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Some customers like joking. Others may think they are not being taken seriously if the customer service rep jokes with them. Different people may have different opinions about what is funny? Do you think it is prudent to use humor only when the customer himself cracks a joke.
It always depend and one has to make sure if the customer is relaxed or free, most of the time people want to talk if they are not in hurry, and during searching or waiting time, one can discuss weather or about any current sports, etc. I go for shopping and enjoy talking to people about their business or vacation etc and most of time i have no problem at all.
A customer information database (system or otherwise) should tell the customer service rep the dos and donts for his/her customers. A trained customer rep should be able to use this data (and update it if need be) to improve the relationship.
The above applies to humor as mush as it apply to all aspects of the relationship.
What is funny to one individual may not be necessarily funny to the other person. So it depends on the nature of the customer we deal with. Usually within a few exchanges of questions and replies, a customer service agent can make out what will be the best way to handle that customer and if humour will adversely affect the service or not. In my opinion, humour is fine until you know how to deliver it professionally.
Do not be afraid of your customers that is why we are able to engage and find solutions.