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Write an expired-listing letter that doesn't trash the last agent

Practice: Getting the tone right. About 5 minutes.

About this exercise

You're writing to a homeowner whose listing just expired without selling. Keep it under 100 words, plain text: open with one specific fact from the listing history, make one concrete offer (a free pricing review), and never criticize the previous agent or their photos. No "I'm sorry your home didn't sell" opener and no pressure language. Write a prompt that gets you exactly that.

Common mistakes when you ask AI for this

  • Trusting the AI to count words. AI is bad at counting. Ask for "under 100 words" and it often lands well over. Try: Cap each part instead: "5 sentences, each under 18 words."
  • Opening with sympathy. The AI's default is "I'm sorry to see your home didn't sell," which every letter in his mailbox says. Try: Add: "Open with one specific fact from the listing history."
  • Making a vague offer. "Let's chat about your options" gives him nothing to say yes to. Try: Add: "Offer a free 30-minute pricing review and give my number."
  • Trashing the competition. The AI points out the dark photos or overpricing to look smart. Try: Add: "Don't criticize the previous agent or guess why it didn't sell."
  • Ignoring where it will be pasted. AI loves bold and headings, which show up as stray ** and # symbols in the letter. Try: Name the place and the format: "For the letter. Plain text, no bold or headings."

What a strong prompt includes

  • Opens with a fact
  • Makes one concrete offer
  • Rules out criticism
  • Bans pressure
  • Sets a word limit

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