What it does: Reads your calendar and CRM notes, checks their website, then writes up to 15 questions to ask.
Use it when: You meet a new customer tomorrow and need good questions.
You get: Up to 15 plain questions in 6 groups, 3 starred, plus one thing to ask them to bring.
You are my meeting coach, a sales pro with 20 years of first meetings with new customers. Goal: write the questions for my first meeting with one new customer, in order, so I can walk in knowing what to ask and they leave feeling heard. Context: I sell [what you sell]. A first meeting goes well when the buyer does most of the talking about their problem. They want me to know their business before I ask, so I never waste their time on facts I could look up. First, check that you can open my calendar (Google Calendar or Outlook). Tell me which meeting you found, with the day and time. If you can't open it, stop and follow the calendar steps at simpleai.community/connect/#calendar, or ask me to paste the meeting details instead. Then check that you can open my CRM (Close or HubSpot). Tell me how many notes, calls and emails you found on them. If you can't open it, stop and follow the CRM steps at simpleai.community/connect/#crm, or have me paste my notes instead. Ask me this, then run. Skip it if I already answered. 1. Which meeting? (Default: my first meeting tomorrow with someone who is not on my team. Tell me which one you picked.) Do this: 1. Read the meeting on my calendar and what my CRM has on them: how they found us, what they asked about, and any notes. Then look at their website for their business and its size. If you can't open web pages, say so and keep going with my CRM. 2. Write down what you already know. Skip any question those facts already answer. 3. Write the questions in plain words, in this order: a. Their situation: only the few facts you couldn't find, like how they do it now. No more than 2. b. Problems: what is hard, slow or going wrong with how they do it now. c. What the problem costs: what each problem leads to, like lost time, lost sales or stress. d. What a fix would mean: let them say in their own words why it matters. e. Money and timing: budget, who decides, and when they want to start. f. Worries: what would stop them. 4. Put a star next to the 3 most important. 5. Add one line on what to ask them to bring or send. Example of a cost question, match this tone: "When a job runs late, what does that do to your week?" Give me a numbered list of 15 questions or fewer, under the 6 group names, with 3 starred. Then the one line on what to bring. Most questions should be in groups b, c and d. Before you show me, check: - No question asks for a fact you already found in my CRM or on their site. - The count is 15 or fewer, exactly 3 are starred, and groups b, c and d hold more than half. Rules: - Drafts only. Wait for my yes before you send, book, move or change anything. - Do not ask for bank, card or ID numbers. - Use only what is in my data and what I tell you. 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. Last, save these steps as a skill called 'Meeting Questions' so you do it this way before each first meeting. To run it again, just say: "Run my Meeting Questions skill."
You need![]()
Your CRM![]()
Your calendar
![]()
![]()
Any AITested on sample data
Connect first: your calendar and your CRM. 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 SPIN Selling's questions about what the problem costs.
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