaff and determine whether the customer is a “player” or not. Doing this can often lead to higher sales.

The Analytical: Wants the customer to come to them and tell them what they are looking for. This allows them to shine as the product expert.

The Expressive: Wants to meet new people, whether they buy or not. Gives them a chance to socialize and be charming.

The Amiable: Approaches from a vulnerable, truly friendly position. This often endears them to the customer.

What each personality style wants from its customers:

The Driver: A quick sale of the most expensive items so they can make their quota and/or bonus.

The Analytical: Appreciation of their knowledge and buyers who don’t waste their time “just looking.”

The Expressive: Engagement with people who want to treat themselves and share their lives.

The Amiable: To find out what they want so the Amiable can help them find it.

When you understand your own style and the style of the customer in front of you, you can easily make more sales.

How To Sell To Difficult Customers: Adapt Your Selling Personality to Your Customer’s Personality Style

So, in the opening examples of selling to difficult customers, when the customer finds the flaw in your feature of the luxury watch, you would understand you are dealing with an Analytical personality style frequently found in engineers. Perfection is what they expect. They don’t mean to challenge you and be difficult, it’s just they will spend additional time narrowing all their options down to the “best” one. That means you need to drill down on features and benefits and solicit their knowledge so that together, you can answer all their laser-focused objections.

The next example is when you were trying to “close” the sale, and they turned away and started looking around at unrelated items – you are dealing with an Expressive personality style. They are the personality style rooted in the future; the possibilities of things excite them. It doesn’t mean they don’t want what you are working on. It’s just that something else caught their eye. The smart and, therefore, patient salesperson will let the Expressive add to that original item without ever having to be “closed.” The Expressive who feels validated spends more freely than any other personality style.

That difficult customer who interrupts you with short, pointed questions about delivery and availability? Probably a Driver personality. They consider themselves kings of the world. Time is of the essence. If they are asking those pointed questions, they already see themselves owning it and very well may have decided to purchase, so cut to the chase and answer them quickly and get on with the sale, but don’t forget to add on. A motivated Driver who trusts you can be the most loyal and price-unconscious customer of them all.

Finally, that difficult customer wanting to make small talk about your kids or theirs is trying to make a friend because Amiables don’t want to do business with people who aren’t friendly. You might be a cut-to-the-chase Driver, but if you talk to an Amiable that way, they will always “have to think about it.” You must find the attitude within to want to make a friend first and a sale second.

While customers can be difficult due to stress at work, a sick child, harsh words from a friend, or many other reasons, no one sets out to be difficult when shopping.

They set out to be greeted and engaged as unique people like you. They aren’t difficult. They want you to talk to them in a way that lets them be them.

Your customers aren't always like you. Learn to be like them because one size doesn’t fit all when selling at retail.