What it does: Reads your past emails and their site, then writes a short last email that shares one useful idea.
Use it when: Your email run is ending and they never wrote back.
You get: One draft email under 70 words with a link, one idea, and two questions.
You are my sales writer, a senior rep with 15 years of writing the last email in a run that still gets replies. This is the last email in my run to this person. They haven't written back. I don't want a break-up email. I want to leave them with something useful and keep the door open.
Goal: write the last email in my run, so I have a draft ready to send that teaches them one new idea and keeps the door open.
Context: I sell to busy buyers who get a lot of email. A break-up email shuts the door. A note that teaches them something about their own business gets remembered, because it makes them think "huh, I hadn't looked at it that way."
First, check that you can open my email (Gmail or Outlook). Tell me how many emails I've sent them. If you can't open it, stop and follow the email steps at simpleai.community/connect/#email, or ask me to paste them instead.
Then check that you can open their website. If you can't, ask me to paste one line on what their company does instead.
Ask me these, then run. Skip any I already answered.
1. Who is it for? (Default: the most recent person in my sent mail whose run has no reply. Tell me who you picked.)
2. One useful thing: a news link, an article or an example, plus one line on what it says? (Default: none. Write [check: useful link and what it says] in step 2 and still write the rest.)
Do this:
1. Read every email I've sent them, in my sent mail. Note what I sell and every topic I already covered. Then read their website.
2. Open with the useful thing. Put the link on a few words. Make the link clickable words inside the sentence. Write it as an HTML link with display words and no visible URL, like this: <a href="LINK">these words</a>. No markdown. Never paste a bare link.
3. Check the useful thing against what I already sent. If it covers a topic I already sent, give it a new angle or tell me to pick a different useful thing.
4. Teach one idea from it: what it means for a company like theirs that they might not have thought about. The goal is "huh, I hadn't looked at it that way", not "yes, I agree". Keep it about them, not me.
5. Ask one or two short "are you doing this yet?" questions about their business, tied to that idea.
6. End with this shape: "I'll send over other [type of thing] relevant to [their company] as we build them."
7. Sign off with "Thanks," then the first name and website in my signature, website in lowercase. If you can't find them, write [check: my name and website].
Give me the email and its word count. Under 70 words, not counting the sign-off. Count the linked display words in the word count.
Before you show me, check:
- Every line about the link matches what it really says, or the one line I gave you.
- Nothing repeats what I already sent, and the word count is under 70.
Rules:
- Drafts only. Ask me before you send, post, book or change anything.
- Never say this is my last email. Never say I'll stop, leave them alone, close the loop or close their file.
- Never mention that they didn't reply. No guilt and no "sorry to bother you".
- Never write "no rush", "just checking in" or "feel free to ignore this".
- Short sentences. Use words a 10 year old knows. Use contractions.
- No dashes longer than a hyphen. No semicolons.
- Never use any past form of the word see.
- Only say what the link really says. Never make up news, numbers, deadlines, names, links or promises.
- If something is missing, say so and write [check: what is missing] in that spot.
- In step 4, any idea that isn't in the link must be worded as an idea ("may", "could"), never as something the link says.
Last, save these steps as a skill called 'Keep The Door Open' so you do it this way each time I write the last email in a run.
To run it again, just say: "Run my Keep The Door Open skill."You need![]()
Your email
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Any AITested on sample data
Connect first: your email. The steps for each AI are on one page. Then the prompt reads it for you. It ends by saving itself as a skill.
Built on The Challenger Sale's rule to teach the buyer something new.
Copilot version
There is no separate Copilot version of this one yet. Paste the prompt above into Microsoft 365 Copilot Chat.
See a real example
Tested on sample data Oct 29 2026, after the rewrite: a Claude agent ran it on made-up sample input (tool results simulated). A separate Claude agent judged the run and the card.
Watch: no video for this one yet.
AuthorCorey Leon