Rebuild the missing context
Assume the recipient will not remember every date, promise, or earlier conversation. For a message about how to reconnect with a former board member, use this factual base: remind the person where you worked together, when, and what current topic makes the contact relevant.
Say what needs to happen next
State the decision, information, or practical action you need and include a real deadline only when one exists. Make one modest request and give enough information for them to decline or redirect it. Make the immediate next step clear enough that the recipient can answer without reconstructing the entire history.
Avoid making urgency into pressure
Do not imply endorsement, exploit a former hierarchy, or send confidential material from the old relationship. Use official business, privacy, conflict, and procurement rules when commercial or regulated information is involved. Do not make the other person responsible for reducing the discomfort that prompted you to write.