How to Close Sales deals
with Skeptical Customers

Table of Content


“I’m sorry, but I don’t see what makes your product different from the others we’ve seen.”
“We hear that your company’s quality has been dropping of late. Is there any reason why we should still buy from you?”
“What guarantee can you give me that your strategy is a 100% foolproof?”

As salesmen, we’ve all had clients that ask uncomfortable questions.
Sure, you might have the answers ready, but it’s a road you’d rather not take.
And you’ve also certainly had a deal fall apart at the eleventh hour due to some last-minute objections from a client such as this. Selling any product is a process of give and take. But with some clients, there’s more to give before you can begin to receive anything. It’s an ugly fact, but the truth nonetheless.

Difficult customers are everywhere, and they’re not going anywhere, anytime soon.
But, ask any salesman, and they’ll all agree: It’s far more gratifying to close a sales deal with a skeptical customer than it is to reel-in an “easy sell.” Additionally, you’ll be able to win their trust and loyalty, which cements your relationship with them.

And what’s better than an endorsement from a sales prospect who’s got a reputation for being difficult?
Read and remember these seven tips, and you’ll be able to convince even the most hardened skeptic to sign on the dotted line.

1.Demonstrate What You Sell

Who doesn’t like free goodies and trials?
There’s something about the word “free” that magically attracts interest and attention.

They’ll also remember you fondly the next time they see your brand.
Leverage this fact to your advantage.
Give your clients a product demonstration or a first-hand experience of your services.
Car salesmen have been doing this for decades.
By letting sales prospects go for a test drive, they cement mutual trust between both parties, while also letting them experience your product first-hand.

This is the easiest way to stall a sales deal.  

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2. Introduce Verifiable Evidence

There’s nothing more satisfying to a skeptic than cold, hard data that supports what they want to believe.
Don’t hesitate to gloat about something as long as it’s verifiable and true.
It’s the best way to lend credibility to yourself and your organization.

Think about what you’re planning to say during your next meeting, and go over anything that may appear misleading.
If you’re making a tall claim, always ensure you have the statistics to back it up.
If you don’t, you could get called out, and this will leave you red-faced to say the least.

They’ll certainly appreciate you for it.
It’ll also go a long way in closing sales deals with such customers.

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3. Provide Testimonials and Expert Reviews

Everybody loves an expert.
We’re instinctually programmed to listen to more authoritative figures. Expertise in a domain lends credibility to your work, and that’s why it’s necessary to share an expert’s review of your product with a difficult client.

Clients appreciate and pay attention when someone who’s a thought leader or is influential in their industry, shares their inputs.
They lower their defense, and start taking you more seriously.
Also remember to include testimonials and customer reviews.
They are an unbiased evaluation of your product, and a happy customer’s review is worth its weight in gold.

4. Explain the “Why’s”

If you’re dealing with a skeptic, you can be certain that they’ll have a lot of questions.
The key to answering them lies in dismantling their decision-making process.
Even the most difficult customer first makes decisions based on their emotions.
They then justify their choices using rationale and logical analysis.

When you give your client a reason as to why they should buy your product, make sure you have a valid reason for the same.
For example, they might ask why you’re offering a free 14-day product trial. Your answer can be anything from “We want to ensure that you know you’re making the right choice” to “It’s the way our company has always offered products.”

It doesn’t matter as long as you’re telling the truth and answer their questions.
The most important thing is to reassure them they’ve made the right choice. It takes you a step closer to closing that sales deal.

5. Be Specific

When you’re short on accurate data and can’t prove the point you’re trying to make, you’ll try beating around the bush.
Skeptical sales prospects earn their reputation from being able to detect this behavior right from the onset.
It’s essential that you don’t say anything that is ambiguous.
Be direct, specific and exact – nothing a skeptic loves more!
When you’re presenting, make sure you include facts, numbers, and quotes.
They improve the credibility of what you’re saying.
If you have statistics that are vague, find a better alternative or avoid using them altogether.

Bad: We’ve received positive feedback from most of our clients about this product.

Good: 84% of our clients have rated our product 4 or more stars out of 5. 

Best: 52% of our clients have rated our product 5/5, and 32% have rated it 4. We’ve had a few negative reviews, but we’ve connected with those respective clients and have taken care of their grievances in a manner that they are satisfied with. 

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6. Exploit Similarities

The fact is that we subconsciously divide society into some groups we’re part of and others we are not.
Naturally, we’re biased towards groups we belong to.
Your message should ideally reflect such similarities between you and your client.
But don’t try to fake it.
You should never go out of character when trying to close sales deals.
Remember, skeptics are hard to convince.
If you’re being insincere, they’ll be able to call you out with little to no effort.

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    7. Differentiate your Product

    This is a must for any customer, but it takes on added value with a skeptic. It could also be the biggest challenge for you.
    15% of salesmen believe that differentiating their product from that of their competitor is the biggest challenge they face when aiming to close a deal.–
    Richardson Study
    It’s necessary to show that your product stands out from the rest of the competition and explain why it’s the best fit.
    Most products in a given market are pale imitations of each other, and that’s not a good enough reason for your client to choose you.
    The process begins well before the sales cycle starts.
    Create your product by keeping a customer’s desires, fears and ambitions in mind.
    Your product must satisfy and fuel their demands, and this will keep them coming back for more.
    Unless your product aligns with a customer’s demands and trends, it simply won’t fare well.

    For example:

    Take a feather out of Apple’s hat, and design your product keeping this example in mind.
    You’ll find it a lot easier to attract sales prospects and to close a greater number sales deals.


    Regardless of how good it is, no product can sell itself.
    Irrespective of how brilliant you think you are, convincing a skeptic to purchase your product is the hardest thing to do in sales.
    But once you’re done, it’s also the most satisfying.
    Not only do you win over a sales prospect who’s picky, but you also polish your organization’s credibility.
    It can seem like it isn’t worth it, but you’d be surprised.
    Create a compelling pitch based on hard evidence, customer testimonials and expert inputs.
    Address their pain points, and be specific about the problems you’re trying to resolve.
    Try to identify with them, and get to know them inside out.
    Empathize with them, and show them you care.
    Follow these tips to the word, and before you know it, you’ll find it a lot easier to talk to them.
    Once that’s the case, you’ll be able to convert even the harshest cynic into a happy-to-pay customer.
    Remember, there’s always light at the end of the funnel!

    An established author and former B2B content marketer, Joseph has been around long enough to see content marketing grow from a buzzword to an industry. Currently a freelancer, he also plays an advisory role with ReachStream’s content team. During his time off, he enjoys a quiet day by the beach with his three dogs.

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