Account for the relationship as it is now
Use a tone that fits the present relationship, not the closeness, authority, or access that existed in the past. For a message about how to follow up to ask why a deal was lost, use this factual base: name the product, proposal, meeting, commercial question, and last agreed next step.
Ask without assigning an obligation
Explain what you hope for while making decline, delay, or a different format genuinely acceptable. 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.
Keep the ending honest
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. Avoid future promises, guilt, flattery, or nostalgia that imply the recipient owes you access.