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How to deal with difficult customer service requests

The most difficult customer service requests can challenge even the most experienced agent. Read our four steps for dealing with them – from start to finish.

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June 6, 2022

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5 min read

The majority of the time, working in customer service is a fulfilling and satisfying experience.

But, occasionally, it can feel like you’re at the sharp end of customers’ ire. This means your agents need to have the right skills to deal with those tough situations when they do arise – whether caused by an angry customer or a piece of negative feedback.

On top of that, a customer service interaction is often the only way for you to build a meaningful relationship with your customers. So how your agents address difficult situations is crucial to building brand loyalty and trust.

So let’s break down the four main steps for dealing with difficult customer requests for your eCommerce business.

First up, the great customer service paradox

It’s commonly assumed that a customer service agent's inbox can be – at times – a pretty negative place, filled with complaints about defects, delays, and shipping mistakes. After all, customers only get in touch when something has gone wrong, right?

Strangely, the ‘Service Recovery Paradox’ tells us that the impression of your business held by a customer who’s had a problem solved can actually be higher than a customer who had an uneventful service from the outset. That means customers will feel happier – and be more loyal to your company – once something’s gone wrong (and been fixed) than if no problem had ever occurred. In fact, an astonishing 89% of consumers are more likely to make another purchase after a positive customer service experience.

So it’s essential when an error occurs that you give your customers the care, attention, and help that they need. Because for that customer, this singular interaction will shape their entire impression of your brand.

The fact that they’ve reached out gives you an incredible opportunity to build a relationship that you might otherwise never have forged.

The four steps to a happy resolution

So how do you deal with difficult requests?

There are four main steps: greeting the customer, relating to them, resolving their problem, and leaving the door open for them to return.

Let’s take a look through each one in detail.

Step One: Greet

Whatever platform the customer has reached out on, a greeting is essential. Usually, this simply means using the customer’s first name, and where variants apply it’s best to use the form they included in their initial request. If you’re still uncertain, go for a more generic greeting (such as ‘Hi there’) to be safe.

Depending on your system, watch out for macros with a dynamic name field, as this may fetch a company name rather than the customer’s (depending on how the ticket was created). It can also be easy to mistake random names assigned anonymously to visitors for their real first name.

Step Two: Relate

When a customer gets in touch, they want to be understood and empathized with. Agents need to think through what precisely is making the customer unhappy, and to connect with that reason.

For example, rather than saying “I’m sorry you’re unhappy,” it’s far better to be specific. Try “I’m sorry to hear your present is arriving late, I understand how sensitive it is since it’s for your wife’s birthday.”

Use words that signal agreement (such as ‘okay’ and ‘uh huh’), and – so long as it aligns with your brand’s tone of voice – speak as an individual (using ‘I’, ‘me’, and ‘my’) rather than on behalf of the company (‘we’ or ‘our’). This will increase the customer’s perception of your care and empathy.

Also, if you can mirror the customer’s word choice, you’ll increase trust. So if they refer to their ‘shipment’, use the same language as they did – even if that’s not the word you’d typically use.


- Don’t neglect their feelings by saying, for example, “It could be worse.”
- And don’t blame others by saying, for example, “We aren’t responsible for delivery; your order was shipped from our warehouse on time.”

Step Three: Resolve

Now that you’re established rapport with the customer, it’s time to resolve their issue as efficiently and favorably as possible. After all, they don’t just want empathy, they want firm action.

Linguistically, that means taking charge of the conversation and forming a plan of action, to express confidence that you’re on the case. Use solving verbs such as ‘get,’ ‘go,’ ‘call,’ ‘do,’ ‘put,’ ‘need,’ ‘permit,’ ‘allow,’ and ‘resolve’. Take a moment to visualize where the solution lies, and the steps needed to get you both there.

At the same time, it’s important to let go of the idea of solving everything. That simply might not be possible. Especially when a customer is being difficult, agents might feel reluctant to challenge them for fear of risking the relationship. Using more assertive language such as ‘must,’ ‘confirm,’ and ‘action’ can help, rather than getting stuck in an apology.

At the end of the day, an agent’s job is to listen, understand, and discern the next steps – not to immediately produce a solution. That means addressing every issue the customer has and setting proper expectations around when things will be resolved. It’s crucial to avoid making promises that you can’t keep here – for example, even if the tracking link says the package will be delivered before the customer leaves for the airport at 11am, you can’t be 100% sure that will happen.

Finally, try wrapping up with a ‘thank you’ rather than yet another apology, which helps the customer feel confident that their problem has been – or will be – sorted.

Step Four: Leave the ending open

When you end a conversation with an agitated customer, it’s always important to thank them for their patience and understanding. If their problem hasn’t been fixed yet, for example if you’re waiting for a response from the billing department, it’s best to sign off with an open ending that includes what will happen next, such as:

“I'll get back to you via email immediately when I hear back from the billing department. Please let me know if there is something I can do for you in the meantime.”

If on the other hand you have been able to fully resolve their issue, make it clear that you’d love to hear from them again. That way, you’ll solidify the relationship that you’ve now established, and they’ll feel able to get back in touch should they need to.


“Let me know if there is anything else I can help with!”


“Always feel free to write in if you have questions or need help along the way!”

Difficult requests, resolved

By taking customers through the right journey, and using the right language, difficult requests can quickly be transformed from high-pressure situations into golden opportunities to build deeper relationships with your customers. Paradoxically, these interactions can raise customers’ loyalty and satisfaction levels beyond those of the silent majority.

And remember, 93% of customers are likely to make repeat purchases with you if you offer excellent customer service.

To make sure your customer service is not only up to scratch, but is also working to grow your business, book a free Discovery Call with Dream Support. We’d love to get to know you and your business.

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