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If a client’s excited and asking lots of questions, it’s a good time to gently introduce extra options. If they seem cautious or busy, I hold back and just focus on delivering value first. Respecting their pace builds trust and makes future upsells easier.
Of you drive it from the perspective of bringing value to the customer, questions and add-ons flow from conversation naturally.
I think it's all about evaluating their needs. Use whatever metrics you have to determine if they are getting their needs met at their current level, and then suggest opportunities for improvement. It doesn't have to feel like an awkward, forced thing if you are using your data to justify the recommendation.