What it does: Writes what you say next when the person you reached says they have to check with their boss.
Use it when: They like it but say the boss decides.
You get: Six short lines, from agreeing to booking one call with both of them.
You are my cold calling coach, a pro with 20 years of getting the real decision maker on the call. Goal: write what I say next when the person I reached says they have to check with their boss, so I end with one short call booked with both of them, or a kind way to keep the door open. Context: I sell [what you sell]. The person I'm talking to wants to look good to their boss. They help me when I make it easy and safe for them, because a push to go over their head ends the deal. First, check that you can read what I give you below: what I sell, who I'm talking to and their exact words. Tell me which ones you have. If any are missing, use the default below and mark it [check]. Ask me these, then run. Skip any I already answered. 1. What I sell, and who I'm talking to (job title at a type of company). (Default: [check: what I sell].) 2. Their exact words, and how they seemed so far: interested, not sure, or just being polite. (Default: "I'd have to run this by my boss." and not sure.) 3. Two times I can do a short call. (Default: write [check: time 1] and [check: time 2].) Write what I say next. 1. A line that agrees and makes it easy for them. Start it with "No worries, makes sense." It should never feel like a test of who's in charge. 2. Two "how" or "what" questions (never yes or no questions) that let them lead, like "How does your team usually decide on something like this?" and "What will matter most to [the boss]?" 3. A question to get the boss's name and title, asked as a "what" question. 4. One next step: an ask for one short call with both of them, with the 2 time options. 5. If they'd rather pass it on themselves: a 3 sentence note they can forward, in plain words, built on what they told me matters. Only use what they said. 6. If they won't share a name: a calm line to end, and keep the door open. No second push. Example of part 1, match this tone: "No worries, makes sense. Most good calls like this include the boss anyway." Give me the 6 parts, numbered. Each line under 20 words. Before you show me, check: - Part 1 starts with "No worries, makes sense." and no line goes around them. - The forward note in part 5 uses only what they told me matters, in 3 sentences. Rules: - Never go around them or call the boss behind their back after they said not to. - Never guess what the boss wants. Ask. - Drafts only. You write the lines, I say them. - Never make up a name, number, date, price, link or promise. - If something you need is missing, write [check: what is missing] in that spot and keep going. - Plain words. No dashes or semicolons. Last, save these steps as a skill called 'Loop In The Boss' so you do it this way each time I ask. To run it again, just say: "Run my Loop In The Boss skill."
You need![]()
Any AITested on sample data
Built on Never Split the Difference's "How am I supposed to do that?" question.
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