The discovery call: 15 questions to ask before you quote

A discovery call earns its name when you leave with one task written in the owner's words, the systems it touches, the people who approve it, the number you'll measure, and the risks that must never happen. Fifteen questions in five blocks get you there in thirty minutes. Ask about the day before you ask about AI, listen for the sentence with the sigh in it, and don't quote until the last block is answered.

Before the call

Read the website and the Google reviews; both tell you what the business promises and where customers complain. Write down your one guess about the painful task. Then let the call prove you wrong.

Block 1: the day

1. "Walk me through a normal Tuesday, from the first customer contact to closing."
2. "Which of those things happens more than five times a day?"
3. "Who does each of them, and what do they use to do it?"

You are listening for repetition and for the tool names that come up unprompted.

Block 2: the pain

4. "Which of those would you happily never do again?"
5. "What happens when it's done late, or wrong?"
6. "Has that cost you a customer, or money, that you know of?"

The answer to 5 is the value of the project; the answer to 6 is the sentence for your case study, if they let you use it.

Block 3: the systems

7. "Where does the information live: WhatsApp, a CRM, a calendar, a sheet, paper?"
8. "Who has the passwords, and who is allowed to give me access?"
9. "Is there anything you're already paying for that you don't really use?"

Question 9 often reveals a CRM or a WhatsApp Business account that nobody set up, which is where the build will live.

Block 4: the people

10. "Who decides whether we go ahead?"
11. "Who would approve an automated message before it goes out, if anyone?"
12. "Who else's day changes if this works?"

If the person on the call isn't the answer to 10, ask for a second call with that person before quoting.

Block 5: the risks

13. "What must this never do?" (Send the wrong price, contact a patient about results, promise a date.)
14. "What kind of message or request would you want a person to handle, always?"
15. "How would you know, a month in, that it's working?"

Question 15 hands you the measurement. If the owner can't answer it, propose one and check it lands.

The questions to skip

• "What's your budget?" Ask later, after the shape is clear; early, it anchors both of you to a number that has no scope behind it.
• "Have you tried AI tools?" Irrelevant and slightly condescending.
• Anything about models, prompts or architecture. That's your homework, not their interview.

Ending the call

Repeat the task back in one sentence. Say what happens next: a one-page brief within two days, with the shape of the engagement and the price, for a one-line approval. Book the follow-up before you hang up. Then write the brief while the sentences are fresh.

Best fit and not a good fit

Best fit: first calls with businesses that have not bought automation before. Not a good fit: a client with a finished spec; there, review the spec against Block 5 and quote from it.

What to do this week

Put the 15 questions on one page. On your next call, tick them off and write the owner's exact sentence next to each block. That page becomes the brief.