How to Upsell a Customer on Live Chat in Stealth Mode?

Upselling is an approach that businesses of all sizes use with the core objective to offer additional products or services through customer support and in marketing campaigns. However, doing this is sometimes inappropriate, especially if you are using the customer support channel. But, with the right approach, this can bring desired results.

The most important reason why businesses choose to upsell is the power of customer retention. First of all, it is much cheaper to do business with a returning customer, as acquiring a new one costs a lot more. On the other hand, making a sale with a returning customer is 50% more likely than with a new customer, a certain level of trust already exists, making it easier to close the sale.

Let’s take a look at a couple of principles to follow if you want your upselling game to be better.

Analyze the collected data

Technology has provided business with a lot of software tools that help capture an abundance of useful data about customer behavior. This has a perfect application in upselling strategies, as live chat software agents can take a look at data and conclude which of the products he or she might upsell to the customers.

Therefore, to pick the right approach, it is first necessary to take a look at data and create documentation that pairs certain products with others. This will allow for the customer support agent to naturally upsell a product, without sounding pushy. This is the first way to make upselling effective, as prediction allows companies to promote the right product.

Pick the right circumstances for upselling

Some companies train their live chat software customer support to be very aggressive. This is a poor approach because live chat agents forget about the importance of actually helping the customer and then upsell a product.

Not knowing when to upsell can cause a lot of problems for a business, as customers will perceive the brand as being too pushy and only worrying about its profits. Remember that your customers are people with emotions and reason, and every wrong upselling approach will be noticed and judged, lowering the chances of them returning to your business.

For example, imagine a customer who is experiencing problems with your product or service, and while the agent is helping the customer, he is also upselling another product. The approach is wrong because the customer is agitated and will only become more angry with the upselling efforts you are making. In such scenarios, the complete focus of your customer support agent should remain on solving an issue and skipping the upsell process.

On the other hand, once the problem is solved, an agent should evaluate the situation and either skip the approach or make an attempt to upsell. This can be easily deduced from the tone of the customer.

You can always mention promotions

Mentioning products which are on sale is not an overly aggressive approach if your agents can mention it in the right tone and with the right approach.

What is the right approach?

  • Tone of the voice – The tone of the customer agent should always remain formal, as it shows respect to the customer. The customer will look at your agents more seriously and take a higher interest in what he or she has to say.
  • Using the customer’s name – When you address someone by their name, things get more personal. This is why it is important to always try and use the customer’s name in the conversation, it makes the communication private and builds up some level of trust.
  • Only promoting once the customer has been serviced – Never upsell if a customer is agitated. Always make sure to solve the issue that caused the customer to reach out to you, it will lower the tension, increase happiness and open a possible window of time when you can mention some of the products or services which are currently on discount.

Doing this will allow you to increase sales, without pushing your customer, the agent simply shares information with him or her, the decision is completely up to them.

Pick a relaxed approach

What is a relaxed approach? Well, sometimes, companies can be quite pushy. That turns out to be counter-effective as customers will decide to move away from your brand than stay with it. This is something you should avoid as much as possible. There is no need for your customer to feel forced into buying more products or services from you.

Simply mention the product and explain why it might be helpful to the customer and continue the normal flow of a conversation, without repeating all the benefits and why he or she should purchase more.

With this approach, your live chat agents should actually offer help through other products without insisting too much on buying it. A simple mention will get the customer thinking and that is the true beauty of upselling.

When upselling, stay with a relevant product

Many companies make the mistake of pushing their products and services on clients who don’t really need them. This will not only negatively affect your sales figures but also make the customers perceive you as another pushy company that just wants to sell the product.

For example, don’t have your live chat software agents offer a product or service aimed at enterprise businesses to smaller business. It simply doesn’t makes sense as the small business doesn’t need that type of a product.

Therefore, to make the upselling process look natural, it is best to offer products and services that someone actually might need. Yes, it is a cheaper product, but it actually has a chance of being sold, making a profit for your business and helping the customer.


These are the best approaches for upselling through live chat software. The point is to make the whole process natural, with the intent of helping a customer. It is the best way to achieve higher results, as being too pushy will actually lead to negative results.