The best upsell doesn't feel like one
Upselling in chat has a bad reputation because it is usually done badly — pushing a bigger plan at someone who just wants help. Done well, it is indistinguishable from good service: the customer wanted an outcome, and the add-on genuinely gets them there faster. The goal is not to sell more; it is to solve better, and sometimes solving better costs a little more.
Spot the genuine opportunity
A real upsell opportunity announces itself in what the customer says: they are hitting a limit, describing a need the bigger option fills, or asking about something the add-on provides. That is the moment a recommendation is welcome. A customer who is just troubleshooting a bug is not that moment — reading the difference is the entire skill.
Recommend, don't push
The line between helpful and pushy is honesty and a graceful exit. Explain why the option fits their stated need, give the real trade-off, and make “no thanks” completely comfortable. A recommendation the customer can easily decline builds trust; one they feel cornered by burns it, and a burned customer costs far more than the upsell was worth.
Know when NOT to sell
Sometimes the right move is to sell nothing — when the customer is frustrated, when the cheaper option genuinely suits them, when they came in with a problem and not a purchase. An agent who tells someone “honestly, the plan you have is the right one” earns a loyalty no upsell can buy. Restraint is part of selling well.
How MyLiveChat fits
MyLiveChat lets you recognize returning and higher-intent visitors, route them to the right person, and keep canned product explainers handy so a recommendation is accurate and fast. The judgment of when to recommend — and when to hold back — stays with your agents; the tool just makes the helpful version easy to deliver.