Rebuild the missing context
Assume the recipient will not remember every date, promise, or earlier conversation. For a message about how to follow up before a free trial ends, use this factual base: name the product, proposal, meeting, commercial question, and last agreed next step.
Say what needs to happen next
State the decision, information, or practical action you need and include a real deadline only when one exists. Add one relevant update and ask whether to proceed, defer, change scope, or close the opportunity. Make the immediate next step clear enough that the recipient can answer without reconstructing the entire history.
Avoid making urgency into pressure
Do not hide an unsubscribe request, invent scarcity, or escalate around the named decision maker. Follow privacy, consent, procurement, and recordkeeping rules for commercial communication. Do not make the other person responsible for reducing the discomfort that prompted you to write.